Find Lamivudine manufacturers, exporters & distributors on PharmaCompass

PharmaCompass

Chemistry

Click the arrow to open the dropdown
read-moreClick the button for full data set
Also known as: 134678-17-4, Epivir, Zeffix, Heptovir, Epivir-hbv, 136891-12-8
Molecular Formula
C8H11N3O3S
Molecular Weight
229.26  g/mol
InChI Key
JTEGQNOMFQHVDC-NKWVEPMBSA-N
FDA UNII
2T8Q726O95

Lamivudine
A reverse transcriptase inhibitor and ZALCITABINE analog in which a sulfur atom replaces the 3' carbon of the pentose ring. It is used to treat HIV disease.
Lamivudine is a Hepatitis B Virus Nucleoside Analog Reverse Transcriptase Inhibitor and Human Immunodeficiency Virus Nucleoside Analog Reverse Transcriptase Inhibitor. The mechanism of action of lamivudine is as a Nucleoside Reverse Transcriptase Inhibitor.
1 2D Structure

Lamivudine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one
2.1.2 InChI
InChI=1S/C8H11N3O3S/c9-5-1-2-11(8(13)10-5)6-4-15-7(3-12)14-6/h1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7+/m0/s1
2.1.3 InChI Key
JTEGQNOMFQHVDC-NKWVEPMBSA-N
2.1.4 Canonical SMILES
C1C(OC(S1)CO)N2C=CC(=NC2=O)N
2.1.5 Isomeric SMILES
C1[C@H](O[C@H](S1)CO)N2C=CC(=NC2=O)N
2.2 Other Identifiers
2.2.1 UNII
2T8Q726O95
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2',3' Dideoxy 3' Thiacytidine

2. 2',3'-dideoxy-3'-thiacytidine

3. 2(1h)-pyrimidinone, 4-amino-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-, (2r-cis)-

4. 3tc Lamivudine

5. Bch 189

6. Bch-189

7. Bch189

8. Epivir

9. Gr 109714x

10. Gr-109714x

11. Gr109714x

12. Lamivudine, (+)-cis-

13. Lamivudine, (+-)-trans-

14. Lamivudine, (2s-cis)-isomer

15. Lamivudine, 3tc

2.3.2 Depositor-Supplied Synonyms

1. 134678-17-4

2. Epivir

3. Zeffix

4. Heptovir

5. Epivir-hbv

6. 136891-12-8

7. 3tc

8. Bch-189

9. Heptodin

10. 4-amino-1-((2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1h)-one

11. (-)-2'-deoxy-3'-thiacytidine

12. Virolam

13. Gr-109714x

14. 3'-thia-2',3'-dideoxycytidine

15. Gr109714x

16. (-)-bch-189

17. Beta-l-2',3'-dideoxy-3'-thiacytidine

18. Beta-l-3'-thia-2',3'-dideoxycytidine

19. 2',3'-dideoxy-3'-thiacytidine

20. Gr 109714x

21. Lamivudine Teva

22. 4-amino-1-[(2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one

23. (-)ngpb-21

24. Bch 189, (-)-

25. (-)-1-((2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)cytosine

26. 4-amino-1-(cis-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1h)-one

27. 4-amino-1-[(2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one

28. Hepitec

29. 4-amino-1-[(2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2(1h)-one

30. 4-amino-1-[(2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1h)-pyrimidinone

31. Chebi:63577

32. (-)-1-[(2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine

33. 4-amino-1-((2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-2(1h)-pyrimidinone

34. 2(1h)-pyrimidinone, 4-amino-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-, (2r-cis)-

35. 2t8q726o95

36. Nsc-760061

37. Heptivir

38. Lamivir

39. Zefix

40. Bch 189

41. Lamivudine [usan:ban:inn]

42. (-)-(2'r,5's)-1-[2'-hydroxymethyl-5'-(1,3-oxathiolanyl)]cytosine

43. 2(1h)-pyrimidinone, 4-amino-1-((2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-

44. 2(1h)-pyrimidinone, 4-amino-1-[(2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-

45. Epivir(tm)

46. Hha & Lamivudine

47. Lamivudine & Gna

48. Smr000466319

49. Epivir (tn)

50. (-)-bch 189

51. Dthc

52. Chembl141

53. Hsdb 7155

54. Drg-0126

55. 3tc And Nv-01

56. (-)-sddc

57. Lamivudeine

58. Lamivudinum

59. Lamivudine (jan/usp/inn)

60. 3tc & Gna

61. 3tc & Sst

62. Hha & 3tc

63. (+/-)-sddc

64. Ccris 9274

65. Nsc620753

66. Unii-2t8q726o95

67. Bch-790

68. Lamivudine [usan:usp:inn:ban]

69. Rac-cis-lamivudine

70. Ncgc00159341-04

71. Lamivudine- Bio-x

72. Gg-714

73. Mfcd00869739

74. Lamivudine (epivir)

75. Cpd000466319

76. Lamivudine [mi]

77. (+/-)-3tc

78. (+/-)-bch-189

79. Lamivudine [inn]

80. Lamivudine [jan]

81. Lamivudine [hsdb]

82. Lamivudine [usan]

83. Lamivudine [vandf]

84. Lamivudine [mart.]

85. Lamivudine [usp-rs]

86. Lamivudine [who-dd]

87. Lamivudine [who-ip]

88. Mls000759424

89. Mls001424097

90. Mls006011910

91. Bidd:gt0033

92. Lamivudine [ema Epar]

93. Schembl109675

94. Amy384

95. Dtxsid7023194

96. Lamivudine [ep Impurity]

97. Lamivudine [orange Book]

98. Zinc12346

99. Lamivudine [ep Monograph]

100. Kivexa Component Lamivudine

101. Hms2051d21

102. Hms3259f08

103. Hms3713c16

104. Lamivudine [usp Monograph]

105. Epzicom Component Lamivudine

106. Lamivudinum [who-ip Latin]

107. Temixys Component Lamivudine

108. Triumeq Component Lamivudine

109. Combivir Component Lamivudine

110. Hy-b0250

111. Lamivudine Teva Pharma B.v.

112. Trizivir Component Lamivudine

113. Bbl033871

114. Bdbm50366817

115. Delstrigo Component Lamivudine

116. Mfcd00870542

117. S1706

118. Stk801940

119. Lamivudine & Tnf-alpha & Ifn-gamma

120. Telura Component Of Lamivudine

121. Akos005622556

122. Akos015854841

123. Lamivudine Component Of Epzicom

124. Lamivudine Component Of Temixys

125. Lamivudine Component Of Triumeq

126. Lamivudine, >=98% (hplc), Powder

127. (-)-bch189

128. Ac-1416

129. Ccg-100984

130. Db00709

131. Ks-1073

132. Lamivudine Component Of Combivir

133. Lamivudine Component Of Dutrebis

134. Lamivudine Component Of Trizivir

135. Nc00234

136. Nc00705

137. Nsc 760061

138. Lamivudine Component Of Delstrigo

139. Ncgc00159341-05

140. Ncgc00159341-18

141. Ncgc00159341-20

142. Bl164607

143. Emtricitabine Impurity C [who-ip]

144. L0217

145. Rac-cis-lamivudine ((2rs,5sr)-lamivudine)

146. Sw197614-3

147. C07065

148. D00353

149. P17147

150. Ab00639995-06

151. Ab00639995-08

152. Ab00639995_09

153. Lamivudeine 100 Microg/ml In Acetonitrile:water

154. 678l174

155. Q422631

156. Sr-01000759420

157. J-700183

158. Q-201275

159. Sr-01000759420-5

160. Lamivudine/zidovudine Teva Component Lamivudine

161. Lamivudine Component Of Lamivudine/zidovudine Teva

162. Lamivudine, British Pharmacopoeia (bp) Reference Standard

163. Lamivudine, European Pharmacopoeia (ep) Reference Standard

164. (2r,5s)-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine

165. .beta.-l-(-)-2',3'-dideoxy-3'-thiacytidine & Sho-saiko-to

166. Lamivudine, United States Pharmacopeia (usp) Reference Standard

167. (+/-) (cis)-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine

168. (-)-l-2',3'-dideoxy-3'-thiacytidine; Lamivudine; Epivir

169. Lamivudine, 1.0 Mg/ml In Methanol, Certified Reference Material

170. Lamivudine, Pharmaceutical Secondary Standard; Certified Reference Material

171. (+/-)-(cis)-4-amino-1-(2-hydroxymethyl-1,3-oxathiolan-5-yl)-(1h)-pyrimidin-2-one

172. 2(1h)-pyrimidinone, 4-amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl], (+/-) (cis)

173. 4-amino-1-[(2r,5s)-2-(hydroxymethyl)-[1,3]-oxathiolan-5-yl]-(1h)-pyrimidin-2-one

174. 4-amino-1-[(2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-(1h)-pyrimidin-2-one

175. Cis(+/-)-4-amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1h)-pyrimidinone

176. Lamivudine For System Suitability 1, European Pharmacopoeia (ep) Reference Standard

177. Lamivudine For System Suitability 2, European Pharmacopoeia (ep) Reference Standard

178. 1117764-41-6

179. 2(1h)-pyrimidinone, 4-amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl], (-)(2r,5s) & Galanthus Nivalis Agglutinin (gna)

180. 2(1h)-pyrimidinone, 4-amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl], (-)(2r,5s) & Hippeastrum Hybrid Agglutinin( Hha)

181. 4-amino-1-((2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1h)-one [who-ip]

2.4 Create Date
2005-08-01
3 Chemical and Physical Properties
Molecular Weight 229.26 g/mol
Molecular Formula C8H11N3O3S
XLogP3-0.9
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Exact Mass229.05211239 g/mol
Monoisotopic Mass229.05211239 g/mol
Topological Polar Surface Area113 Ų
Heavy Atom Count15
Formal Charge0
Complexity331
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 Drug Information
1 of 6  
Drug NameEpivir
Drug LabelEPIVIR-HBV is a brand name for lamivudine, a synthetic nucleoside analogue with activity against hepatitis B virus (HBV) and HIV. Lamivudine was initially developed for the treatment of HIV infection as EPIVIR. Please see the complete prescribing inf...
Active IngredientLamivudine
Dosage FormTablet; Solution
RouteOral
Strength300mg; 150mg; 10mg/ml
Market StatusPrescription
CompanyViiv Hlthcare

2 of 6  
Drug NameEpivir-hbv
PubMed HealthLamivudine (By mouth)
Drug ClassesAntiretroviral Agent, Antiviral
Drug LabelEPIVIR-HBV is a synthetic nucleoside analogue with activity against HBV. The chemical name of lamivudine is (2R,cis)-4-amino-1-(2-hydroxymethyl-1,3-oxathiolan-5-yl)-(1H)-pyrimidin-2-one. Lamivudine is the (-)enantiomer of a dideoxy analogue of cytidi...
Active IngredientLamivudine
Dosage FormTablet; Solution
RouteOral
Strength5mg/ml; 100mg
Market StatusPrescription
CompanyGlaxosmithkline

3 of 6  
Drug NameLamivudine
PubMed HealthLamivudine (By mouth)
Drug ClassesAntiretroviral Agent, Antiviral
Drug LabelEPIVIR-HBV is a brand name for lamivudine, a synthetic nucleoside analogue with activity against hepatitis B virus (HBV) and HIV. Lamivudine was initially developed for the treatment of HIV infection as EPIVIR. Please see the complete prescribing inf...
Active IngredientLamivudine
Dosage FormTablet; Solution
Routeoral; Oral
Strength150mg; 10mg/ml; 300mg; 100mg
Market StatusTentative Approval; Prescription
CompanyRanbaxy; Hetero Labs Ltd V; Macleods Pharma; Apotex; Aurobindo; Hetero Labs Ltd Iii; Alkem Labs; Aurobindo Pharma; Invagen Pharms; Cipla; Matrix Labs; Teva Pharms; Strides Arcolab; Micro Labs

4 of 6  
Drug NameEpivir
Drug LabelEPIVIR-HBV is a brand name for lamivudine, a synthetic nucleoside analogue with activity against hepatitis B virus (HBV) and HIV. Lamivudine was initially developed for the treatment of HIV infection as EPIVIR. Please see the complete prescribing inf...
Active IngredientLamivudine
Dosage FormTablet; Solution
RouteOral
Strength300mg; 150mg; 10mg/ml
Market StatusPrescription
CompanyViiv Hlthcare

5 of 6  
Drug NameEpivir-hbv
PubMed HealthLamivudine (By mouth)
Drug ClassesAntiretroviral Agent, Antiviral
Drug LabelEPIVIR-HBV is a synthetic nucleoside analogue with activity against HBV. The chemical name of lamivudine is (2R,cis)-4-amino-1-(2-hydroxymethyl-1,3-oxathiolan-5-yl)-(1H)-pyrimidin-2-one. Lamivudine is the (-)enantiomer of a dideoxy analogue of cytidi...
Active IngredientLamivudine
Dosage FormTablet; Solution
RouteOral
Strength5mg/ml; 100mg
Market StatusPrescription
CompanyGlaxosmithkline

6 of 6  
Drug NameLamivudine
PubMed HealthLamivudine (By mouth)
Drug ClassesAntiretroviral Agent, Antiviral
Drug LabelEPIVIR-HBV is a brand name for lamivudine, a synthetic nucleoside analogue with activity against hepatitis B virus (HBV) and HIV. Lamivudine was initially developed for the treatment of HIV infection as EPIVIR. Please see the complete prescribing inf...
Active IngredientLamivudine
Dosage FormTablet; Solution
Routeoral; Oral
Strength150mg; 10mg/ml; 300mg; 100mg
Market StatusTentative Approval; Prescription
CompanyRanbaxy; Hetero Labs Ltd V; Macleods Pharma; Apotex; Aurobindo; Hetero Labs Ltd Iii; Alkem Labs; Aurobindo Pharma; Invagen Pharms; Cipla; Matrix Labs; Teva Pharms; Strides Arcolab; Micro Labs

4.2 Therapeutic Uses

Lamivudine is indicated in the treatment of chronic hepatitis B associated with evidence of hepatitis B viral replication and active liver inflammation. This use is based on 1-year histologic and serologic responses in patients with compensated chronic hepatitis B. /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. 1646


Lamivudine is indicated, in combination with zidovudine or other antiretroviral agents, in the treatment of HIV infection or AIDS when therapy is warranted based on clinical and/or immunological evidence of disease progression. /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. 1646


Lamivudine may be used prophylactically in health care workers at risk of acquiring HIV infection after occupational exposure to the virus. It is being used in combination with zidovudine and, in some cases, a protease inhibitor. /NOT 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. 1646


The safety, pharmacokinetics, and antiretroviral activity of lamivudine alone and in combination with zidovudine was studied in pregnant women infected with human immunodeficiency virus type 1 (HIV-1) and their neonates. Women received the drugs orally from week 38 of pregnancy to 1 week after delivery. Neonate therapy began 12 h after delivery and continued for 1 week. Both treatment regimens were well-tolerated in women and newborns. Lamivudine and zidovudine pharmacokinetics in pregnant women were similar to those in nonpregnant adults. Lamivudine and zidovudine freely crossed the placenta and were secreted in breast milk. Neonatal lamivudine clearance was about half that in pediatric patients; zidovudine clearance was consistent with previous reports. HIV-1 RNA could be quantified in 17 of the 20 women. At the onset of labor/delivery, mean virus load had decreased by approximately 1.5 log10 copies/mL in both treatment cohorts. Although not definitive for HIV-1 infection status, all neonates had HIV-1 RNA levels below the limit of quantification at birth and at ages 1 and 2 weeks.

PMID:9780252 Moodley J et al; J Infect Dis 178 (5): 1327-33 (1998)


4.3 Drug Warning

Safety and efficacy of lamivudine in the treatment of chronic