Stavudine
Title: Stavudine
CAS Registry Number: 3056-17-5
CAS Name: 2¢,3¢-Didehydro-3¢-deoxythymidine
Additional Names: 1-(2,3-dideoxy-b-glycero-pent-2-enofuranosyl)thymine; 3¢-deoxy-2¢-thymidinene; D4T
Manufacturers' Codes: BMY-27857
Trademarks: Zerit (BMS)
Molecular Formula: C10H12N2O4
Molecular Weight: 224.21
Percent Composition: C 53.57%, H 5.39%, N 12.49%, O 28.54%
Literature References: Analog of thymidine, q.v.; reverse transcriptase inhibitor. Prepn: J. P. Horwitz et al., J. Org. Chem. 31, 205 (1966); J. W. Beach et al., ibid. 57, 3887 (1992). Large scale production: J. E. Starrett et al., EP 334368; eidem, US 5130421 (1989, 1992 both to Bristol-Myers). In vitro activity against HIV and toxicology: M. M. Mansuri et al., Antimicrob. Agents Chemother. 34, 637 (1990). Mechanism of action study: H.-T. Ho, M. J. M. Hitchcock, ibid. 33, 844 (1989). Disposition and metabolism: E. M. Cretton et al., ibid. 37, 1816 (1993). Clinical pharmacokinetics: M. N. Dudley et al., J. Infect. Dis. 166, 480 (1992). HPLC determn in plasma and urine: J. S. Janiszewski et al., J. Chromatogr. 577, 151 (1992). Clinical evaluation in AIDS and ARC: M. J. Browne et al., J. Infect. Dis. 167, 21 (1993).
Properties: Colorless, granular solid from ethanol/benzene, mp 165-166° (Horwitz). Also reported as crystals from ethanol-ether, mp 174° (Beach). uv max (water): 266 nm (e 10149). [a]D25 -39.4° (c = 0.701 in water); [a]D20 -46.1° (c = 0.7 in water).
Melting point: mp 165-166° (Horwitz); mp 174° (Beach)
Optical Rotation: [a]D25 -39.4° (c = 0.701 in water); [a]D20 -46.1° (c = 0.7 in water)
Absorption maximum: uv max (water): 266 nm (e 10149)
Therap-Cat: Antiviral.
Keywords: Antiviral; Purines/Pyrimidinones; Reverse Transcriptase Inhibitor.

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