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
Molecular Formula | C8H13N2O5P |
Molecular Weight | 248.173 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | H2O |
Molecular Weight | 18.0153 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
---|---|---|---|
Target ID: Carbonyl stress |
|||
Target ID: GO:0034440 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10801874 |
|||
Target ID: GO:0072593 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15905958 |
|||
Target ID: Advanced glycation end products |
|||
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 |
|||
Primary | Unknown Approved UseUnknown |
|||
PubMed
Title | Date | PubMed |
---|---|---|
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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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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FT-IR study of pyridoxamine 5' phosphate. | 2003 Apr 11 |
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Inhibition of diphenolase activity of tyrosinase by vitamin b(6) compounds. | 2003 Apr 23 |
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LR-90 a new advanced glycation endproduct inhibitor prevents progression of diabetic nephropathy in streptozotocin-diabetic rats. | 2003 Aug |
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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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Structure and properties of recombinant human pyridoxine 5'-phosphate oxidase. | 2003 Jul |
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Inhibitory effect of pyridoxal 5'-phosphate on endothelial cell proliferation, replicative DNA polymerase and DNA topoisomerase. | 2003 Jul |
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Synthesis of a novel radical trapping and carbonyl group trapping anti-AGE agent: a pyridoxamine analogue for inhibiting advanced glycation (AGE) and lipoxidation (ALE) end products. | 2003 Jul 24 |
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Origin of lipid A species modified with 4-amino-4-deoxy-L-arabinose in polymyxin-resistant mutants of Escherichia coli. An aminotransferase (ArnB) that generates UDP-4-deoxyl-L-arabinose. | 2003 Jul 4 |
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Expression of a Brassic napus glutamate 1-semialdehyde aminotransferase in Escherichia coli and characterization of the recombinant protein. | 2003 Jun |
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The AGE inhibitor pyridoxamine inhibits lipemia and development of renal and vascular disease in Zucker obese rats. | 2003 Jun |
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[The role of nonenzymatic glycation and glyco-oxidation in the development of diabetic vascular complications]. | 2003 May |
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The biosynthesis of GDP-L-colitose: C-3 deoxygenation is catalyzed by a unique coenzyme B6-dependent enzyme. | 2003 May 14 |
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Biosynthesis of Vitamin B(6) in yeast. Incorporation pattern of trioses. | 2003 May 2 |
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Pyridoxamine, an inhibitor of advanced glycation and lipoxidation reactions: a novel therapy for treatment of diabetic complications. | 2003 Nov 1 |
|
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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Stereochemistry of the reactions of glutamate-1-semialdehyde aminomutase with 4,5-diaminovalerate. | 2003 Oct 17 |
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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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Paradoxical impact of antioxidants on post-Amadori glycoxidation: Counterintuitive increase in the yields of pentosidine and Nepsilon-carboxymethyllysine using a novel multifunctional pyridoxamine derivative. | 2003 Oct 3 |
|
Dendrimeric pyridoxamine enzyme mimics. | 2003 Oct 8 |
|
Antioxidant activities of chitobiose and chitotriose. | 2003 Sep |
|
Advanced glycation end products in clinical nephrology. | 2004 |
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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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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 |
|
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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[Carbonyl stress inhibitor towards new therapeutic interventions in diabetic nephropathy]. | 2004 May |
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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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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 |
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:11:44 GMT 2023
by
admin
on
Fri Dec 15 16:11:44 GMT 2023
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Record UNII |
QWW7V29814
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C45812
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C81633
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DTXSID001005188
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300000008628
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C010627
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QWW7V29814
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DBSALT002045
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CHEMBL1235353
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE | |||
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ANHYDROUS->SOLVATE |