5352. Lamivudine

Nomenclature

CAS number: 134678-17-4
(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; ()-BCH-189; GR-109714X; Epivir (GSK); Zeffix (GSK).
C8H11N3O3S; mol wt 229.26.
C 41.91%, H 4.84%, N 18.33%, O 20.94%, S 13.99%.

Description and 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); of clinical experience in chronic hepatitis B and cirrhosis: C. Hanché, J-P Villeneuve, Expert Opin. Pharmacother. 7, 1835-1843 (2006).

Chemical structure

Properties

Crystals from boiling ethanol, mp 160-162°. [α]D21 135° (c = 0.38 in methanol). Soly in water (20°): ≈70 mg/ml.

Therapeutic Category

Antiretroviral.

Keywords

Reverse Transcriptase Inhibitor; Antiretroviral; Reverse Transcriptase Inhibitors; Nucleosides/Nucleotides