Title: Emtricitabine
CAS Registry Number: 143491-57-0
CAS Name: 4-Amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone
Additional Names: (-)-cis-4-amino-5-fluoro-1-(2-hydroxymethyl-1,3-oxathiolan-5-yl)-(1H)-pyrimidin-2-one; (-)-(2R,5S)-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine; (-)-b-2¢,3¢-dideoxy-5-fluoro-3¢-thiacytidine; (-)-FTC
Manufacturers' Codes: 524W91; BW-524W91
Trademarks: Coviracil (Triangle); Emtriva (Gilead)
Molecular Formula: C8H10FN3O3S
Molecular Weight: 247.25
Percent Composition: C 38.86%, H 4.08%, F 7.68%, N 16.99%, O 19.41%, S 12.97%
Literature References: Reverse transcriptase inhibitor; nucleoside analog structurally related to lamivudine, q.v. Prepn: D. C. Liotta et al., WO 9214743 (1992 to Emory University); G. Dionne, US 5538975 (1996 to BioChem Pharma, Inc.); L. S. Jeong et al., J. Med. Chem. 36, 181 (1993). Absolute configuration: P. van Roey et al., Antiviral Chem. Chemother. 4, 369 (1993). HPLC-NMR determn of urinary metabolites: J. P. Shockcor et al., Xenobiotica 26, 189 (1996). Comparative efficacy of enantiomers vs HIV: R. F. Schinazi et al., Antimicrob. Agents Chemother. 36, 2423 (1992). Pharmacokinetics: L. W. Frick et al., ibid. 38, 2722 (1994). Mechanism of action study: J. Y. Feng et al., FASEB J. 13, 1511 (1999). Clinical study in combination with didanosine and efavirenz: J.-M. Molina et al., J. Infect. Dis. 182, 599 (2000). Review: P. Cahn, Expert Opin. Invest. Drugs 13, 55-68 (2004).
Properties: White solid from ether and methanol, mp 136-140°. [a]D25 -133.60° (c = 0.23 in MeOH). uv max (water): 287.8 nm (pH 2); 280.0 nm (pH 7); 279.8 nm (pH 11) (e 14210, 11090, 11810).
Melting point: mp 136-140°
Optical Rotation: [a]D25 -133.60° (c = 0.23 in MeOH)
Absorption maximum: uv max (water): 287.8 nm (pH 2); 280.0 nm (pH 7); 279.8 nm (pH 11) (e 14210, 11090, 11810)
Therap-Cat: Antiviral.
Keywords: Antiviral; Purines/Pyrimidinones; Reverse Transcriptase Inhibitor. |