Title: Zalcitabine
CAS Registry Number: 7481-89-2
CAS Name: 2¢,3¢-Dideoxycytidine
Additional Names: dideoxycytidine; ddCyd
Trademarks: Hivid (Roche)
Molecular Formula: C9H13N3O3
Molecular Weight: 211.22
Percent Composition: C 51.18%, H 6.20%, N 19.89%, O 22.72%
Literature References: Pyrimidine nucleoside analog with antiviral activity. Prepn: J. P. Horwitz et al., J. Org. Chem. 32, 817 (1967); R. Marumoto, M. Honjo, Chem. Pharm. Bull. 22, 128 (1974). Prepn and structure-activity study: T.-S. Lin et al., J. Med. Chem. 30, 440 (1987). In vitro inhibition of viral DNA synthesis: P. C. van der Vliet, M. M. Kwant, Biochemistry 20, 2628 (1981); of HIV-1 virus replication: H. Mitsuya, S. Broder, Proc. Natl. Acad. Sci. USA 83, 1911 (1986). Phosphorylation by human cells: D. A. Cooney et al., Biochem. Pharmacol. 35, 2065 (1986). Metabolism by human cells: M. C. Starnes, Y. Cheng, J. Biol. Chem. 262, 988 (1987). Potential application in acquired immunodeficiency syndrome (AIDS): E. De Clercq, J. Med. Chem. 29, 1561 (1986).
Properties: Crystals from ethanol + benzene, mp 215-217° (Horwitz); also reported as mp 209-210° (Lin). [a]D25 +81° (c = 0.635 in water). uv max in 0.1N HCl: 280 nm (e 17720); in 0.1N NaOH: 270 nm (e 8410).
Melting point: mp 215-217° (Horwitz); mp 209-210° (Lin)
Optical Rotation: [a]D25 +81° (c = 0.635 in water)
Absorption maximum: uv max in 0.1N HCl: 280 nm (e 17720); in 0.1N NaOH: 270 nm (e 8410)
Therap-Cat: Antiviral.
Keywords: Antiviral; Purines/Pyrimidinones; Reverse Transcriptase Inhibitor. |