Details
Stereochemistry | ACHIRAL |
Molecular Formula | C8H13N2O5P.2H2O |
Molecular Weight | 284.2035 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.CC1=C(O)C(CN)=C(COP(O)(O)=O)C=N1
InChI
InChIKey=XYFGQXNREWPENX-UHFFFAOYSA-N
InChI=1S/C8H13N2O5P.2H2O/c1-5-8(11)7(2-9)6(3-10-5)4-15-16(12,13)14;;/h3,11H,2,4,9H2,1H3,(H2,12,13,14);2*1H2
DescriptionSources: http://www.efsa.europa.eu/sites/default/files/scientific_output/files/main_documents/760.pdfhttps://www.ncbi.nlm.nih.gov/pubmed/16037308 | https://www.ncbi.nlm.nih.gov/pubmed/15905958 | http://www.nephrogenex.com/ | https://www.ncbi.nlm.nih.gov/pubmed/19434047Curator's Comment: description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/12542535 | https://www.ncbi.nlm.nih.gov/pubmed/479950
Sources: http://www.efsa.europa.eu/sites/default/files/scientific_output/files/main_documents/760.pdfhttps://www.ncbi.nlm.nih.gov/pubmed/16037308 | https://www.ncbi.nlm.nih.gov/pubmed/15905958 | http://www.nephrogenex.com/ | https://www.ncbi.nlm.nih.gov/pubmed/19434047
Curator's Comment: description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/12542535 | https://www.ncbi.nlm.nih.gov/pubmed/479950
Pyridoxamine (PM) is one of three natural forms of vitamin B6. It is a critical transient intermediate in catalysis of transamination reactions by vitamin B6-dependent enzymes. In preclinical or clinical trials PM has demonstrated pharmacological potential
for treatment of diabetic nephropathy, diabetic retinopathy, and hyperlipidemia, and
for use in kidney stone preventive therapies. Although its precise mode of action in
vivo is not yet clear, it is likely that at least three mechanisms are at play: inhibition
of post-Amadori steps of the Maillard reaction; scavenging of reactive carbonyl
compounds; and inhibition of toxic effects of ROS. Pyridoxamine was marketed as a dietary supplement, often as the hydrochloride salt, pyridoxamine dihydrochloride. However, in the United States, the FDA ruled in January 2009 that pyridoxamine must be regulated as a pharmaceutical drug because it is the active ingredient in Pyridorin, a drug designed to prevent the progression of diabetic nephropathy.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23970548
Curator's Comment: Pyridoxamine (PM) crosses the blood-brain barrier in mice
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20259097https://www.ncbi.nlm.nih.gov/pubmed/16037308
Curator's Comment: Pyridoxamine (PM) was purified from animal tissues and identified in 1944 in the laboratory of Esmond Snell during the study of microbiological assays for vitamin B6
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: Carbonyl stress |
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Target ID: GO:0034440 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10801874 |
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Target ID: GO:0072593 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15905958 |
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Target ID: Advanced glycation end products |
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Target ID: 1.00521112E8 Gene Symbol: PNPO Sources: https://www.ncbi.nlm.nih.gov/pubmed/6243300 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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PubMed
Title | Date | PubMed |
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Inhibition of gp120-CD4 interaction and human immunodeficiency virus type 1 infection in vitro by pyridoxal 5'-phosphate. | 1994 Oct |
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Crystal structure of histidinol phosphate aminotransferase (HisC) from Escherichia coli, and its covalent complex with pyridoxal-5'-phosphate and l-histidinol phosphate. | 2001 Aug 24 |
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Seizures induced by intracerebral administration of pyridoxal-5'-phosphate: effect of GABAergic drugs and glutamate receptor antagonists. | 2001 Oct |
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Tryptophan metabolism via transamination. In vitro aminotransferase assay using dinitrophenylhydrazine method. | 2003 |
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Clinical potential of advanced glycation end-product inhibitors in diabetes mellitus. | 2003 |
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The effect of vitamin B6 on cognition. | 2003 |
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Antioxidant activity of a Schiff base of pyridoxal and aminoguanidine. | 2003 Dec 1 |
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The nature of the rate-limiting steps in the refolding of the cofactor-dependent protein aspartate aminotransferase. | 2003 Dec 12 |
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Pyridoxal 5'-phosphate is a selective inhibitor in vivo of DNA polymerase alpha and epsilon. | 2003 Dec 26 |
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Pyridoxamine, an inhibitor of advanced glycation and lipoxidation reactions: a novel therapy for treatment of diabetic complications. | 2003 Nov 1 |
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Involvement of advanced lipooxidation end products (ALEs) and protein oxidation in the apoptotic actions of nitric oxide in insulin secreting RINm5F cells. | 2003 Nov 15 |
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Treponema denticola cystalysin catalyzes beta-desulfination of L-cysteine sulfinic acid and beta-decarboxylation of L-aspartate and oxalacetate. | 2003 Nov 20 |
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Modification of proteins in vitro by physiological levels of glucose: pyridoxamine inhibits conversion of Amadori intermediate to advanced glycation end-products through binding of redox metal ions. | 2003 Nov 21 |
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Catalytic enantioselective transamination of alpha-keto esters: an organic approach to enzymatic reactions. | 2003 Oct 21 |
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Pyridoxamine traps intermediates in lipid peroxidation reactions in vivo: evidence on the role of lipids in chemical modification of protein and development of diabetic complications. | 2003 Oct 24 |
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Dendrimeric pyridoxamine enzyme mimics. | 2003 Oct 8 |
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Antioxidant activities of chitobiose and chitotriose. | 2003 Sep |
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Advanced glycation end-products and the progress of diabetic vascular complications. | 2004 |
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Advanced glycation end products in clinical nephrology. | 2004 |
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Regulation of glomerular endothelial cell proteoglycans by glucose. | 2004 Apr |
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Conformational changes in the reaction of pyridoxal kinase. | 2004 Apr 23 |
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Expression, purification, and kinetic constants for human and Escherichia coli pyridoxal kinases. | 2004 Aug |
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Vigabatrin inhibits pyridoxine-5'-phosphate oxidase, not pyridoxal kinase in the hippocampus of seizure prone gerbils. | 2004 Feb |
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Disruption of the plr1+ gene encoding pyridoxal reductase of Schizosaccharomyces pombe. | 2004 Feb |
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Effect of vitamin B6 on oxygen radicals, mitochondrial membrane potential, and lipid peroxidation in H2O2-treated U937 monocytes. | 2004 Feb 15 |
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American society of nephrology-36th annual meeting and renal week 2003. | 2004 Jan |
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Inactivation of gamma-aminobutyric acid aminotransferase by (S)-4-amino-4,5-dihydro-2-furancarboxylic acid does not proceed by the expected aromatization mechanism. | 2004 Jan 5 |
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Gateways to clinical trials. | 2004 Jan-Feb |
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A molecularly imprinted polymer-based synthetic transaminase. | 2004 Jul 14 |
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Bacillus subtilis GabR, a protein with DNA-binding and aminotransferase domains, is a PLP-dependent transcriptional regulator. | 2004 Jul 16 |
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3-hydroxypyridine chromophores are endogenous sensitizers of photooxidative stress in human skin cells. | 2004 Jul 16 |
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Transamination reactions with multiple turnovers catalyzed by hydrophobic pyridoxamine cofactors in the presence of polyethylenimine polymers. | 2004 Jul 7 |
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Genomic organization, tissue distribution and deletion mutation of human pyridoxine 5'-phosphate oxidase. | 2004 Jun |
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Integrative annotation of 21,037 human genes validated by full-length cDNA clones. | 2004 Jun |
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Pyridoxamine: an extremely potent scavenger of 1,4-dicarbonyls. | 2004 Mar |
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[Carbonyl stress inhibitor towards new therapeutic interventions in diabetic nephropathy]. | 2004 May |
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Structural studies of the catalytic reaction pathway of a hyperthermophilic histidinol-phosphate aminotransferase. | 2004 May 14 |
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N,N'-ethylenebis(pyridoxylideneiminato) and N,N'-ethylenebis(pyridoxylaminato): synthesis, characterization, potentiometric, spectroscopic, and DFT studies of their vanadium(IV) and vanadium(V) complexes. | 2004 May 3 |
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Amelioration of the beta-cell dysfunction in diabetic APA hamsters by antioxidants and AGE inhibitor treatments. | 2004 May-Jun |
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Identification of a pyridoxine (pyridoxamine) 5'-phosphate oxidase from Arabidopsis thaliana. | 2007 Feb 6 |
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Metabolic profiling of an Echinostoma caproni infection in the mouse for biomarker discovery. | 2008 Jul 2 |
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Molecular evolution of B6 enzymes: binding of pyridoxal-5'-phosphate and Lys41Arg substitution turn ribonuclease A into a model B6 protoenzyme. | 2008 Jun 19 |
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Poisoning pyridoxal 5-phosphate-dependent enzymes: a new strategy to target the malaria parasite Plasmodium falciparum. | 2009 |
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Vitamin B6 deficient plants display increased sensitivity to high light and photo-oxidative stress. | 2009 Nov 10 |
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Application of the high-performance liquid chromatography method with coulometric detection for determination of vitamin B(6) in human plasma and serum. | 2009 Oct 1 |
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Vitamin B6 metabolism in chronic kidney disease--relation to transsulfuration, advanced glycation and cardiovascular disease. | 2010 |
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Crystal structure of glutamate-1-semialdehyde aminotransferase from Bacillus subtilis with bound pyridoxamine-5'-phosphate. | 2010 Nov 12 |
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Identification of novel thermostable taurine-pyruvate transaminase from Geobacillus thermodenitrificans for chiral amine synthesis. | 2016 Apr |
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Biochemical and Structural Insights into the Aminotransferase CrmG in Caerulomycin Biosynthesis. | 2016 Apr 15 |
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Molecular dynamics simulations of apo, holo, and inactivator bound GABA-at reveal the role of active site residues in PLP dependent enzymes. | 2016 Jul |
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NCI_THESAURUS |
C45812
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C81633
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DTXSID001005188
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C010627
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QWW7V29814
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DBSALT002045
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CHEMBL1235353
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD