134678-17-4 Lamivudine AKSci J10244
 
 
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  J10244    
Lamivudine, >98% (HPLC), powder
 
2',3'-Dideoxy-3'-thiacytidine
3TC
Zeffix
more..
IDENTITY
CAS Number:134678-17-4
MDL Number:MFCD00869739
MF:C8H11N3O3S
MW:229.26
BRN:5480511
SPECIFICATIONS & PROPERTIES
Min. Purity Spec:>98% (HPLC), powder
Physical Form (at 20°C):Solid
Melting Point:173-179°C
Optical Rotation:-148° - -137° (c=1,MeOH)
Long-Term Storage:Store long-term at 2-8°C
DOT/IATA TRANSPORT INFORMATION
Not hazardous material

BIOLOGICAL INFO
Solubility:DMSO: 46mg/mL; H2O: 46mg/mL; EtOH: <1mg/mL
Application(s):Nucleoside analog reverse transcriptase inhibitor (nRTI)
Form:Free base

REVIEW
 Lamivudine is a potent, single enantiomer nucleoside analog reverse-transcriptase inhibitor (NRTI) antiviral drug. It has been used for treatment of chronic hepatitis B at a lower dose than for treatment of HIV. Long-term use of lamivudine unfortunately leads to emergence of a resistant hepatitis B virus (YMDD) mutant. Despite this, lamivudine is still used widely as it is well tolerated. Lamivudine is an analog of cytidine and can inhibit both types of HIV reverse transcriptase and also the reverse transcriptase of hepatitis B. It is phosphorylated intracellularly to lamivudine triphosphate, which competes for incorporation into viral DNA. It inhibits HIV reverse transcriptase and HBV polymerase enzymes competitively and acts as a chain terminator of DNA synthesis. The lack of a 3''-OH group in the incorporated nucleoside analog prevents the formation of the 5'' to 3'' phosphodiester linkage essential for DNA chain elongation, and therefore, the viral DNA growth is terminated.

REFERENCES
[1]Yousef Y, Beland K, Mas E, Lapierre P, Bouron Dal Soglio D, Alvarez F (2012). Predictive factors of lamivudine treatment success in an hepatitis B virus-infected pediatric cohort: a 10-year study. Can J Gastroenterol. 26(7):429-35. PMID 22803017.
[2] Yang FQ, Yu YY, Wang GQ, Chen J, Li JH, Li YQ, Rao GR, Mo GY, Luo XR, Chen GM (2012). A pilot randomized controlled trial of dual-plasmid HBV DNA vaccine mediated by in vivo electroporation in chronic hepatitis B patients under lamivudine chemotherapy. J Viral Hepat. 19(8):581-93. PMID 22762143.
[3] Goodyear, Michael David; Dwyer, P. Owen; Hill, Malcolm Leithead; Whitehead, Andrew Jonathan; Hornby, Roy; Hallett, Peter Diastereoselective synthesis of oxathiolane nucleoside analogs. PCT Int. Appl. (1995), WO 9529174 A1 19951102.
[4] Katlama C, Havlir DV.Newer nucleosides: lamivudine and stavudine. AIDS. 1996;10 Suppl A:S135-43.

GLOBALLY HARMONIZED SYSTEM (GHS)

Pictograms

Signal Word
Warning

Hazard Statements
H361

Precautionary Statements
P201; P202; P281; P308+P313; P405; P501

Current as of April 26, 2024


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CATEGORIES
 APIs and Bioactives > Antivirals, Antiretrovirals, NRTIs


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