1. Beta-hch
2. 1,2,3,4,5,6-hexachlorocyclohexane
3. Gamma-hch
4. Alpha-hch
5. 58-89-9
6. Hexachlorane
7. Kwell
8. Gamma-bhc
9. Beta-bhc
10. Benzene Hexachloride
11. Epsilon-hch
12. Beta-hexachlorocyclohexane
13. Hexicide
14. Gamene
15. Scabene
16. Delta-bhc
17. Delta-hch
18. Gamma-hexachlorocyclohexane
19. Beta-lindane
20. 319-85-7
21. Aalindan
22. Aphtiria
23. Jacutin
24. Gexane
25. 319-86-8
26. 319-84-6
27. Agrocide
28. Aparasin
29. Chloresene
30. Codechine
31. Entomoxan
32. Gammalin
33. Gammaterr
34. Hexachloran
35. Hexaverm
36. Hexyclan
37. Kokotine
38. Lindafor
39. Lindosep
40. Lorexane
41. Nicochloran
42. Ovadziak
43. Owadziak
44. Pedraczak
45. Pflanzol
46. Quellada
47. Streunex
48. Aficide
49. Aplidal
50. Arbitex
51. Celanex
52. Devoran
53. Gamacid
54. Hortex
55. Lendine
56. Lentox
57. Lidenal
58. Lindex
59. Lintox
60. Linvur
61. Mszycol
62. Omnitox
63. Alpha-hexachlorocyclohexane
64. Bexol
65. Nexit
66. Viton
67. Alpha-lindane
68. Beta-1,2,3,4,5,6-hexachlorocyclohexane
69. Hcch
70. 608-73-1
71. Agrocide Wp
72. Agrocide Iii
73. Ben-hex
74. Ameisentod
75. Benhexol
76. Gammexane
77. Heclotox
78. Lasochron
79. Lindatox
80. Gammalin 20
81. Neo-scabicidol
82. Gamma-lindane
83. Nexit-stark
84. Bentox 10
85. Milbol 49
86. Nexen Fb
87. Alpha-bhc
88. Alpha-1,2,3,4,5,6-hexachlorocyclohexane
89. Nexol-e
90. Delta-hexachlorocyclohexane
91. Dol Granule
92. Gamacarbatox
93. Lindagrain
94. Lindagranox
95. Lindapoudre
96. Spruehpflanzol
97. (+)-alpha-hch
98. Agronexit
99. Esoderm
100. Gallogama
101. Gamaphex
102. Geobilan
103. Hexatox
104. Hilbeech
105. Lindagam
106. Novigam
107. Silvanol
108. Gamiso
109. Inexit
110. Isotox
111. Lindan
112. Gamma-col
113. Spritz-rapidin
114. Forst-nexen
115. Sang Gamma
116. Mglawik L
117. Agrocide 7
118. Hungaria L7
119. Ameisenmittel Merck
120. Tri-6
121. Spritzlindane
122. Lindanum
123. Delta-lindane
124. Gamma-1,2,3,4,5,6-hexachlorocyclohexane
125. Geolin G 3
126. Verindal Ultra
127. Gamma Benzene Hexachloride
128. Gamma-benzene Hexachloride
129. Tap 85
130. Detox 25
131. Alpha-hexachlorane
132. Agrocide 6g
133. Hexachlorcyclohexan
134. 6108-10-7
135. Drilltox-spezial Aglukon
136. Beta-benzene Hexachloride
137. Hexachlorocyclohexanes
138. Gammallin
139. Gammaxene
140. Gamma-hexachlorobenzene
141. .delta.-hexachlorocyclohexane
142. Delta-benzenehexachloride
143. .alpha.-lindane
144. .delta.-lindane
145. Ent 9,234
146. Alpha-benzene Hexachloride
147. Delta-benzene Hexachloride
148. .alpha.-bhc
149. .delta.-bhc
150. Epsilon-hexachlorocyclohexane
151. Bhc (mixed Isomers)
152. Ent 7,796
153. Ent 9,232
154. Latka 666
155. Gamma-hexachlorzyklohexan
156. 119911-69-2
157. Hch
158. Latka 666 [czech]
159. Benzene Hexachloride-alpha-isomer
160. Hexachlorocyclohexane, Gamma-isomer
161. Benzene Hexachloride, Gamma
162. Zeta-hch
163. .beta.-hexachlorocyclohexane
164. Hexachlorocyclohexane, Technical Grade
165. .alpha.-hexachlorocyclohexane
166. .alpha.-hexachloran
167. .alpha.-hch
168. .delta.-hch
169. .alpha.-hexachlorane
170. Bbh
171. Benzene Hexachloride (ambiguous)
172. 1a,2a,3b,4a,5b,6b-hexachlorocyclohexane
173. Benzene Hexachloride Gamma
174. (1r,2r,3r,4r,5r,6r)-1,2,3,4,5,6-hexachlorocyclohexane
175. 59nee7pcab
176. Bhc,mixtureofisomers(alpha
177. Ym80odm9pd
178. Hgi
179. Nsc-755895
180. .alpha.-hexachlorcyclohexane
181. .delta.-benzene Hexachloride
182. 88rhn9khn8
183. Ivm9a2n49k
184. (1alpha,2beta,3alpha,4beta,5alpha,6beta)-1,2,3,4,5,6-hexachlorocyclohexane
185. Yv2d256z3n
186. Hexapoudre
187. Benzanex
188. Gamacide
189. Hexablanc
190. Hexachlor
191. Hexamul
192. Hexcidum
193. (1r,2r,3r,4r,5s,6s)-1,2,3,4,5,6-hexachlorocyclohexane
194. (1r,2r,3s,4r,5r,6s)-1,2,3,4,5,6-hexachlorocyclohexane
195. Chebi:24536
196. Chebi:28428
197. Chebi:32888
198. Chebi:39095
199. Chebi:39096
200. Dolmix
201. Gamtox
202. Isatox
203. Submar
204. Gyben
205. Beta-hexachloran
206. Arcotal S
207. Trives-t
208. Gamma Bhc
209. Hch-.delta.
210. Lacco Hi Lin
211. Nsc-11808
212. Cyclohexane, 1,2,3,4,5,6-hexachloro-, (1.alpha.,2.alpha.,3.alpha.,4.beta.,5.alpha.,6.beta.)-
213. Cyclohexane, 1,2,3,4,5,6-hexachloro-, (1.alpha.,2.alpha.,3.beta.,4.alpha.,5.alpha.,6.beta.)-
214. Cyclohexane, 1,2,3,4,5,6-hexachloro-, (1.alpha.,2.alpha.,3.beta.,4.alpha.,5.beta.,6.beta.)-
215. Bhc-.delta. Isomer
216. Gamacide 20
217. Bhc, .delta.
218. Hecoltox
219. Epsilon-hch 100 Microg/ml In Methanol
220. Ncgc00094546-04
221. Ameisenatod
222. Benhexachlor
223. Gammahexane
224. Aphtitria
225. Epsilon-hch 10 Microg/ml In Cyclohexane
226. Exagama
227. Gammahexa
228. Gammopaz
229. Lindalo
230. Lindamul
231. Lindano
232. Lindaterra
233. Novigan
234. Benzex
235. Beta-hexachlorobenzene
236. Forlin
237. Gammex
238. (1r,2r,3s,4s,5r,6s)-1,2,3,4,5,6-hexachlorocyclohexane
239. Bhc Or Hch
240. Delta-1,2,3,4,5,6-hexachlorocyclohexane
241. Detmol-extrakt
242. Epsilon-hch 100 Microg/ml In Cyclohexane
243. Fenoform Forte
244. Trans-1,2,3,4,5,6-hexachlorocyclohexane
245. Nexen-fb
246. Detmol Extract
247. Dsstox_cid_685
248. Dsstox_cid_686
249. Dsstox_cid_687
250. Borer Spray
251. .alpha.-1,2,3,4,5,6-hexachlorocyclohexane
252. .gamma.-1,2,3,4,5,6-hexachlorocyclohexane
253. Alpha-hexachloran
254. Alpha-benzenehexachloride
255. (1alpha,2alpha,3alpha,4beta,5alpha,6beta)-1,2,3,4,5,6-hexachlorocyclohexane
256. (1alpha,2alpha,3beta,4alpha,5alpha,6beta)-1,2,3,4,5,6-hexachlorocyclohexane
257. Agrocide 2
258. Kwell-r
259. Dsstox_rid_75733
260. Dsstox_rid_75734
261. Dsstox_rid_75735
262. Dsstox_gsid_20685
263. Dsstox_gsid_20686
264. Dsstox_gsid_20687
265. Bhc (insecticide)
266. Hch [bsi]
267. Hch [iso]
268. Cyclohexane, 1,2,3,4,5,6-hexachloro-, .alpha.-
269. Cyclohexane, 1,2,3,4,5,6-hexachloro-, .beta.-
270. Cyclohexane, 1,2,3,4,5,6-hexachloro-, .delta.-
271. Gamma-mean 400
272. Agrisol G-20
273. T-hch
274. Caswell No. 079
275. Caswell No. 527
276. Gamma-benzohexachloride
277. Cyclohexane, 1,2,3,4,5,6-hexachloro-, .gamma.-isomer
278. (1r,2c,3t,4c,5c,6t)-1,2,3,4,5,6-hexachlorocyclohexane
279. (1r,2r,3s,4r,5s,6s)-1,2,3,4,5,6-hexachlorocyclohexane
280. (1r,2t,3c,4t,5c,6t)-1,2,3,4,5,6-hexachlorocyclohexane
281. 1alpha,2alpha,3beta,4alpha,5beta,6beta-hexachlorocyclohexane
282. Scabecid
283. Gamma Hexachlor
284. Lindanum [inn-latin]
285. Pepsin
286. Gamma-benzenehexachloride
287. Gamma-hexachloro-cyclohexane
288. Atlas Steward
289. Lindano [inn-spanish]
290. Sang-gamma
291. Gamma-hch Or Gamma-bhc
292. Gamma-hexachlorcyclohexanum
293. Rcra Waste Number U129
294. Technical Hch
295. Gamma-hexachlorane
296. Theta-hch
297. Cas-58-89-9
298. Hexachlorocyclohexane, Beta-
299. Hexachlorcyclohexan [german]
300. Ent 8,601
301. Ent 9,233
302. Hexachlorocyclohexane, Alpha-
303. Hexachlorocyclohexane, Delta-
304. Hexachlorocyclohexane, Gamma-
305. 6108-11-8
306. 6108-12-9
307. Cas-319-85-7
308. Cas-608-73-1
309. Smr000857321
310. Smr000875266
311. Ccris 327
312. Ccris 328
313. Ccris 329
314. Technical Hexachlorocyclohexane
315. Trans-alpha-benzenehexachloride
316. .gamma.-bhc
317. Benzenehexachloride-alpha-isomer
318. Ccris 1449
319. Hsdb 646
320. .beta.-bhc
321. 1,2,3,4,5,6-hexachlorocyclohexane (hch)
322. D-bhc
323. .delta.,1,2,3,4,5,6-hexachlorocyclohexane
324. Lindane (gamma-hch)
325. Benzene Hexachloride-gamma Isomer
326. Cyclohexane, 1,2,3,4,5,6-hexachloro-
327. Hsdb 1606
328. Hsdb 6029
329. Hsdb 6183
330. Hsdb 6184
331. (-)-alpha-hch
332. Benzenehexachloride, Mixed Isomers
333. Gamma-bhc Benhexachlor
334. Benzene-cis-hexachloride
335. Nci-c00204
336. Eta-hexachlorocyclohexane
337. Hexachlorocyclohexane, Gamma Isomer
338. Cyclohexane, .delta.,1,2,3,4,5,6-hexachloro-
339. Hexachlorocyclohexane (all Isomers)
340. Sr-05000001837
341. Zeta-hexachlorocyclohexane
342. Drill Tox-spezial Aglukon
343. Murfume Grain Store Smoke
344. Einecs 200-401-2
345. Einecs 206-270-8
346. Einecs 206-271-3
347. Einecs 206-272-9
348. Einecs 210-168-9
349. Unii-59nee7pcab
350. Unii-ym80odm9pd
351. Epsilon-benzenehexachloride
352. Hexachlorocyclohexane (mixed Isomers)
353. Nsc 11808
354. Theta-hexachlorocyclohexane
355. .delta.-(aeeee)-1,2,3,4,5,6-hexachlorocyclohexane
356. Kwell (tn)
357. Rcra Waste No. U129
358. Unii-ivm9a2n49k
359. Cyclohexane, 1,2,3,4,5,6-hexachloro-, .delta.-isomer
360. Epa Pesticide Chemical Code 009001
361. Hexachlorocyclohexane (technical Grade)
362. Brn 1907331
363. Brn 1907334
364. Brn 1907337
365. Brn 1907338
366. Brn 3195880
367. Kanodane
368. Detmol Extrakt
369. Ai3-07796
370. Ai3-08601
371. Ai3-09232
372. Ai3-09233
373. Ai3-09234
374. H.c.h.
375. Nexit Stark
376. Lindane [hexachlorocyclohexanes]
377. 1.alpha.,2.alpha.,3.alpha.,4.beta.,5.alpha.,6.beta.-hexachlorocyclohexane
378. Benzene Hexachloride-gamma-isomer
379. Unii-5477b350ek
380. .gamma.-lindane
381. Lindane [usan:usp:inn:ban]
382. Benzene Hexachloride, All Isomers
383. Theta-bhc
384. Cyclohexane, Beta-1,2,3,4,5,6-hexachloro-
385. Cyclohexane, Delta-1,2,3,4,5,6-hexachloro-
386. Hexachlorzyklohexan
387. Beta-hch [hexachlorocyclohexanes]
388. Nexol E
389. Hch (technical)
390. Alpha-hch [hexachlorocyclohexanes]
391. D-alpha-bhc
392. Gamma-hch [hexachlorocyclohexanes]
393. Sang-.gamma.
394. Delta -bhc
395. Eta-bhc
396. Eta-hch
397. 1,2,3,4,5,6-hexachlorocyclohexane, (1.alpha.,2.alpha.,3.alpha.,4.beta.,5.alpha.,6.beta.)-
398. Cyclohexane, 1,2,3,4,5,6-hexachloro-, Alpha-
399. Cyclohexane, 1,2,3,4,5,6-hexachloro-, Gamma-
400. Lindane,(s)
401. 1,2,3,4,5,6-hexachlorocyclohexane, Gamma-isomer
402. Delta-(aeeeee)-1,2,3,4,5,6-hexachlorocyclohexane
403. Einecs 228-068-9
404. .gamma.-hexachloran
405. .gamma.-hch
406. Bhc .alpha.
407. Hch-.alpha.
408. .gamma.-hexachlorane
409. Bhc-.alpha. Isomer
410. Cyclohexane, 1,2,3,4,5,6-hexachloro-, Alpha-isomer
411. Cyclohexane, 1,2,3,4,5,6-hexachloro-, Beta-isomer
412. Cyclohexane, 1,2,3,4,5,6-hexachloro-, Delta-isomer
413. Cyclohexane, 1,2,3,4,5,6-hexachloro-, Gamma-isomer
414. Bhc(.gamma.)
415. G-bhc-.delta.
416. Hch, Technical Grade
417. Lindane (gama-hch)
418. Lindane, 97%
419. 1,2,3,4,5,6-hexachlorocyclohexane (mixture Of Isomers)
420. Cyclohexane, 1,2,3,4,5,6-hexachloro-, (mixed Isomers)
421. Lindane (usp/inn)
422. Gammahexachlorcyclohexane
423. Spectrum_001929
424. 1a,2b,3a,4b,5a,6b-hexachlorocyclohexane
425. .beta.-lindane
426. 1alpha,2alpha,3beta,4alpha,5alpha,6beta-hexachlorocyclohexane
427. Lindane [hsdb]
428. Lindane [iarc]
429. Lindane [usan]
430. .epsilon.-bhc
431. Ai3-15109
432. Bhc, Epsilon-
433. Lindane [inn]
434. Alpha-hexachlorcyclohexane
435. Lindane [mi]
436. .gamma.-benzohexachloride
437. .gamma.-hexachlorobenzene
438. Dsstox_cid_684
439. Lindane [mart.]
440. Spectrum2_001864
441. Spectrum3_000860
442. Spectrum4_000700
443. Spectrum5_001586
444. .epsilon.-lindane
445. Bhc, Delta-
446. .beta.-hch
447. 1-alpha,2-alpha,3-alpha,4-beta,5-alpha,6-beta-hexachlorocyclohexane
448. 1-alpha,2-beta,3-alpha,4-beta,5-alpha,6-beta-hexachlorocyclohexane
449. Dsstox_cid_4134
450. Lindane [usp-rs]
451. Lindane [who-dd]
452. Lindane [who-ip]
453. .beta.-hexachloran
454. Hch, Technical Grade [hexachlorocyclohexanes]
455. Gamma Benzene Hydrochloride
456. Unii-88rhn9khn8
457. (1alpha,2alpha,3beta,4alpha,5beta,6beta)-1,2,3,4,5,6-hexachlorocyclohexane
458. Epsilon-benzene Hexachloride
459. Bhc, .alpha.-
460. Cyclohexane, 1,2,3,4,5,6-hexachloro-, (1alpha,2alpha,3beta,4alpha,5alpha,6beta)-
461. Cyclohexane, 1,2,3,4,5,6-hexachloro-, (1alpha,2beta,3alpha,4beta,5alpha,6beta)-
462. Dsstox_rid_75732
463. Unii-yv2d256z3n
464. .alpha.-benzene Hexachloride
465. .gamma.-benzene Hexachloride
466. 1,2,3,4,5,6-hexachlorocyclohexane Gamma Isomer
467. Benzene-1,2,3,4,5,6-hexachloride (ambiguous)
468. Bhc, .beta.-
469. Bidd:pxr0097
470. Cyclohexane, 1,2,3,4,5,6-hexachloro-, Delta-
471. Dsstox_gsid_20684
472. Dsstox_gsid_24134
473. Schembl25895
474. Schembl25896
475. Schembl75689
476. .gamma.-hexachlorocyclohexane
477. Bspbio_002479
478. Kbiogr_001199
479. Kbioss_002471
480. Spectrum330071
481. 2-05-00-00011 (beilstein Handbook Reference)
482. 4-05-00-00056 (beilstein Handbook Reference)
483. 4-05-00-00058 (beilstein Handbook Reference)
484. 4-05-00-00060 (beilstein Handbook Reference)
485. 4-05-00-00061 (beilstein Handbook Reference)
486. Mls001333088
487. Mls001335969
488. Mls001335970
489. Mls001361319
490. Beta-bhc, Analytical Standard
491. Bidd:er0090
492. Bidd:er0091
493. Bidd:er0449
494. Bidd:er0558
495. Bidd:gt0634
496. Chembl15891
497. Divk1c_000701
498. Lindane [orange Book]
499. Schembl140812
500. Schembl140813
501. Schembl472088
502. Benzene Hexachloride, .gamma.
503. Spbio_001708
504. .epsilon.-hexachlorocyclohexane
505. Delta-bhc, Analytical Standard
506. Gamma-bhc, Analytical Standard
507. Lindane [usp Impurity]
508. Chembl389022
509. Schembl7647849
510. Schembl8469477
511. Schembl9120917
512. Zinc1621
513. (+)-alpha-hexachlorocyclohexane
514. .beta.-hexachlorobenzene
515. Lindane [usp Monograph]
516. Chembl1200921
517. Chembl1714528
518. Chembl1874247
519. Chembl2272381
520. Dtxsid0024135
521. Dtxsid2020684
522. Dtxsid2020686
523. Dtxsid5024134
524. Dtxsid7020685
525. Dtxsid7020687
526. Hexachlorocyclohexane (q-isomer)
527. Hexachlorocyclohexane (z-isomer)
528. Hexachlorocyclohexane [h-isomer]
529. Lindanum [who-ip Latin]
530. Schembl10795898
531. .alpha.-666
532. .alpha.-benzohexachloride
533. .delta.-666
534. Hms502d03
535. Kbio1_000701
536. Kbio2_002464
537. Kbio2_005032
538. Kbio2_007600
539. Kbio3_001979
540. 1,2,3,4,5,6-hexachlorocyclohexane (all Stereo Isomers)
541. Nsc7909
542. Nsc8093
543. (+/-)-.alpha.-hch
544. Ninds_000701
545. (1r,2r,3s,4s,5s,6s)-1,2,3,4,5,6-hexachlorocyclohexane
546. .alpha.-benzenehexachloride
547. .beta.-666
548. Dtxsid901310407
549. Hms1923k17
550. Hms2091e05
551. Hms2230c24
552. Hms2231a06
553. Hms3369j21
554. Pharmakon1600-00330071
555. .beta.-benzene Hexachloride
556. Benzene Hexachloride-.alpha.-isomer
557. Hy-a0085
558. Nsc-7909
559. Nsc-8093
560. Nsc11807
561. Nsc11808
562. A-hexachlorocyclohexane (hch, Bhc)
563. Benzene Hexachloride (gamma-isomer)
564. Hexachlorocyclohexane,.gamma.-isomer
565. Tox21_111294
566. Tox21_200676
567. Tox21_201777
568. Tox21_202069
569. Tox21_202290
570. Tox21_300624
571. Tox21_300953
572. Tox21_302925
573. Tox21_303873
574. Bdbm50410525
575. Beta-hch 100 Microg/ml In Toluene
576. Ccg-39862
577. Nsc-11807
578. Nsc755895
579. .epsilon.-benzene Hexachloride
580. Alpha-hch 100 Microg/ml In Acetone
581. (1alpha,2alpha,3alpha,4beta,5beta,6beta)-1,2,3,4,5,6-hexachlorocyclohexane
582. 1,2,3,4,5,6-hexachlorocyclohexane (1alpha,2alpha,3beta,4alpha,5alpha,6beta)
583. 1,2,3,4,5,6-hexachlorocyclohexane (all Stereo Isomers, Including Lindane)
584. Akos015903494
585. Akos015914103
586. Akos024390982
587. Beta-hch 1000 Microg/ml In Toluene
588. Cyclohexane,2,3,4,5,6-hexachloro-
589. Gamma-hexachlorocyclohexane [lindane And Other Hexachlorocyclohexane Isomers]
590. Zinc100068484
591. Zinc100076865
592. Zinc100076868
593. Zinc100899052
594. Zinc245204924
595. Zinc263584078
596. 1,2,3,4,5,6-hexachloro-cyclohexane
597. 5477b350ek
598. Alpha-hch 1000 Microg/ml In Toluene
599. Beta-hch 10 Microg/ml In Cyclohexane
600. Db00431
601. Delta-hch 1000 Microg/ml In Toluene
602. Gamma-hch 1000 Microg/ml In Toluene
603. Nsc 755895
604. (1alpha,2alpha,3alpha,4alpha,5alpha,6beta)-1,2,3,4,5,6-hexachlorocyclohexane
605. Alpha-hch 10 Microg/ml In Cyclohexane
606. Beta-hch 1000 Microg/ml In N-hexane
607. Bhc (mixture Of Hexachlorocyclohexanes)
608. Cyclohexane, 1,2,3,4,5,6-hexachloro-, (1alpha,2alpha,3alpha,4alpha,5alpha,6beta)-
609. Cyclohexane, 1,2,3,4,5,6-hexachloro-, (1alpha,2alpha,3alpha,4beta,5alpha,6beta)-
610. Cyclohexane, 1,2,3,4,5,6-hexachloro-, (1alpha,2alpha,3alpha,4beta,5beta,6beta)-
611. Cyclohexane, 1,2,3,4,5,6-hexachloro-, (1alpha,2alpha,3beta,4alpha,5beta,6beta)-
612. Cyclohexane, L,2,3,4,5,6-hexachloro-, (1alpha,2alpha,3beta,4alpha,5beta,6beta)-
613. Delta-hch 10 Microg/ml In Cyclohexane
614. G-1,2,3,4,5,6-hexachlorocyclohexane
615. Gamma-hch 10 Microg/ml In Cyclohexane
616. Gamma-hch 1000 Microg/ml In Methanol
617. Idi1_000701
618. (.+/-.)-.alpha.-hexachlorocyclohexane
619. Alpha-hch 100 Microg/ml In Cyclohexane
620. Alpha-hch 1000 Microg/ml In N-hexane
621. Beta-hexachlorocyclohexane [hsdb]
622. Cyclohexane,1,2,3,4,5,6-hexachloro-
623. Delta-hch 100 Microg/ml In Cyclohexane
624. Delta-hch 1000 Microg/ml In N-hexane
625. Gamma-hch 100 Microg/ml In Cyclohexane
626. Gamma-hch 1000 Microg/ml In N-hexane
627. Ncgc00094546-01
628. Ncgc00094546-02
629. Ncgc00094546-03
630. Ncgc00094546-05
631. Ncgc00094546-06
632. Ncgc00094546-07
633. Ncgc00094546-08
634. Ncgc00094546-09
635. Ncgc00094546-10
636. Ncgc00094546-11
637. Ncgc00159386-02
638. Ncgc00159386-03
639. Ncgc00159386-04
640. Ncgc00159386-05
641. Ncgc00163943-01
642. Ncgc00163943-02
643. Ncgc00163943-03
644. Ncgc00163943-04
645. Ncgc00163943-05
646. Ncgc00163943-06
647. Ncgc00248792-01
648. Ncgc00254541-01
649. Ncgc00254855-01
650. Ncgc00256383-01
651. Ncgc00258230-01
652. Ncgc00259326-01
653. Ncgc00259618-01
654. Ncgc00259839-01
655. Ncgc00348372-01
656. Ncgc00357135-01
657. 119911-70-5
658. 55963-79-6
659. 6108-13-0
660. Ac-11679
661. Cas-319-84-6
662. Cas-319-86-8
663. Cyclohexane, 1,2,3,4,5,6-hexachloro-, (1.alpha.,2.beta.,3.alpha.,4.beta.,5.alpha.,6.beta.)-
664. Gammahexachlorcyclohexane [who-ip]
665. Sbi-0051430.p003
666. .delta.,2,3,4,5,6-hexachlorocyclohexane
667. Gamma Benzene Hexachloride [who-ip]
668. Lindane Related Compound A [usp-rs]
669. Lindane, Pestanal(r), Analytical Standard
670. (+/-)-.alpha.-hexachlorocyclohexane
671. (+/-)-.beta.-hexachlorocyclohexane
672. .alpha.-1,2,3,4,5,6-hexachlorcyclohexane
673. Cs-0450994
674. Ft-0603490
675. Ft-0606175
676. Ft-0647466
677. H0056
678. Hch (technical) 10 Microg/ml In Isooctane
679. Hch (technical) 100 Microg/ml In N-hexane
680. Wln: L6tj Ag Bg Cg Dg Eg Fg .delta.
681. 1,2,3,4,5,6-.gamma.-hexachlorocyclohexane
682. Alpha-hch, Pestanal(r), Analytical Standard
683. Beta-hch, Pestanal(r), Analytical Standard
684. Delta-hch, Pestanal(r), Analytical Standard
685. C06988
686. C07075
687. C18738
688. D00360
689. 1,2,3,4,5,6-hexachlorocyclohexane (.gamma.)
690. 1,3,4,5,6-hexachlorcyclohexane, .beta. Isomer
691. Ab00052031_02
692. Cyclohexane,2,3,4,5,6-hexachloro-, .delta.-
693. Delta-bhc, Vial Of 100 Mg, Analytical Standard
694. 1,3,4,5,6-hexachlorocyclohexane, .gamma. Isomer
695. Alpha-1,2,3,4,5,6-hexachlorocyclohexane, 99%
696. Cyclohexane, .alpha.-1,2,3,4,5,6-hexachloro-
697. Q282003
698. .beta.-1,2,3,4,5,6-hexachlorocyclohexane
699. .delta.-(aeeee)-1,3,4,5,6-hexachlorocyclohexane
700. 1,2,3,4,5,6-hexachlorocyclohexane (gamma-isomer)
701. Cyclohexane, 1,2,3,4,5,6-hexachloro-, .gamma.-
702. J-018587
703. J-018588
704. J-018589
705. Q6445839
706. Sr-05000001837-1
707. Sr-05000001837-4
708. .delta.-1,2,3,4,5,6-hexachlorocyclohexane
709. .epsilon.-1,2,3,4,5,6-hexachlorocyclohexane
710. Alpha-hch, Certified Reference Material, Tracecert(r)
711. Cyclohexane,2,3,4,5,6-hexachloro-, .delta.-isomer
712. Q10860138
713. Q23014122
714. Cyclohexane, 1,2,3,4,5,6-hexachloro-, .alpha.-isomer
715. (1r,2c,3c,4t,5c,6t)-1,2,3,4,5,6-hexachlorocyclohexane
716. (1r,2c,3t,4t,5c,6t)-1,2,3,4,5,6-hexachlorocyclohexane
717. (1s,2r,3r,4s,5s,6s)-1,2,3,4,5,6-hexachlorocyclohexane
718. Lindane, United States Pharmacopeia (usp) Reference Standard
719. Lindane, Pharmaceutical Secondary Standard; Certified Reference Material
720. (1.alpha.,3.alpha.,4.beta.,5.alpha.,6.beta.)-1,2,3,4,5,6-hexachlorocyclohexane
721. (1.alpha.,3.beta.,4.alpha.,5.alpha.,6.beta)-1,2,3,4,5,6-hexachlorocyclohexane
722. (1alpha,2alpha,3alpha,4alpha,5alpha,6alpha)-1,2,3,4,5,6-hexachlorocyclohexane
723. (1alpha,2alpha,3alpha,4alpha,5beta,6beta)-1,2,3,4,5,6-hexachlorocyclohexane
724. (1alpha,2alpha,3beta,4beta,5alpha,6beta)-1,2,3,4,5,6-hexachlorocyclohexane
725. 1-.alpha.,2-.alpha.,3-.beta.,4-.alpha.,5-.beta.,6-.beta.-hexachlorocyclohexane
726. 1.alpha.,2.alpha.,3.beta.,4.alpha.,5.alpha.,6.beta.-hexachlorocyclohexane
727. Beta-hch Solution, 100 Mug/ml In Methanol, Pestanal(r), Analytical Standard
728. Cyclohexane, 1,2,3,4,5,6-hexachloro-, (1alpha,2alpha,3alpha,4alpha,5alpha,6alpha)-
729. Cyclohexane, 1,2,3,4,5,6-hexachloro-, (1alpha,2alpha,3alpha,4alpha,5beta,6beta)-
730. (1.alpha.,2.alpha.,3.beta.,4.alpha.,5.alpha.,6.beta.)-1,2,3,4,5,6-hexachlorocyclohexane
731. 1,2,3,4,5,6-hexachlorocyclohexane, (1.alpha.,2.alpha.,3.beta.,4.alpha.,5.beta.,6.beta.)-
732. Cyclohexane, 1,2,3,4,5,6-hexachloro-, (1.alpha.,2.alpha.,3.alpha.,4.beta.,5.beta.,6.beta.)-
733. Cyclohexane,2,3,4,5,6-hexachloro-, (1.alpha.,2.alpha.,3.alpha.,4.beta.,5.alpha.,6.beta.)-
734. Hch, Pestanal(r), Analytical Standard, Mixture Of Isomers (alpha:beta:gamma:delta=1:1:1:1)
| Molecular Weight | 290.8 g/mol |
|---|---|
| Molecular Formula | C6H6Cl6 |
| XLogP3 | 3.8 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 0 |
| Rotatable Bond Count | 0 |
| Exact Mass | 289.857116 g/mol |
| Monoisotopic Mass | 287.860066 g/mol |
| Topological Polar Surface Area | 0 Ų |
| Heavy Atom Count | 12 |
| Formal Charge | 0 |
| Complexity | 104 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
| 1 of 2 | |
|---|---|
| Drug Name | Lindane |
| PubMed Health | Lindane (On the skin) |
| Drug Classes | Pediculicide, Scabicide |
| Active Ingredient | Lindane |
| Dosage Form | Shampoo; Lotion |
| Route | Topical |
| Strength | 1% |
| Market Status | Prescription |
| Company | Wockhardt; Olta Pharms |
| 2 of 2 | |
|---|---|
| Drug Name | Lindane |
| PubMed Health | Lindane (On the skin) |
| Drug Classes | Pediculicide, Scabicide |
| Active Ingredient | Lindane |
| Dosage Form | Shampoo; Lotion |
| Route | Topical |
| Strength | 1% |
| Market Status | Prescription |
| Company | Wockhardt; Olta Pharms |
Insecticides
National Library of Medicine's Medical Subject Headings. Lindane. Online file (MeSH, 2016). Available from, as of December 7, 2016: https://www.nlm.nih.gov/mesh/2016/mesh_browser/MBrowser.html
/CLINICAL TRIALS/ ClinicalTrials.gov is a registry and results database of publicly and privately supported clinical studies of human participants conducted around the world. The Web site is maintained by the National Library of Medicine (NLM) and the National Institutes of Health (NIH). Each ClinicalTrials.gov record presents summary information about a study protocol and includes the following: Disease or condition; Intervention (for example, the medical product, behavior, or procedure being studied); Title, description, and design of the study; Requirements for participation (eligibility criteria); Locations where the study is being conducted; Contact information for the study locations; and Links to relevant information on other health Web sites, such as NLM's MedlinePlus for patient health information and PubMed for citations and abstracts for scholarly articles in the field of medicine. Lindane is included in the database.
NIH/NLM; ClinicalTrials.Gov. Available from, as of February 1, 2017: https://clinicaltrials.gov/ct2/results?term=lindane&Search=Search
Lindane is used for the topical treatment of pediculosis capitis (head lice infestation) and pediculosis pubis (pubic lice infestation) and for the topical treatment of scabies.
American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016
MEDICATION: Pediculicide, scabicide
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1023
For more Therapeutic Uses (Complete) data for Lindane (6 total), please visit the HSDB record page.
/CLINICAL TRIALS/ ClinicalTrials.gov is a registry and results database of publicly and privately supported clinical studies of human participants conducted around the world. The Web site is maintained by the National Library of Medicine (NLM) and the National Institutes of Health (NIH). Each ClinicalTrials.gov record presents summary information about a study protocol and includes the following: Disease or condition; Intervention (for example, the medical product, behavior, or procedure being studied); Title, description, and design of the study; Requirements for participation (eligibility criteria); Locations where the study is being conducted; Contact information for the study locations; and Links to relevant information on other health Web sites, such as NLM's MedlinePlus for patient health information and PubMed for citations and abstracts for scholarly articles in the field of medicine. Hexachlorohexanes are included in the database.
NIH/NLM; ClinicalTrials.Gov. Available from, as of February 1, 2017: https://clinicaltrials.gov/ct2/results?term=HEXACHLOROCYCLOHEXANES&Search=Search
Adverse CNS effects, including dizziness and seizures, have been reported with lindane. While seizures generally have been associated with ingestion or misuse of lindane, seizures and deaths rarely have been reported following a single application of lindane shampoo or lotion used according to the manufacturers' directions. Infants, children, geriatric patients, patients weighing less than 50 kg, and patients with certain other skin conditions may be at greater risk of serious neurotoxicity than other individuals. Although the relationship to lindane is unknown, headache, pain, and paresthesia have been reported with lindane shampoo or lotion.
American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016
Alopecia, dermatitis, pruritus, and urticaria have been reported in patients using lindane shampoo or lotion.
American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016
In patients with scabies or pediculosis, pruritus (caused by an acquired sensitivity to the ectoparasites and their products) frequently persists for one to several weeks following treatment with the drug; this reaction does not indicate treatment failure and is not an indication for further treatment. Oral antihistamines and/or topical corticosteroids may be used to help relieve pruritus.
American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016
Aplastic anemia has been reported with prolonged administration of lindane lotion. Inhalation of lindane vapors may produce headache, nausea, vomiting, and irritation of eyes, nose, and throat.
American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016
For more Drug Warnings (Complete) data for Lindane (17 total), please visit the HSDB record page.
Fatal oral dose: Adults: 28 g
Lelkin, J.B., Paloucek, F.P., Poisoning & Toxicology Compendium. LEXI-COMP Inc. & American Pharmaceutical Association, Hudson, OH 1998., p. 354
For the treatment of patients infested with Sarcoptes scabiei or pediculosis capitis who have either failed to respond to adequate doses, or are intolerant of other approved therapies.
Used as a pancreatic enzyme replacement in pancreatic insufficiency. It is intended to mimic naturally produced human pepsin. Pepsin powder is prepared from the gastric mucosa of pigs, cattle or sheep. In the laboratory, it is primarily used for the unspecific hydrolysis of proteins and peptides in acidic media. In addition, it provides limited hydrolysis of native immunoglobulins, yielding biologically active fragments. In certain supplements, pepsin may be combined with betaine and HCl (hydrochloric acid) to aid in digestion in various gastrointestinal conditions,.
Scabies is a common, highly pruritic infestation of the skin caused by Sarcoptes scabiei (lice). It is a very contagious condition with specific lesions, such as burrows, and nonspecific lesions, such as papules, vesicles and excoriations. The typical areas of the body it affects are finger webs, scalp (hair), wrists, axillary folds, abdomen, buttocks, inframammary folds and genitalia (males). It is characterized by intense night-time itching. Scabies is spread through close personal contact (relatives, sexual partners, schoolchildren, chronically ill patients and crowded communities). Scabies infestations and the corresponding symptoms can be eliminated by killing the scabies with topical insecticides or scabicides. Lindane is a scabicide that is essentially an organochloride insecticide.
Pepsin digests protein. It classified by the FDA that is characterizing enzyme activity is that of a peptide _hydrolase_.
A - Alimentary tract and metabolism
A09 - Digestives, incl. enzymes
A09A - Digestives, incl. enzymes
A09AA - Enzyme preparations
A09AA03 - Pepsin
P - Antiparasitic products, insecticides and repellents
P03 - Ectoparasiticides, incl. scabicides, insecticides and repellents
P03A - Ectoparasiticides, incl. scabicides
P03AB - Chlorine containing products
P03AB02 - Lindane
Absorption
Lindane is absorbed significantly through the skin. A mean peak blood concentration of 28 nanograms per mL occurred in infants and children 6 hours after total body application of lindane lotion for scabies.
/MILK/ The present study was conducted to highlight the existing level of organochlorine-pesticides (OCPs) from human milk (n=45) and blood serum (n=40) of female workers who pick cotton in Khanewal District, southern Punjab, Pakistan. Source apportionment, congener-specific analysis, and risk surveillance of OCPs are reported from human milk and blood samples. Levels of OCPs in milk and blood serum samples ranged from 15.7 ppb to 538.3 ppb and from 16.4 ppb to 747.1 ppb, respectively, and were lower than previously published reports from other regions of the globe. Congener-specific analysis revealed that DDTs were predominant, followed by hexachlorocyclohexane, chlordane, and hexachlorobenzene. Calculated results for source apportionment analysis suggested that contamination load was a new input of DDTs as well as the historic use of lindane in the study area. Levels of OCPs in milk and blood serum were significantly (p<0.05) correlated with age, time period of picking cotton, and number of children. Health risk revealed that female workers had risk of cancer among 1 per million; however, noncarcinogenic risks were not considerable.
PMID:27684504 Yasmeen H et al; Environ Toxicol Chem doi: 10.1002/etc.3633 (Epub ahead of print) (2016)
A 1% lindane cream (Kwell) was applied to skin of 9 voluteers, left on for 12 hours and washed off with soap and water. Plasma concentratioin increased to 10.3 ng/mL (range 2-24 ng/mL).
PMID:6153210 Hosler J et al; J Invest Dermatol 74 (1): 51-3 (1980)
... Serum concentrations of lindane were determined in infants and children with and without scabies infection following application of 1% lindane lotion to the body surface area /for 24 hours instead of the maximum of 12 hours/ prescribed by the label. Studies were performed on 20 infected and noninfected patients who averaged 33 to 64 months of age ... Specimens of blood for determination of lindane concentrations were obtained at 0, 2, 4, 6, 8, 12, 24, and 48 hours after topical application of 1% lotion. The highest measured blood concentration from the clinical study was 0.064 ug/mL /at 6 hours/.
USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document - Lindane. p.19 September 25, 2002. Available from, as of December 8, 2016: https://www.epa.gov/pesticides/reregistration/status.htm
... Transplacental passage ... has been established ...
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V20 220 (1979)
For more Absorption, Distribution and Excretion (Complete) data for Lindane (22 total), please visit the HSDB record page.
Chronically, lindane is the least likely to bioaccumulate ... The alpha, beta, and delta isomers have a low degree of acute toxicity, but are retained in body tissues for a longer period than lindane.
Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V5 667
BHC is absorbed through all portals including the intact skin. ... In rats given BHC by mouth ... 80% /was/ absorbed when given as a solution in olive oil but only 6% absorbed when given as aqueous suspension. Highest concn were found in adipose tissue and lowest in blood and muscle. Peak values were reached in 2-5 days. By 2 wk after ip admin, 34% of dose was recovered in feces mostly unchanged and only 5% in urine.
Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. III-240
Trace amt of HCH have been detected in human milk and blood, and transplacental passage of HCH has been established.
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V20 220 (1979)
/MILK/ Concentrations of < / = 4 ppm of BHC have been found in the milk of ewes after they were dipped with Entomoxan (0.5% BHC).
Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V5 668
For more Absorption, Distribution and Excretion (Complete) data for Hexachlorocyclohexanes (14 total), please visit the HSDB record page.
When single doses of (36)Cl-labelled alpha-HCH ... were given ip to rats at level of 200 mg/kg body weight ... approx 80% of total radioactivity was excreted in urine and 20% in feces. ... Pretreatment of rats with phenobarbital accelerated rate of excretion ...
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V20 218 (1979)
In rats fed 800 mg/kg diet ... for 20 months, 3.5 mg/g ...were found in adipose tissue; levels in other tissues were lower by factor of 5-10. ... Upon cessation of dietary exposure ... /alpha isomer/ disappeared from fat depots within 3 wk. ... /It is/ stored in adipose tissue of dogs ... to lesser degree in liver.
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V20 218 (1979)
ln feeding experiments with broiler breeder hens, the ratio of the level of HCH in the animal fat to the level in the feed was 1.8 for alpha-HCH ... . The ratio of the level of HCH in eggs to the level in the feed was 0.10 for alpha-HCH ... on a whole egg basis
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V20 206 (1979)
In rats, 65% of ip dose of (14)C-alpha-HCH was excreted in urine and 16% in feces within 4 wk. ... Chlorothiophenols were also detected in urine, and proportion incr when animals were pretreatd with alpha-HCH.
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V20 219 (1979)
For more Absorption, Distribution and Excretion (Complete) data for alpha-Hexachlorocyclohexane (15 total), please visit the HSDB record page.
When labelled beta-hexachlorocyclohexane was administered orally to female Sprague-Dawley rats, 80% was ... absorbed. ... Beta-HCH fed at 100 mg/kg diet for 20 months was stored to greater extent /than alpha- or delta-HCH/, the concentration in adipose tissue being 1.9 mg/g; brain contained 130 ug/g and liver only 20 ug/g. Upon cessation of dietary exposure ... it persisted in adipose tissue in small amt after 14 wk. ... It is stored to lesser degree in ... kidneys and adrenals ... .
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V20 218 (1979)
In rats preadapted by feeding ... beta-hexachlorocyclohexane at dietary level of 10 ppm for 10 days and then given single oral dose of radioactive beta-BHC, total of 12.2 to 13.0% of radioactive material was recovered in urine and 5.4 to 5.8% in feces during 1st 10 days after ingestion.
Hayes, Wayland J., Jr. Pesticides Studied in Man. Baltimore/London: Williams and Wilkins, 1982., p. 216
Experiments with alpha-, beta-, and gamma-hexachlorocyclohexane showed that the absorption rates of the isomers were approx equal. In 30-day feeding studies with rats, adipose tissue took up the alpha-HCH faster than beta-HCH, and much faster than gamma-HCH. Accumulation of beta-HCH in mammals is related to its low rate of metabolism and transport.
Macholz R; Nahrung 26 (9): 747-57 (1982)
The time at which beta-hexachlorocyclohexane reaches storage equilibrium in fat /of rats/ is not less than 8 weeks. In mice it reaches a constant level after 12 weeks of feeding at dietary levels less than 50 ppm. ... BHC is transferred by way of the placenta, but the rate is negligible. ... Only 1.6 to 2.2% of carbon-14 beta-BHC admin to pregnant mice was retained by the fetuses, while the dams retained 33.2 to 53.7%. ... /However,/ a high proportion of (carbon-14 beta-BHC admin to dams during lactation was secreted in ... milk so that at end of lactation the young retained 60.0 to 63.8% of total dose, while very little remained in the mothers.
Hayes, Wayland J., Jr. Pesticides Studied in Man. Baltimore/London: Williams and Wilkins, 1982., p. 214
For more Absorption, Distribution and Excretion (Complete) data for beta-Hexachlorocyclohexane (19 total), please visit the HSDB record page.
In rats fed 800 mg/kg diet ... delta-HCH ... for 20 months ... 0.55 mg/kg ... was found in adipose tissue; levels in other tissues were lower by factor of 5-10. ... Upon cessation of dietary exposure ... it disappeared from fat depots within 3 weeks ...
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V20 218 (1979)
Umbilical cord and venous blood samples were collected at the time of delivery from 52 mothers living in urban and rural areas of the Atoya River basin, Nicaragua ... /and/ analyzed for 13 organochlorine pesticides: 1,1,1-trichloro-2,2-bis(4-chlorophenyl)ethane (pp'-DDT); 1,1-dichloro-2,2-bis(p-chlorophenyl)ethylene (pp'-DDE); pp'-dichlorophenyldichlorodiene (pp'-DDD); alpha-hexachlorocyclohexane (alpha-HCH); beta-hexachlorocyclohexane (beta-HCH); gamma-hexachlorocyclohexane (gamma-HCH); delta-hexachlorocyclohexane (delta-HCH); toxaphene; dieldrin; endrin; aldrin; heptachlor; and heptachlor epoxide. In venous blood only pp'-DDE (100% of samples), pp'-DDT (1.92%), dieldrin (15.38%), heptachlor (15.38%), gamma-HCH (7.69%), beta-HCH (11.53%), and delta-HCH (1.92%) were found, whereas in cord blood only pp'-DDE (100%), pp'-DDT (3.84%), dieldrin (19.23%), and heptachlor (9.16%), were found.
PMID:11453673 Dorea JG et al; Environ Res 86 (3): 229-37 (2001)
The accumulation of hexachlorocyclohexane, one of the most commonly used chlorinated insecticides, was studied in a high-risk group of people who are exposed during its manufacturing process. The serum HCH concentration was estimated by quantitating its alpha, beta, gamma, and delta-isomers with the help of GLC analysis. Exposed workers involved in maintenance work were found to have 3 times higher HCH residues than the controls, while in the plant operators and supervisors the levels were 5 times higher. The most severely exposed were the handlers who are in direct contact with the insecticide. The level of serum HCH residues in them was found to be about 12 times higher than those in the controls. The percentage composition of the insecticide, with respect to the different isomers, varied up to 20% for the gamma-isomer, up to 30% for alpha-isomer and had between 60%-100% of the beta-isomer in the samples. The serum levels of the insecticides were clearly related to the workers' job-related close contact, intensity, frequency, and the duration of their exposure. The total of HCH residues in the sera studied were in the range of 0.143-1.152 ppm. ...
PMID:2423460 Nigam SK et al; Int Arch Occup Environ Health 57: 315-20 (1986)
The chronic toxicity for isomers of BHC decreases in the order beta > alpha > gamma > delta and is directly related to their tissue retention, and inversely to rates of metabolism. This contrasts with the order of acute toxicities, which are in the decreasing order of gamma > alpha > delta > beta.
Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V5 668
... Chronically, lindane is the least likely to bioaccumulate ... The alpha, beta, and delta isomers have a low degree of acute toxicity, but are retained in body tissues for a longer period than lindane.
Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V5 667
Primarily hepatic through dechlorination leading to 2-chlorophenol, 0-chlorophenol, chlorocyclohexane, chlorocyclohexanol.
Pepsin is the first of several enzymes that digest proteins. In the stomach, polypeptide chains bind in the deep active site groove of pepsin, and are then digested into smaller pieces. Following this, a variety of proteases and peptidases in the intestine complete the process. The small fragments, which are amino acids and dipeptides, are then absorbed by cells for use as metabolic energy or construction of new proteins.
Metabolism of gamma-Hexachlorocyclohexane (HCH) was studied examining 21 workers producing this insecticide. Using gas chromatography in combination with ECD and mass spectrometry 14 mono-, di-, tri- and tetrachlorophenols were identified in the urine samples of the workers. Seven dihydroxychlorobenzenes of still unknown configuration were detected by mass spectrometry. Ten of the more abundant metabolites, di-, tri- and tetrachlorophenols were determined quantitatively in all urine samples. 2,4,6-; 2,3,5- and 2,4,5-trichlorophenol turned out to be the main metabolites of gamma-HCH. They were excreted in nearly equal quantities. ...
PMID:6192092 Angerer J et al; Int Arch Occup Environ Health 52 (1): 59-68 (1983)
The primary metabolites of lindane are chlorophenols and chlorobenzenes. Chlorinated metabolites in the urine have been found in lindane production workers. The major metabolite is trichlorophenol, which accounted for approximately 58% of lindane metabolites identified in the urine. Other metabolites are dichlorophenols, tetrachlorophenols, hexachlorobenzene, tetrachlorocyclohexanol, and pentachlorocyclohexene. Pentachlorophenol has also been identified as a urinary metabolite in humans after occupational exposure.
Sullivan, J.B., Krieger G.R. (eds). Clinical Environmental Health and Toxic Exposures. Second edition. Lippincott Williams and Wilkins, Philadelphia, Pennsylvania 1999., p. 1065
Human liver microsomes metabolized lindane to 4 primary metabolites, gamma-1,2,3,4,5,6-hexachlorocyclohex-1-ene; gamma-1,3,4,5,6-pentachlorocyclohex-1-ene; beta-1,3,4,5,6-pentachlorocyclohex-1-ene; and 2,4,6-trichlorophenol. The secondary metabolites, 2,3,4,6-tetrachlorophenol and pentachlorobenzene were also formed.
PMID:6180560 Fitzloff JF et al; Xenobiotica 12 (3): 197-202 (1982)
In mice, urinary metabolites of single ip injection ... accounted for 57% of dose ... and consisted mostly of glucuronide and sulfate conjugates of 2,4,6-trichlorophenol and 2,4-dichlorophenol. No mercapturic acid conjugates were detected. When ... administered ip to rats, 2,3,5- and 2,4,5-trichlorophenol were identified in urine ... free or as conjugates with glucuronic and/or sulfuric acid. When weanling Sprague-Dawley rats were fed 400 mg/kg diet lindane, 3,4-dichlorophenol, 2,4,6-trichlorophenol, 2,3,4,5- and 2,3,4,6-tetrachlorophenol and 2,3,4,5,6-pentachloro-2-cyclohexene-1-ol were identified in urine. Pentachlorobenzene, 2,3,4,6- and 2,3,5,6-tetrachlorophenol and 2,4,6-trichlorophenol were excreted in urine of rats given oral doses ... pretreatment of rats with other organochlorine pesticides modified lindane metabolism.
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V20 218 (1979)
For more Metabolism/Metabolites (Complete) data for Lindane (12 total), please visit the HSDB record page.
Mammalian biotransformation of BHC isomers involves formation of chlorophenols (trichlorophenol, tetrachlorophenol and pentachlorophenol), which are excreted free and as conjugates of sulfuric and glucuronic acids.
National Research Council. Drinking Water & Health Volume 1. Washington, DC: National Academy Press, 1977., p. 585
The primary urinary metabolites are chlorophenols and 1,1,4-trichlorocyclohexane-4,5-epoxide. The conversion occurs mainly by the action of hepatic enzymes.
DHHS/ATSDR; Toxicological Profile for alpha-, beta-, gamma-, and delta-Hexachlorocyclohexane p. 115 PB2006-100003 (August 2005). Available from, as of December 8, 2016: https://www.atsdr.cdc.gov/toxprofiles/tp.asp?id=754&tid=138
...The urine of occupationally exposed workers (apparently to technical-grade HCH in manufacturing processes), /was analyzed and found to contain/, apart from alpha-, beta-, gamma-, and delta-HCH, traces of hexa- and pentachlorobenzene, gamma- and delta-pentachlorocyclohexane, pentachlorophenol, 2,3,4,5-, 2,3,4,6-, and 2,3,5,6-tetrachlorophenol, and several trichlorophenols, as well as the glucuronides of several of these metabolites. The pentachlorocyclohexenes, tetrachlorophenol, hexachlorobenzene, and pentachlorophenol were also identified in the blood.
WHO; Environ Health Criteria 123: alpha and beta-Hexachlorocyclohexanes (1991). Available from, as of March 28, 2017: https://www.inchem.org/documents/ehc/ehc/ehc123.htm
Conjugated 2,4,6-trichlorophenol was major urinary metabolite /of alpha-HCH/ ...
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V20 219 (1979)
Sphingomonas paucimobilis B90A is able to degrade the alpha-, beta-, gamma-, and delta-isomers of hexachlorocyclohexane (HCH). It contains the genes linA, linB, linC, linD, linE, and linR, which have been implicated in HCH degradation. In this study, dynamic expression of the lin genes was measured in chemostat-grown S. paucimobilis B90A by RNA dot blot hybridization and real-time reverse transcriptase PCR upon exposure to a pulse of different HCH isomers. Irrespective of the addition of HCH, linA, linB, and linC were all expressed constitutively. In contrast, linD and linE were induced with alpha-HCH (2 mg/liter) and gamma-HCH (7 mg/liter). A sharp increase in mRNA levels for linD and linE was observed from 10 to 45 min after the addition of alpha- or gamma-HCH. Induction of linD and linE was not detectable upon the addition of 0.7 mg of gamma-HCH per liter, although the compound was degraded by the cells. The addition of beta-HCH (5 mg/liter) or delta-HCH (20 mg/liter) did not lead to linE and linD induction, despite the fact that 50% of the compounds were degraded. This suggests that degradation of beta- and delta-HCH proceeds by a different pathway than that of alpha- and gamma-HCH.
PMID:15528530 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC525160 Suar M et al; Appl Environ Microbiol 70 (11): 6650-6 (2004)
Perdeuterated analogs were used in the study of the in vivo and in vitro metabolism of ... alpha-hexachlorocyclohexane ... In vivo, the rate of disappearance from depot fat, the major body store of HCH, was markedly slowed by perdeuteration in the case of alpha-HCH (H/D 6.3).
Portig J; Pestic Chem: Hum Welfare Environ, Proc Int Congr Pestic Chem, 5th 3: 401-405 (1983)
When alpha-hexachlorocyclohexane was applied to plants, the level of beta-HCH on the plants was shown to increase, showing transformation of alpha-HCH to beta-HCH.
Menzie, C.M. Metabolism of Pesticides-Update III. Special Scientific Report- Wildlife No. 232. Washington, DC: U.S.Department of the Interior, Fish and Wildlife Service, 1980., p. 77
For more Metabolism/Metabolites (Complete) data for alpha-Hexachlorocyclohexane (6 total), please visit the HSDB record page.
... /In rats/ 2,4,6-trichlorophenol is a ... metabolite ... of ... beta-hexachlorocyclohexane. Pathway favored ... is by way of hydroxylation of 1,3,5-trichlorobenzene, one of products of dehydrochlorination ... an alternative pathway /is proposed/ involving direct hydroxylation ... to alpha-chlorohydrins, which, following rapid, spontaneous loss of HCL yielded one of the isomers of pentachlorocyclohexanone; loss therefrom of two molecules of HCL led directly to 2,4,6-trichlorophenol. ... /Also it is an/ in vitro metabolite of ... beta-HCH in rat-liver microsomes ... the reaction is oxidative and catalyzed by cytochrome p450.
The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 5: A Review of the Literature Published during 1976 and 1977. London: The Chemical Society, 1979., p. 463
In rats fed 600-3000 mg/kg beta hexachlorocyclohexane the following metabolites were identified in urine, liver, and kidney: 2,3,5-trichloroanisole, 2,3,6-trichloroanisole, 3,4,5-trichloroanisole, 2,3,4,6-tetrachloroanisole, 2,3,4,5-tetrachloroanisole, 2,4,6-trichlorophenol, 2,3,5-trichlorophenol, 2,3,6-trichlorophenol, 2,4,5-trichlorophenol, 3,4,5-trichlorophenol, & 2,3,4-trichlorophenol.
PMID:6180701 Macholz RM et al; Arch Toxicol 50 (1): 85-8 (1982)
... /In rats/ 2,4,6-trichlorophenol is ... metabolite ... of ... delta-hexachlorocyclohexane. Pathway favored ... for formation ... /is/ by way of hydroxylation of 1,3,5-trichlorobenzene, one of products of dehydrochlorination ... an alternative pathway /is proposed/ involving direct hydroxylation ... to alpha-chlorohydrins, which, following rapid, spontaneous loss of HCl yielded one of the isomers of pentachlorocyclohexanone; loss therefrom of two mols of HCl led directly to 2,4,6-trichlorophenol.
The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 5: A Review of the Literature Published during 1976 and 1977. London: The Chemical Society, 1979., p. 463
... 2,4,6-Trichlorophenol is /an/ ... in vitro metabolite of ... delta-HCH in rat-liver microsomes ... the reaction is oxidative and catalyzed by cytochrome p450. ...Purification of ... /glutathione-dependent/ dechlorinating enzyme from rat-liver cytosol has been achieved.
The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 5: A Review of the Literature Published during 1976 and 1977. London: The Chemical Society, 1979., p. 463
d-Hexachlorocyclohexane (d-HCH), one of the prevalent isomers of technical HCH, was enantioselectively dehydrochlorinated by the dehydrochlorinases LinA1 and LinA2 from Sphingobium indicum B90A to the very same d-pentachlorocyclohexene enantiomer. Racemic d-pentachlorocyclohexene, however, was transformed with opposite enantioselectivities by the two enzymes. A transformation pathway based on an anti-1,2-elimination, followed by a syn-1,4-elimination and a subsequent syn-1,2-elimination is postulated.
PMID:23872559 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3811360 Geueke B et al; Appl Environ Microbiol 79 (19): 6180-3 (2013)
18 hours
Gamma-HCH (Lindane) is rapidly metabolized; beta-HCH has been detected in serum 10-15 years after exposure; [TDR, p. 753]
TDR - Ryan RP, Terry CE, Leffingwell SS (eds). Toxicology Desk Reference: The Toxic Exposure and Medical Monitoring Index, 5th Ed. Washington DC: Taylor & Francis, 1999., p. 753
Half-life: Children: 17-22 hours
Lelkin, J.B., Paloucek, F.P., Poisoning & Toxicology Compendium. LEXI-COMP Inc. & American Pharmaceutical Association, Hudson, OH 1998., p. 353
The elimination half-life of lindane is 21 hours in adults.
Goldfrank, L.R., Goldfrank's Toxicologic Emergencies 9th Ed. 2011., McGraw-Hill, New York, N.Y., p. 1479
The half-life of lindane in blood is approximately 18 hours.
American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016
... We present a case of a massive suicidal ingestion of lindane in which the patient survived the ingestion, though he did expire shortly thereafter from an unrelated cause pre-discharge. Pharmacokinetic analysis of serum lindane concentrations was performed with Phoenix WinNONLIN. The estimated distribution half-life for lindane was 10.3 hr, and the terminal half-life was 162.9 hr ... .
PMID:24805102 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4371023 Wiles DA et al; J Med Toxicol 11 (1): 106-9 (2015)
For more Biological Half-Life (Complete) data for Lindane (6 total), please visit the HSDB record page.
The half-life for the clearance of alpha-HCH from depot fat was found to be 6.9 days in female rats and 1.6 days in male rats. ...After a single oral dose of 200 mg/kg body weight /to Wistar rats/, the approximate half-life in females for the elimination from brain was 6 days.
WHO; Environ Health Criteria 123: alpha and beta-Hexachlorocyclohexanes p.46 (1991). Available from, as of June 8, 2006: https://www.inchem.org/documents/ehc/ehc/ehc123.htm
... After administration of a single oral dose of 200 mg/kg bw /beta-HCH to Wistar rats/; the approximate half-life for elimination from the brain was 20 days in females.
WHO; Environ Health Criteria 123: alpha and beta-Hexachlorocyclohexanes p. 109 (1991). Available from, as of March 30, 2017: https://www.inchem.org/documents/ehc/ehc/ehc123.htm
...The absorption of beta-HCH from the gastrointestinal tract in mice was 80-95%, most of this being accumulated in adipose tissue. The elimination followed a 2-stage mechanism, the half-life for the first stage being 2.5 days and that for the second stage being 18 days. The half-life for clearance from blood in rats (sex not specified) was 1 month, and the half-life for clearance from fat was 14 days in male rats and 28 days in female rats. ...A half-life for clearance from "internal organs" of 22 days in female rats /was reported/. A half-life of 20 days for the clearance from the brain of female rats was reported. In cows the half-life for clearance from fat was 4.2-22.0 weeks. The elimination in humans was slow after continuous exposure ceased, the concentration in fatty tissues decreasing only slightly over several years.
WHO; Environ Health Criteria 123: alpha and beta-Hexachlorocyclohexanes p. 97 (1991). Available from, as of March 30, 2017: https://www.inchem.org/documents/ehc/ehc/ehc123.htm
Lindane is an organochloride insecticide that has similar neurotoxic protperties to DDT. It exerts its parasiticidal action by being directly absorbed through the parasite's exoskeleton (primarily lice, or scabies) and their ova. The gamma-aminobutyric acid (GABA(1)) receptor/chloride ionophore complex is the primary site of action for lindane, and other insecticides such as endosulfan, and fipronil. Blockage of the GABA-gated chloride channel reduces neuronal inhibition, which leads to hyperexcitation of the central nervous system. This results in paralysis, convulsions, and death. Lindane has very low ovicidal activity.
Glands present in the mucous membrane lining of the stomach produce and store an inactive protein named _pepsinogen_. Impulses from the vagus nerve and the hormonal secretions of the hormones _gastrin_ and _secretin_ promote the release of pepsinogen into the stomach, where it is mixed with hydrochloric acid and quickly converted to the active enzyme _pepsin_. The digestive potency of pepsin is highest at the acidic pH of normal gastric juice. In the intestine, the gastric acids are then neutralized, and pepsin is no longer effective. Pepsin, the proteolytic enzyme of the stomach is normally responsible for less than 20% of the protein digestion occuring the gastrointestinal tract. It is an endopeptidase enzyme that metabolizes proteins to peptides. It preferentially hydrolyzes peptide linkages where one of the amino acids is aromatic. Pepsin, like other protease enzymes, is produced from an inactive precursor, _pepsinogen_, which is stored in granule form in the chief cells of the stomach and are released by a process called _exocytosis_. In the digestive tract, pepsin activity only contributes to the partial breakdown of proteins into smaller units called peptides, which then either are absorbed from the intestine into the bloodstream or are broken down further by pancreatic enzymes.
gamma-HCH interacts with cellular membranes and may produce several generalized cytotoxic effects associated with impaired membrane function. In rat renal cortical tubules, glucose uptake and cyclic AMP accumulation were altered by gamma-HCH treatment. Transport of D-galactose and L-leucine across enterocytes was decreased in chickens injected daily with gamma-HCH for 7 days. Rats exposed orally to 5 mg/kg/day technical-grade HCH 5 days/week, for 3-6 months, exhibited significantly decreased levels of phosphatidylinositol, phosphatidylinositol 4-phosphate, and phosphatidylinositol 4,5-bisphosphate in the erythrocyte membrane and cerebrum. An in vitro study showed that gamma-HCH altered the action potential and transmembrane currents in frog heart (atrial) myocytes. gamma-HCH also has been shown to block gap junctional intercellular communication in Sertoli cells by inducing the aberrant endocytosis of Connexin 43 and zonula occludens-1 within Rab5 positive endosomes via the activation of the extracellular signal-regulated kinases. Inhibition of intercellular communication could potentially lead to uncontrolled cell growth and tumor promotion. gamma-HCH inhibited gap junction and intercellular communication in myometrial cell cultures isolated from rats on gestation day 10 by creating an oxidative stress environment. gamma-HCH also inhibited spontaneous phasic contractions in late gestation rat uterus.
DHHS/ATSDR; Toxicological Profile for alpha-, beta-, gamma-, and delta-Hexachlorocyclohexane p.136 PB2006-100003 (August 2005). Available from, as of December 8, 2016: https://www.atsdr.cdc.gov/toxprofiles/tp.asp?id=754&tid=138
Oxidative stress in the liver has been suggested as a mechanism of gamma-HCH-induced hepatotoxicity. This condition is characterized in the rat liver by a reduction in hepatic glutathione content, lipid peroxidation, the microsomal generation of superoxide radical coupled to cytochrome P-450 induction, and a decrement in superoxide dismutase and catalase activity. Dose-dependent inhibition of intercellular communication in cultured rat hepatocytes, with subsequent reversal by addition of vitamin E or superoxide dismutase, indicates oxidative stress as a hepatotoxic mechanism. Species differences exist in the activities of hepatic metabolizing enzymes, and it has been demonstrated that gamma-HCH at a dose of 10 mg/kg/day for 6 days increased the hepatic cytochrome P-450 as well as glutathione-S-transferase in the rat, but not in the rabbit or monkey. Thus, oxidative stress and hepatotoxicity are produced with gamma-HCH treatment in rats, but not in the rabbit and monkey. Inhibition of Mg2+-ATPase activity has also been observed in rat liver tissue, suggesting an ATPase enzyme sensitivity to the action of gamma-HCH. The researchers suggested that some toxic effects appearing in mammals as a result of gamma-HCH exposure may arise from its influence on this ATPase activity. An in vitro study in mammalian CHO-K1 cells indicated that both gamma-HCH and an unspecified HCH isomer mixture induced glutathione peroxidase and glutathione reductase activities as a defense mechanism against oxidative stress.
DHHS/ATSDR; Toxicological Profile for alpha-, beta-, gamma-, and delta-Hexachlorocyclohexane p.137 PB2006-100003 (August 2005). Available from, as of December 8, 2016: https://www.atsdr.cdc.gov/toxprofiles/tp.asp?id=754&tid=138
In rat cortical neurons, expression of the protooncogene c-fos, which is associated with seizure activity and is induced by elevated intracellular calcium levels, was increased by gamma-HCH treatment but decreased by delta-HCH treatment. Treatment-related changes in c-fos expression suggested that gamma-HCH induces seizures through the activation of calcium channels, while inhibition of calcium channels by delta-HCH results in anticonvulsant effects. ...In a study on the cytotoxic action of delta-HCH and gamma-HCH in cultured rat cerebellar granule neurons, both isomers were found to induce an increase in the free intracellular Ca2+ concentration. ...delta-HCH may exert its action by stimulating a large influx of Ca2+. delta-HCH was found to be more potent and active as a cytotoxic agent then gamma-HCH, and the differences in cytotoxicity and neurotoxic action may be related to their action on the different Ca2+ pools. Other suggestive data concerning mechanisms by which HCH causes neurological effects in animals include enhanced synaptic activity, altered GABA functional activity, and inhibition of, or oxidative damage to Na+- K+-ATPase activity. In general, the mechanism of toxicity of HCH on the nervous system appears to be similar to those of other neurotoxic organochlorine insecticides.
DHHS/ATSDR; Toxicological Profile for alpha-, beta-, gamma-, and delta-Hexachlorocyclohexane p.136 PB2006-100003 (August 2005). Available from, as of December 8, 2016: https://www.atsdr.cdc.gov/toxprofiles/tp.asp?id=754&tid=138
Several isomers of hexachlorocyclohexanes (HCHs) have been shown to be toxic to mammals. Previous studies have revealed that the delta isomer (delta-HCH) was particularly potent toward disrupting Ca2+ homeostasis in a variety of excitable and nonexcitable cells and altering contractility of cardiac muscle. The effects of the delta and gamma isomers of HCH were further investigated on isolated ventricular myocytes from guinea pig and on single cardiac ryanodine receptor (RyR2) Ca2+-release channels from cardiac SR vesicles. Intracellular Ca2+ transients were examined in electrically stimulated cells using the fluorescent dye indo-1, and twitch contractions of myocytes were analyzed using a video-based edge motion detection system. Exposure of myocytes to delta- but not gamma-HCH depressed the peak of intracellular Ca2+ transients and prolonged recovery time. These effects were correlated with the ability of delta-HCH to inhibit the binding of [3H]ryanodine, a conformationally sensitive probe for RyR2 function, to SR preparations (IC50 = 2 and 18 uM for high- and low-affinity interactions, respectively). Measurements of single-channel gating kinetics under voltage-clamp provided direct evidence of a potent isoform-selective activation of RyR2 by delta-HCH. Results from these studies revealed that delta-HCH alters Ca2+ homeostasis and contractility in cardiac myocytes and that the mechanism can be ascribed, at least in part, to a direct interaction with the RyR2 channel complex.
PMID:10087040 Buck ED et al; J Pharmacol Exp Ther 289 (1): 477-85 (1999)
Patch clamp experiments using rat dorsal root ganglia (DRG) neurons showed differential actions of the 4 HCH isomers. Gamma-HCH had a weak potentiating action and a strong inhibitory action on gamma-aminobutyric acid (GABA)-induced currents. Delta-HCH had a strong potentiating action and an inhibitory action. Alpha-HCH and Beta-HCH had little or no effect on GABA-induced currents. The differential modulation of GABA response by HCH isomers accounts for variable symptoms of poisoning in insects and mammals. However, somewhat different results were obtained for the effects of HCH isomers on the alpha 1-beta 3-gamma 2S (short splice variants of the gamma 2 subunit) and alpha 6-beta 3-gamma 2S subunit combinations of GABA-A receptors expressed in Xenopus oocytes. GABA responses were inhibited by gamma-HCH, potentiated by alpha- and delta-HCH, and not affected by beta-HCH. Furthermore, the alpha subunit composition had no influence on these effects of HCH isomers. These differences in the responses to chemicals represent an example of the dissimilarity between native receptors and receptors expressed in xenopus oocytes which is often encountered.
Krieger, R. (ed.). Handbook of Pesticide Toxicology. Volume 1, 2nd ed. 2001. Academic Press, San Diego, California., p. 343
Gamma-aminobutyric acid-induced (36)Cl(-) flux /into membrane microsacs/ was inhibited by several cyclodienes and gamma-BHC with the following order of decreasing potency: endosulfan I > endrin I > endosulfan II > dieldrin > heptachlor epoxide > gamma-BHC > heptachlor. The non-insecticidal beta-BHC had no effect, while the IC50 (concn of insecticide that inhibits 50% of the binding of 2 nM (35)S-tert-butylbicyclophosphorothionate to rat brain membranes) values for gamma-BHC and alpha-BHC were 1 and 0.2 uM, respectively.
PMID:3009836 Abalis IM et al; J Toxicol Environ Health 18 (1): 13-23 (1986)
Alpha-hexachlorocyclohexane (alpha-HCH) is one of eight structural isomers that have been used worldwide as insecticides. Although no longer produced or used agriculturally in the United States, exposure to HCH isomers is of continuing concern due to legacy usage and persistence in the environment. The U.S. Environmental Protection Agency (EPA) classifies alpha-HCH as a probable human carcinogen and provides a slope factor of 6.3 (mg/kg-day)(-1) for the compound, based on hepatic nodules and hepatocellular carcinomas observed in male mice and derived using a default linear approach for modeling carcinogens. EPA's evaluation, last updated in 1993, does not consider more recently available guidance that allows for the incorporation of mode of action (MOA) for determining a compound's dose-response. Contrary to the linear approach assumed by EPA, the available data indicate that alpha-HCH exhibits carcinogenicity via an MOA that yields a nonlinear, threshold dose-response. In our analysis, we conducted an MOA evaluation and dose-response analysis for alpha-HCH-induced liver carcinogenesis. We concluded that alpha-HCH causes liver tumors in rats and mice through an MOA involving increased promotion of cell growth, or mitogenesis.
PMID:26713892 Bradley AE et al; Regul Toxicol Pharmacol 76: 152-73 (2016)
The mechanisms of tumor promotion in liver by various xenobiotics of diverse structure are not well understood. However, these tumor promoters share the ability to exert growth-stimulatory effects on hepatocytes. Our laboratory has been utilizing normal rat hepatocytes under defined conditions of primary cultures, to investigate growth-stimulatory actions of liver tumor promoters. We have shown that most, if not all, of the liver tumor promoters tested stimulate hepatocyte DNA synthesis when added in combination with epidermal growth factor (EGF), insulin, and glucocorticoids. In the present study, /the authors/ sought evidence for the role of the Na(+)/H(+) antiporter and cytoplasmic alkalinization in the direct growth-stimulatory actions of tumor promoters on hepatocytes. Hepatocytes cultured under conditions (bicarbonate-buffered medium) where intracellular pH (pH(i)) was independent of extracellular pH (pH(e)), EGF- and insulin-stimulated rates of DNA synthesis were unaffected by modest changes in pH(e). However, under conditions (HEPES-buffered medium) where pH(i) varied in a linear fashion with pH(e), rates of EGF- and insulin-stimulated DNA synthesis were highly dependent on pH(e). Similarly, 12-O-tetradecanoylphorbol-13-acetate (TPA) and alpha-hexachlorocyclohexane (HCH)-stimulated DNA synthesis were pH(e)-dependent but were stimulatory over different pH(e) ranges, suggesting that these promoters may act by distinct mechanisms. Chemicals that are capable of inducing rapid cytoplasmic alkalinization, ammonium chloride (1 and 15 mM) and monensin (0.5 microM), were found to stimulate hepatocyte DNA synthesis. The role of the Na(+)/H(+) antiport in controlling pH(i) of hepatocytes was demonstrated by artificially acidifying 2',7'-bis(carboxyethyl)-5,6-carboxyfluorescein acetoxymethyl (BCECF)-loaded isolated hepatocytes with 20 mM sodium acetate and the use of specific inhibitors. Amiloride and its analogues inhibited pH(i) recovery from the acid load in a dose dependent manner and the relative potency of these inhibitors paralleled their K(i) values for the Na(+)/H(+) antiport. At concentrations that stimulate hepatocyte DNA synthesis, some liver tumor promoters phenobarbital (PB) and HCH, were found to cause a rapid rise pH(i) in isolated hepatocytes which was sensitive to amiloride and its analogues. Taken together, our data suggest that activation of Na(+)/H(+) antiport activity may be one mechanism whereby some liver tumor promoters stimulate hepatocytes DNA synthesis.
PMID:12599209 Lee CH et al; J Cell Physiol 195 (1): 61-9 (2003)
Patch clamp experiments using rat dorsal root ganglia (DRG) neurons showed differential actions of the 4 HCH isomers. Gamma-HCH had a weak potentiating action and a strong inhibitory action on gamma-aminobutyric acid (GABA)-induced currents. Delta-HCH had a strong potentiating action and an inhibitory action. Alpha-HCH and Beta-HCH had little or no effect on GABA-induced currents. The differential modulation of GABA response by HCH isomers accounts for variable symptoms of poisoning in insects and mammals. However, somewhat different results were obtained for the effects of HCH isomers on the alpha 1-beta 3-gamma 2S (short splice variants of the gamma 2 subunit) and alpha 6-beta 3-gamma 2S subunit combinations of GABA-A receptors expressed in Xenopus oocytes. GABA responses were inhibited by gamma-HCH, potentiated by alpha- and delta-HCH, and not affected by beta-HCH. Furthermore, the alpha subunit composition had no influence on these effects of HCH isomers. These differences in the responses to chemicals represent an example of the dissimilarity between native receptors and receptors expressed in xenopus oocytes which is often encountered.
Krieger, R. (ed.). Handbook of Pesticide Toxicology. Volume 1, 2nd ed. 2001. Academic Press, San Diego, California., p. 343
Patch clamp experiments using rat dorsal root ganglia (DRG) neurons showed differential actions of the 4 HCH isomers. Gamma-HCH had a weak potentiating action and a strong inhibitory action on gamma-aminobutyric acid (GABA)-induced currents. Delta-HCH had a strong potentiating action and an inhibitory action. Alpha-HCH and Beta-HCH had little or no effect on GABA-induced currents. The differential modulation of GABA response by HCH isomers accounts for variable symptoms of poisoning in insects and mammals. However, somewhat different results were obtained for the effects of HCH isomers on the alpha 1-beta 3-gamma 2S (short splice variants of the gamma 2 subunit) and alpha 6-beta 3-gamma 2S subunit combinations of GABA-A receptors expressed in Xenopus oocytes. GABA responses were inhibited by gamma-HCH, potentiated by alpha- and delta-HCH, and not affected by beta-HCH. Furthermore, the alpha subunit composition had no influence on these effects of HCH isomers. These differences in the responses to chemicals represent an example of the dissimilarity between native receptors and receptors expressed in xenopus oocytes which is often encountered.
Krieger, R. (ed.). Handbook of Pesticide Toxicology. Volume 1, 2nd ed. 2001. Academic Press, San Diego, California., p. 343
/Delta-HCH causes/ sustained elevation of cytosolic Ca+2 /by acting as a/ ryanodine receptor activator /and/ inducing Ca+2 influx into cytoplasm from the endoplasmic reticulum. /From table/
Klaassen, C.D. (ed). Casarett and Doull's Toxicology. The Basic Science of Poisons. 6th ed. New York, NY: McGraw-Hill, 2001., p. 60
Delta-HCH altered calcium homeostasis and contractility of cardiac myocytes through interaction with ryanodine receptors. Delta-HCH also induced a profound increase in ionic permeability in lipid bilayers, and the calcium-dependent current produced by delta-HCH was selective for mono-valent cations (K+ >> Cs+ > Na+).
Krieger, R. (ed.). Handbook of Pesticide Toxicology. Volume 1, 2nd ed. 2001. Academic Press, San Diego, California., p. 344
Patch clamp experiments using rat dorsal root ganglia (DRG) neurons showed differential actions of the 4 HCH isomers. Gamma-HCH had a weak potentiating action and a strong inhibitory action on gamma-aminobutyric acid (GABA)-induced currents. Delta-HCH had a strong potentiating action and an inhibitory action. Alpha-HCH and Beta-HCH had little or no effect on GABA-induced currents. The differential modulation of GABA response by HCH isomers accounts for variable symptoms of poisoning in insects and mammals. However, somewhat different results were obtained for the effects of HCH isomers on the alpha 1-beta 3-gamma 2S (short splice variants of the gamma 2 subunit) and alpha 6-beta 3-gamma 2S subunit combinations of GABA-A receptors expressed in Xenopus oocytes. GABA responses were inhibited by gamma-HCH, potentiated by alpha- and delta-HCH, and not affected by beta-HCH. Furthermore, the alpha subunit composition had no influence on these effects of HCH isomers. These differences in the responses to chemicals represent an example of the dissimilarity between native receptors and receptors expressed in xenopus oocytes which is often encountered.
Krieger, R. (ed.). Handbook of Pesticide Toxicology. Volume 1, 2nd ed. 2001. Academic Press, San Diego, California., p. 343
delta-Hexachlorocyclohexane (delta-HCH) interacts with cardiac ryanodine-sensitive Ca2+ channels (RyR2), accounting in part for altered Ca2+ transients and contractility. Analysis of channel gating kinetics in the presence of delta-HCH also revealed a nonfluctuating membrane current that remained even after RyR2 channels were blocked. /The authors/ further elucidated the nature of a direct interaction between delta-HCH and biological membranes by measuring ionic currents across planar lipid bilayers made from defined lipids lacking cellular protein using voltage-clamp. Dimethyl sulfoxide, in the presence or absence of 50 uM ... delta-HCH, produced negligible steady-state current with symmetric 100 mM CsCl in the range of +/-50 mV. However, the addition of 50 uM Ca2+ to the bilayer chamber in the presence of delta-HCH induced a profound increase in ionic permeability ... . Significantly, the permeability increase 1) was proportional with increasing Ca2+ to approximately 600 uM and saturated between 1 and 2 mM Ca2+ regardless of holding potential, 2) occurred only when delta-HCH and Ca2+ were added to the same side of the membrane, and 3) was independent of the order of addition or of the side of the membrane to which delta-HCH and Ca2+ was added. The Ca2+-dependent current produced by delta-HCH was highly selective for monovalent cations (K+ >> Cs+ > Na+), with negligible conductance for Ca2+ or Cl-. In symmetric 100 mM K+, the conductance induced with 50 uM concentration each of delta-HCH and Ca2+ was 4.25 pA/mV. The results show that delta-HCH increases the ionic permeability of phospholipid membranes by two distinct Ca2+-dependent mechanisms: one mediated through RyR and the other mediated by a unique ionophore activity.
PMID:10087041 Buck ED, Pessah IN; J Pharmacol Exp Ther 289 (1): 486-93 (1999)
Several isomers of hexachlorocyclohexanes (HCHs) have been shown to be toxic to mammals. Previous studies have revealed that the delta isomer (delta-HCH) was particularly potent toward disrupting Ca2+ homeostasis in a variety of excitable and nonexcitable cells and altering contractility of cardiac muscle. The effects of the delta and gamma isomers of HCH were further investigated on isolated ventricular myocytes from guinea pig and on single cardiac ryanodine receptor (RyR2) Ca2+-release channels from cardiac SR vesicles. Intracellular Ca2+ transients were examined in electrically stimulated cells using the fluorescent dye indo-1, and twitch contractions of myocytes were analyzed using a video-based edge motion detection system. Exposure of myocytes to delta- but not gamma-HCH depressed the peak of intracellular Ca2+ transients and prolonged recovery time. These effects were correlated with the ability of delta-HCH to inhibit the binding of [3H]ryanodine, a conformationally sensitive probe for RyR2 function, to SR preparations (IC50 = 2 and 18 uM for high- and low-affinity interactions, respectively). Measurements of single-channel gating kinetics under voltage-clamp provided direct evidence of a potent isoform-selective activation of RyR2 by delta-HCH. Results from these studies revealed that delta-HCH alters Ca2+ homeostasis and contractility in cardiac myocytes and that the mechanism can be ascribed, at least in part, to a direct interaction with the RyR2 channel complex.
PMID:10087040 Buck ED et al; J Pharmacol Exp Ther 289 (1): 477-85 (1999)
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