CAS No 39809-25-1 , 2-amino-9-[4-hydroxy-3-(hydroxymethyl)butyl]-3H-purin-6-one

Title: Penciclovir
CAS Registry Number: 39809-25-1
CAS Name: 2-Amino-1,9-dihydro-9-[4-hydroxy-3-(hydroxymethyl)butyl]-6H-purin-6-one
Synonyms: 9-[4-hydroxy-3-(hydroxymethyl)but-1-yl]guanine; PCV
Manufacturers' Codes: BRL-39123
Trademarks: Denavir (SKB); Vectavir (SKB)
Molecular Formula: C10H15N5O3
Molecular Weight: 253.26
Percent Composition: C 47.42%, H 5.97%, N 27.65%, O 18.95%
Literature References: Carba analog of ganciclovir, q.v., active against several herpes viruses. Prepn: U. K. Pandit et al., Synth. Commun. 2, 345 (1972); R. L. Jarvest, M. R. Harnden, US 5075445 (1991 to Beecham). Synthesis: M. R. Harnden et al., J. Med. Chem. 30, 1636 (1987); J. Hannah et al., J. Heterocycl. Chem. 26, 1261 (1989). Crystal and molecular structures: M. R. Harnden et al., Nucleosides Nucleotides 9, 499 (1990). In vitro activity of enantiomers in comparison with acyclovir, q.v.: G. Abele et al., Antiviral Chem. Chemother. 2, 163 (1991); against herpes simplex viruses: A. Weinberg et al., Antimicrob. Agents Chemother. 36, 2037 (1992). Clinical pharmacokinetics: S. E. Fowles et al., Eur. J. Clin. Pharmacol. 43, 513 (1992). HPLC determn in plasma and urine: J. R. McMeekin et al., Anal. Proc. 29, 178 (1992). Review of development and antiviral activity: M. R. Harnden, Drugs Future 14, 347-358 (1989).
Properties: White crystalline solid from water, (monohydrate), mp 275-277°; also reported as colorless matted needles, mp 272-275°. uv max (in water): 253 nm (e 11500). uv max (aq 0.01N NaOH): 215, 268 nm (e 18140, 10710). Sol in water (20°): 1.7 mg/ml, pH 7.
Melting point: mp 275-277°; mp 272-275°
Absorption maximum: uv max (in water): 253 nm (e 11500); uv max (aq 0.01N NaOH): 215, 268 nm (e 18140, 10710)
 
Derivative Type: Sodium salt
Manufacturers' Codes: BRL-39123A
Properties: Occurs as monohydrate, stable crystalline solid. Sol in water (20°): >200 mg/ml. 30 mg/ml soln has pH 11.
 
Therap-Cat: Antiviral.
Keywords: Antiviral; Purines/Pyrimidinones.