9899. Valacyclovir
Nomenclature
CAS number: 124832-26-4
l-Valine 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]ethyl ester; l-valine ester with 9-[(2-hydroxyethoxy)methyl]guanine; valaciclovir; ValACV. C13H20N6O4; mol wt 324.34.
C 48.14%, H 6.22%, N 25.91%, O 19.73%.
Description and references
l-Valine ester prodrug of acyclovir, q.v. Prepn: T. A. Krenitsky et al., EP 308065; L. M. Beauchamp, US 4957924 (1989, 1990 both to Wellcome). Evaluation as prodrug: L. M. Beauchamp et al., Antivir. Chem. Chemother. 3, 157 (1992). Clinical pharmacokinetics: S. Weller et al., Clin. Pharmacol. Ther. 54, 595 (1993). Review of pharmacology and clinical efficacy in herpes virus infections: C. M. Perry, D. Faulds, Drugs 52, 754-772 (1996). Clinical trial to prevent cytomegalovirus disease in renal transplantation: D. Lowance et al., N. Engl. J. Med. 340, 1462 (1999); to prevent transmission of genital herpes: L. Corey et al., ibid. 350, 11 (2004).
Derivative
Hydrochloride.Nomenclature
CAS number: 124832-27-5
256U; BW-256U87; BW-256; Valtrex (GSK). Properties
Crystalline solid, occurs as hydrate. uv max (water): 252.8 nm (ε 8530). Soly in water: 174 mg/ml.Therapeutic Category
Antiviral.
Keywords
Antiviral; Nucleosides/Nucleotides