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L1295

Sigma-Aldrich

Lamivudine

≥98% (HPLC), powder

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Synonym(s):
2′,3′-Dideoxy-3′-thiacytidine, 3TC, Epivir, Epivir-HBV, Heptovir, Zeffix
Empirical Formula (Hill Notation):
C8H11N3O3S
CAS Number:
134678-17-4
Molecular Weight:
229.26
MDL number:
MFCD00869739
UNSPSC Code:
12352200
PubChem Substance ID:
329817388
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

water: 10 mg/mL, clear

originator

GlaxoSmithKline

storage temp.

room temp

SMILES string

NC1=NC(=O)N(C=C1)[C@@H]2CS[C@H](CO)O2

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

InChI key

JTEGQNOMFQHVDC-NKWVEPMBSA-N

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Application

Lamivudine has been used to deplete the Hepatitis B Virus (HBV) covalently closed circular DNA (cccDNA) forms for the preparation of inverse nested PCR.

Biochem/physiol Actions

Lamivudine is a potent nucleoside analog reverse transcriptase inhibitor (nRTI). It is an analogue of cytidine, and can inhibit both types (1 and 2) of HIV reverse transcriptase as well as the reverse transcriptase of hepatitis B. It needs to be phosphorylated to its triphosphate form before it is active. 3TC-triphosphate also inhibits cellular DNA polymerase.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by GlaxoSmithKline. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H361

Hazard Classifications

Repr. 2

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Chia-Yen Dai et al.
The Journal of antimicrobial chemotherapy, 68(10), 2332-2338 (2013-06-27)
For hepatitis B e antigen (HBeAg)-positive patients, continuing therapy (consolidation) for 6-12 months before cessation of nucleos(t)ide analogues (NAs) was recommended. This study aimed to investigate whether a longer period of lamivudine consolidation therapy leads to better outcomes and the
Raph L Hamers et al.
Journal of acquired immune deficiency syndromes (1999), 64(2), 174-182 (2013-07-31)
This study assessed HIV-hepatitis B virus (HBV) coinfection in southern Africa in terms of prevalence, viral characteristics, occult HBV, and the effect of lamivudine- versus tenofovir-containing first-line combination antiretroviral treatment (cART) on HBV-related outcomes. A multicenter prospective cohort of HIV-infected
Sharon L Walmsley et al.
The New England journal of medicine, 369(19), 1807-1818 (2013-11-08)
Dolutegravir (S/GSK1349572), a once-daily, unboosted integrase inhibitor, was recently approved in the United States for the treatment of human immunodeficiency virus type 1 (HIV-1) infection in combination with other antiretroviral agents. Dolutegravir, in combination with abacavir-lamivudine, may provide a simplified
Hepatitis B virus DNA integration occurs early in the viral life cycle in an in vitro infection model via NTCP-dependent uptake of enveloped virus particles
Tu T, et al.
Journal of virology, JVI-02007 (2018)
François Raffi et al.
The Lancet. Infectious diseases, 13(11), 927-935 (2013-10-01)
In the primary analysis of SPRING-2 at week 48, dolutegravir showed non-inferior efficacy to and similar tolerability to raltegravir in adults infected with HIV-1 and naive for antiretroviral treatment. We present the 96 week results. SPRING-2 is an ongoing phase
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