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2D Structure
Also known as: 56-75-7, Chloromycetin, Chlornitromycin, Levomycetin, Chloroamphenicol, Halomycetin
Molecular Formula
C11H12Cl2N2O5
Molecular Weight
323.13  g/mol
InChI Key
WIIZWVCIJKGZOK-RKDXNWHRSA-N
FDA UNII
66974FR9Q1

An antibiotic first isolated from cultures of Streptomyces venequelae in 1947 but now produced synthetically. It has a relatively simple structure and was the first broad-spectrum antibiotic to be discovered. It acts by interfering with bacterial protein synthesis and is mainly bacteriostatic. (From Martindale, The Extra Pharmacopoeia, 29th ed, p106)
Chloramphenicol is an Amphenicol-class Antibacterial.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
2.1.2 InChI
InChI=1S/C11H12Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h1-4,8-10,16-17H,5H2,(H,14,18)/t8-,9-/m1/s1
2.1.3 InChI Key
WIIZWVCIJKGZOK-RKDXNWHRSA-N
2.1.4 Canonical SMILES
C1=CC(=CC=C1C(C(CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]
2.1.5 Isomeric SMILES
C1=CC(=CC=C1[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]
2.2 Other Identifiers
2.2.1 UNII
66974FR9Q1
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Amphenicol

2. Amphenicols

3. Chlornitromycin

4. Chlorocid

5. Chloromycetin

6. Cloranfenicol

7. Detreomycin

8. Kloramfenikol

9. Levomycetin

10. Ophthochlor

11. Syntomycin

2.3.2 Depositor-Supplied Synonyms

1. 56-75-7

2. Chloromycetin

3. Chlornitromycin

4. Levomycetin

5. Chloroamphenicol

6. Halomycetin

7. Levomicetina

8. Chlorocid

9. Globenicol

10. Alficetyn

11. Chloramex

12. Chlorocol

13. Detreomycin

14. Oleomycetin

15. Fenicol

16. Amphenicol

17. Aquamycetin

18. Chloramficin

19. Chloramfilin

20. Chloroptic

21. Cloramicol

22. D-chloramphenicol

23. Econochlor

24. Enteromycetin

25. Juvamycetin

26. Leukomycin

27. Novomycetin

28. Ophthochlor

29. Sificetina

30. Amphicol

31. Mychel

32. Chloramphenicolum

33. Chloronitrin

34. Ciplamycetin

35. Detreomycine

36. Intramycetin

37. Laevomycetinum

38. Levomitsetin

39. Mediamycetine

40. Micochlorine

41. Novophenicol

42. Stanomycetin

43. Synthomycetin

44. Amseclor

45. Anacetin

46. Austracil

47. Austracol

48. Biocetin

49. Biophenicol

50. Chemicetin

51. Chemicetina

52. Chlomycol

53. Chloramsaar

54. Chlorasol

55. Chloricol

56. Chlorocaps

57. Chlorocide

58. Chlorovules

59. Cidocetine

60. Cloramficin

61. Cloramidina

62. Clorocyn

63. Cloromisan

64. Clorosintex

65. Comycetin

66. Cylphenicol

67. Doctamicina

68. Embacetin

69. Erbaplast

70. Farmicetina

71. Hortfenicol

72. Isicetin

73. Ismicetina

74. Isophenicol

75. Kemicetina

76. Kemicetine

77. Leukomyan

78. Loromisin

79. Mastiphen

80. Medichol

81. Micloretin

82. Micoclorina

83. Microcetina

84. Rivomycin

85. Ambofen

86. Catilan

87. Chlomin

88. Desphen

89. Emetren

90. Enicol

91. Ertilen

92. Glorous

93. Kamaver

94. Klorita

95. Isopto Fenicol

96. Chlora-tabs

97. Chlorocidin C

98. Chloroject L

99. Normimycin V

100. Chlorocid S

101. Klorocid S

102. Mychel-vet

103. Chloramfenikol

104. Cloramfenicol

105. Novochlorocap

106. Sintomicetina

107. Chloromax

108. Oftalent

109. Otachron

110. Pantovernil

111. Pentamycetin

112. Quemicetina

113. Romphenil

114. Ronphenil

115. Septicol

116. Chloro-25 Vetag

117. Mycinol

118. Opclor

119. Otophen

120. Paraxin

121. Sintomicetine R

122. Sno-phenicol

123. Chlorocidin C Tetran

124. Chlorofair

125. Cloroamfenicolo

126. Optomycin

127. D-(-)-chloramphenicol

128. Chloromycetny

129. Dextromycetin

130. Synthomycetine

131. Treomicetina

132. Tevcocin

133. Tifomycine

134. Unimycetin

135. Veticol

136. Viceton

137. Tiromycetin

138. Leukamycin

139. Loromisan

140. Tifomycin

141. D-(-)-threo-chloramphenicol

142. Tega-cetin

143. 2,2-dichloro-n-[(1r,2r)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide

144. I 337a

145. U-6062

146. Nci-c55709

147. Nsc 3069

148. D-threo-chloramphenicol

149. 2,2-dichloro-n-[(1r,2r)-2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]acetamide

150. D(-)-threo-chloramphenicol

151. D-(-)-threo-1-p-nitrophenyl-2-dichloroacetylamino-1,3-propanediol

152. Caf

153. Cloramfen

154. Ak-chlor

155. Chebi:17698

156. Nsc3069

157. Nsc-3069

158. D-(-)-2,2-dichloro-n-(beta-hydroxy-alpha-(hydroxymethyl)-p-nitrophenylethyl)acetamide

159. D-(-)-threo-1-p-nitrophenyl-2-dichloracetamido-1,3-propanediol

160. Acetamide, 2,2-dichloro-n-(2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl)-, (r-(r*,r*))-

161. Chloramphenicol (chloromycetin)

162. 125440-98-4

163. Cloramfenicolo

164. Syntomycin

165. D-(-)-threo-2-dichloroacetamido-1-p-nitrophenyl-1,3-propanediol

166. D-(-)-threo-1-(4-nitrophenyl)-2-dichloroacetamido-1,3-propanediol

167. D-threo-(1r,2r)-1-p-nitrophenyl-2-dichloroacetamido-1,3-propanediol

168. Chloramphenicol-[ring-3,5-3h]

169. Acetamide, 2,2-dichloro-n-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]-, [r-(r*,r*)]-

170. 66974fr9q1

171. Ncgc00091011-05

172. Caf (pharmaceutical)

173. Dsstox_cid_265

174. Chloramfenikol [czech]

175. Chloromycetny [polish]

176. Cloramfenicolo [dcit]

177. D-threo-n-(1,1'-dihydroxy-1-p-nitrophenylisopropyl)dichloroacetamide

178. 2,2-dichloro-n-((1r,2r)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl)acetamide

179. Chlorbiotic (veterinary)

180. Chloramphenicol 100 Microg/ml In Ethyl Acetate

181. Cloroamfenicolo [italian]

182. Dsstox_rid_75473

183. Chloramphenicol Crystalline

184. Dsstox_gsid_20265

185. Elase-chloromycetin

186. Gloveticol

187. Mycochlorin

188. Ocuphenicol

189. Sintomicetin

190. Tyfomycine

191. Chlorocin

192. Halcetin

193. Levocin

194. Levoplast

195. Levosin

196. Levovetin

197. Myclocin

198. Soluthor

199. Chloramphenicol, D-

200. Chloroptic S.o.p.

201. Cloramfenicol [inn-spanish]

202. Chloramphenicolum [inn-latin]

203. Ophtochlor

204. Synthomycine

205. Tevcosin

206. Opelor

207. D(-)-threo-2-dichloroacetamido-1-p-nitrophenyl-1,3-propanediol

208. (-)-chloramphenicol

209. Acetamide, 2,2-dichloro-n-((1r,2r)-2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl)-

210. Econochlor (tn)

211. Amphicol (tn)

212. Ophthocort (salt/mix)

213. Acetamide, 2,2-dichloro-n-[(1r,2r)-2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]-

214. Smr000471851

215. Chloromyxin (salt/mix)

216. Chloromycetin (tn)

217. Ccris 3922

218. Hsdb 3027

219. Sr-01000761450

220. Einecs 200-287-4

221. Elase-chloromycetin (salt/mix)

222. Brn 2225532

223. Chioramphenicol

224. Chloramphenicole

225. Ai3-25003

226. Unii-66974fr9q1

227. Cas-56-75-7

228. Ncgc00094620-01

229. Thiamphenicol,(s)

230. 2,2-dichloro-n-((1r,2r)-2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl)acetamide

231. 2787-09-9

232. D-(-)-threo-2,2-dichloro-n-(.beta.-hydroxy-.alpha.-(hydroxymethyl))-p-nitrophenethylacetamide

233. D-(-)-threo-2,2-dichloro-n-[.beta.-hydroxy-.alpha.-(hydroxymethyl)]-p-nitrophenethylacetamide

234. Chloramphenicol [usp:inn:ban:jan]

235. Chloramphenicol,(s)

236. Mfcd00078159

237. Prestwick3_000031

238. Chembl130

239. Epitope Id:114066

240. Pork Muscle-chloramphenicol

241. Chloramphenicol [mi]

242. Schembl16111

243. Bspbio_000121

244. Chloramphenicol [inn]

245. Chloramphenicol [jan]

246. Wln: Wnr Dyqy1qmvygg

247. 4-13-00-02742 (beilstein Handbook Reference)

248. Mls001055372

249. Mls001066397

250. Mls001332385

251. Mls001332386

252. Mls002222155

253. Bidd:gt0145

254. Chloramphenicol [hsdb]

255. Chloramphenicol [iarc]

256. Divk1c_000544

257. Chloramphenicol [vandf]

258. Bpbio1_000135

259. Chloramphenicol [mart.]

260. Chloramphenicolum [hpus]

261. Chloramphenicol [usp-rs]

262. Chloramphenicol [who-dd]

263. Chloramphenicol [who-ip]

264. D-(-)-threo-1-(p-nitrophenyl)-2-(dichloroacetylamino)-1,3-propanediol

265. D-(-)-threo-n-dichloroacetyl-1-p-nitrophenyl-2-amino-1,3-propanediol

266. Dtxsid7020265

267. Bdbm23447

268. Chloramphenicol, Gamma-irradiated

269. Gtpl10901

270. Hms501l06

271. Kbio1_000544

272. Ninds_000544

273. Chloramphenicol (jp17/usp/inn)

274. Hms2090m15

275. Hms2095g03

276. Hms2269n06

277. Hms3712g03

278. Zinc113382

279. Chloramphenicol, >=98% (hplc)

280. Acetamide, 2,2-dichloro-n-(.beta.-hydroxy-.alpha.-(hydroxymethyl)-p-nitrophenethyl)-, D-(-)-threo-

281. Acetamide, 2,2-dichloro-n-[.beta.-hydroxy-.alpha.-(hydroxymethyl)-p-nitrophenethyl]-, D-threo-(-)-

282. Bcp12150

283. D-(-)-threo-2,2-dichloro-n-(.beta.-hydroxy-.alpha.-(hydroxymethyl)-p-nitrophenyl-ethyl)acetamide

284. D-threo-n-dichloroacetyl-1-p-nitrophenyl-2-amino-1,3-propanediol

285. Hy-b0239

286. Rkl10087

287. Chloramphenicol [green Book]

288. Tox21_111306

289. Tox21_400061

290. Chloramphenicol [orange Book]

291. D-(-)-threo-2-dichloroacetamido-1-(4-nitrophenyl)-1,3-propanediol

292. S1677

293. Chloramphenicol [ep Monograph]

294. Akos005111001

295. Chloramphenicol For Peak Identification

296. Porcine Muscle-chloramphenicol (blank)

297. Ccg-220031

298. Chloramphenicol [usp Monograph]

299. Db00446

300. Chloramphenicolum [who-ip Latin]

301. D-threo-(-)-2,2-dichloro-n-(beta-hydroxy-alpha-(hydroxymethyl)-p-nitrophenethyl)acetamide

302. Idi1_000544

303. Smp1_000065

304. Ncgc00091011-01

305. Ncgc00091011-02

306. Ncgc00091011-03

307. Ncgc00091011-04

308. Ncgc00091011-06

309. Ncgc00091011-08

310. Ncgc00091011-09

311. Ncgc00091011-20

312. Acetamide, 2,2-dichloro-n-(2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl)-, (theta-(theta,theta))-

313. Acetamide, 2,2-dichloro-n-(beta-hydroxy-alpha-(hydroxymethyl)-p-nitrophenethyl)-, D-(-)-threo-

314. As-14683

315. Nci60_002620

316. Ophthocort Component Chloramphenicol

317. Chloramphenicol, Puriss., 98.0-102.0%

318. Chloromyxin Component Chloramphenicol

319. Ab00374860

320. Chloramphenicol 10 Microg/ml In Acetonitrile

321. Chloramphenicol, Tested According To Ph.eur.

322. Sw198497-2

323. Chloramphenicol 100 Microg/ml In Acetonitrile

324. Chloramphenicol Component Of Ophthocort

325. C-3307

326. C00918

327. Chloramphenicol Component Of Chloromyxin

328. D00104

329. Ab00374860-13

330. Ab00374860-14

331. Ab00374860_15

332. Chloramphenicol, Meets Usp Testing Specifications

333. Q274515

334. Chloramphenicol, Vetranal(tm), Analytical Standard

335. Elase-chloromycetin Component Chloramphenicol

336. Sr-01000761450-2

337. Sr-01000761450-3

338. Sr-01000761450-5

339. Brd-k08111712-001-02-7

340. Brd-k08111712-001-16-7

341. Chloramphenicol Component Of Elase-chloromycetin

342. Chloramphenicol, Antibiotic For Culture Media Use Only

343. Chloroptic-p S.o.p. Component Chloramphenicol

344. Chloramphenicol Component Of Chloroptic-p S.o.p.

345. Chloramphenicol, Bioreagent, Suitable For Plant Cell Culture

346. Chloramphenicol, Certified Reference Material, Tracecert(r)

347. Chloromycetin Hydrocortisone Component Chloramphenicol

348. Chloramphenicol Component Of Chloromycetin Hydrocortisone

349. Chloramphenicol, British Pharmacopoeia (bp) Reference Standard

350. Chloramphenicol, European Pharmacopoeia (ep) Reference Standard

351. Chloramphenicol, United States Pharmacopeia (usp) Reference Standard

352. D-threo-1-(p-nitrophenyl)-2-(dichloroacetylamino)-1,3-propanediol

353. 2,2-dichloro-n-[(1r,2r)-1,3-dihydroxy-1-(4-nitrophenyl)-2-propyl]acetamide

354. Acetamide,2,2-dichloro-n-[(1r,2r)-2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]-

355. Acetamide,2-dichloro-n-[.beta.-hydroxy-.alpha.-(hydroxymethyl)-p-nitrophenethyl]

356. Chloramphenicol, Biotechnology Performance Certified, Suitable For Plant Cell Culture

357. D-(-)-2,2-dichloro-n-(.beta.-hydroxy-.alpha.-(hydroxymethyl)-p-nitrophenyl-ethyl)acetamide

358. 2,2-dichloro-n-(2-hydroxy-1-(hydroxymethyl)-2-(4-(hydroxy(oxido)amino)phenyl)ethyl)acetamide, (1r, 2r)-

359. Acetamide, 2,2-dichloro-n-(2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl)-, (r*,r*)-(+-)-

360. Acetamide,2-dichloro-n-[.beta.-hydroxy-.alpha.-(hydroxymethyl)-p-nitrophenethyl]-, D-threo-(-)-

361. Acetamide,2-dichloro-n-[.beta.-hydroxy-.alpha.-(hydroxymethyl)-p-nitrophenethyl]-,d-(-)-threo-

362. Acetamide,2-dichloro-n-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]-, [r-(r*,r*)]-

363. Chloramphenicol 10 Microg/ml In Acetonitrile. Short Expiry Date Due To Chemical Nature Of Component(s)

364. D-(-)-threo-alpha, Alpha-dichloro-n-(beta-hydroxy-alpha-(hydroxymethyl)-p-nitrophenethyl)acetamide

365. D-threo-(-)-2,2-dichloro-n-(.beta.-hydroxy-.alpha.-(hydroxymethyl)-p-nitrophenethyl)acetamide

2.3.3 Other Synonyms

1. Chloramphenicol Succinate

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 323.13 g/mol
Molecular Formula C11H12Cl2N2O5
XLogP31.1
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count5
Exact Mass322.0123269 g/mol
Monoisotopic Mass322.0123269 g/mol
Topological Polar Surface Area115 Ų
Heavy Atom Count20
Formal Charge0
Complexity342
Isotope Atom Count0
Defined Atom Stereocenter Count2
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

Anti-Bacterial Agents; Protein Synthesis Inhibitors

National Library of Medicine's Medical Subject Headings. Chloramphenicol. Online file (MeSH, 2017). Available from, as of April 10, 2017: https://www.nlm.nih.gov/mesh/2017/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. Chloramphenicol is included in the database.

NIH/NLM; ClinicalTrials.Gov. Available from, as of April 10, 2017: https://clinicaltrials.gov/


Chloramphenicol is an antibiotic produced by Streptomyces venezuelae ... recommended for serious infections in which the location of the infection, susceptibility of the pathogen or poor response to other therapy indicate restricted antimicrobial option. It has been used since the 1950s for a wide range of microbial infections, including typhoid fever and other forms of salmonellosis, and central nervous system, anaerobic and ocular infections ... .

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. V50 171 (1990)


(VET): Chloramphenicol Tablets are recommended for oral treatment of the following conditions in dogs: Bacterial pulmonary infections caused by susceptible microorganisms such as: Staphylococcus aureus, Streptococcus pyogenes and Brucella bronchiseptica; infections of the urinary tract caused by susceptible microorganisms such as: Escherichia coli, Proteus vulgaris, Corynebacterium renale, Streptococcus spp., and hemolytic Staphylococcus; enteritis caused by susceptible microorganisms such as: E. coli, Proteus spp., Salmonella spp., and Pseudomonas spp.; infections associated with canine distemper caused by susceptible microorganims such as: B. bronchiseptica, E. coli, P. aeruginosa, Proteus spp., Shigella spp. and Neisseria catarrhalis. Additional adjunctive therapy should be used when indicated. Most susceptible infectious disease organisms will respond to chloramphenicol therapy in three to five days when the recommended dosage regimen is followed. If no response to chloramphenicol therapy is obtained in three to five days, discontinue its use and review the diagnosis. Also, a change of therapy should be considered. Laboratory tests should be conducted including in vitro culturing and susceptibility tests on samples collected prior to treatment.

NIH; DailyMed. Current Medication Information for Viceton- chloramphenicol tablet, coated (veterinary drug) (Updated: November 2015). Available from, as of April 13, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=698aaa0a-9fd3-40c2-ec93-0dc2170a75ba&audience=consumer3


For more Therapeutic Uses (Complete) data for Chloramphenicol (38 total), please visit the HSDB record page.


4.2 Drug Warning

/BOXED WARNING/ WARNING Serious and fatal blood dyscrasias (aplastic anemia, hypoplastic anemia, thrombocytopenia and granulocytopenia) are known to occur after the administration of chloramphenicol. In addition, there have been reports of aplastic anemia attributed to chloramphenicol which later terminated in leukemia. Blood dyscrasias have occurred after both short-term and prolonged therapy with this drug. Chloramphenicol must not be used when less potentially dangerous agents will be effective, as described in the INDICATIONS AND USAGE section. It must not be used in the treatment of trivial infections or where it is not indicated, as in colds, influenza, infections of the throat; or as a prophylactic agent to prevent bacterial infections. Precautions: It is essential that adequate blood studies be made during treatment with the drug. While blood studies may detect early peripheral blood changes, such as leukopenia, reticulocytopenia, or granulocytopenia, before they become irreversible, such studies cannot be relied on to detect bone marrow depression prior to development of aplastic anemia. To facilitate appropriate studies and observation during therapy, it is desirable that patients be hospitalized.

NIH; DailyMed. Current Medication Information for Chloramphenicol sodium succinate injection (Updated: January 2017). Available from, as of April 12, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=aed29594-211d-49ef-813f-131975a8d0e3


/BOXED WARNING/ WARNING Bone marrow hypoplasia including aplastic anemia and death has been reported following topical application of chloramphenicol. Chloramphenicol should not be used when less potentially dangerous agents would be expected to provide effective treatment.

NIH; DailyMed. Current Medication Information for Chloromycetin Ophthalmic Ointment (Updated: October 2006). Available from, as of April 13, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=698aaa0a-9fd3-40c2-ec93-0dc2170a75ba&audience=consumer3


/Chloramphenicol/ is not recommended for the routine treatment of the typhoid carrier state.

NIH; DailyMed. Current Medication Information for Chloramphenicol sodium succinate injection (Updated: January 2017). Available from, as of April 12, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=aed29594-211d-49ef-813f-131975a8d0e3


Chloramphenicol is contraindicated in individuals with a history of previous hypersensitivity and/or toxic reaction to it. It must not be used in the treatment of trivial infections or where it is not indicated, as in colds, influenza, infections of the throat; or as a prophylactic agent to prevent bacterial infections.

NIH; DailyMed. Current Medication Information for Chloramphenicol sodium succinate injection (Updated: January 2017). Available from, as of April 12, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=aed29594-211d-49ef-813f-131975a8d0e3


For more Drug Warnings (Complete) data for Chloramphenicol (44 total), please visit the HSDB record page.


4.3 Drug Indication

Used in treatment of cholera, as it destroys the vibrios and decreases the diarrhea. It is effective against tetracycline-resistant vibrios. It is also used in eye drops or ointment to treat bacterial conjunctivitis.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Chloramphenicol is a broad-spectrum antibiotic that was derived from the bacterium Streptomyces venezuelae and is now produced synthetically. Chloramphenicol is effective against a wide variety of microorganisms, but due to serious side-effects (e.g., damage to the bone marrow, including aplastic anemia) in humans, it is usually reserved for the treatment of serious and life-threatening infections (e.g., typhoid fever). Chloramphenicol is bacteriostatic but may be bactericidal in high concentrations or when used against highly susceptible organisms. Chloramphenicol stops bacterial growth by binding to the bacterial ribosome (blocking peptidyl transferase) and inhibiting protein synthesis.


5.2 MeSH Pharmacological Classification

Protein Synthesis Inhibitors

Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins. (See all compounds classified as Protein Synthesis Inhibitors.)


Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
CHLORAMPHENICOL
5.3.2 FDA UNII
66974FR9Q1
5.3.3 Pharmacological Classes
Amphenicols [EXT]
5.4 ATC Code

S01AA01

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


D - Dermatologicals

D06 - Antibiotics and chemotherapeutics for dermatological use

D06A - Antibiotics for topical use

D06AX - Other antibiotics for topical use

D06AX02 - Chloramphenicol


D - Dermatologicals

D10 - Anti-acne preparations

D10A - Anti-acne preparations for topical use

D10AF - Antiinfectives for treatment of acne

D10AF03 - Chloramphenicol


G - Genito urinary system and sex hormones

G01 - Gynecological antiinfectives and antiseptics

G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids

G01AA - Antibiotics

G01AA05 - Chloramphenicol


J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01B - Amphenicols

J01BA - Amphenicols

J01BA01 - Chloramphenicol


S - Sensory organs

S01 - Ophthalmologicals

S01A - Antiinfectives

S01AA - Antibiotics

S01AA01 - Chloramphenicol


S - Sensory organs

S02 - Otologicals

S02A - Antiinfectives

S02AA - Antiinfectives

S02AA01 - Chloramphenicol


S - Sensory organs

S03 - Ophthalmological and otological preparations

S03A - Antiinfectives

S03AA - Antiinfectives

S03AA08 - Chloramphenicol


5.5 Absorption, Distribution and Excretion

Absorption

Rapidly and completely absorbed from gastrointestinal tract following oral administration (bioavailability 80%). Well absorbed following intramuscular administration (bioavailability 70%). Intraocular and some systemic absorption also occurs after topical application to the eye.


Hepatic metabolism to the inactive glucuronide is the major route of elimination. This metabolite and chloramphenicol itself are excreted in the urine following filtration and secretion.

Brunton, L. Chabner, B, Knollman, B. Goodman and Gillman's The Pharmaceutical Basis of Therapeutics, Twelth Edition, McGraw Hill Medical, New York, NY. 2011, p. 1527


Chloramphenicol administered orally is absorbed rapidly from the intestinal tract. In controlled studies in adult volunteers using the recommended dosage of 50 mg/kg/day, a dosage of 1 g every 6 hours for 8 doses was given. Using the microbiological assay method, the average peak serum level was 11.2 ug/mL one hour after the first dose. A cumulative effect gave a peak rise to 18.4 ug/mL after the fifth dose of 1 g. Mean serum levels ranged from 8 to 14 ug/mL over the 48-hour period. Total urinary excretion of chloramphenicol in these studies ranged from a low of 68% to a high of 99% over a three-day period. From 8% to 12% of the antibiotic excreted is in the form of free chloramphenicol; the remainder consists of microbiologically inactive metabolites, principally the conjugate with glucuronic acid. Since the glucuronide is excreted rapidly, most chloramphenicol detected in the blood is in the microbiologically active free form. Despite the small proportion of unchanged drug excreted in the urine, the concentration of free chloramphenicol is relatively high, amounting to several hundred mcg/mL in patients receiving divided doses of 50 mg/kg/day. Small amounts of active drug are found in bile and feces. Chloramphenicol diffuses rapidly, but its distribution is not uniform. Highest concentrations are found in liver and kidney, and lowest concentrations are found in brain and cerebrospinal fluid. Chloramphenicol enters cerebrospinal fluid even in the absence of meningeal inflammation, appearing in concentrations about half of those found in the blood. Measurable levels are also detected in pleural and in ascitic fluids, saliva, milk, and in the aqueous and vitreous humors. Transport across the placental barrier occurs with somewhat lower concentration in cord blood of neonates than in maternal blood.

NIH; DailyMed. Current Medication Information for Chloramphenicol sodium succinate injection (Updated: January 2017). Available from, as of April 12, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=aed29594-211d-49ef-813f-131975a8d0e3


Chloramphenicol achieves maximum serum levels very rapidly following oral, intravenous and intraperitoneal administration. Intramuscular injection with chloramphenicol, except certain soluble forms, results in a somewhat delayed absorption and lower serum levels than when given by the oral, intravenous, or intraperitoneal route. Chloramphenicol diffuses readily into all body tissues, but at different concentrations. Highest concentrations are found in the liver and kidney of dogs indicating that these organs are the main route of inactivation and excretion of the metabolites. The lungs, spleen, heart and skeletal muscles contain concentrations similar to that of the blood. Chloramphenicol reaches significant concentration in the aqueous and vitreous humors of the eye from the blood. A significant difference from other antibiotics is its marked ability to diffuse into the cerebrospinal fluid. Within three to four hours after administration, the concentration in the cerebrospinal fluid has reached, on the average, 50% of the concentration in the serum. If the meninges are inflamed, the percentage may be even higher. Chloramphenicol diffuses readily into milk, pleural and ascitic fluids and crosses the placenta attaining concentrations of about 75% of that of the maternal blood.

NIH; DailyMed. Current Medication Information for Viceton- chloramphenicol tablet, coated (veterinary drug) (Updated: November 2015). Available from, as of April 13, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=698aaa0a-9fd3-40c2-ec93-0dc2170a75ba&audience=consumer3


Approximately 55% of a single daily dose can be recovered from the urine of a treated dog. A small fraction of this is in the form of unchanged chloramphenicol.

NIH; DailyMed. Current Medication Information for Viceton- chloramphenicol tablet, coated (veterinary drug) (Updated: November 2015). Available from, as of April 13, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=698aaa0a-9fd3-40c2-ec93-0dc2170a75ba&audience=consumer3


For more Absorption, Distribution and Excretion (Complete) data for Chloramphenicol (21 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Hepatic, with 90% conjugated to inactive glucuronide.


Chloramphenicol is rather rapidly metabolized, mainly in the liver, by conjugation with glucuronic acid.

NIH; DailyMed. Current Medication Information for Viceton- chloramphenicol tablet, coated (veterinary drug) (Updated: November 2015). Available from, as of April 13, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=698aaa0a-9fd3-40c2-ec93-0dc2170a75ba&audience=consumer3


Yields d-threo-2-amino-1-(p-nitrophenyl)-1,3-propanediol and chloramphenicol-beta-d-glucuronide in man. In rat. /from table/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. C-14


... /undergoes/ direct conjugation. Formation of glucuronide was shown to occur at primary rather than at secondary alcoholic group ... its major reaction of inactivation and detoxication of drug in man, and any factor which decreases its importance ... results in greatly increased toxicity. ... In newborns ... bilirubin ... acts as competitive endogenous acceptor.

Testa, B. and P. Jenner. Drug Metabolism: Chemical & Biochemical Aspects. New York: Marcel Dekker, Inc., 1976., p. 191


Chloramphenicol 3-glucuronide was the major metabolite of chloramphenicol produced by isolated rat hepatocytes although a minor metabolite was also formed.

Siliciano RF et al; Biochem Pharmacol 27 (23): 2759 (1978)


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


5.7 Biological Half-Life

Half-life in adults with normal hepatic and renal function is 1.5 - 3.5 hours. In patients with impaired renal function half-life is 3 - 4 hours. In patients with severely impaired hepatic function half-life is 4.6 - 11.6 hours. Half-life in children 1 month to 16 years old is 3 - 6.5 hours, while half-life in infants 1 to 2 days old is 24 hours or longer and is highly variable, especially in low birth-weight infants.


Chloramphenicol has a half-time /in humans/ ranging from 1.6 to 4.6 hr; using different techniques and in different adult patients, apparent volumes of distribution ranging from 0.2 to 3.1 l/kg have been measured ... . The half-time is considerably longer in neonates ... in 1- to 8-day-old infants the half-life ranged from 10 to over 48 hr, and in 11-day to 8-wk-old infants the range was 5-16 hr ... .

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. V50 178 (1990)


The plasma half-life of chloramphenicol in adults with normal renal and hepatic function is 1.5-4.1 hours. ... The plasma half-life is 24 hours or longer in infants 1-2 days of age and approximately 10 hours in infants 10-16 days of age. The plasma half-life of chloramphenicol is prolonged in patients with markedly reduced hepatic function. In patients with impaired renal function, the plasma half-life of chloramphenicol is not significantly prolonged, although half-lives of the inactive conjugated derivatives may be prolonged.

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 196


5.8 Mechanism of Action

Chloramphenicol is lipid-soluble, allowing it to diffuse through the bacterial cell membrane. It then reversibly binds to the L16 protein of the 50S subunit of bacterial ribosomes, where transfer of amino acids to growing peptide chains is prevented (perhaps by suppression of peptidyl transferase activity), thus inhibiting peptide bond formation and subsequent protein synthesis.


Chloramphenicol inhibits protein synthesis in bacteria, and to a lesser extent, in eukaryotic cells. The drug readily penetrates bacterial cells, probably by facilitated diffusion. Chloramphenicol acts primarily by binding reversibly to the 50S ribosomal subunit (near the binding site for the macrolide antibiotics and clindamycin, which chloramphenicol inhibits competitively). Although binding of tRNA at the codon recognition site on the 30S ribosomal subunit is undisturbed, the drug apparently prevents the binding of the amino acid-containing end of the aminoacyl tRNA to the acceptor site on the 50S ribosomal subunit. The interaction between peptidyltransferase and its amino acid substrate cannot occur, and peptide bond formation is inhibited.

Brunton, L. Chabner, B, Knollman, B. Goodman and Gillman's The Pharmaceutical Basis of Therapeutics, Twelth Edition, McGraw Hill Medical, New York, NY. 2011, p. 1527


Chloramphenicol ... can inhibit mitochondrial protein synthesis in mammalian cells, perhaps because mitochondrial ribosomes resemble bacterial ribosomes (both are 70S) more than they do the 80S cytoplasmic ribosomes of mammalian cells. The peptidyltransferase of mitochondrial ribosomes, but not of cytoplasmic ribosomes, is inhibited by chloramphenicol. Mammalian erythropoietic cells are particularly sensitive to the drug.

Brunton, L. Chabner, B, Knollman, B. Goodman and Gillman's The Pharmaceutical Basis of Therapeutics, Twelth Edition, McGraw Hill Medical, New York, NY. 2011, p. 1527


/Chloramphenicol/ inhibits bacterial protein synthesis by interfering with the transfer of activated amino acids from soluble RNA to ribosomes. In vitro, chloramphenicol exerts mainly a bacteriostatic effect on a wide range of gram-negative and gram-positive bacteria.

NIH; DailyMed. Current Medication Information for Chloramphenicol sodium succinate injection (Updated: January 2017). Available from, as of April 12, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=aed29594-211d-49ef-813f-131975a8d0e3


/Chloramphenicol/ acts by inhibition of protein synthesis by interfering with the transfer of activated amino acids from soluble RNA to ribosomes.

NIH; DailyMed. Current Medication Information for Chloromycetin Ophthalmic Ointment (Updated: October 2006). Available from, as of April 13, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=698aaa0a-9fd3-40c2-ec93-0dc2170a75ba&audience=consumer3


For more Mechanism of Action (Complete) data for Chloramphenicol (9 total), please visit the HSDB record page.