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Also known as: Ethynylestradiol, 57-63-6, Ethinylestradiol, Ethynyl estradiol, Ethinyloestradiol, 17-ethinylestradiol
Molecular Formula
C20H24O2
Molecular Weight
296.4  g/mol
InChI Key
BFPYWIDHMRZLRN-SLHNCBLASA-N
FDA UNII
423D2T571U

Ethinyl Estradiol
A semisynthetic alkylated ESTRADIOL with a 17-alpha-ethinyl substitution. It has high estrogenic potency when administered orally, and is often used as the estrogenic component in ORAL CONTRACEPTIVES.
Ethinyl estradiol is an Estrogen. The mechanism of action of ethinyl estradiol is as an Estrogen Receptor Agonist.
1 2D Structure

Ethinyl Estradiol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(8R,9S,13S,14S,17R)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
2.1.2 InChI
InChI=1S/C20H24O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,5,7,12,16-18,21-22H,4,6,8-11H2,2H3/t16-,17-,18+,19+,20+/m1/s1
2.1.3 InChI Key
BFPYWIDHMRZLRN-SLHNCBLASA-N
2.1.4 Canonical SMILES
CC12CCC3C(C1CCC2(C#C)O)CCC4=C3C=CC(=C4)O
2.1.5 Isomeric SMILES
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=C3C=CC(=C4)O
2.2 Other Identifiers
2.2.1 UNII
423D2T571U
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 19-norpregna-1,3,5(10)-trien-20-yne-3,17-diol, (17alpha)-

2. Estinyl

3. Estradiol, Ethinyl

4. Estradiol, Ethynyl

5. Ethinyl Estradiol Hemihydrate

6. Ethinyl Estradiol, (8 Alpha)-isomer

7. Ethinyl Estradiol, (8 Alpha,17 Alpha)-isomer

8. Ethinyl Estradiol, (8 Alpha,9 Beta,13 Alpha,14 Beta)-isomer

9. Ethinyl Estradiol, (9 Beta,17 Alpha)-isomer

10. Ethinyl Oestradiol Effik

11. Ethinyl-oestradiol Effik

12. Ethinylestradiol Jenapharm

13. Ethinyloestradiol

14. Ethynyl Estradiol

15. Hemihydrate, Ethinyl Estradiol

16. Jenapharm, Ethinylestradiol

17. Lynoral

18. Microfollin

19. Microfollin Forte

20. Progynon C

2.3.2 Depositor-Supplied Synonyms

1. Ethynylestradiol

2. 57-63-6

3. Ethinylestradiol

4. Ethynyl Estradiol

5. Ethinyloestradiol

6. 17-ethinylestradiol

7. Estinyl

8. 17alpha-ethynylestradiol

9. Ginestrene

10. Lynoral

11. Progynon C

12. Ethinoral

13. Eticyclin

14. Eticyclol

15. Etinestrol

16. Etinestryl

17. Etinoestryl

18. Etistradiol

19. Follicoral

20. Novestrol

21. Orestralyn

22. Spanestrin

23. Amenoron

24. Dyloform

25. Ertonyl

26. Estigyn

27. Estoral

28. Estorals

29. Ethidol

30. Feminone

31. Inestra

32. Linoral

33. Menolyn

34. Oradiol

35. Primogyn

36. Esteed

37. Neo-estrone

38. Primogyn C

39. Primogyn M

40. Nogest-s

41. Eston-e

42. Palonyl

43. Perovex

44. 17alpha-ethinylestradiol

45. 17-ethynylestradiol

46. Diogyn E

47. Chee-o-genf

48. Chee-o-gen

49. 17-ethinyl-3,17-estradiol

50. Ethynyloestradiol

51. 17-ethinyl-3,17-oestradiol

52. 17-ethynyloestradiol

53. Estoral (orion)

54. 17alpha-ethinyl Estradiol

55. Diognat-e

56. Diogyn-e

57. Eticylol

58. Kolpolyn

59. Orestrayln

60. Ylestrol

61. Anovlar

62. Etivex

63. 17a-ethynylestradiol

64. Progynon M

65. Ethinylestradiolum

66. Estradiol, 17-ethynyl-

67. Nsc-10973

68. Ethinyl Estradiol [usp]

69. 17.alpha.-ethinylestradiol

70. 17.alpha.-ethynylestradiol

71. Estoral [orion]

72. 17.alpha.-ethynyloestradiol

73. Microfollin

74. 17a-ethinylestradiol

75. 17 Alpha-ethinyestradiol

76. Ethinyl Estradiol (usp)

77. Diprol

78. (8r,9s,13s,14s,17r)-17-ethynyl-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6h-cyclopenta[a]phenanthrene-3,17-diol

79. Ee

80. Chembl691

81. 17-alpha-ethynyl Estradiol

82. 17.alpha.-ethinyl-17.beta.-estradiol

83. Ethinyl-oestranol

84. 17.alpha.-ethynyl-17.beta.-oestradiol

85. Norinyl

86. Mls000028479

87. Aethinyloestradiolum

88. Chebi:4903

89. Ee2

90. Estopherol

91. Prosexol

92. Ethinyl E2

93. 17.alpha.-ethynylestradiol-l7.beta.

94. 423d2t571u

95. (8r,9s,13s,14s,17r)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthrene-3,17-diol

96. 17.alpha.-ethynyloestradiol-17.beta.

97. Estoral (van)

98. (17beta)-17-ethynylestra-1(10),2,4-triene-3,17-diol

99. Aethinyoestradiol [german]

100. Ncgc00091533-04

101. Etinilestradiol

102. Certostat

103. Smr000058319

104. 19-norpregna-1,3,5(10)-trien-20-yne-3,17-diol, (17a)-

105. Etinilestradiolo

106. Dsstox_cid_576

107. Aethinyoestradiol

108. 19-norpregna-1,3,5(10)-trien-20-yne-3,17-diol, (17.alpha.)-

109. Etinilestradiol [inn-spanish]

110. Ee(sub 2)

111. Ethinylestradiolum [inn-latin]

112. Etinilestradiolo [dcit]

113. 17alpha-ethynyloestradiol

114. Dsstox_rid_75668

115. 17-alpha-ethynylestradiol

116. Dsstox_gsid_20576

117. 17alpha-ethynylestra-1,3,5(10)-triene-3,17beta-diol

118. 17alpha-ethinyl-estra-1,3,5(10)-triene-3,17beta-diol

119. 17-ethynyl-3,17-dihydroxy-1,3,5-oestratriene

120. 19-nor-17.alpha.-pregna-1,3,5(10)-trien-20-yne-3,17-diol

121. 17alpha-ethinylestradiol-17beta

122. Ethinylestradiol [inn:ban:jan]

123. 17-alpha-ethynylestradiol-17-beta

124. Cas-57-63-6

125. 17-alpha-ethinyl-17-beta-estradiol

126. (1s,10r,11s,14r,15s)-14-ethynyl-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol

127. 17-alpha-ethynyl-17-beta-oestradiol

128. Component Of Oracon

129. Component Of Ortrel

130. Ccris 286

131. Estinyl (tn)

132. Component Of Demulen

133. Hsdb 3587

134. Einecs 200-342-2

135. Mfcd00003690

136. Ovulen-21

137. Ovulen-28

138. Estra-1,5(10)-triene-3,17.beta.-diol, 17-ethynyl-

139. Estra-1,5[10]-triene-3,17.beta.-diol, 17-ethynyl-

140. Brn 2419975

141. Ethinyloestradiol [steroidal Oestrogens]

142. Ylestol

143. 19-nor-17.alpha.-pregna-1,5(10)-trien-20-yne-3,17-diol

144. 19-nor-17.alpha.-pregna-1,5[10]-trien-20-yne-3,17-diol

145. Ai3-52941

146. Ethinyl-estradiol

147. Ethynyl-estradiol

148. Unii-423d2t571u

149. 17alpha-ethinyl-17beta-estradiol

150. 19-norpregna-1,3,5(10)-trien-20-yne-3,17-diol, (17alpha)-

151. Component Of Ovral

152. 3wf

153. Levlen (salt/mix)

154. Oracon (salt/mix)

155. Ortrel (salt/mix)

156. 17-alpha-ethynyl-1,3,5-oestratriene-3,17-beta-diol

157. Anovlar (salt/mix)

158. Desogen (salt/mix)

159. 17a-ethynyloestradiol

160. Estoral {[orion]}

161. 17alpha-ethinylestra-1,3,5(10)-triene-3,17beta-diol

162. 17alpha-ethinyloestra-1,3,5(10)-triene-3,17beta-diol

163. Nordette (salt/mix)

164. Secrovin (salt/mix)

165. 17-alpha-ethinylestra-1,3,5(10)-triene-3,17-beta-diol

166. 17-alpha-ethynyl-1,3,5(10)-estratriene-3,17-beta-diol

167. Seasonale (salt/mix)

168. Triphasil (salt/mix)

169. 17-alpha-ethinyloestra-1,3,5(10)-triene-3,17-beta-diol

170. 17-alpha-ethynyl-1,3,5(10)-oestratriene-3,17-beta-diol

171. 17alpha-ethinyl-3,17-dihydroxy-delta(sup1,3,5)-estratriene

172. 17alpha-ethinyl-3,17-dihydroxy-delta(sup1,3,5)oestratriene

173. 3,17beta-dihydroxy-17alpha-ethynyl-1,3,5(10)-estratriene

174. 3,17beta-dihydroxy-17alpha-ethynyl-1,3,5(10)-oestratriene

175. Estopherol (salt/mix)

176. Estra-1,3,5(10)-triene-3,17beta-diol, 17alpha-ethynyl-

177. Seasonique (salt/mix)

178. 17-alpha-ethinyl-3,17-dihydroxy-delta(sup 1,3,5)-estratriene

179. 17-ethynylestradiol Ram

180. 19-nor-17alpha-pregna-1,3,5(10)-trien-20-yne-3,17-diol

181. 3,17-beta-dihydroxy-17-alpha-ethynyl-1,3,5(10)-estratriene

182. 3,17-beta-dihydroxy-17-alpha-ethynyl-1,3,5(10)-oestratriene

183. Estra-1,3,5(10)-triene-3,17-beta-diol, 17-alpha-ethynyl-

184. Ortho Evra (salt/mix)

185. Tri-levlen (salt/mix)

186. (17-alpha)-19-norpregna-1,3,5(10)-trien-20-yne-3,17,diol

187. 17alpha-ethinyl-delta(sup1,3,5(10))oestratriene-3,17-beta -diol

188. 17alpha-ethynyloestradiol-17beta; 17beta-estradiol, 17-ethynyl-

189. 19-nor-17-alpha-pregna-1,3,5(10)-triene-20-yne-3,17-diol

190. Opera_id_1808

191. 17a-ethynylestradiol-l7b

192. 17-alpha-ethinyl-delta(sup 1,3,5(10))oestratriene-3,17-beta-diol

193. Ortho-cyclen (salt/mix)

194. 17a-ethynyloestradiol-17b

195. Schembl4071

196. 17a-ethinyl-17b-estradiol

197. 17a-ethynyl-17b-oestradiol

198. Mls000758274

199. Mls001424011

200. Bidd:er0162

201. Ethinylestradiol [inn]

202. Ethinylestradiol [jan]

203. Ethinyl Estradiol [mi]

204. Ethinylestradiol (jp17/inn)

205. Ethinylestradiol [inci]

206. Gtpl7071

207. Sgcut00127

208. 17alpha-ethynyl-1,3,5(10)-estratriene-3,17beta-diol

209. Dtxsid5020576

210. Ethinyl Estradiol [hsdb]

211. Ethinylestradiol [mart.]

212. Ethinyl Estradiol [vandf]

213. Ethinylestradiol [who-dd]

214. Ethinylestradiol [who-ip]

215. Hms2051i19

216. Hms2235j09

217. Hms3715j09

218. 17alpha-ethynylestradiol, >=98%

219. Ethinyl Estradiol [usp-rs]

220. (17alpha)-19-norpregna-1,3,5(10)-trien-20-yne-3,17-diol

221. 17.beta.-estradiol, 17-ethynyl-

222. 19-nor-17-alpha-pregna-1,3,5(10)-trien-20-yne-3,17-diol

223. Hy-b0216

224. Nsc10973

225. To_000048

226. Zinc3812897

227. Tox21_111147

228. Tox21_201291

229. Tox21_300413

230. Bdbm50187243

231. Ethinyl Estradiol [ema Epar]

232. Lmst02010036

233. S1625

234. 17

235. A-ethynylestradiol;ethynylestradiol

236. Akos015894925

237. Tox21_111147_1

238. Yaz Component Ethinyl Estradiol

239. Ac-2169

240. Ccg-100819

241. Db00977

242. Ethinyl Estradiol [orange Book]

243. Ethinylestradiol [ep Monograph]

244. Ks-5257

245. Nc00069

246. 17.alpha.-ethinyl-3,3,5)oestratriene

247. Beyaz Component Ethinyl Estradiol

248. Ovral Component Ethinyl Estradiol

249. Zovia Component Ethinyl Estradiol

250. 17.alpha.-ethinyl-3,3,5)-estratriene

251. Alesse Component Ethinyl Estradiol

252. Aviane Component Ethinyl Estradiol

253. Ethinyl Estradiol [usp Monograph]

254. Ethinylestradiolum [who-ip Latin]

255. Femhrt Component Ethinyl Estradiol

256. Kariva Component Ethinyl Estradiol

257. Kelnor Component Ethinyl Estradiol

258. Levora Component Ethinyl Estradiol

259. Lybrel Component Ethinyl Estradiol

260. Ncgc00091533-01

261. Ncgc00091533-05

262. Ncgc00091533-07

263. Ncgc00091533-08

264. Ncgc00091533-09

265. Ncgc00091533-10

266. Ncgc00254514-01

267. Ncgc00258843-01

268. Portia Component Ethinyl Estradiol

269. Preven Component Ethinyl Estradiol

270. Twirla Component Ethinyl Estradiol

271. Vienva Component Ethinyl Estradiol

272. Volnea Component Ethinyl Estradiol

273. Xulane Component Ethinyl Estradiol

274. Yasmin Component Ethinyl Estradiol

275. Bekyree Component Ethinyl Estradiol

276. Desogen Component Ethinyl Estradiol

277. Enskyce Component Ethinyl Estradiol

278. Ethinyl Estradiol Component Of Yaz

279. Kurvelo Component Ethinyl Estradiol

280. Lessina Component Ethinyl Estradiol

281. Levlite Component Ethinyl Estradiol

282. Nci60_000234

283. Norinyl Component Ethinyl Estradiol

284. Pimtrea Component Ethinyl Estradiol

285. Safyral Component Ethinyl Estradiol

286. Trivora Component Ethinyl Estradiol

287. Velivet Component Ethinyl Estradiol

288. Viorele Component Ethinyl Estradiol

289. Vyfemla Component Ethinyl Estradiol

290. Altavera Component Ethinyl Estradiol

291. Annovera Component Ethinyl Estradiol

292. Aranelle Component Ethinyl Estradiol

293. Brevicon Component Ethinyl Estradiol

294. Cryselle Component Ethinyl Estradiol

295. Cyclessa Component Ethinyl Estradiol

296. Elifemme Component Ethinyl Estradiol

297. Enpresse Component Ethinyl Estradiol

298. Isibloom Component Ethinyl Estradiol

299. Levonest Component Ethinyl Estradiol

300. Marlissa Component Ethinyl Estradiol

301. Mircette Component Ethinyl Estradiol

302. Nordette Component Ethinyl Estradiol

303. Nuvaring Component Ethinyl Estradiol

304. Orsythia Component Ethinyl Estradiol

305. Previfem Component Ethinyl Estradiol

306. Quasense Component Ethinyl Estradiol

307. Setlakin Component Ethinyl Estradiol

308. Sprintec Component Ethinyl Estradiol

309. Taytulla Component Ethinyl Estradiol

310. Ethinyl Estradiol Component Of Beyaz

311. Ethinyl Estradiol Component Of Ovral

312. Introvale Component Ethinyl Estradiol

313. Quartette Component Ethinyl Estradiol

314. Seasonale Component Ethinyl Estradiol

315. Triphasil Component Ethinyl Estradiol

316. Ethinyl Estradiol Component Of Alesse

317. Ethinyl Estradiol Component Of Desogen

318. Ethinyl Estradiol Component Of Femhrt

319. Ethinyl Estradiol Component Of Kariva

320. Ethinyl Estradiol Component Of Kelnor

321. Ethinyl Estradiol Component Of Levlite

322. Ethinyl Estradiol Component Of Lybrel

323. Ethinyl Estradiol Component Of Preven

324. Ethinyl Estradiol Component Of Safyral

325. Ethinyl Estradiol Component Of Twirla

326. Ethinyl Estradiol Component Of Velivet

327. Ethinyl Estradiol Component Of Yasmin

328. Femcon Fe Component Ethinyl Estradiol

329. Ortho-cept Component Ethinyl Estradiol

330. Seasonique Component Ethinyl Estradiol

331. 17-ethynyl-3-17-dihydroxy-1,5-oestratriene

332. 17alpha-ethynylestradiol, >=98.0% (hplc)

333. Ethinyl Estradiol Component Of Altavera

334. Ethinyl Estradiol Component Of Annovera

335. Ethinyl Estradiol Component Of Aranelle

336. Ethinyl Estradiol Component Of Cryselle

337. Ethinyl Estradiol Component Of Cyclessa

338. Ethinyl Estradiol Component Of Levonest

339. Ethinyl Estradiol Component Of Mircette

340. Ethinyl Estradiol Component Of Nuvaring

341. Ethinyl Estradiol Component Of Previfem

342. Ethinyl Estradiol Component Of Quasense

343. Ethinyl Estradiol Component Of Setlakin

344. Ethinyl Estradiol Component Of Sprintec

345. Norquest Fe Component Ethinyl Estradiol

346. C07534

347. D00554

348. Estrostep Fe Component Ethinyl Estradiol

349. Ethinyl Estradiol Component Of Femcon Fe

350. Ethinyl Estradiol Component Of Introvale

351. Ethinyl Estradiol Component Of Seasonale

352. H11762

353. Loseasonique Component Ethinyl Estradiol

354. Tri-previfem Component Ethinyl Estradiol

355. Tri-sprintec Component Ethinyl Estradiol

356. 17-ethynyl-3-17-dihydroxy-1,3,5-oestratriene

357. Ab00441335-11

358. Ab00441335_12

359. Ethinyl Estradiol Component Of Ortho-cept

360. Ethinyl Estradiol Component Of Seasonique

361. Tri-legest Fe Component Ethinyl Estradiol

362. Wln: L E5 B666ttt&j E1 Fq F1uu1 Oq

363. 003e690

364. Ethinyl Estradiol Component Of Estrostep Fe

365. Ethinyl Estradiol Component Of Loseasonique

366. Ethinyl Estradiol Component Of Norquest Fe

367. Ethinyl Estradiol Component Of Tri-previfem

368. Ethinyl Estradiol Component Of Tri-sprintec

369. Lo Loestrin Fe Component Ethinyl Estradiol

370. Lo Minastrin Fe Component Ethinyl Estradiol

371. Q415563

372. Sr-01000721903

373. Tri Lo Sprintec Component Ethinyl Estradiol

374. 17-ethynylestra-1,3,5(10)-triene-3,17beta-diol

375. 17a-ethinylestradiol 100 Microg/ml In Acetonitrile

376. Ethinyl Estradiol Component Of Lo Loestrin Fe

377. Ethinyl Estradiol Component Of Tri-legest Fe

378. Minastrin 24 Fe Component Ethinyl Estradiol

379. Ortho Tri-cyclen Component Ethinyl Estradiol

380. Q-201076

381. Sr-01000721903-3

382. 17-ethynyloestra-1,5(10)-triene-3,17.beta.-diol

383. 17.alpha.-ethynyl-1,5-estratriene-3,17.beta.-diol

384. 17.alpha.-ethynyl-1,5-oestratriene-3,17.beta.-diol

385. 17a-ethinylestradiol 100 Microg/ml In Methanol/water

386. 17alpha-ethinyl-1,3,5(10)-estratriene-3,17-diol

387. Brd-k48195008-001-19-9

388. Ethinyl Estradiol Component Of Ortho Tri-cyclen

389. Ethinyl Estradiol Component Of Tri Lo Sprintec

390. 17-ethynyloestra-1,3,5(10)-triene-3,17.beta.-diol

391. 17.alpha.-ethinyl-1,3,5(10)-estratriene-3,17-diol

392. Z1541638513

393. 17.alpha.-ethinylestra-1,5(10)-triene-3,17.beta.-diol

394. 17.alpha.-ethinyloestra-1,5(10)-triene-3,17.beta.-diol

395. 17.alpha.-ethynylestra-1,5(10)-triene-3,17.beta.-diol

396. 17.alpha.-ethynyloestra-1,5(10)-triene-3,17.beta.-diol

397. 17.alpha.-ethinylestra-1,3,5(10)-triene-3,17.beta.-diol

398. 17.alpha.-ethinyloestra-1,3,5(10)-triene-3,17.beta.-diol

399. 17.alpha.-ethynyl-1,3,5(10)-estratriene-3,17.beta.-diol

400. 17.alpha.-ethynyl-1,3,5(10)-oestratriene-3,17.beta.-diol

401. 17.alpha.-ethynylestra-1,3,5(10)-triene-3,17.beta.-diol

402. 17.alpha.-ethynyloestra-1,3,5(10)-triene-3,17.beta.-diol

403. 17alpha-ethynylestradiol, Vetranal(tm), Analytical Standard

404. 19-nor-17.alpha.-pregna-1,5(10)-trien-2-yne-3,17-diol

405. Estra-1,5(10)-triene-3,17.beta.-diol, 17.alpha.-ethynyl-

406. 17.alpha.-ethinyl-3,17-dihydroxy-.delta.(sup1,3,5)-estratriene

407. 17.alpha.-ethinyl-3,17-dihydroxy-.delta.(sup1,3,5)oestratriene

408. 19-nor-17.alpha.-pregna-1,3,5(10)-trien-20-yn-3,17-diol

409. 19-norpregna-1,5(10)-trien-20-yne-3,17-diol, (17.alpha.)-

410. 3,17.beta.-dihydroxy-17.alpha.-ethynyl-1,3,5(10)-estratriene

411. 3,17.beta.-dihydroxy-17.alpha.-ethynyl-1,3,5(10)-oestratriene

412. Estra-1,3,5(10)-triene-3,17.beta.-diol, 17.alpha.-ethynyl-

413. Ethinylestradiol, European Pharmacopoeia (ep) Reference Standard

414. 17.alpha.-ethinyl-.delta.(sup1,3,5(10))oestratriene-3,17-.beta. -diol

415. 17.alpha.-ethinyl-.delta.(sup1,5(10))oestratriene-3,17-.beta.-diol

416. 19-nor-17.alpha.-pregna-1,3,5(10)-trien-20-yne-3,17.beta.-diol

417. Ethinyl Estradiol, United States Pharmacopeia (usp) Reference Standard

418. (9beta,13alpha,14beta,17alpha)-17-ethynylestra-1(10),2,4-triene-3,17-diol

419. Ethinyl Estradiol, Pharmaceutical Secondary Standard; Certified Reference Material

420. Ethinylestradiol For System Suitability, European Pharmacopoeia (ep) Reference Standard

421. 1050678-65-3

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 296.4 g/mol
Molecular Formula C20H24O2
XLogP33.7
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Exact Mass296.177630004 g/mol
Monoisotopic Mass296.177630004 g/mol
Topological Polar Surface Area40.5 Ų
Heavy Atom Count22
Formal Charge0
Complexity505
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Estrogens

National Library of Medicine's Medical Subject Headings online file (MeSH, 2009)


Ethinyl estradiol /is indicated in combination with an oral progestin/ for the prevention of pregnancy in women who elect to use this product as a method of contraception. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information CESIA (desogestrel and ethinyl estradiol) kit (February 2009). Available from, as of March 10, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=9373


Femhrt (norethindrone acetate/ethinyl estradiol) is indicated in women with an intact uterus for the treatment of moderate to severe vasomotor symptoms associated with the menopause. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information FEMHRT (norethindrone acetate/ethinyl estradiol) tablet (October 2008). Available from, as of March 10, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=23194


Femhrt (norethindrone acetate/ethinyl estradiol) is indicated in women with an intact uterus for the prevention of postmenopausal osteoporosis. When prescribing solely for the prevention of postmenopausal osteoporosis, therapy should only be considered for women at significant risk of osteoporosis. Non-estrogen medications should be carefully considered. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information FEMHRT (norethindrone acetate/ethinyl estradiol) tablet (October 2008). Available from, as of March 10, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=23194


Ethinyl estradiol is used frequently in combination with progestins for oral contraception.

Briggs, G.G, R.K. Freeman, S.J. Yaffe. A Reference Guide to Fetal and Neonatal Risk. Drugs in Pregnancy and Lactation. 4th ed. Baltimore, MD: Williams & Wilkins 1994., p. 354


4.2 Drug Warning

/BOXED WARNING/ WARNING: Estrogens and progestins should not be used for the prevention of cardiovascular disease or dementia. The Women's Health Initiative (WHI) study reported increased risks of myocardial infarction, stroke, invasive breast cancer, pulmonary emboli, and deep vein thrombosis in postmenopausal women (50 to 79 years of age) during 5 years of treatment with oral conjugated estrogens (CE 0.625 mg) combined with medroxyprogesterone acetate (MPA 2.5 mg) relative to placebo. The Women's Health Initiative Memory Study (WHIMS), a substudy of WHI, reported increased risk of developing probable dementia in postmenopausal women 65 years of age or older during 4 years of treatment with oral conjugated estrogens plus medroxyprogesterone acetate relative to placebo. It is unknown whether this finding applies to younger postmenopausal women. Other doses of oral conjugated estrogens with medroxyprogesterone acetate, and other combinations and dosage forms of estrogens and progestins were not studied in the WHI clinical trials and, in the absence of comparable data, these risks should be assumed to be similar. Because of these risks, estrogens with or without progestins should be prescribed at the lowest effective doses and for the shortest duration consistent with treatment goals and risks for the individual woman.

US Natl Inst Health; DailyMed. Current Medication Information FEMHRT (norethindrone acetate/ethinyl estradiol) tablet (October 2008). Available from, as of March 10, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=23194


ESTROGENS INCREASE THE RISK OF ENDOMETRIAL CANCER: Close clinical surveillance of all women taking estrogens is important. Adequate diagnostic measures, including endometrial sampling when indicated, should be undertaken to rule out malignancy in all cases of undiagnosed persistent or recurring abnormal vaginal bleeding. There is no evidence that the use of "natural" estrogens results in a different endometrial risk profile than synthetic estrogens at equivalent estrogen doses.

US Natl Inst Health; DailyMed. Current Medication Information FEMHRT (norethindrone acetate/ethinyl estradiol) tablet (October 2008). Available from, as of March 10, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=23194


Other doses of oral conjugated estrogens with medroxyprogesterone acetate, and other combinations and dosage forms of estrogens and progestins were not studied in the WHI clinical trials and, in the absence of comparable data, these risks should be assumed to be similar. Because of these risks, estrogens with or without progestins should be prescribed at the lowest effective doses and for the shortest duration consistent with treatment goals and risks for the individual woman.

US Natl Inst Health; DailyMed. Current Medication Information FEMHRT (norethindrone acetate/ethinyl estradiol) tablet (October 2008). Available from, as of March 10, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=23194


FDA Pregnancy Risk Category: X /CONTRAINDICATED IN PREGNANCY. Studies in animals and or humans, or investigational or post-marketing reports, have demonstrated positive evidence of fetal abnormalities or risk which clearly outweighs any possible benefit to the patient./

US Natl Inst Health; DailyMed. Current Medication Information FEMHRT (norethindrone acetate/ethinyl estradiol) tablet (October 2008). Available from, as of March 10, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=23194


For more Drug Warnings (Complete) data for ETHINYLESTRADIOL (38 total), please visit the HSDB record page.


4.3 Drug Indication

Ethinylestradiol is combined with other drugs for use as a contraceptive, premenstrual dysphoric disorder, moderate acne, moderate to severe vasomotor symptoms of menopause, prevention of postmenopausal osteoporosis.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Ethinylestradiol is a synthetic estrogen that decreases luteinizing hormone to decrease endometrial vascularization, and decreases gonadotrophic hormone to prevent ovulation. It has a long duration of action as it is taken once daily, and a wide therapeutic index as overdoses are generally not associated with serious adverse effects. Patients should be counselled regarding the risks of thrombotic events.


5.2 MeSH Pharmacological Classification

Contraceptives, Oral, Hormonal

Oral contraceptives which owe their effectiveness to hormonal preparations. (See all compounds classified as Contraceptives, Oral, Hormonal.)


Estrogens

Compounds that interact with ESTROGEN RECEPTORS in target tissues to bring about the effects similar to those of ESTRADIOL. Estrogens stimulate the female reproductive organs, and the development of secondary female SEX CHARACTERISTICS. Estrogenic chemicals include natural, synthetic, steroidal, or non-steroidal compounds. (See all compounds classified as Estrogens.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
ETHINYL ESTRADIOL
5.3.2 FDA UNII
423D2T571U
5.3.3 Pharmacological Classes
Mechanisms of Action [MoA] - Estrogen Receptor Agonists
5.4 ATC Code

G03AA07

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


G - Genito urinary system and sex hormones

G03 - Sex hormones and modulators of the genital system

G03C - Estrogens

G03CA - Natural and semisynthetic estrogens, plain

G03CA01 - Ethinylestradiol


L - Antineoplastic and immunomodulating agents

L02 - Endocrine therapy

L02A - Hormones and related agents

L02AA - Estrogens

L02AA03 - Ethinylestradiol


5.5 Absorption, Distribution and Excretion

Absorption

A 30g oral dose of ethinylestradiol reaches a Cmax of 74.135.6pg/mL, with a Tmax of 1.50.5h, and an AUC of 487.4166.6pg\*h/mL. A 1.2mg dose delivered via a patch reaches a Cmax of 28.810.3pg/mL, with a Tmax of 8631h, and an AUC of38951423pg\*h/mL.


Route of Elimination

Ethinylestradiol is 59.2% eliminated in the urine and bile, while 2-3% is eliminated in the feces. Over 90% of ethinylestradiol is eliminated as the unchanged parent drug.


Volume of Distribution

A 30g oral dose has an apparent volume of distribution of 625.3228.7L and a 1.2mg topical dose has an apparent volume of distribution of 11745.315934.8L.


Clearance

Ethinylestradiol has an intravenous clearance of 16.47L/h, and an estimated renal clearance of approximately 2.1L/h. A 30g oral dose has a clearance of 58.019.8L/h and a 1.2mg topical dose has a clearance of 303.5100.5L/h.


Ethinyl estradiol is rapidly and almost completely absorbed. When the lowest and highest tablet strengths, 0.100 mg desogestrel/0.025 mg ethinyl estradiol and 0.150 mg desogestrel/0.025 mg ethinyl estradiol, were compared to solution, the relative bioavailability of ethinyl estradiol was 92% and 98%, respectively.

US Natl Inst Health; DailyMed. Current Medication Information CESIA (desogestrel and ethinyl estradiol) kit (February 2009). Available from, as of March 10, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=9373


The distribution of exogenous estrogens is similar to that of endogenous estrogens. Estrogens are widely distributed in the body and are generally found in higher concentrations in the sex hormone target organs. Ethinyl estradiol circulates in the blood largely bound to ... albumin. ... Although ethinyl estradiol does not bind to SHBG, it induces SHBG synthesis.

US Natl Inst Health; DailyMed. Current Medication Information FEMHRT (norethindrone acetate/ethinyl estradiol) tablet (October 2008). Available from, as of March 10, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=23194


Estradiol, estrone, and estriol are excreted in the urine along with glucuronide and sulfate conjugates.

US Natl Inst Health; DailyMed. Current Medication Information FEMHRT (norethindrone acetate/ethinyl estradiol) tablet (October 2008). Available from, as of March 10, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=23194


25 healthy women of reproductive age who had not previously used oral contraceptive steroids, were each given a single tablet containing 50, 80, or 100 ug of mestranol or 50 or 80 ug of ethinyl estradiol. Blood samples were obtained before taking the tablets and at intervals of 1, 2, 4, and 24 hours afterward. Anti-ethinyl-estradiol antibody in 1 to 100,000 initial dilution was used. Details of techniques employed are given. With ethinyl estradiol, the 1-hour sampling yielded the maximum plasma levels. At 24 hours, the plasma level was not detectable in 4 of 5 subjects given 50 ug or in 1 of 5 given 80 ug. With mestranol, the disappearance curve was more variable with the peak levels usually at 2 hours but occasionally at 4 hours. At all 3 dose levels of mestranol, measurable serum ethinyl estradiol levels were found at 24 hours. These levels were reached more slowly and were lower than when ethinyl estradiol was given. In contrast to natural estrogens ethinyl, estrogens are bound to plasma proteins chiefly by nonspecific binding and are therefore less likely to affect the metabolism of the ethinyl estrogens than are the endogenous steroids. Also, significant amounts of ethinyl estradiol are was given. In contrast to natural estrogens ethinyl, estrogens are bound di-ethynylated in vitro. The pharmacokinetics of ethinyl estrogens differ from those of natural estrogens. This complicates interpretation of plasma or urinary estrone and estradiol measurements.

PMID:1154455 de la Pena A et al; Steroids 25 (6): 773-80 (1975)


For more Absorption, Distribution and Excretion (Complete) data for ETHINYLESTRADIOL (7 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Ethinylestradiol can be glucuronidated by UGT1A1, UGT1A3, UGT1A4, UGT1A9, and UGT2B7. Ethinylestradiol is also sulfated by SULT1A1, SULT1A3, and SULT1E1. Ethinylestradiol can also be hydroxylated at positions 2, 4, 6, 7, and 16 by CYP3A4, CYP3A5, CYP2C8, CYP2C9, and CYP1A2. These hydroxylated metabolites can be methylated by catechol-O-methyltransferase. The methoxy metabolites can in turn be sulfated or glucuronidated.


Exogenous estrogens are metabolized in the same manner as endogenous estrogens. Circulating estrogens exist in a dynamic equilibrium of metabolic interconversions. These transformations take place mainly in the liver. Estradiol is converted reversibly to estrone, and both can be converted to estriol, which is the major urinary metabolite. Estrogens also undergo enterohepatic recirculation via sulfate and glucuronide conjugation in the liver, biliary secretion of conjugates into the intestine, and hydrolysis in the gut followed by reabsorption. In postmenopausal women, a significant proportion of the circulating estrogens exist as sulfate conjugates, especially estrone sulfate, which serves as a circulating reservoir for the formation of more active estrogens.

US Natl Inst Health; DailyMed. Current Medication Information FEMHRT (norethindrone acetate/ethinyl estradiol) tablet (October 2008). Available from, as of March 10, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=23194


Ethinyl estradiol is extensively metabolized, both by oxidation and by conjugation with sulfate and glucuronide. Sulfates are the major circulating conjugates of ethinyl estradiol and glucuronides predominate in urine. The primary oxidative metabolite is 2-hydroxy ethinyl estradiol, formed by the CYP3A4 isoform of cytochrome P450. Part of the first-pass metabolism of ethinyl estradiol is believed to occur in gastrointestinal mucosa. Ethinyl estradiol may undergo enterohepatic circulation.

US Natl Inst Health; DailyMed. Current Medication Information FEMHRT (norethindrone acetate/ethinyl estradiol) tablet (October 2008). Available from, as of March 10, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=23194


Ethinyl estradiol is cleared much more slowly ... due to decreased hepatic metabolism.

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 1420


Studies on the metabolism of ethinylestradiol have been carried out in rats, rabbits, guinea-pigs, dogs and monkeys. It is very rapidly and effectively absorbed from rat intestine; no appreciable metabolic transformation is reported to take place during the absorption process. The main metabolic pathway of ethinylestradiol in rats is by aromatic 2-hydroxylation; hydroxylations at ring B (C-6/C-7) are of only minor importance. Rat liver forms 2-hydroxyethinylestradiol and the methyl ethers thereof, 2-methoxyethinylestradiol and 2-hydroxyethinylestradiol-3-methy1 ether, as its major metabolic products. This pathway is also important in humans. Metabolites of ethinylestradiol in rats are excreted almost exclusively in the feces.

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. V21 245 (1979)


For more Metabolism/Metabolites (Complete) data for ETHINYLESTRADIOL (10 total), please visit the HSDB record page.


Ethinylestradiol has known human metabolites that include 17-Ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-2,3,17-triol and 17-Ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,4,17-triol.

Ethinylestradiol is a known human metabolite of Mestranol.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.7 Biological Half-Life

A 30g oral dose has a half life of 8.44.8h and a 1.2mg topical dose has a half life of 27.734.2h.


The pharmacokinetics of 19-nor-17 alpha-pregna-1,3,5(10)-trien-20-yne-3,17-diol (ethinylestradiol, Progynon C) (EE2) has been studied after intravenous administration of 0.1 or 0.01 mg/kg and after intragastric administration of 1 mg/kg in female rats, rabbits, beagle dogs, rhesus monkeys and baboons. After intravenous administration disposition of unchanged drug in the plasma was biphasic with initial half-lives between 0.3 and 0.5 hr and terminal half-lives between 2.3 and 3.0 hr. Total plasma clearance was of the same magnitude as total plasma liver flow or even higher rat) indicating a rapid biotransformation of the estrogen in the liver. Systemic availability of intragastric EE2 amounted to 3% in the rat, 0.3% in the rabbit, 9% in the dog, 0.6% in rhesus monkeys and 2% in the baboon and was considerably lower than in humans (40%). Differences in the pharmacokinetics and in the systemic availability of EE2 between laboratory animals and man should be taken into account in the retrospective interpretation of pharmacological and toxicological data and in the design of new studies.

PMID:3778555 Dusterberg B et al; Arzneimittelforschung 36 (8): 1187-90 (1986)


... The elimination phase half-life has been reported ... to be 13 to 27 hours.

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 1420


5.8 Mechanism of Action

Ethinylestradiol is a synthetic estrogenic compound. Use of estrogens have a number of effects on the body including reduced bone density. Combined oral contraceptives suppress ovulation by suppressing gonadotrophic hormone, thickening cervical mucus to prevent the travel of sperm, and preventing changes in the endometrium required for implantation of a fertilized egg. Ethinylestradiol decreases luteinizing hormone, decreasing vascularity in the endometrium. It also increases sex hormone binding globulin.


Endogenous estrogens are largely responsible for the development and maintenance of the female reproductive system and secondary sexual characteristics. Although circulating estrogens exist in a dynamic equilibrium of metabolic interconversions, estradiol is the principal intracellular human estrogen and is substantially more potent than its metabolites estrone and estriol at the receptor level. ... After menopause, most endogenous estrogen is produced by conversion of androstenedione, secreted by the adrenal cortex, to estrone by peripheral tissues. Thus, estrone and the sulfate conjugated form, estrone sulfate, are the most abundant circulating estrogens in postmenopausal women. The pharmacologic effects of ethinyl estradiol are similar to those of endogenous estrogens. Estrogens act through binding to nuclear receptors in estrogen-responsive tissues. To date, two estrogen receptors have been identified. These vary in proportion from tissue to tissue. Circulating estrogens modulate the pituitary secretion of the gonadotropins, luteinizing hormone (LH) and follicle stimulating hormone (FSH) through a negative feedback mechanism. Estrogens act to reduce the elevated levels of these hormones seen in postmenopausal women.

US Natl Inst Health; DailyMed. Current Medication Information FEMHRT (norethindrone acetate/ethinyl estradiol) tablet (October 2008). Available from, as of March 10, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=23194


Estrogens have an important role in the reproductive, skeletal, cardiovascular, and central nervous systems in women, and act principally by regulating gene expression. Biologic response is initiated when estrogen binds to a ligand-binding domain of the estrogen receptor resulting in a conformational change that leads to gene transcription through specific estrogen response elements (ERE) of target gene promoters; subsequent activation or repression of the target gene is mediated through 2 distinct transactivation domains (ie, AF-1 and AF-2) of the receptor. The estrogen receptor also mediates gene transcription using different response elements (ie, AP-1) and other signal pathways. Recent advances in the molecular pharmacology of estrogen and estrogen receptors have resulted in the development of selective estrogen receptor modulators (eg, clomiphene, raloxifene, tamoxifen, toremifene), agents that bind and activate the estrogen receptor but that exhibit tissue-specific effects distinct from estrogen. Tissue-specific estrogen-agonist or -antagonist activity of these drugs appears to be related to structural differences in their estrogen receptor complex (eg, specifically the surface topography of AF-2 for raloxifene) compared with the estrogen (estradiol)-estrogen receptor complex. A second estrogen receptor also has been identified, and existence of at least 2 estrogen receptors (ER-alpha, ER-beta) may contribute to the tissue-specific activity of selective modulators. While the role of the estrogen receptor in bone, cardiovascular tissue, and the CNS continues to be studied, emerging evidence indicates that the mechanism of action of estrogen receptors in these tissues differs from the manner in which estrogen receptors function in reproductive tissue. /Estrogen General Statement/

American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 3130


Intracellular cytosol-binding proteins for estrogens have been identified in estrogen-responsive tissues including the female genital organs, breasts, pituitary, and hypothalamus. The estrogen-binding protein complex (ie, cytosol-binding protein and estrogen) distributes into the cell nucleus where it stimulates DNA, RNA, and protein synthesis. The presence of these receptor proteins is responsible for the palliative response to estrogen therapy in women with metastatic carcinoma of the breast. /Estrogen General Statement/

American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 3130


Estrogens have generally favorable effects on blood cholesterol and phospholipid concentrations. Estrogens reduce LDL-cholesterol and increase HDL-cholesterol concentrations in a dose-related manner. The decrease in LDL-cholesterol concentrations associated with estrogen therapy appears to result from increased LDL catabolism, while the increase in triglyceride concentrations is caused by increased production of large, triglyceride-rich, very-low-density lipoproteins (VLDLs); changes in serum HDL-cholesterol concentrations appear to result principally from an increase in the cholesterol and apolipoprotein A-1 content of HDL2- and a slight increase in HDL3-cholesterol. /Estrogen General Statement/

American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 3130


For more Mechanism of Action (Complete) data for ETHINYLESTRADIOL (7 total), please visit the HSDB record page.


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MAHARASHTRA","supplier":"ASPEN API","supplierCountry":"NETHERLANDS","foreign_port":"AMSTERDAM, SCHIPHOL","customer":"GLENMARK PHARMACEUTICALS","customerCountry":"INDIA","quantity":"0.17","actualQuantity":"0.168","unit":"KGS","unitRateFc":"62500","totalValueFC":"11628.3","currency":"EUR","unitRateINR":"5778125","date":"18-Jun-2024","totalValueINR":"970725","totalValueInUsd":"11628.3","indian_port":"Bombay Air","hs_no":"29372300","bill_no":"4063977","productDescription":"API","marketType":"REGULATED MARKET","country":"NETHERLANDS","selfForZScoreResived":"Micronized","supplierPort":"AMSTERDAM, SCHIPHOL","supplierAddress":"KLOOSTERSTRAAT 6,5349 AB OSS.SDNFSDNF NETHERLANDS","customerAddress":"B\/2 MAHALAXMI CHAMBERS"}]
19-Mar-2021
18-Jun-2024
KGS
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Average Price (USD/KGS)

Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country Total Quantity
(KGS)
Average Price
(USD/KGS)
Number of Transactions

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DOSAGE - TABLET;ORAL-21 - 0.03MG;1.5MG

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USFDA APPLICATION NUMBER - 203667

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USFDA APPLICATION NUMBER - 208612

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DOSAGE - TABLET;ORAL - 0.0025MG;0.5MG

USFDA APPLICATION NUMBER - 21065

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DOSAGE - TABLET;ORAL - 0.01MG,0.01MG;1MG,N/A

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