4363. Ganciclovir

Nomenclature

CAS number: 82410-32-0
2-Amino-1,9-dihydro-9-[[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl]-6H-purin-6-one; 9-[(1,3-dihydroxy-2-propoxy)methyl]guanine; 2′-nor-2′-deoxyguanosine; DHPG; 2′NDG; BIOLF-62; BW-B759U; BW-759; BW-759U; RS-21592.
C9H13N5O4; mol wt 255.23.
C 42.35%, H 5.13%, N 27.44%, O 25.07%.

Description and references

Nucleoside analog structurally related to acyclovir, q.v. Prepn: J. P. Verheyden, J. C. Martin, US 4355032 (1982 to Syntex); K. K. Ogilvie et al., Can. J. Chem. 60, 3005 (1982); W. T. Ashton et al., Biochem. Biophys. Res. Commun. 108, 1716 (1982); J. C. Martin et al., J. Med. Chem. 26, 759 (1983). Antiviral spectrum in vitro: K. O. Smith et al., Antimicrob. Agents Chemother. 22, 55 (1982). Mode of action study: Y.-C. Cheng et al., Proc. Natl. Acad. Sci. USA 80, 2767 (1983). Clinical treatment of cytomegalovirus infection in immunodeficient patients: S. H. Koretz et al., N. Engl. J. Med. 314, 801 (1986). Symposium on pharmacology and clinical efficacy vs cytomegalovirus: Rev. Infect. Dis. 10, Suppl. 3, S457-S572 (1988). Review: C. S. Crumpacker, N. Engl. J. Med. 335, 721-729 (1996).

Chemical structure

Properties

Crystals from methanol, mp 250° (dec) (Verheyden, Martin); also reported as crystalline monohydrate from water, mp 248-249° (dec) (Ashton); crystals from water, mp >300° (Martin). uv max (methanol): 254 nm (ε 12880). Soly in water (25°): 4.3 mg/ml at pH 7. LD50 i.p. in mice: 1-2 g/kg (Martin).

Derivative

Sodium salt.

Nomenclature

CAS number: 107910-75-8
Cymevan (Syntex); Cymevene (Syntex); Cytovene (Syntex); Denosine (Syntex); Vitrasert (Chiron).
C9H12N5NaO4; mol wt 277.21.
C 38.99%, H 4.36%, N 25.26%, Na 8.29%, O 23.09%.

Therapeutic Category

Antiviral.

Keywords

Antiviral; Nucleosides/Nucleotides