Cidofovir

Title: Cidofovir
CAS Registry Number: 113852-37-2
CAS Name: [[(1S)-2-(4-Amino-2-oxo-1(2H)-pyrimidinyl)-1-(hydroxymethyl)ethoxy]methyl]phosphonic acid
Additional Names: (S)-1-[3-hydroxy-2-(phosphonylmethoxy)propyl]cytosine; (S)-HPMPC
Manufacturers' Codes: GS-504
Trademarks: Vistide (Gilead)
Molecular Formula: C8H14N3O6P
Molecular Weight: 279.19
Percent Composition: C 34.42%, H 5.05%, N 15.05%, O 34.38%, P 11.09%
Literature 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., Antiviral Chem. Chemother. 7, 115-127 (1996). Review of clinical potential in poxvirus infections: E. De Clercq, Trends Pharmacol. Sci. 23, 456-458 (2002).
Properties: Fluffy white powder, mp 260° (dec). [a]D20 -97.3° (c = 0.80 in water). Monohydrate, uv max (pH 2): 279 nm (e 13000).
Melting point: mp 260° (dec)
Optical Rotation: [a]D20 -97.3° (c = 0.80 in water)
Absorption maximum: uv max (pH 2): 279 nm (e 13000)
Therap-Cat: Antiviral.
Keywords: Antiviral; Purines/Pyrimidinones.
Cifenline Ciguatoxins Cilansetron Cilastatin Cilazapril

Cidofovir
Cidofovir2DACS.svg
Cidofovir3Dan.gif
Systematic (IUPAC) name
({[(S)-1-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxypropan-2-yl]oxy}methyl)phosphonic acid
Clinical data
Trade names Vistide
AHFS/Drugs.com monograph
Licence data EMA:Link, US FDA:link
Pregnancy cat. D (AU) C (US)
Legal status Prescription Only (S4) (AU) -only (CA) POM (UK) -only (US)
Routes IV
Pharmacokinetic data
Bioavailability complete
Protein binding <6%
Half-life 2.6 hours
Excretion renal
Identifiers
CAS number 113852-37-2 YesY
ATC code J05AB12
PubChem CID 60613
DrugBank DB00369
ChemSpider 54636 YesY
UNII 768M1V522C YesY
ChEBI CHEBI:3696 YesY
ChEMBL CHEMBL152 YesY
NIAID ChemDB 001049
Chemical data
Formula C8H14N3O6P 
Mol. mass 279.187 g/mol
Physical data
Melt. point 260 °C (500 °F)
Spec. rot -97.3
 YesY (what is this?)  (verify)

Cidofovir (brand name Vistide) is an injectable antiviral medication primarily used as a the treatment for cytomegalovirus (CMV) retinitis (an infection of the retina of the eye) in people with AIDS.[1][2]