7083. Penciclovir

Nomenclature

CAS number: 39809-25-1
2-Amino-1,9-dihydro-9-[4-hydroxy-3-(hydroxymethyl)butyl]-6H-purin-6-one; 9-[4-hydroxy-3-(hydroxymethyl)but-1-yl]guanine; PCV; BRL-39123; Denavir (SKB); Vectavir (SKB).
C10H15N5O3; mol wt 253.26.
C 47.42%, H 5.97%, N 27.65%, O 18.95%.

Description and 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., Antivir. 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).

Chemical structure

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 (ε 11500). uv max (aq 0.01N NaOH): 215, 268 nm (ε 18140, 10710). Sol in water (20°): 1.7 mg/ml, pH 7.

Derivative

Sodium salt.

Nomenclature

BRL-39123A.

Properties

Occurs as monohydrate, stable crystalline solid. Sol in water (20°): >200 mg/ml. 30 mg/ml soln has pH 11.

Therapeutic Category

Antiviral.

Keywords

Antiviral; Nucleosides/Nucleotides