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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 hepatitis B have not been established in patients with decompensated liver disease or organ transplants; pediatric patients; or patients dually infected with hepatitis B and hepatitis C, hepatitis delta, or HIV; or for a treatment period greater than 1 year.

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


Although lamivudine generally is well tolerated, serious adverse effects such as peripheral neuropathy, pancreatitis, and lactic acidosis and severe hepatomegaly with steatosis have been reported. Adverse GI effects are the most common adverse effects in patients receiving lamivudine alone or in conjunction with zidovudine. Information on adverse effects of lamivudine has been obtained from clinical studies in HIV-infected adults who received the drug in conjunction with other antiretroviral agents ... . In addition, information on adverse effects of lamivudine in patients with compensated chronic hepatitis B virus (HBV) infection has been obtained from 3 placebo-controlled studies where the drug was used alone for up to 68 weeks.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 668


Peripheral neuropathy, the major dose-limiting toxicity associated with zalcitabine therapy, has been reported in adults receiving lamivudine, but has rarely resulted in interruption or discontinuance of therapy. In clinical studies... in HIV-infected adults receiving lamivudine in conjunction with zidovudine, neuropathy was reported in 12% of the patients. Paresthesia, weakness, and peripheral neuropathy have been reported in patients receiving lamivudine during postmarketing surveillance. ... In clinical studies in adults who received lamivudine for the treatment of chronic /hepatitis B virus/ (HBV) infection, malaise, fatigue, and headache were reported in 24, 24, and 21% of patients, respectively.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 668


In HIV-infected adults receiving lamivudine in conjunction with zidovudine, headache, malaise, fatigue, insomnia and other sleep disorders, dizziness, and depressive disorders were reported in 35, 27, 27, 11, 10, and 9%, respectively.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 668


For more Drug Warnings (Complete) data for LAMIVUDINE (20 total), please visit the HSDB record page.


4.4 Drug Indication

For the treatment of HIV infection and chronic hepatitis B (HBV).


FDA Label


Epivir is indicated as part of antiretroviral combination therapy for the treatment of human-immunodeficiency-virus (HIV)-infected adults and children.


Lamivudine Teva Pharma B. V. is indicated as part of antiretroviral combination therapy for the treatment of human-immunodeficiency-virus (HIV)-infected adults and children.


Zeffix is indicated for the treatment of chronic hepatitis B in adults with:

- compensated liver disease with evidence of active viral replication, persistently elevated serum alanine aminotransferase (ALT) levels and histological evidence of active liver inflammation and / or fibrosis. Initiation of lamivudine treatment should only be considered when the use of an alternative antiviral agent with a higher genetic barrier is not available or appropriate;

- decompensated liver disease in combination with a second agent without cross-resistance to lamivudine.


Lamivudine Teva is indicated for the treatment of chronic hepatitis B in adults with:

- compensated liver disease with evidence of active viral replication, persistently elevated serum alanine aminotransferase (ALT) levels and histological evidence of active liver inflammation and / or fibrosis. Initiation of lamivudine treatment should only be considered when the use of an alternative antiviral agent with a higher genetic barrier is not available or appropriate (see in section 5. 1).


5 Pharmacology and Biochemistry
5.1 Pharmacology

Lamivudine is a nucleoside reverse transcriptase inhibitor (NRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1) and hepatitis B (HBV) to disrupt viral DNA synthesis. When phosphorylated, lamivudine can form active metabolites that compete for incorporation into viral DNA. Via DNA incorporation, lamivudine metabolites competitively inhibit the activity of the HIV reverse transcriptase enzyme and act as a chain terminator of DNA synthesis. Due to the lack of a 3'-OH group, incorporated nucleoside analogues prevent the formation of a 5' to 3' phosphodiester linkage that is essential for DNA chain elongation.


5.2 MeSH Pharmacological Classification

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
LAMIVUDINE
5.3.2 FDA UNII
2T8Q726O95
5.3.3 Pharmacological Classes
Human Immunodeficiency Virus Nucleoside Analog Reverse Transcriptase Inhibitor [EPC]; Nucleoside Analog [EXT]; Nucleoside Reverse Transcriptase Inhibitors [MoA]; Hepatitis B Virus Nucleoside Analog Reverse Transcriptase Inhibitor [EPC]
5.4 ATC Code

J05AF05


J05AF05


J05AF05


J05AF05


J - Antiinfectives for systemic use

J05 - Antivirals for systemic use

J05A - Direct acting antivirals

J05AF - Nucleoside and nucleotide reverse transcriptase inhibitors

J05AF05 - Lamivudine


5.5 Absorption, Distribution and Excretion

Absorption

Lamivudine was rapidly absorbed after oral administration in HIV-infected patients. Absolute bioavailability in 12 adult patients was 86% 16% (mean SD) for the 150-mg tablet and 87% 13% for the oral solution. The peak serum lamivudine concentration (Cmax) was 1.5 0.5 mcg/mL when an oral dose of 2 mg/kg twice a day was given to HIV-1 patients. When given with food, absorption is slower, compared to the fasted state.


Route of Elimination

The majority of lamivudine is eliminated unchanged in urine by active organic cationic secretion. 5.2% 1.4% (mean SD) of the dose was excreted as the trans-sulfoxide metabolite in the urine. Lamivudine is excreted in human breast milk and into the milk of lactating rats.


Volume of Distribution

Apparent volume of distribution, IV administration = 1.3 0.4 L/kg. Volume of distribution was independent of dose and did not correlate with body weight.


Clearance

Renal clearance = 199.7 56.9 mL/min [300 mg oral dose, healthy subjects]

Renal clearance = 280.4 75.2 mL/min [single IV dose, HIV-1-infected patients]

Total clearance = 398.5 69.1 mL/min [HIV-1-infected patients]


Lamivudine crosses the placenta and has been detected in the fetal circulation.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1359


Lamivudine has high oral bioavailability with or without food and reaches peak plasma levels within approximately 1 hour.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1359


5.6 Metabolism/Metabolites

Metabolism of lamivudine is a minor route of elimination. In man, the only known metabolite of lamivudine is the trans-sulfoxide metabolite. This biotransformation is catalyzed by sulfotransferases.


5.7 Biological Half-Life

5 to 7 hours (healthy or HBV-infected patients)


5.8 Mechanism of Action

Lamivudine is a synthetic nucleoside analogue and is phosphorylated intracellularly to its active 5'-triphosphate metabolite, lamivudine triphosphate (L-TP). This nucleoside analogue is incorporated into viral DNA by HIV reverse transcriptase and HBV polymerase, resulting in DNA chain termination.


Lamivudine enters cells by passive diffusion and is phosphorylated to its active metabolite, lamivudine triphosphate. Lamivudine triphosphate competes with deoxycytidine triphosphate for binding to reverse transcriptase, and incorporation into DNA results in chain termination. Lamivudine has very low affinity for human alpha and omega DNA polymerases, moderate affinity for beta DNA polymerase, and higher affinity for gamma DNA polymerase.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1358


NDC API

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01

26th North American ISSX
Not Confirmed
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26th North American ISSX
Not Confirmed

LAMIVUDINE

NDC Package Code : 65862-577

Start Marketing Date : 2024-01-11

End Marketing Date : 2025-12-31

Dosage Form (Strength) : POWDER (50kg/50kg)

Marketing Category : BULK INGREDIENT

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02

Cipla Ltd.

India
26th North American ISSX
Not Confirmed
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Cipla Ltd.

India
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26th North American ISSX
Not Confirmed

LAMIVUDINE

NDC Package Code : 53104-7538

Start Marketing Date : 2016-01-01

End Marketing Date : 2024-12-31

Dosage Form (Strength) : POWDER (25kg/25kg)

Marketing Category : BULK INGREDIENT

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03

Cipla Ltd.

India
26th North American ISSX
Not Confirmed
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Cipla Ltd.

India
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26th North American ISSX
Not Confirmed

LAMIVUDINE

NDC Package Code : 53104-7677

Start Marketing Date : 2016-01-01

End Marketing Date : 2024-12-31

Dosage Form (Strength) : POWDER (25kg/25kg)

Marketing Category : BULK INGREDIENT

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04

26th North American ISSX
Not Confirmed
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26th North American ISSX
Not Confirmed

LAMIVUDINE

NDC Package Code : 52482-003

Start Marketing Date : 2014-03-13

End Marketing Date : 2024-12-31

Dosage Form (Strength) : POWDER (1kg/kg)

Marketing Category : BULK INGREDIENT

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05

26th North American ISSX
Not Confirmed
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26th North American ISSX
Not Confirmed

LAMIVUDINE

NDC Package Code : 68554-0043

Start Marketing Date : 1995-11-17

End Marketing Date : 2024-12-31

Dosage Form (Strength) : POWDER (1kg/kg)

Marketing Category : BULK INGREDIENT

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06

26th North American ISSX
Not Confirmed
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26th North American ISSX
Not Confirmed

LAMIVUDINE

NDC Package Code : 68554-0016

Start Marketing Date : 1995-11-17

End Marketing Date : 2024-12-31

Dosage Form (Strength) : POWDER (1kg/kg)

Marketing Category : BULK INGREDIENT

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07

26th North American ISSX
Not Confirmed
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26th North American ISSX
Not Confirmed

LAMIVUDINE

NDC Package Code : 42385-714

Start Marketing Date : 2017-07-07

End Marketing Date : 2024-12-31

Dosage Form (Strength) : POWDER (1kg/kg)

Marketing Category : BULK INGREDIENT

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08

26th North American ISSX
Not Confirmed
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26th North American ISSX
Not Confirmed

LAMIVUDINE

NDC Package Code : 67835-0017

Start Marketing Date : 2019-11-01

End Marketing Date : 2024-12-31

Dosage Form (Strength) : POWDER (1kg/kg)

Marketing Category : BULK INGREDIENT

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09

26th North American ISSX
Not Confirmed
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26th North American ISSX
Not Confirmed

LAMIVUDINE

NDC Package Code : 65015-756

Start Marketing Date : 2015-01-13

End Marketing Date : 2024-12-31

Dosage Form (Strength) : POWDER (1kg/kg)

Marketing Category : BULK INGREDIENT

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10

26th North American ISSX
Not Confirmed
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26th North American ISSX
Not Confirmed

LAMIVUDINE

NDC Package Code : 65015-701

Start Marketing Date : 2015-01-13

End Marketing Date : 2024-12-31

Dosage Form (Strength) : POWDER (1kg/kg)

Marketing Category : BULK INGREDIENT

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03-Jan-2021
22-Aug-2024
KGS
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