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Chemistry

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Also known as: Azidothymidine, 30516-87-1, 3'-azido-3'-deoxythymidine, Retrovir, Azt, Zidovudinum

Molecular Formula

C₁₀H₁₃N₅O₄

Molecular Weight

267.24 g/mol

InChI Key

HBOMLICNUCNMMY-XLPZGREQSA-N

FDA UNII

4B9XT59T7S

A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.

Zidovudine is a Human Immunodeficiency Virus Nucleoside Analog Reverse Transcriptase Inhibitor. The mechanism of action of zidovudine is as a Nucleoside Reverse Transcriptase Inhibitor.

1 2D Structure

Zidovudine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione

2.1.2 InChI

InChI=1S/C10H13N5O4/c1-5-3-15(10(18)12-9(5)17)8-2-6(13-14-11)7(4-16)19-8/h3,6-8,16H,2,4H2,1H3,(H,12,17,18)/t6-,7+,8+/m0/s1

2.1.3 InChI Key

HBOMLICNUCNMMY-XLPZGREQSA-N

2.1.4 Canonical SMILES

CC1=CN(C(=O)NC1=O)C2CC(C(O2)CO)N=[N+]=[N-]

2.1.5 Isomeric SMILES

CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO)N=[N+]=[N-]

2.2 Other Identifiers

2.2.1 UNII

4B9XT59T7S

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3' Azido 2',3' Dideoxythymidine

2. 3' Azido 3' Deoxythymidine

3. 3'-azido-2',3'-dideoxythymidine

4. 3'-azido-3'-deoxythymidine

5. Antiviral Azt

6. Azidothymidine

7. Azt (antiviral)

8. Azt Antiviral

9. Azt, Antiviral

10. Bw A509u

11. Bwa 509u

12. Bwa-509u

13. Bwa509u

14. Retrovir

2.3.2 Depositor-Supplied Synonyms

1. Azidothymidine

2. 30516-87-1

3. 3'-azido-3'-deoxythymidine

4. Retrovir

5. Azt

6. Zidovudinum

7. Thymidine, 3'-azido-3'-deoxy-

8. Compound S

9. Trizivir

10. Zidovudine [azt]

11. Zidovudina

12. Bw A509u

13. Zidovudin

14. Bwa509u

15. Zdv

16. 3'-deoxy-3'-azidothymidine

17. Bw-a509u

18. Bw-a-509u

19. Nsc 602670

20. 3'-azt

21. 1-((2r,4s,5s)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1h,3h)-dione

22. Chembl129

23. 1-(3-azido-2,3-dideoxy-beta-d-ribofuranosyl)thymine

24. 1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione

25. Mls000028548

26. 4b9xt59t7s

27. Chebi:10110

28. Azidothymidine (azt)

29. Ncgc00023945-05

30. Zidovudinum [latin]

31. Smr000058351

32. Zidovudina [spanish]

33. Dsstox_cid_127

34. Dsstox_rid_75386

35. Dsstox_gsid_20127

36. 1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

37. Propolis+azt

38. Nsc-602670

39. 3'-azido-2',3'-dideoxythymidine

40. Drg-0004

41. Retrovir(tm)

42. Azt & Li & Epo

43. Retrovir (tn)

44. Ccris 105

45. Cpd S

46. Intron A & Azt

47. Hsdb 6515

48. Racemic Liposomal Azt

49. Liposomal Azt-sn-1

50. Liposomal Azt-sn-3

51. Zidovudine+pro 140

52. Pc-sod+azt

53. Azt & Srcd4

54. Azt & Rifn.alpha.2

55. Azt & Rst4

56. Rifn-beta Seron & Azt

57. Mfcd00006536

58. 3'-azido-3'-deoxythymidine (aids)

59. Azt & Epo

60. Azt & Gm-csf

61. Azt & Hpa

62. Azt & Scd4

63. Azt & Sst

64. Zudovidine

65. Unii-4b9xt59t7s

66. Azt & Li & Gm-csf

67. Azt+pro 140

68. Met-sdf-1.beta. & Azt

69. Azt & Li & Il-1

70. Azt & Li & Il-6

71. Azt & Il-1

72. Azt & Il-2

73. Azt & Il-6

74. Azt & Interferon-.alpha.-2

75. Azt & Concanavalin A (cona)

76. Azt & Lymphoblastoid Interferon

77. Azt & Pm-19

78. Met-sdf-1.beta. & Zidovudine

79. 4lhm

80. 1-(4-azido-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1h-pyrimidine-2,4-dione (azt)

81. 1-(4-azido-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1h-pyrimidine-2,4-dione [azt]

82. Azt & Rscd4 & Rifn.alpha.a

83. 3'-azido-3'-deoxythymidine, Azt

84. Ds-4152 & Azt

85. 1-((2r,4r,5s)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1h,3h)-dione

86. 1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione

87. 5-methyl-1-[rac-(2r,4s,5s)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione

88. Azt & Colony-stimulating Factor 2

89. Azt & Np (from Phca Or Hsa)

90. 3''-azido-thymidine

91. K7 [p Ti2 W10 O40]

92. Zidovudine [usan:usp:inn:ban:jan]

93. Zidovudine & Ifnl1

94. Zidovudine & Ifnl2

95. Zidovudine & Ifnl3

96. Zidovudine (retrovir)

97. Compound-s

98. Spectrum_001348

99. Azt & Cd4(178)-pe 40

100. Azt & Ifn.alpha.

101. Zidovudine & Il-29

102. Zidovudine [mi]

103. Zidovudine & Il-28a

104. Zidovudine & Il-28b

105. Zidovudine [inn]

106. Zidovudine [jan]

107. Azt & Interleukin 29

108. Opera_id_1602

109. Prestwick3_000333

110. Spectrum2_000927

111. Spectrum3_001507

112. Spectrum4_000332

113. Spectrum5_001101

114. 3'azido-3'deoxythymidine

115. Zidovudine [hsdb]

116. Zidovudine [iarc]

117. Zidovudine [usan]

118. 3'-azido-3'-deoxythymidine & Erythropoietin

119. 3'-azido-3'-deoxythymidine & Sho-saiko-to

120. Azidothymidine; Zidovudine

121. Interferon Ad + 3'-azido-3'-deoxythymidine

122. Azt & Interleukin 28a

123. Azt & Interleukin 28b

124. 3'-azido-3'-deoxythymidine & Concanavalin A

125. 3'-azido-3'-deoxythymidine & Interleukin-1

126. 3'-azido-3'-deoxythymidine & Interleukin-2

127. 3'-azido-3'-deoxythymidine & Interleukin-6

128. Zidovudine [vandf]

129. 3'-azido3'-deoxythymidine

130. Azt & Ifnl1

131. Azt & Ifnl2

132. Azt & Ifnl3

133. Zidovudine [mart.]

134. 1-(3-azido-2,3-dideoxy-beta-d-ribofuranosyl)-5-methylpyrimidine-2,4-(1h,3h)-dione

135. Azt & Interferon Lambda-1

136. Azt & Interferon Lambda-2

137. Azt & Interferon Lambda-3

138. Zidovudine [usp-rs]

139. Zidovudine [who-dd]

140. Zidovudine [who-ip]

141. 3''-deoxy-3-azidothymidine

142. Bspbio_000365

143. Bspbio_003153

144. Kbiogr_000703

145. Kbioss_001828

146. 399024-19-2

147. Mls001055351

148. Mls001076358

149. Mls002153202

150. Mls002222249

151. Zidovudine & Interleukin 29

152. Divk1c_000524

153. Spectrum1502109

154. Zidovudine [ema Epar]

155. 3'-deoxy-3'-azido-thymidine

156. Spbio_000834

157. Zidovudine & Interleukin 28a

158. Zidovudine & Interleukin 28b

159. Azt & Il-28a

160. Azt & Il-28b

161. Bpbio1_000403

162. Gtpl4825

163. Zidovudine (jp17/usp/inn)

164. 3'-azido-3'-deoxythymidine & Lithium & Erythropoietin

165. 3'-azido-3'-deoxythymidine & Lithium & Interleukin-1

166. 3'-azido-3'-deoxythymidine & Lithium & Interleukin-6

167. 3'-azido-3'-deoxythymidine & Lymphoblastoid Interferon

168. Dtxsid8020127

169. Schembl14615088

170. Sn-1-dipalmitoylglycerophospho-azt (in A Lipid Vesicle)

171. Sn-3-dipalmitoylglycerophospho-azt (in A Lipid Vesicle)

172. Zidovudine [ep Impurity]

173. Zidovudine [orange Book]

174. Azt & Il-29

175. Hms501k06

176. Kbio1_000524

177. Kbio2_001828

178. Kbio2_004396

179. Kbio2_006964

180. Kbio3_002653

181. 3'-azido-3'-deoxythymidine & Heteropolyoxotungstate Pm-19

182. Racemic-dipalmitoylglycerophospho-azt (in A Lipid Vesicle)

183. Zidovudine [ep Monograph]

184. 3''-azido-3''-deoxy-thymidine

185. Ninds_000524

186. Zidovudine & Interferon Lambda-1

187. Zidovudine & Interferon Lambda-2

188. Zidovudine & Interferon Lambda-3

189. Hms1921j20

190. Hms2090g11

191. Hms2092d06

192. Hms2096c07

193. Hms2234k17

194. Hms3259h17

195. Hms3713c07

196. Pharmakon1600-01502109

197. Zidovudine [usp Monograph]

198. Zidovudinum [who-ip Latin]

199. Combivir Component Zidovudine

200. Trizivir Component Zidovudine

201. Zinc3779042

202. 3''azido-2''3''-dideoxythymidine

203. Tox21_110062

204. Tox21_110894

205. Tox21_202203

206. Tox21_300578

207. Bbl033764

208. Bdbm50002692

209. Ccg-39924

210. Nsc758185

211. Stk801891

212. Akos005622576

213. Akos015842610

214. Tox21_110062_1

215. 3''-azido-2'',3''-dideoxythymidine

216. Db00495

217. Nc00666

218. Nsc-758185

219. Zidovudine Component Of Combivir

220. Zidovudine Component Of Trizivir

221. Idi1_000524

222. Ncgc00014918-01

223. Ncgc00023945-03

224. Ncgc00023945-04

225. Ncgc00023945-06

226. Ncgc00023945-07

227. Ncgc00023945-08

228. Ncgc00023945-09

229. Ncgc00023945-10

230. Ncgc00023945-12

231. Ncgc00023945-13

232. Ncgc00023945-24

233. Ncgc00023945-25

234. Ncgc00178237-01

235. Ncgc00178237-02

236. Ncgc00254276-01

237. Ncgc00259752-01

238. 1-((2r,4s,5s)-4-azido-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1h-pyrimidine-2,4-dione

239. As-13019

240. Sbi-0051731.p002

241. Propolis & Thymidine, 3'-azido-3'-deoxy-

242. S2579

243. Sw198799-2

244. En300-52518

245. 3'-azido-3'-deoxythymidine, >=98% (hplc)

246. C07210

247. D00413

248. D88500

249. 3'-azido-3'deoxythymidine & Interferon .alpha.

250. 3'-azido-3'-deoxythymidine, >=99.0% (hplc)

251. A820413

252. Q198504

253. Sr-01000000098

254. Sr-05000001587

255. J-700147

256. Sr-01000000098-3

257. Sr-05000001587-1

258. Brd-k72903603-001-04-6

259. Brd-k72903603-001-14-5

260. Lamivudine/zidovudine Teva Component Zidovudine

261. Z1723414428

262. Zidovudine Component Of Lamivudine/zidovudine Teva

263. Zidovudine, European Pharmacopoeia (ep) Reference Standard

264. 3'-azido-3'-deoxythymidine & Recombinant Interferon-.alpha.-2

265. Zidovudine, United States Pharmacopeia (usp) Reference Standard

266. 3'-azido-3'-deoxythymidine & Cd4-pseudomonas Exotoxin A Hybrid

267. Beta Interferon(rifn-beta Seron) & 3'-azido-3'-deoxythymidine(azt)

268. Lecithinized Superoxide Dismutase & Thymidine, 3'-azido-3'-deoxy-

269. 3'-azido-2',3'-dideoxythymidine & Scd4(soluble Recombinant Protein)

270. Sulfated Polysaccharide-peptidoglycan Ds-4152 & 3'-azido-3'-deoxythymidine

271. Thymidine, 3'-azido-3'-deoxy- & Pro 140 (anti-ccr5 Monoclonal Antibody)

272. Zidovudine, Pharmaceutical Secondary Standard; Certified Reference Material

273. (azt) 1-(4-azido-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1h-pyrimidine-2,4-dione

274. (azt)1-(4-azido-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1h-pyrimidine-2,4-dione

275. 1-(4-azido-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1h-pyrimidine-2,4-dione

276. 1-(4-azido-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1h-pyrimidine-2,4-dione(azt)

277. 3'-azido-3'-deoxythymidine & Granulocyte-macrophage Colony-stimulating Factor

278. 3'-azido-3'-deoxythymidine & Lithium & Granulocyte-macrophage Colony-stimulating Factor

279. 3'-azido-3'deoxythymidine & Recombinant Soluble Cd4 & Recombinant Interferon.alpha.a

280. 4-(4-azido-5-hydroxy-tetrahydro-furan-2-yl)-5-methyl-3h-pyrazine-2,6-dione

281. Met-stromal Cell-derived Factor-1.beta. (human) & 3'-azido-3'-deoxythymidine

282. 1-((2r,4s,5s)-4-(diazoamino)-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1h,3h)-dione

283. 1-((2r,4s,5s)-4-azido-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1h,3h)-dione

284. 1-((2r,5s)-4-azido-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1h-pyrimidine-2,4-dione

285. 1-((2s,4r,5r)-4-azido-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1h-pyrimidine-2,4-dione

286. 1-(4-azido-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1h-pyrimidine-2,4-dione (azddthd, Azt)

287. 1-(4-azido-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1h-pyrimidine-2,4-dione (n3ddthd)

288. 1-(4-azido-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1h-pyrimidine-2,4-dione(3''-azido-2'',3''-dideoxythymidine)

289. 1-(4-azido-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1h-pyrimidine-2,4-dione(azidothymidine, Azt)

290. 1-(4-azido-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1h-pyrimidine-2,4-dione(zidovudine, Azt)

291. 146426-54-2

292. 3'-azido-3'deoxythymidine & Nanoparticles (from Human Serum Albumin Or Polyhexylcyanoacrylate)

293. 3-((2s,3s,5r)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl)tetrahydrofuran-3-yl)triaz-1-en-2-ium-1-ide

294. 3-azido-1,2,3-trideoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2h)-pyrimidinyl)-d-erythro- Pentofuranuronic Acid

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₀H₁₃N₅O₄
Molecular Weight	267.24 g/mol
XLogP3	0
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	3
Exact Mass	267.09675391 g/mol
Monoisotopic Mass	267.09675391 g/mol
Topological Polar Surface Area	93.2 Å²
Heavy Atom Count	19
Formal Charge	0
Complexity	484
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Retrovir
PubMed Health	Zidovudine
Drug Classes	Antiretroviral Agent
Drug Label	RETROVIR is the brand name for zidovudine (formerly called azidothymidine [AZT]), a pyrimidine nucleoside analogue active against HIV. RETROVIR IV Infusion is a sterile solution for intravenous infusion only. Each mL contains 10mg zidovudine in Wat...
Active Ingredient	Zidovudine
Dosage Form	Syrup; Capsule; Injectable
Route	Injection; Oral
Strength	50mg/5ml; 10mg/ml; 100mg
Market Status	Prescription
Company	Viiv Hlthcare

2 of 4
Drug Name	Zidovudine
PubMed Health	Zidovudine
Drug Classes	Antiretroviral Agent
Drug Label	RETROVIR is the brand name for zidovudine (formerly called azidothymidine [AZT]), a pyrimidine nucleoside analogue active against HIV. RETROVIR IV Infusion is a sterile solution for intravenous infusion only. Each mL contains 10mg zidovudine in Wat...
Active Ingredient	Zidovudine
Dosage Form	Tablet; Syrup; Capsule; Injectable
Route	oral; Injection; Oral
Strength	50mg/5ml; 10mg/ml; 300mg; 100mg
Market Status	Tentative Approval; Prescription
Company	Mylan Pharms; Aurobindo; Hetero Labs Ltd Iii; Aurobindo Pharma; Cipla; Roxane; Sunshine Lake; Luitpold; Barr

3 of 4
Drug Name	Retrovir
PubMed Health	Zidovudine
Drug Classes	Antiretroviral Agent
Drug Label	RETROVIR is the brand name for zidovudine (formerly called azidothymidine [AZT]), a pyrimidine nucleoside analogue active against HIV. RETROVIR IV Infusion is a sterile solution for intravenous infusion only. Each mL contains 10mg zidovudine in Wat...
Active Ingredient	Zidovudine
Dosage Form	Syrup; Capsule; Injectable
Route	Injection; Oral
Strength	50mg/5ml; 10mg/ml; 100mg
Market Status	Prescription
Company	Viiv Hlthcare

4 of 4
Drug Name	Zidovudine
PubMed Health	Zidovudine
Drug Classes	Antiretroviral Agent
Drug Label	RETROVIR is the brand name for zidovudine (formerly called azidothymidine [AZT]), a pyrimidine nucleoside analogue active against HIV. RETROVIR IV Infusion is a sterile solution for intravenous infusion only. Each mL contains 10mg zidovudine in Wat...
Active Ingredient	Zidovudine
Dosage Form	Tablet; Syrup; Capsule; Injectable
Route	oral; Injection; Oral
Strength	50mg/5ml; 10mg/ml; 300mg; 100mg
Market Status	Tentative Approval; Prescription
Company	Mylan Pharms; Aurobindo; Hetero Labs Ltd Iii; Aurobindo Pharma; Cipla; Roxane; Sunshine Lake; Luitpold; Barr

4.2 Therapeutic Uses

Anti-HIV Agents; Antimetabolites; Antimetabolites, Antineoplastic; Reverse Transcriptase Inhibitors

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

Zidovudine is indicated in combination with other antiretroviral agents for the treatment of HIV infection. ... /Included in US product labeling/

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 23rd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2003. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 2787

Zidovudine is indicated for the prevention of mother-to-child transmission of HIV-1 infection as part of a regimen that includes oral zidovudine beginning between 14 and 34 weeks gestation, continuous intravenous infusion of zidovudine during labor, and administration of zidovudine syrup to the neonate for the first 6 weeks of life. However, transmission to infants may still occur in some cases despite the use of this regimen. /Included in US product labeling/

Zidovudine has been used prophylactically in health care workers at risk of acquiring HIV infection after occupational exposure to the virus. Risk of transmission from a single needlestick is approximately 0.3%. Efficacy, and optimal dose and duration of prophylactic treatment are unknown at this time; however, HIV infection has occurred in persons who received zidovudine prophylaxis after a needlestick or other parenteral exposure. /NOT included in US product labeling/

For more Therapeutic Uses (Complete) data for ZIDOVUDINE (7 total), please visit the HSDB record page.

4.3 Drug Warning

Adverse systemic effects reported with IV zidovudine are similar to those reported with oral zidovudine. However, clinical experience with IV zidovudine has been more limited than experience with oral zidovudine and the drug has generally been administered IV only for short periods of time. Long-term IV zidovudine therapy (i.e., longer than 2-4 weeks) has not been evaluated in adults and may enhance adverse hematologic effects.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 727

The most common adverse effects of zidovudine are hematologic effects (i.e., anemia, neutropenia), nausea, and headache. Because HIV-infected patients receiving zidovudine generally have serious underlying disease with multiple baseline symptomatology and clinical abnormalities and because many adverse effects that occurred in zidovudine-treated patients also occurred in patients receiving placebo, many reported effects may not be directly attributable to zidovudine. The frequency and severity of adverse effects associated with use of zidovudine in adults are greater in patients with more advanced disease at the time of initiation of therapy. In one study in asymptomatic patients receiving 100 mg of the drug orally 5 times daily for an average of longer than 1 year (range: 4 months to 2 years), only nausea occurred more frequently in patients receiving zidovudine than in those receiving placebo. Adverse effects reported with use of zidovudine in women, IV drug users, and racial minorities are similar to those reported with use of the drug in white males.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 727

Four patients with the acquired immunodeficiency syndrome, and a history of Pneumocystis carinii pneumonia developed severe pancytopenia (hemoglobin, less than 85 g/l; granulocytes, less than or equal to 0.5 X 10(9)/L; platelets, less than or equal to 30 X 10(9)/L) 12 to 17 weeks after the initiation of azidothymidine (AZT) therapy. The bone marrow was markedly hypocellular in three patients and moderately hypocellular in the fourth. Partial bone marrow recovery was documented within 4 to 5 weeks in three patients, but no marrow recovery has yet occurred in one patient during the more than 6 months since AZT treatment was discontinued.

PMID:3477107 Gill PS et al; Ann Intern Med 107 (4): 502-5 (1987)

Hematologic toxicity is causally related to zidovudine therapy, being directly related to dosage and duration of therapy with the drug, and has been reported most frequently in patients with advanced symptomatic HIV infection or low pretreatment hemoglobin concentrations, neutrophil counts, and helper/inducer (CD4+, T4+) T-cell counts. Patients with low serum folate or vitamin B12 concentrations may be at increased risk for developing bone marrow toxicity during zidovudine therapy. There also are limited data suggesting that bone marrow of patients with fulminant acquired immunodeficiency syndrome (AIDS) may be more sensitive to zidovudine-induced toxicity than that of patients with less advanced disease (e.g., AIDS-related complex (ARC)).

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 727

For more Drug Warnings (Complete) data for ZIDOVUDINE (43 total), please visit the HSDB record page.

4.4 Drug Indication

Used in combination with other antiretroviral agents for the treatment of human immunovirus (HIV) infections.

FDA Label

Trizivir is indicated for the treatment of human-immunodeficiency-virus (HIV) infection in adults.

This fixed combination replaces the three components (abacavir, lamivudine and zidovudine) used separately in similar dosages. It is recommended that treatment is started with abacavir, lamivudine,and zidovudine separately for the first six to eight weeks. The choice of this fixed combination should be based not only on potential adherence criteria, but mainly on expected efficacy and risk related to the three nucleoside analogues.

The demonstration of the benefit of Trizivir is mainly based on results of studies performed in treatment naive patients or moderately antiretroviral experienced patients with non-advanced disease.

In patients with high viral load (> 100,000 copies/ml) choice of therapy needs special consideration.

Overall, the virologic suppression with this triple nucleoside regimen could be inferior to that obtained with other multitherapies notably including boosted protease inhibitors or non-nucleoside reverse-transcriptase inhibitors, therefore the use of Trizivir should only be considered under special circumstances (e. g. co-infection with tuberculosis).

Before initiating treatment with abacavir, screening for carriage of the HLA-B*5701 allele should be performed in any HIV-infected patient, irrespective of racial origin. Screening is also recommended prior to re-initiation of abacavir in patients of unknown HLA-B*5701 status who have previously tolerated abacavir (see 'management after an interruption of Trizivir therapy'). Abacavir should not be used in patients known to carry the HLA-B*5701 allele, unless no other therapeutic option is available in these patients, based on the treatment history and resistance testing.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Zidovudine is a nucleoside reverse transcriptase inhibitor (NRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Zidovudine is phosphorylated to active metabolites that compete for incorporation into viral DNA. They inhibit the HIV reverse transcriptase enzyme competitively and act as a chain terminator of DNA synthesis. The lack of a 3'-OH group in the incorporated nucleoside analogue prevents the formation of the 5' to 3' phosphodiester linkage essential for DNA chain elongation, and therefore, the viral DNA growth is terminated.

5.2 MeSH Pharmacological Classification

Antimetabolites

Drugs that are chemically similar to naturally occurring metabolites, but differ enough to interfere with normal metabolic pathways. (From AMA Drug Evaluations Annual, 1994, p2033) (See all compounds classified as Antimetabolites.)

Anti-HIV Agents

Agents used to treat AIDS and/or stop the spread of the HIV infection. These do not include drugs used to treat symptoms or opportunistic infections associated with AIDS. (See all compounds classified as Anti-HIV Agents.)

Reverse Transcriptase Inhibitors

Inhibitors of reverse transcriptase (RNA-DIRECTED DNA POLYMERASE), an enzyme that synthesizes DNA on an RNA template. (See all compounds classified as Reverse Transcriptase Inhibitors.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

ZIDOVUDINE

5.3.2 FDA UNII

4B9XT59T7S

5.3.3 Pharmacological Classes

Nucleoside Analog [EXT]; Nucleoside Reverse Transcriptase Inhibitors [MoA]; Human Immunodeficiency Virus Nucleoside Analog Reverse Transcriptase Inhibitor [EPC]

5.4 ATC Code

J05AR04

J05AF01

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

J - Antiinfectives for systemic use

J05 - Antivirals for systemic use

J05A - Direct acting antivirals

J05AF - Nucleoside and nucleotide reverse transcriptase inhibitors

J05AF01 - Zidovudine

5.5 Absorption, Distribution and Excretion

Absorption

Rapid and nearly complete absorption from the gastrointestinal tract following oral administration; however, because of first-pass metabolism, systemic bioavailability of zidovudine capsules and solution is approximately 65% (range, 52 to 75%). Bioavailability in neonates up to 14 days of age is approximately 89%, and it decreases to approximately 61% and 65% in neonates over 14 days of age and children 3 months to 12 years, respectively. Administration with a high-fat meal may decrease the rate and extent of absorption.

Route of Elimination

As in adult patients, the major route of elimination was by metabolism to GZDV. After intravenous dosing, about 29% of the dose was excreted in the urine unchanged and about 45% of the dose was excreted as GZDV.

Volume of Distribution

Apparent volume of distribution, HIV-infected patients, IV administration = 1.6 0.6 L/kg

Clearance

0.65+/- 0.29 L/hr/kg [HIV-infected, Birth to 14Days of Age]

1.14+/- 0.24 L/hr/kg [HIV-infected, 14Days to 3 Months of Age]

1.85 +/- 0.47 L/hr/kg [HIV-infected, 3 Months to 12Years of Age]. The transporters, ABCB1, ABCC4, ABCC5, and ABCG2 are involved with the clearance of zidovudine.

In patients with impaired renal function, plasma concentrations of zidovudine may be increased and the half-life prolonged. In one study in adults with impaired renal function (creatinine clearances ranging from 6-31 ml/minute) without HIV infections beta half life of zidovudine averaged 1.4 hours and was similar to that reported for adults with HIV infections who had normal renal function. However, the beta half life of glucuronide in these adults with impaired renal function averaged 8 hours and was considerably prolonged compared with that reported for adults with HIV infections who had normal renal function. In one study in adults with hemophilia and HIV infections who had elevated serum concentrations of aspartate aminotransferase (serum glutamic-oxaloacetic transaminase), alanine aminotransferase (serum glutamic-pyruvic transaminase), pharmacokinetics of zidovudine after a single 300 mg oral dose showed considerable interindividual variation.