Title: Lamivudine
CAS Registry Number: 134678-17-4
CAS Name: (2R-cis)-4-Amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone
Additional Names: (-)-2¢-deoxy-3¢-thiacytidine; (-)-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cystosine; 3¢-thia-2¢,3¢-dideoxycytidine; 3TC
Manufacturers' Codes: (-)-BCH-189; GR-109714X
Trademarks: Epivir (GSK); Zeffix (GSK)
Molecular Formula: C8H11N3O3S
Molecular Weight: 229.26
Percent Composition: C 41.91%, H 4.84%, N 18.33%, O 20.94%, S 13.99%
Literature References: Reverse transcriptase inhibitor. Prepn: J. A. V. Coates et al., WO 9117159 C.A. 117, 111989 (1991). Synthesis of enantiomers: J. W. Beach et al., J. Org. Chem. 57, 2217 (1992); of (-)-enantiomer: D. C. Humber et al., Tetrahedron Lett. 33, 4625 (1992). HPLC determn in urine: D. M. Morris, K. Selinger, J. Pharm. Biomed. Anal. 12, 255 (1994). Clinical trial in hepatitis B: F. Nevens et al., Gastroenterology 113, 1258 (1997). Review of pharmacology and clinical efficacy in HIV infection: C. M. Perry, D. Faulds, Drugs 53, 657-680 (1997).
Properties: Crystals from boiling ethanol. mp 160-162°. [a]D21 -135° (c = 0.38 in methanol). Soly in water (20°): ~70 mg/ml.
Melting point: mp 160-162°
Optical Rotation: [a]D21 -135° (c = 0.38 in methanol)
Therap-Cat: Antiviral.
Keywords: Antiviral; Purines/Pyrimidinones; Reverse Transcriptase Inhibitor. |