({[(2S)-1-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxypropan-2-yl]oxy}methyl)phosphonic acid

• ChemBase ID: 253
• Molecular Formular: C8H14N3O6P
• Molecular Mass: 279.187021
• Monoisotopic Mass: 279.06202181
• SMILES: P(=O)(O)(O)CO[C@@H](Cn1ccc(nc1=O)N)CO
• Canonical SMILES: OC[C@H](Cn1ccc(nc1=O)N)OCP(=O)(O)O
• InChI: InChI=1S/C8H14N3O6P/c9-7-1-2-11(8(13)10-7)3-6(4-12)17-5-18(14,15)16/h1-2,6,12H,3-5H2,(H2,9,10,13)(H2,14,15,16)/t6-/m0/s1
• InChIKey: VWFCHDSQECPREK-LURJTMIESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ({[(2S)-1-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxypropan-2-yl]oxy}methyl)phosphonic acid
• IUPAC Traditional name: cidofovir
• Brand Name: HPMPC; Vistide
• Synonyms: CDV; Cidofovir Anhydrous; Cidofovir; Vistide; [[(1S)-2-(4-Amino-2-oxo-1(2H)-pyrimidinyl)-1-(hydroxymethyl)ethoxy]methyl]phosphonic Acid Hydrate; 1-[(S)-3-Hydroxy-2-(phosphonomethoxy)propyl]cytosine Hydrate; (S)-[[2-(4-Amino-2-oxo-1(2H)-pyrimidinyl)-1-(hydroxymethyl)ethoxy]methyl]phosphonic Acid Hydrate; (S)-1-(3-hydroxy-2-phosphonomethoxypropyl)cytosine Hydrate; (S)-HPMPC Hydrate; Cidovir Hydrate; GS 0504 Hydrate; Vistide Hydrate; Cidofovir Hydrate

Database IDs

• CAS Number: 113852-37-2
• PubChem SID: 160963716; 46506054
• PubChem CID: 60613

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.0463051
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -4.5788546
• LogD (pH = 7.4): -4.7014484
• Log P: -2.9908068
• Molar Refractivity: 60.4279 cm^3
• Polarizability: 23.452892 Å^3
• Polar Surface Area: 145.68 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.12
• LOG S: -1.38
• Solubility (Water): 1.15e+01 g/l

PROPERTIES

Physical Property

• Solubility: =170 mg/mL at pH 6-8; DMSO (Sparingly); Water (Sparingly)
• Apperance: White Solid
• Melting Point: 256-260°C (dec.)
• Hydrophobicity(logP): -3.9

Safety Information

• Storage Condition: -20°C; Refrigerator

Product Information

• Salt Data: Free Base

DETAILS

DrugBank - DB00369

• Drug Groups: approved
• Description: Cidofovir is an injectable antiviral medication for the treatment of cytomegalovirus (CMV) retinitis in patients with AIDS. It suppresses CMV replication by selective inhibition of viral DNA synthesis. [Wikipedia]
• Indication: For the treatment of CMV retinitis in patients with acquired immunodeficiency syndrome (AIDS)
• Pharmacology: Cidofovir is a new anti-viral drug. It is classified as a nucleotide analogue and is active against herpes cytomegalovirus (CMV) retinitis infection. Most adults are infected with CMV. Cidofovir suppresses cytomegalovirus (CMV) replication by selective inhibition of viral DNA synthesis.
• Toxicity: Kidney damage, fall in the number of white blood cells, decreased platelets
• Affected Organisms: Human Immunodeficiency Virus
• Absorption: 100%
• Half Life: 2.4 to 3.2 hours
• Protein Binding: 6%
• Distribution: * 537 ± 126 mL/kg [VISTIDE ADMINISTERED WITHOUT PROBENECID]; * 410 ± 102 mL/kg [VISTIDE ADMINISTERED WITH PROBENECID]
• Clearance: * 179 +/- 23.1 mL/min/1.73 m2 [WITHOUT PROBENECID]; * 148 +/- 38.8 mL/min/1.73 m2 [WITH PROBENECID]
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1516

Research Area: Infection
Biological Activity:
Cidofovir(Vistide) is an injectable antiviral medication for the treatment of cytomegalovirus (CMV) retinitis. (IC50= 0.94 μM) [1][2] A wild type HCMV laboratory strain (AD 169) and 3 ganciclovir-resistant clinical isolates(generated as a result of Ganciclovir therapy) that are cross-resistant to cidofovir were also included in the cidofovir susceptibility assays. AD 169 showed a cidofovir IC50 value of 0.6 pM, and the ganciclovir- resistant isolates showed cidofovir IC50 values ranging from 2.3 to 16 pM. [3]

Toronto Research Chemicals - C433500

An injectable antiviral medication for the treatment of cytomegalovirus (CMV) retinitis in patients with AIDS. It suppresses CMV replication by selective inhibition of viral DNA polymerase and therefore prevention of viral replication and transcription. I

REFERENCES

• http://en.wikipedia.org/wiki/Cidofovir
• Rahal, F.M. et al.: Ann. Internal Med., 125, 98 (1996)
• Johnson, J.A. et al.: Antimicrob. Agents Chemother., 43, 1190 (1996)
• Ho, H.T. et al.: Mol. Pharmacol., 41, 197 (1996)