CAS No 104227-87-4 , [2-(acetyloxymethyl)-4-(2-aminopurin-9-yl)butyl] acetate

Title: Famciclovir
CAS Registry Number: 104227-87-4
CAS Name: 2-[2-(2-Amino-9H-purin-9-yl)ethyl]-1,3-propanediol diacetate (ester)
Synonyms: 9-[4-acetoxy-3-(acetoxymethyl)but-1-yl]-2-aminopurine; FCV
Manufacturers' Codes: BRL-42810
Trademarks: Oravir (SKB); Famvir (SKB)
Molecular Formula: C14H19N5O4
Molecular Weight: 321.33
Percent Composition: C 52.33%, H 5.96%, N 21.79%, O 19.92%
Literature References: Prodrug of penciclovir, q.v. Prepn: M. R. Harnden, R. L. Jarvest, AU 85 47560; eidem, US 5246937 (1986, 1993 both to Beecham); M. R. Harnden et al., J. Med. Chem. 32, 1738 (1989). HPLC determn in plasma and urine: J. R. McMeekin et al., Anal. Proc. 29, 178 (1992). Review of metabolism and mode of action: R. A. Vere Hodge, Antiviral Chem. Chemother. 4, 67-84 (1993). Series of articles on pharmacology and pharmacokinetics: ibid. Suppl. 1, 37-68 (1993). Review of clinical efficacy in herpes zoster and genital herpes: R. Circelli et al., Antiviral Res. 29, 141-151 (1996).
Properties: White shiny plates from ethyl acetate-hexane, mp 102-104°. uv max (methanol): 222, 244, 309 nm (e 27500, 4890, 7160). Sol in water (25°): >25% w/v initially; rapidly ppts as sparingly sol monohydrate (2-3% w/v). Freely sol in acetone, methanol; sparingly sol in ethanol, isopropanol.
Melting point: mp 102-104°
Absorption maximum: uv max (methanol): 222, 244, 309 nm (e 27500, 4890, 7160)
Therap-Cat: Antiviral.
Keywords: Antiviral; Purines/Pyrimidinones.