Title: Clevudine
CAS Registry Number: 163252-36-6
CAS Name: 1-(2-Deoxy-2-fluoro-b-L-arabinofuranosyl)-5-methyl-2,4-(1H,3H)-pyrimidinedione
Additional Names: 1-(2-deoxy-2-fluoro-b-L-arabinofuranosyl)thymine; 2¢-fluoro-5-methyl-b-L-arabinofuranosyluridine; L-FMAU
Molecular Formula: C10H13FN2O5
Molecular Weight: 260.22
Percent Composition: C 46.16%, H 5.04%, F 7.30%, N 10.77%, O 30.74%
Literature References: Nucleoside analog; specific inhibitor of viral DNA synthesis. Prepn: C. K. Chu et al., WO 9520595; eidem, US 5587362 (1995, 1996 both to Univ. Georgia Res. Found.; Yale Univ.); T. Ma et al., J. Med. Chem. 39, 2835 (1996). Synthesis: M. L. Sznaidman et al., Nucleosides Nucleotides Nucleic Acids 21, 155 (2002). In vitro antiviral activity: C. K. Chu et al., Antimicrob. Agents Chemother. 39, 979 (1995). Pharmacokinetics: J. D. Wright et al., Pharm. Res. 12, 1350 (1995). Mechanism of action study: Y. Chong, C. K. Chu, Bioorg. Med. Chem. Lett. 12, 3459 (2002). Clinical evaluation in chronic hepatitis B: P. Marcellin et al., Hepatology 40, 140 (2004). Review of preclinical pharmacology: C. K. Chu et al. in Therapies for Viral Hepatitis, R. F. Schinazi et al., Eds. (Int. Med. Press, London, 1998) pp 303-312; of development and clinical experience: G. R. Painter et al. in Frontiers in Viral Hepatitis, R. F. Schinazi et al., Eds. (Elsevier, New York, 2003) pp 281-300.
Properties: Crystals from methanol/chloroform, mp 184-185°. [a]D25 -111.77° (c = 0.23 in methanol). uv max in water: 265.0 (pH 2), 265.5 (pH 7), 265.5 nm (pH 11) (e 9695, 9647, 7153). LD50 in mice, rats (mg/kg): >5000, >3000 orally (Painter).
Melting point: mp 184-185°
Optical Rotation: [a]D25 -111.77° (c = 0.23 in methanol)
Absorption maximum: uv max in water: 265.0 (pH 2), 265.5 (pH 7), 265.5 nm (pH 11) (e 9695, 9647, 7153)
Toxicity data: LD50 in mice, rats (mg/kg): >5000, >3000 orally (Painter)
Derivative Type: Triphosphate
CAS Registry Number: 174625-00-4
Additional Names: L-FMAU-TP
Molecular Formula: C10H16FN2O14P3
Molecular Weight: 500.16
Percent Composition: C 24.01%, H 3.22%, F 3.80%, N 5.60%, O 44.78%, P 18.58%
Therap-Cat: Antiviral.
Keywords: Antiviral; Purines/Pyrimidinones. |