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
Inhibition of herpes simplex virus replication by phosphonoacetic acid.	1974 Sep	15830487
Inhibitors of human immunodeficiency virus type 1 reverse transcriptase target distinct phases of early reverse transcription.	2001 Apr	11238836
Gene amplification in fibroblasts from ataxia telangiectasia (AT) patients and in X-ray hypersensitive AT-like Chinese hamster mutants.	2001 Jan	11159752
Increased gene amplification in immortal rodent cells deficient for the DNA-dependent protein kinase catalytic subunit.	2001 Jun 1	11389084
The allosteric activator Mg-ATP modifies the quaternary structure of the R-state of Escherichia coli aspartate transcarbamylase without altering the T<-->R equilibrium.	2001 Jun 8	11397099
Pharmacological cyclin-dependent kinase inhibitors inhibit replication of wild-type and drug-resistant strains of herpes simplex virus and human immunodeficiency virus type 1 by targeting cellular, not viral, proteins.	2002 Aug	12097601
Induction of gene amplification as a gain-of-function phenotype of mutant p53 proteins.	2002 Jun 1	12036943
Caspase-dependent cleavage of carbamoyl phosphate synthetase II during apoptosis.	2002 Mar	11854437
Phosphine and methane generation by the addition of organic compounds containing carbon-phosphorus bonds into incubated soil.	2002 Nov	12430652
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
Down-regulation of MHC class I expression by equine herpesvirus-1.	2003 Feb	12560560
Phosphonoacetic acid as a building block in supramolecular chemistry: salts with organic polyamines.	2003 Feb	12554975
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
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
Cyclic sulfamidates as vehicles for the synthesis of substituted lactams.	2004 Dec 9	15575671
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
In vitro selection of drug-resistant varicella-zoster virus (VZV) mutants (OKA strain): differences between acyclovir and penciclovir?	2004 Mar	15168799
Efficient synthesis of fluorothiosparfosic acid analogues with potential antitumoral activity.	2005 Aug 15	15975800
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
Phosphonate catabolism by Campylobacter spp.	2005 Feb	15647906
A facile synthesis of novel chiral phosphonoacetates bearing a stereogenic phosphorus atom.	2005 Jan	15635249
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
Susceptibilities of several clinical varicella-zoster virus (VZV) isolates and drug-resistant VZV strains to bicyclic furano pyrimidine nucleosides.	2005 Mar	15728906
Functional inaccessibility of quiescent herpes simplex virus genomes.	2005 Nov 21	16300675
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
Continued survival of more than ten years, without resection of metastatic disease, in patients with metastatic colorectal cancer treated with biomodulated fluorouracil: report of two cases.	2006 Mar	16475032
Phosphonoacetate hydrolase from Penicillium oxalicum: purification and properties, phosphate starvation-independent expression, and partial sequencing.	2006 Mar	16129582
Synergistic antiviral activity of acyclovir and vidarabine against herpes simplex virus types 1 and 2 and varicella-zoster virus.	2006 Nov	16797734
Selective excision of chain-terminating nucleotides by HIV-1 reverse transcriptase with phosphonoformate as substrate.	2006 Sep 22	16829515
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
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