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Lamivudine

Catalog No. DB00709 Name DrugBank
CAS Number 134678-17-4 Website http://www.ualberta.ca/
M. F. C8H11N3O3S Telephone (780) 492-3111
M. W. 229.25624 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 590

SYNONYMS

IUPAC name
4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one
IUPAC Traditional name
lamivudine
Brand Name
3TC
Epivir-HBV
Zeffix
Epivir
Heptovir
Hepitec
Synonyms
Lamivudine [Usan:Ban:Inn]

DATABASE IDS

PubChem SID 46507855
CAS Number 134678-17-4
PubChem CID 60825

PROPERTIES

Hydrophobicity(logP) -1.4
Solubility 70 mg/ml

DETAILS

Description (English)
Item Information
Drug Groups approved; investigational
Description 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 Human Immunodeficiency Virus Type 1 (HIV-1) and hepatitis B (HBV).
Indication For the treatment of HIV infection and chronic hepatitis B (HBV).
Pharmacology Lamivudine is a nucleoside reverse transcriptase inhibitor (NRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1) and hepatitis B (HBV). Lamivudine 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.
Affected Organisms
Human Immunodeficiency Virus
Hepatitis B virus
Biotransformation The only detected metabolite of lamivudine is trans-sulfoxide.
Absorption Lamivudine was rapidly absorbed after oral administration in HIV-infected patients. Absolute bioavailability in adults is 86% ± 16% for the tablet and 87% ± 13% for the oral solution.
Half Life 5 to 7 hours
Protein Binding 36%
Elimination The primary routes of elimination of abacavir are metabolism by alcohol dehydrogenase to form the 5′-carboxylic acid and glucuronyl transferase to form the 5′-glucuronide. Lamivudine is excreted in human breast milk and into the milk of lactating rats.
Clearance * Renal cl=280.4?+/-?75.2 mL/min [HIV-infected?patients given a single IV doses ranging from 0.25 to 8 mg/kg]
References
Fox Z, Dragsted UB, Gerstoft J, Phillips AN, Kjaer J, Mathiesen L, Youle M, Katlama C, Hill A, Bruun JN, Clumeck N, Dellamonica P, Lundgren JD: A randomized trial to evaluate continuation versus discontinuation of lamivudine in individuals failing a lamivudine-containing regimen: the COLATE trial. Antivir Ther. 2006;11(6):761-70. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com

REFERENCES

  • Fox Z, Dragsted UB, Gerstoft J, Phillips AN, Kjaer J, Mathiesen L, Youle M, Katlama C, Hill A, Bruun JN, Clumeck N, Dellamonica P, Lundgren JD: A randomized trial to evaluate continuation versus discontinuation of lamivudine in individuals failing a lamivudine-containing regimen: the COLATE trial. Antivir Ther. 2006;11(6):761-70. Pubmed