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Phosphonic Acids

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Definition: Inorganic or organic derivatives of phosphonic acid with the general formula ROP(OH)2 or RP(=O)(OH)2. The tautomeric form of this compound (P(OH)3) is PHOSPHOROUS ACIDS. Nucleoside phosphonates have a phosphate-carbon bond that is more resistant to enzymatic cleavage than the normal phosphate-oxygen bond.  do not confuse with PHOSPHINIC ACIDS; for nucleoside phosphonates coordinate with PURINES or PYRIMIDINES    Other names Esters, Phosphonic Acid; Acids, Phosphonic; Acid Esters, Phosphonic; Phosphonic Acid Esters; Phosphonates
 
SubstanceCAS Registry & nameCategoriesSourceDrugs*
alpha-hydroxyfarnesylphosphonic acid  0   *Phosphonic Acids Farnesol/*analogs & derivatives. Anticancer Res. 2012 Mar;32(3):831-8.
(1R*,2R*)-1,2-dihydroxy-(1-(13)C(1))propylphosphonic acid  0   *Phosphonic Acids Propane/*analogs & derivatives. Chemistry. 2011 Nov 18;17(47):13341-8
phosphonic acid  13598-36-2   *Phosphonic Acids *Phosphorous Acids.
2-amino-4-((3-(carboxymethyl)phenyl)(methyl)phosphono)butanoic acid  0   *Aminobutyric Acids *Phosphonic Acids gamma-Glutamyltransferase/antagonists & inhibitors. J Pharmacol Exp Ther. 2011 Dec;339(3):945-51.
n-propanephosphonic acid anhydride  0   *Phosphonic Acids Propane/*analogs & derivatives. Org Lett. 2011 Oct 7;13(19):5048-51
N1-(4-bis(pivaloyloxymethyl)phosphinylbuten-2-yl)thymine  0   *Phosphonic Acids Thymidine/*analogs & derivatives. J Med Chem 2011 Jan 13;54(1):222-32
diethylcyanophosphonate  0   *Phosphonic Acids. Chemistry 2011 Jun 14;17(25):6931-4
diethyl 2-((furan-2-ylmethyl)carbamoyl)ethylphosphonate  0   *Furans *Phosphonic Acids. Bioorg Med Chem 2011 Feb 1;19(3):1321-7
octadecyloxyethyl-cyclic-cidofovir  0   *Phosphonic Acids Cytosine/*analogs & derivatives. J Ocul Pharmacol Ther 2011 Apr;27(2):157-62
4-pentadecylbenzylphosphonic acid  0   *Phosphonic Acids. ChemMedChem. 2011 May 2;6(5):922-35
glycyl-prolyl-diphenylphosphonic acid  0   *Dipeptides *Phosphonic Acids Dipeptidyl Peptidase 4. Arch Dermatol Res 2010 Dec;302(10):725-31
3-phosphonoalanine  0   *Phosphonic Acids Alanine/*analogs & derivatives. Org Biomol Chem 2011 Jan 7;9(1):111-9
benzenetriyl-1,3,5-tris(methylphosphonic acid)  0   *Benzene Derivatives *Phosphonic Acids. Dalton Trans. 2010 Dec 7;39(45):11008-18
biphenyldiyl-2,2'-bis(methylphosphonic acid)  0   *Biphenyl Compounds *Phosphonic Acids. Dalton Trans. 2010 Dec 7;39(45):11008-18
diethyl (6-amino-9H-purin-9-yl) methylphosphonate  0   *Phosphonic Acids *Purines. Free Radic Res. 2010 Aug;44(8):881-90
(benzoxazol-2-ylmethyl)phosphonic acid  0   *Benzoxazoles *Phosphonic Acids. Inorg Chem. 2010 Oct 18;49(20):9369-79
(5-(2-amino-5-(2-methylpropyl)-4-thiazolyl)-2-furanyl)phosphonic acid  0   *Phosphonic Acids *Thiazoles Fructose-Bisphosphatase/antagonists & inhibitors. Proc Natl Acad Sci U S A 2005 May 31;102(22):7970-5
2-ethylhexyl phosphonic acid mono-2-ethylhexyl ester  0   *Phosphonic Acids. Chemosphere. 2010 Jun;80(4):433-7
octadecyloxyethyl 9-(2-(phosphonomethoxy)ethyl)guanine  0   *Phosphonic Acids Guanine/*analogs & derivatives. Chemotherapy 2010;56(1):54-9
acycloguanosine H-phosphonate  0   *Phosphonic Acids Acyclovir/*analogs & derivatives. Vopr Virusol. 2010 Jan-Feb;55(1):31-4
2-hydroxy-3-imidazo(1,2-a)pyridin-3-yl-2-phosphonopropionic acid  0   *Lactates *Phosphonic Acids. J Med Chem 2010 May 13;53(9):2454-64
hexakis(p-phosphonatophenyl)benzene  0   *Benzene Derivatives *Phosphonic Acids. Angew Chem Int Ed Engl. 2009;48(52):9951-3
poly((mu2-aqua(mu3-1-hydroxy-2-(1H,3H-imidazol-3-ium-1-yl)ethylidenediphosphonato)potassium(I))monohydrate)  0   *Imidazoles *Phosphonic Acids. Acta Crystallogr C. 2010 Jan;66(Pt 1):m13-6
ethyl phosphonate  0   *Phosphonic Acids. Acta Crystallogr Sect F Struct Biol Cryst Commun 2009 Sep 1;65(Pt 9):862-5
((5-methyl-2-pyridinio)aminomethylene)diphosphonate dianion  0   *Phosphonic Acids *Pyridines. Acta Crystallogr C. 2009 Jun;65(Pt 6):o261-6
1-(4-aminobutanoyl)-4-(1,3-bis(dihydroxyphosphoryloxy)propan-2-yloxy)-7-nitroindoline  0   *Indoles *Phosphonic Acids Receptors, GABA-A/antagonists & inhibitors. J Neurosci Methods 2009 Jul 30;181(2):159-69
170Tm-ethylenediamine-tetramethylenephosphonic acid  0   *Organometallic Compounds *Phosphonic Acids Thulium. Nucl Med Biol 2009 Jul;36(5):561-8
4-methylphosphonophenylisothiocyanate  0   *Phosphonic Acids *Isothiocyanates. J Am Soc Mass Spectrom 2009 Mar;20(3):377-84
FTY720-(E)-vinylphosphonate  0   *Vinyl Compounds Sphingosine/*analogs & derivatives Phosphonic Acids. J Org Chem. 2009 Apr 17;74(8):3192-5
hydroxymethylphosphonate  0   *Phosphonic Acids. J Antibiot (Tokyo) 1984 Nov;37(11):1505-8
1-(3-fluoro-2-(phosphonomethoxy)propyl)thymine  0   *Phosphonic Acids Thymine/*analogs & derivatives Thymidine Phosphorylase/antagonists & inhibitors. Biochem Pharmacol 2005 May 15;69(10):1517-21
3-mercaptopropylphosphonic acid  0   *Phosphonic Acids *Sulfhydryl Compounds. Bioelectrochemistry. 2009 Apr;75(1):26-31
propylphosphonic acid anhydride  0   *Anhydrides *Phosphonic Acids. Adv Exp Med Biol 2009;611:193-4
3,5-dimethyl-4-(4'-hydroxy-3'-isopropylbenzyl)phenoxy methylphosphonic acid  0   *Phenols *Phosphonic Acids. Br J Pharmacol 2009 Feb;156(3):454-65
2-((3,5-dimethyl-4-(4'-hydroxy-3'-isopropylbenzyl)phenoxy)methyl)-4-(3-chlorophenyl)-2-oxido(1,3,2)dioxaphosphonane  0   *Phosphonic Acids. J Med Chem 2008 Nov 27;51(22):7075-93
n-octylphosphonic acid  0   *Phosphonic Acids. Langmuir 2008 Dec 2;24(23):13450-6
(4-(tetradecanoylamino)benzyl)phosphonic acid  0   *Anilides *Phosphonic Acids. J Pharmacol Exp Ther 2008 Dec;327(3):809-19
2-hydroxybutylphosphonic acid  0   *Phosphonic Acids. Bioorg Med Chem Lett. 2008 May 15;18(10):3056-9
2-hydroxyethylphosphonic acid  0   *Phosphonic Acids. Bioorg Med Chem Lett. 2008 May 15;18(10):3056-9
2-hydroxypropylphosphonic acid  0   *Phosphonic Acids. Bioorg Med Chem Lett. 2008 May 15;18(10):3056-9
octadecyloxyethyl 9-(3-hydroxy-2-(phosphonomethoxy)propyl)adenine  0   *Phosphonic Acids Adenine/*analogs & derivatives. Antimicrob Agents Chemother 2006 Aug;50(8):2857-9
(6,7-dihydro-5H-cyclopenta(c)pyridin-7-yl(hydroxy)methylene)bis(phosphonic acid)  0   *Phosphonic Acids *Pyridines. Bioorg Med Chem Lett. 2008 May 1;18(9):2878-82
((4-chlorophenyl)-(hydroxyamidophosphinoyl)-methyl) phosphonic acid  0   *Hydrocarbons, Chlorinated *Phosphonic Acids. Eur J Med Chem. 2008 Apr;43(4):885-92
((3-bromo-7-cyano-2-naphthyl)(difluoro)methyl)phosphonic acid  0   *Naphthalenes *Phosphonic Acids. Bioorg Med Chem Lett 2008 Jun 1;18(11):3200-5
2-aminocyclohexylcarbamoylphosphonic acid  0   *Phosphonic Acids Matrix Metalloproteinases/antagonists & inhibitors. J Med Chem 2008 Mar 13;51(5):1406-14
9-(5',5'-difluoro-5'-phosphonopentyl)-9-deazaguanine  0   *Phosphonic Acids Guanine/*analogs & derivatives. Nucleic Acids Symp Ser (Oxf) 2007;(51):431-2
N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-N-oxyl  0   *Phosphonic Acids. Chemphyschem 2008 Feb 1;9(2):272-81
ethane-1,1,2-trisphosphonic acid  0   *Phosphonic Acids Ethane/*analogs & derivatives. Acta Crystallogr C. 2008 Feb;64(Pt 2):o47-9
methyl 1-(bis(4-acetamidophenoxy)phosphoryl)-2-(4-guanidinophenyl)ethylcarbamate  0   *Guanidines *Phosphonic Acids Urokinase-Type Plasminogen Activator/antagonists & inhibitors. J Med Chem 2007 Dec 27;50(26):6638-46
methyl 1-(diphenoxyphosphoryl)-2-(4-guanidinophenyl)ethylcarbamate  0   *Guanidines *Phosphonic Acids Urokinase-Type Plasminogen Activator/antagonists & inhibitors. J Med Chem 2007 Dec 27;50(26):6638-46
2-fluoro-3-(3-pyridinyl)-2-phosphonopropionic acid  0   *Phosphonic Acids *Propionic Acids. J Med Chem 2007 Nov 29;50(24):5967-75
(5-(6-amino-purin-9-yl)-2,5-dihydrofuran-2-yloxymethyl)phosphonic acid  0   *Nucleosides *Phosphonic Acids. Bioorg Med Chem Lett 2007 Dec 15;17(24) (dup#1):6785-9
alpha-ethyl-N-(phosphonomethyl)glycine  0   *Phosphonic Acids Glycine/*analogs & derivatives. Amino Acids 2007 Nov;33(4):695-702
cidofovir hexadecyloxypropyl ester  0   *Phosphonic Acids Cytosine/*analogs & derivatives. Antimicrob Agents Chemother 2007 Nov;51(11):4118-24
methyl linolenoylfluorophosphonate  0   *Phosphonic Acids. J Lipid Res 2007 Nov;48(11):2365-76
hexadecyloxypropyl 9-(2-(phosphonomethoxy)propyl)adenine  0   *Phosphonic Acids Adenine/*analogs & derivatives. Antimicrob Agents Chemother 2007 Oct;51(10):3505-9
O-phenyl (triphenylphosphoniomethyl)phosphonate  0   *Phosphonic Acids. Acta Crystallogr C 2007 Sep;63(Pt 9):o504-6
(4-iodo-phenyl)phenyl phosphinic acid  0   *Phosphonic Acids. Langmuir 2007 Jul 17;23(15):8257-63
1-amino-2-phosphonomethylcyclopropanecarboxylic acid  0   *Amino Acids *Phosphonic Acids Cyclopropanes Receptors, Metabotropic Glutamate/agonists. J Med Chem 2007 Jul 26;50(15):3585-95
cyclohexane-1,2-diamine-N,N,N',N'-tetrakis(methylenephosphonic acid)  0   *Cyclohexylamines *Phosphonic Acids. Dalton Trans 2006 Sep 28;(36):4384-94
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Sources: NLM Medical Subject Headings, NIH UMLS, Drugs@FDA, FDA AERS original data copyright United States Government. No endorsement implied. Last modified 6/6/2012

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