PHOSPHONOACETIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C2H5O5P
Molecular Weight	140.0319
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)CP(O)(O)=O

InChI

InChIKey=XUYJLQHKOGNDPB-UHFFFAOYSA-N

InChI=1S/C2H5O5P/c3-2(4)1-8(5,6)7/h1H2,(H,3,4)(H2,5,6,7)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7069603 | https://www.ncbi.nlm.nih.gov/pubmed/212978

Fosfonet sodium (or phosphonoacetate sodium), an organophosphorus compound, was found to be a specific inhibitor of the virus-induced DNA polymerases and thus could inhibit specifically the replication of herpes-viruses.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA polymerase catalytic subunit 14 Target ID: P04293 Gene ID: 2703462.0 Gene Symbol: NA Target Organism: Human herpesvirus 1 (strain 17) (HHV-1) (Human herpes simplex virus\|\|\|1) Sources: https://www.ncbi.nlm.nih.gov/pubmed/189089 \| https://www.ncbi.nlm.nih.gov/pubmed/172657	Interacts 323

PubMed

Title	Date	PubMed
In vitro antiviral activity of polyoxotungstate (PM-19) and other polyoxometalates against herpes simplex virus.	1991 Dec	1663733
[Embryonal stem cells do not undergo cell cycle arrest upon exposure to damaging factors].	2002	12455372
[The effect of Kagocel on herpes virus reproduction].	2002 Jul-Aug	12271726
Gamma-ray and hydrogen peroxide induction of gene amplification in hamster cells deficient in DNA double strand break repair.	2002 Jun 21	12509235
Phosphine and methane generation by the addition of organic compounds containing carbon-phosphorus bonds into incubated soil.	2002 Nov	12430652
Overexpression of the 18 kDa and 22/24 kDa FGF-2 isoforms results in differential drug resistance and amplification potential.	2002 Oct	12209881
Genomic instability driven by the human T-cell leukemia virus type I (HTLV-I) oncoprotein, Tax.	2002 Oct 17	12370813
Complexation of beryllium(II) ion by phosphinate ligands in aqueous solution. Synthesis and XRPD structure determination of Be[(PhPO2)2CH2](H2O)2.	2003 Apr 7	12665369
Phosphonoacetic acid as a building block in supramolecular chemistry: salts with organic polyamines.	2003 Feb	12554975
Solid-phase chemical synthesis of phosphonoacetate and thiophosphonoacetate oligodeoxynucleotides.	2003 Jan 29	12537492
Design and synthesis of phosphonoacetic acid (PPA) ester and amide bioisosters of ribofuranosylnucleoside diphosphates as potential ribonucleotide reductase inhibitors and evaluation of their enzyme inhibitory, cytostatic and antiviral activity.	2003 Jul	14582847
The purification and characterization of phosphonopyruvate hydrolase, a novel carbon-phosphorus bond cleavage enzyme from Variovorax sp Pal2.	2003 Jun 27	12697754
Herpes simplex virus replication compartments can form by coalescence of smaller compartments.	2003 May 10	12758171
A metal-independent hydrolase from a Penicillium oxalicum strain able to use phosphonoacetic acid as the only phosphorus source.	2003 May 28	12770709
Efficacy of Thai medicinal plant extracts against herpes simplex virus type 1 infection in vitro and in vivo.	2003 Nov	14638393
Synthesis and biological evaluation of S-acyl-3-thiopropyl prodrugs of N-phosphonoacetyl-L-aspartate (PALA).	2003 Oct	14575935
A phase II study of high-dose 24 hour continuous infusion 5-FU and leucovorin and low-dose PALA for patients with advanced pancreatic adenocarcinoma: a Southwest Oncology Group Study.	2004 Aug	15122082
Treatment of intracranial rat glioma model with implant of radiosensitizer and biomodulator drug combined with external beam radiotherapy.	2004 Feb 1	14751523
Suppression of generation and replication of acyclovir-resistant herpes simplex virus by a sensitive virus.	2004 Jan	14635018
Tetrahedral intermediates in thiamin diphosphate-dependent decarboxylations exist as a 1',4'-imino tautomeric form of the coenzyme, unlike the michaelis complex or the free coenzyme.	2004 Jun 1	15157089
A phase II pilot study of high-dose 24-hour continuous infusion of 5-FU and leucovorin and low-dose PALA for patients with colorectal cancer: a Southwest Oncology Group study.	2004 Nov	15292717
Antiviral activity of the marine alga Symphyocladia latiuscula against herpes simplex virus (HSV-1) in vitro and its therapeutic efficacy against HSV-1 infection in mice.	2005 Dec	16327161
Severe cytochrome c oxidase inhibition in vivo does not induce a pyrimidine deficiency; neuroprotective action of oral uridine prodrug PN401 requires supraphysiological levels of uridine.	2005 Dec 20	16330000
The human cytomegalovirus UL78 gene is highly conserved among clinical isolates, but is dispensable for replication in fibroblasts and a renal artery organ-culture system.	2005 Feb	15659748
Phosphonate catabolism by Campylobacter spp.	2005 Feb	15647906
The antiviral activity of the combinations of netropsin derivatives with modified nucleosides and phosphonoacetic acid as estimated in the model of herpesvirus type 1 in a vero cell culture.	2005 Jan-Feb	15846992
Effect of ligand structure on the pathways for iron release from human serum transferrin.	2005 Jul 11	15998048
Anion binding and controlled aggregation of human interleukin-1 receptor antagonist.	2005 Jul 26	16026159
[Photodynamic inhibition of infection caused by herpes simplex virus type 1 in the cultured cells, by using 5-aminolevulinic acid-induced porphyrins].	2005 Jul-Aug	16104524
Aspartate transcarbamylase from the hyperthermophilic archaeon Pyrococcus abyssi. Insights into cooperative and allosteric mechanisms.	2005 Jun	15943802
Sensitivity to phosphonoacetic acid: a new phenotype to probe DNA polymerase delta in Saccharomyces cerevisiae.	2005 Jun	15802517
Genomic instability in Gadd45a-/- cells is coupled with S-phase checkpoint defects.	2005 May	15846075
Adenosine phosphonoacetic acid is slowly metabolized by NDP kinase.	2005 Nov	16787337
Functional inaccessibility of quiescent herpes simplex virus genomes.	2005 Nov 21	16300675
Alpha-herpesvirus infection induces the formation of nuclear actin filaments.	2006 Aug	16933992
A role for carbon catabolite repression in the metabolism of phosphonoacetate by Agromyces fucosus Vs2.	2006 Aug	16842370
Phosphonoacetic acid utilization by fungal isolates: occurrence and properties of a phosphonoacetate hydrolase in some penicillia.	2006 Dec	17123811
Development of a common fully stereocontrolled access to the medicinally important and promising prostacyclin analogues iloprost, 3-oxa-iloprost and cicaprost.	2006 Jul 17	16708414
Bond strength to primed Ti-6Al-7Nb alloy of two acrylic resin adhesives.	2006 Jun	16916231
Fully stereocontrolled syntheses of 3-oxacarbacyclin and carbacyclin by the conjugate addition-azoalkene-asymmetric olefination strategy.	2006 Jun 9	16749799
Phosphonoacetate hydrolase from Penicillium oxalicum: purification and properties, phosphate starvation-independent expression, and partial sequencing.	2006 Mar	16129582
Detection of phosphonoacetate degradation and phnA genes in soil bacteria from distinct geographical origins suggest its possible biogenic origin.	2006 May	16623750
Synergistic antiviral activity of acyclovir and vidarabine against herpes simplex virus types 1 and 2 and varicella-zoster virus.	2006 Nov	16797734
Picosecond dynamics of T and R forms of aspartate transcarbamylase: a neutron scattering study.	2006 Oct	17008138
N-phosphonacetyl-L-isoasparagine a potent and specific inhibitor of Escherichia coli aspartate transcarbamoylase.	2006 Oct 5	17004708
Design, synthesis, and bioactivity of novel inhibitors of E. coli aspartate transcarbamoylase.	2007 Apr 1	17336518
Glycosaminoglycan interactions in murine gammaherpesvirus-68 infection.	2007 Apr 4	17406671
Enriching suicide gene bearing tumor cells for an increased bystander effect.	2007 Jan	17024230
Unique uptake and efflux systems of inorganic phosphate in osteoclast-like cells.	2007 Jan	16971494
Autophagy suppresses tumor progression by limiting chromosomal instability.	2007 Jun 1	17510285

Patents

Name

Type

Language

PHOSPHONOACETIC ACID

Systematic Name

English

NSC-18205

Code

English

FOSFONET

Common Name

English

PHOSPHONOACETATE

Systematic Name

English

Classification Tree Code System Code

WHO-ATC

J05AD02