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CHEBI:127780 - phosphonoformic acid

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ChEBI Name phosphonoformic acid
ChEBI ID CHEBI:127780
Definition Phosphoric acid in which one of the hydroxy groups is replaced by a carboxylic acid group. It is used as the trisodium salt as an antiviral agent in the treatment of cytomegalovirus retinitis (CMV retinitis, an inflamation of the retina that can lead to blindness) and as an alternative to ganciclovir for AIDS patients who require concurrent antiretroviral therapy but are unable to tolerate ganciclovir due to haematological toxicity.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:45085, CHEBI:8158
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Formula CH3O5P
Net Charge 0
Average Mass 126.00530
Monoisotopic Mass 125.972
InChI InChI=1S/CH3O5P/c2-1(3)7(4,5)6/h(H,2,3)(H2,4,5,6)
InChIKey ZJAOAACCNHFJAH-UHFFFAOYSA-N
SMILES OC(=O)P(O)(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): antiviral drug
A substance used in the prophylaxis or therapy of virus diseases.
HIV-1 reverse transcriptase inhibitor
An entity which inhibits the activity of HIV-1 reverse transcriptase.
sodium-dependent Pi-transporter inhibitor
Any substance that inhibits the action of sodium-dependent Pi-transporters.
Application(s): antiviral drug
A substance used in the prophylaxis or therapy of virus diseases.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing phosphonoformic acid (CHEBI:127780) has functional parent formic acid (CHEBI:30751)
phosphonoformic acid (CHEBI:127780) has functional parent phosphonic acid (CHEBI:44976)
phosphonoformic acid (CHEBI:127780) has role antiviral drug (CHEBI:36044)
phosphonoformic acid (CHEBI:127780) has role HIV-1 reverse transcriptase inhibitor (CHEBI:53756)
phosphonoformic acid (CHEBI:127780) has role sodium-dependent Pi-transporter inhibitor (CHEBI:63330)
phosphonoformic acid (CHEBI:127780) is a carboxylic acid (CHEBI:33575)
phosphonoformic acid (CHEBI:127780) is a one-carbon compound (CHEBI:64708)
phosphonoformic acid (CHEBI:127780) is a phosphonic acids (CHEBI:26069)
phosphonoformic acid (CHEBI:127780) is conjugate acid of phosphonatoformate (CHEBI:60268)
phosphonoformic acid (CHEBI:127780) is conjugate acid of phosphonoformate(2−) (CHEBI:91254)
Incoming CMP-5'-phosphonoformic acid (CHEBI:131759) has functional parent phosphonoformic acid (CHEBI:127780)
phosphonatoformate (CHEBI:60268) is conjugate base of phosphonoformic acid (CHEBI:127780)
phosphonoformate(2−) (CHEBI:91254) is conjugate base of phosphonoformic acid (CHEBI:127780)
IUPAC Name
dihydroxyphosphanecarboxylic acid oxide
Synonyms Sources
carboxyphosphonic acid ChemIDplus
Foscarmet KEGG COMPOUND
FOSCARNET ChEMBL
foscarnet ChEMBL
Foscarnet KEGG COMPOUND
PHOSPHONOFORMIC ACID PDBeChem
phosphonomethanoic acid ChEBI
Database Links Databases
C00000800 KNApSAcK
C06456 KEGG COMPOUND
DB00529 DrugBank
Foscarnet Wikipedia
PPF PDBeChem
View more database links
Registry Numbers Types Sources
1756501 Reaxys Registry Number Reaxys
4428-95-9 CAS Registry Number KEGG COMPOUND
4428-95-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11576919 PubMed citation Europe PMC
15182735 PubMed citation Europe PMC
16858125 PubMed citation Europe PMC
19213941 PubMed citation Europe PMC
19288498 PubMed citation Europe PMC
21056575 PubMed citation Europe PMC
21566148 PubMed citation Europe PMC
Last Modified
18 April 2016