131086-21-0

Basic information

• Product Name: Lamivudine
• Synonyms: 2(1H)-Pyrimidinone,4-amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-,(2R-cis)-; (-) 2'-Deoxy-3'-thiacytidine; 2'-Deoxy-3'-thiacytidine; (2R-cis)-4-amino-1-; 3'-thia-2',3'-dideoxcytidine; (-)-BCH-189; Epivir; GR109714X; (-)NGPB-21; (2R-cis)-4-Amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone; (-)-2¢ -deoxy-3¢ -thiacytidine; (-)-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cystosine; 3¢ -thia-2¢ ,3¢ -dideoxycytidine; 3TC; 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2(1H)-one; 4-amino-1-[(2S,5R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2(1H)-one
• CAS NO: 131086-21-0
• Molecular Formula: C₈H₁₁N₃O₃S
• Molecular Weight: 0
• Product Categories: Lamivudine
• Mol File: 131086-21-0.mol
• Article Data: 25

Chemical Properties

• Boiling Point: 475.4°C at 760 mmHg
• Flash Point: 241.3°C
• Appearance: /
• Density: 1.73g/cm³
• Vapor Pressure: 4.91E-11mmHg at 25°C
• Refractive Index: 1.754
• CAS DataBase Reference: Lamivudine(CAS DataBase Reference)
• NIST Chemistry Reference: Lamivudine(131086-21-0)
• EPA Substance Registry System: Lamivudine(131086-21-0)

Safety Data

• Hazardous Substances Data: 131086-21-0(Hazardous Substances Data)

Usage

General Description

Lamivudine is a nucleoside reverse transcriptase inhibitor (NRTI) that is used in the treatment of HIV infection and chronic hepatitis B. It works by inhibiting the activity of the reverse transcriptase enzyme, thereby preventing the virus from replicating and spreading in the body. Lamivudine is often used in combination with other antiretroviral medications to effectively control and manage HIV infection. It is available in oral tablet and oral solution forms and is generally well-tolerated, with common side effects including nausea, headache, and fatigue. Lamivudine is an important component of antiretroviral therapy and has significantly improved the prognosis and quality of life for individuals living with HIV.

InChI:InChI=1/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+/m1/s1

Upstream product

• 136831-90-8 cis-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-(cytosin-1'-yl)-1,3-oxathiolane 
• 14631-20-0 4-N-Acetylcytosine 
• 143919-90-8 2-benzoyloxymethyl-5-acethoxy-1,3-oxathiolane 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 
• 131086-21-0 (+/-)-cis-N-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>cytosine 
• 136794-49-5 (+)-(2S,5R)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N₄-acetylcystosine 
• 1091585-30-6 ((2R,5S)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl benzoate 
• 147126-73-6 (1'S,2'R,5'S)-Menthyl 5(R)-cytosin-1''-yl-1,3-oxathiolane-2(S)-carboxylate 
• 145416-33-7 (+)-(2S,5R)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-cystosine 
• 1346921-53-6 L-menthyl 5-cytosin-1-yl-1,3-oxathiolane-2-carboxylate 
• 358348-70-6 cis/trans-2-benzoyloxymethyl-5-(cytosin-1'-yl)-1,3-oxathiolane 
• 1091585-30-6 cis-2-benzoyloxymethyl-5-(N'4-acetylcytosin-1'-yl)-1,3-oxathiolane 

Downstream Products

• 131086-21-0 lamivudine 
• 134678-17-4 lamivudine 
• 136831-90-8 cis-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-(cytosin-1'-yl)-1,3-oxathiolane 
• 131086-23-2 cis-2-hydroxymethyl-5-(cytosin-1'-yl)-3-oxo-1,3-oxathiolane 
• 172912-08-2 cis-2-(tert-butyldiphenylsilyloxymethyl)-5-4-(Boc-AHPPA-1-oxo-6-aminopentyl)cytosin-1'-yl>-1,3-oxathiolane 

Relevant articles and documents

Synthesis of (±)-cis-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine and its (±)-trans isomer

The title compounds were synthesized by the formation of 2-[(benzyloxy)methyl]-1,3-oxathiolan-5-one and subsequent DIBALH reduction, acetylation, coupling with N-(1,2-dihydro-2-oxo-4-pyrimidinyl)-2-ethylhexanamide and deprotection.

Diastereoselective Synthesis of the Potent Antiviral Agent (-)-2'-Deoxy-3'-thiacytidine and Its Enantiomer

-

Multienzymatic cascade synthesis of an enantiopure (2R,5R)-1,3-oxathiolane anti-HIV agent precursor

An enantiopure (2R,5R)-1,3-oxathiolane was obtained using a multienzymatic cascade protocol. By employing a combination of surfactant-treated subtilisin Carlsberg and Candida antarctica lipase B, the absolute configuration of the resulting 1,3-oxathiolane ring was efficiently controlled, resulting in an excellent enantiomeric excess (>99%). This enantiopure 1,3-oxathiolane derivative is a key precursor to anti-HIV agents, such as lamivudine, through subsequent N-glycosylation.

Efficient asymmetric synthesis of lamivudine via enzymatic dynamic kinetic resolution

The anti-HIV nucleoside lamivudine was asymmetrically synthesized in only three steps via a novel surfactant-treated subtilisin Carlsberg-catalyzed dynamic kinetic resolution protocol. The enantiomer of lamivudine could also be accessed using the same protocol catalyzed by Candida antarctica lipase B.