phosphonoformic acid

• ChemBase ID: 411
• Molecular Formular: CH3O5P
• Molecular Mass: 126.005281
• Monoisotopic Mass: 125.97180983
• SMILES: P(=O)(O)(O)C(=O)O
• Canonical SMILES: OC(=O)P(=O)(O)O
• InChI: InChI=1S/CH3O5P/c2-1(3)7(4,5)6/h(H,2,3)(H2,4,5,6)
• InChIKey: ZJAOAACCNHFJAH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: phosphonoformic acid
• IUPAC Traditional name: foscarnet
• Brand Name: Foscarmet; Foscavir; Triapten
• Synonyms: PFA; Foscarnet sodium; Forscarnet sodium; Dihydroxyphosphinecarboxylic acid oxide; Carboxyphosphonic acid; Phgosphonocarboxylic acid; Phosphonoformate; Phosphonoformic acid; Foscarnet

Database IDs

• CAS Number: 63585-09-1
• PubChem SID: 160963874; 46507873
• PubChem CID: 3415

CALCULATED PROPERTIES

JChem

• Acid pKa: -0.09567522
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -5.199673
• LogD (pH = 7.4): -7.582527
• Log P: -0.8303841
• Molar Refractivity: 19.0731 cm^3
• Polarizability: 7.912969 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.63
• LOG S: -0.88
• Solubility (Water): 1.68e+01 g/l

PROPERTIES

Physical Property

• Solubility: Complete
• Hydrophobicity(logP): -2.1

DETAILS

DrugBank - DB00529

• Drug Groups: approved
• Description: An antiviral agent used in the treatment of cytomegalovirus retinitis. Foscarnet also shows activity against human herpesviruses and HIV. [PubChem]
• Indication: For the treatment of CMV retinitis in patients with acquired immunodeficiency syndrome (AIDS) and for treatment of acyclovir-resistant mucocutaneous HSV infections in immunocompromised patients.
• Pharmacology: Foscarnet is an organic analogue of inorganic pyrophosphate that inhibits replication of herpes viruses in vitro including cytomegalovirus (CMV) and herpes simplex virus types 1 and 2 (HSV-1 and HSV-2). Foscarnet does not require activation (phosphorylation) by thymidine kinase or other kinases and therefore is active in vitro against HSV TK deficient mutants and CMV UL97 mutants. Thus, HSV strains resistant to acyclovir or CMV strains resistant to ganciclovir may be sensitive to foscarnet. However, acyclovir or ganciclovir resistant mutants with alterations in the viral DNA polymerase may be resistant to foscarnet and may not respond to therapy with foscarnet. The combination of foscarnet and ganciclovir has been shown to have enhanced activity in vitro.
• Toxicity: Oral, rat LD₅₀: >2,000 mg/kg. Signs of overdose include renal impairment.
• Affected Organisms: Human Herpes Virus
• Biotransformation: Not metabolized.
• Absorption: Poorly absorbed after oral administration (bioavailability from 12 to 22%).
• Half Life: 3.3-6.8 hours
• Protein Binding: 14-17%
• Clearance: * 2.13 +/- 0.71 mL/min/kg [patients had normal renal function (CrCl > 80 mL/min]; * 68 +/- 8 mL/min/kg [CrCl was 50-80 mL/min]; * 34 +/- 9 mL/min/kg [CrCl was 25-49 mL/min]; * 20 +/- 4 mL/min/kg [CrCl was 10 - 24 mL/min]
• External Links: Wikipedia; RxList; Drugs.com