Lamivudine molecular structure

Lamivudine

Also known as: Epivir, Zeffix, Lamivir, Heptavir (component of Combivir, Triumeq, TLD regimens)

CAS Number: 134678-17-4

Nucleoside Reverse Transcriptase Inhibitor (NRTI)

Pharmacopeia Standards

USPIPEPBPWHO

Mechanism of Action

Lamivudine is the negative enantiomer of a dideoxy analogue of cytidine that is phosphorylated intracellularly to lamivudine triphosphate. The triphosphate competes with deoxycytidine triphosphate for incorporation into viral DNA by HIV-1 reverse transcriptase and hepatitis B polymerase. Its oxathiolane ring lacks a 3-hydroxyl group, so incorporation halts chain elongation and terminates viral DNA synthesis.

Technical Specifications

Generic / INN NameLamivudine
CAS Registry Number134678-17-4
Molecular FormulaC8H11N3O3S
Molecular Weight229.26 g/mol g/mol
Typical PurityNot less than 98.0% on anhydrous basis; enantiomeric purity not less than 99.5%
Storage ConditionsStore below 25 degrees C in well-closed, light-resistant containers; protect from humidity.
Shelf Life48 months from date of manufacture in original sealed packing
CategoryAntiretrovirals (HIV)

Specifications are indicative and intended for sourcing reference only. Always confirm against the supplier's Certificate of Analysis and the applicable pharmacopeial monograph before issuing a purchase specification.

Typical Applications

Bulk API for dual and triple fixed-dose antiretroviral combinations with tenofovir, dolutegravir, zidovudine, abacavir or nevirapine, paediatric dispersible tablets and oral solutions, and single-entity 100 mg chronic hepatitis B tablets.

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