2268. Cidofovir

Nomenclature

CAS number: 113852-37-2
[[(1S)-2-(4-Amino-2-oxo-1(2H)-pyrimidinyl)-1-(hydroxymethyl)ethoxy]methyl]phosphonic acid; (S)-1-[3-hydroxy-2-(phosphonylmethoxy)propyl]cytosine; (S)-HPMPC; GS-504; Vistide (Gilead).
C8H14N3O6P; mol wt 279.19.
C 34.42%, H 5.05%, N 15.05%, O 34.38%, P 11.09%.

Description and references

DNA synthesis inhibitor. Prepn: A. Holy et al., EP 253412; eidem, US 5142051 (1988, 1992 both to Ceskoslov. Akad. Ved; Rega Inst.); and activity vs cytomegalovirus: R. Snoeck et al., Antimicrob. Agents Chemother. 32, 1839 (1988). Syntheses: J. J. Bronson et al., Nucleosides Nucleotides 9, 745 (1990); P. R. Brodfuehrer et al., Tetrahedron Lett. 35, 3243 (1994). Activity vs herpes simplex virus: G. Andrei et al., Eur. J. Clin. Microbiol. Infect. Dis. 11, 143 (1992). Review of pharmacology and clinical studies: M. J. M. Hitchcock et al., Antivir. Chem. Chemother. 7, 115-127 (1996). Review of clinical potential in poxvirus infections: E. De Clercq, Trends Pharmacol. Sci. 23, 456-458 (2002).

Chemical structure

Properties

Fluffy white powder, mp 260° (dec). [α]D20 -97.3° (c = 0.80 in water). Monohydrate, uv max (pH 2): 279 nm (ε 13000).

Therapeutic Category

Antiviral.

Keywords

Antiviral; Nucleosides/Nucleotides