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L1295

Sigma-Aldrich

Lamivudine

≥98% (HPLC), powder

Synonym(s):

2′,3′-Dideoxy-3′-thiacytidine, 3TC, Epivir, Epivir-HBV, Heptovir, Zeffix

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About This Item

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

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Edward J Gane et al.
Liver transplantation : official publication of the American Association for the Study of Liver Diseases and the International Liver Transplantation Society, 19(3), 268-274 (2013-03-01)
Without effective prophylaxis, liver transplantation for hepatitis B virus (HBV)-related liver disease is frequently complicated by severe and rapidly progressive HBV recurrence. Combination prophylaxis with hepatitis B immune globulin (HBIG) and lamivudine (LAM) reduces long-term recurrence rates below 10%; however
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)
Kiyoaki Ito et al.
Hepatology (Baltimore, Md.), 59(1), 89-97 (2013-07-31)
The proportion of patients who progress to chronicity following acute hepatitis B (AHB) varies widely worldwide. Moreover, the association between viral persistence after AHB and hepatitis B virus (HBV) genotypes in adults remains unclear. A nationwide multicenter study was conducted
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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