Structural Formula Vector Image
Title: Zidovudine
CAS Registry Number: 30516-87-1
CAS Name: 3¢-Azido-3¢-deoxythymidine
Additional Names: azidothymidine; AZT
Manufacturers' Codes: BW-A509U
Trademarks: Retrovir (GSK)
Molecular Formula: C10H13N5O4
Molecular Weight: 267.24
Percent Composition: C 44.94%, H 4.90%, N 26.21%, O 23.95%
Literature References: Pyrimidine nucleoside analog; reverse transcriptase inhibitor. Prepn: J. P. Horwitz et al., J. Org. Chem. 29, 2076 (1964); R. P. Glinski et al., ibid. 38, 4299 (1973). See also: J. L. Rideout et al., US 4724232 (1988 to Burroughs Wellcome). Total synthesis: C. K. Chu et al., Tetrahedron Lett. 29, 5349 (1988). In vitro antiviral and antitumor activity: E. De Clercq et al., Biochem. Pharmacol. 29, 1849 (1980); vs HIV-1 virus: H. Mitsuya et al., Proc. Natl. Acad. Sci. USA 82, 7096 (1985). Clinical pharmacokinetics: R. W. Klecker et al., Clin. Pharmacol. Ther. 41, 407 (1987). Toxicology studies: K. M. Ayers, Am. J. Med. 85, Suppl. 2A, 186 (1988). Comprehensive description: M. L. Sethi, Anal. Profiles Drug Subs. 20, 729-765 (1991). Review of clinical experience: G. X. McLeod, S. M. Hammer, Ann. Intern. Med. 117, 487-501 (1992); in prevention of perinatal HIV transmission: R. Sperling, Infect. Dis. Obstet. Gynecol. 6, 197-203 (1998).
Properties: Needles from petr ether, mp 106-112° (Horwitz). Also reported as crystals from water, mp 120-122° (Glinski). [a]D25 +99° (c = 0.5 in water). Soly in water (25°C): 25 mg/ml. uv max (water): 266.5 nm (e 11650). LD50 in male, female mice, male, female rats (mg/kg): 3568, 3062, 3084, 3683 orally; >750 i.v. (all species) (Ayers).
Melting point: mp 106-112° (Horwitz); mp 120-122° (Glinski)
Optical Rotation: [a]D25 +99° (c = 0.5 in water)
Absorption maximum: uv max (water): 266.5 nm (e 11650)
Toxicity data: LD50 in male, female mice, male, female rats (mg/kg): 3568, 3062, 3084, 3683 orally; >750 i.v. (all species) (Ayers)
Therap-Cat: Antiviral.
Keywords: Antiviral; Purines/Pyrimidinones; Reverse Transcriptase Inhibitor.

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