Title: Vidarabine
CAS Registry Number: 5536-17-4
CAS Name: 9-b-D-Arabinofuranosyl-9H-purine-6-amine monohydrate
Additional Names: 9-b-D-arabinofuranosyladenine monohydrate; arabinosyladenine; adenine arabinoside; spongoadenosine; ara-A
Manufacturers' Codes: CI-673
Trademarks: Arasena-A (Mochida); Vira-A (Warner-Lambert)
Molecular Formula: C10H13N5O4.H2O
Molecular Weight: 285.26
Percent Composition: C 42.10%, H 5.30%, N 24.55%, O 28.04%
Literature References: Purine nucleoside first synthesized as a potential anticancer agent: Lee et al., J. Am. Chem. Soc. 82, 2648 (1960); Reist et al., J. Org. Chem. 27, 3274 (1962); Glaudemans, Fletcher, ibid. 28, 3004 (1963); Reist et al., ibid. 29, 3725 (1964). Fermentation process using a strain of Streptomyces antibioticus: GB 1159290; J. D. Howells, A. Ryder, US 3616208 (1969, 1971 both to Parke, Davis). Crystal and molecular structure: Bunick, Voet, Acta Crystallogr. 30B, 1641 (1974). Series of articles on antiviral activity: Antimicrob. Agents Chemother. 1968, 136-179. Toxicity study: S. M. Kurtz et al., ibid. 180. HPLC determn in plasma and urine: W. P. McCann et al., ibid. 28, 265 (1985). Clinical trial in immunocompromised patients: R. J. Whitley et al., J. Infect. Dis. 165, 450 (1992). Book: Adenine Arabinoside: An Antiviral Agent, D. Paven-Langston et al., Eds. (Raven Press, New York, 1975) xviii + 425 pp. Review of pharmacology and clinical experience: R. A. Buchanan, F. Hess, Pharmacol. Ther. 8, 143-171 (1980). Comprehensive description: W. Hong et al., Anal. Profiles Drug Subs. 15, 647-672 (1986).
Properties: Crystals from water, mp 257.0-257.5° (0.4 H2O). [a]D27 -5° (c = 0.25). uv max (pH 1): 257.5 nm (e 12700); pH 7: 259 nm (e 13400); pH 13: 259 nm (e 14000). LD50 in mice (mg/kg): 4677 i.p.; >7950 orally (Kurtz).
Melting point: mp 257.0-257.5° (0.4 H2O)
Optical Rotation: [a]D27 -5° (c = 0.25)
Absorption maximum: uv max (pH 1): 257.5 nm (e 12700); pH 7: 259 nm (e 13400); pH 13: 259 nm (e 14000)
Toxicity data: LD50 in mice (mg/kg): 4677 i.p.; >7950 orally (Kurtz)
Therap-Cat: Antiviral.
Keywords: Antiviral; Purines/Pyrimidinones. |