Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C8H12N2O2.2ClH |
| Molecular Weight | 241.115 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.Cl.CC1=C(O)C(CN)=C(CO)C=N1
InChI
InChIKey=HNWCOANXZNKMLR-UHFFFAOYSA-N
InChI=1S/C8H12N2O2.2ClH/c1-5-8(12)7(2-9)6(4-11)3-10-5;;/h3,11-12H,2,4,9H2,1H3;2*1H
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C8H12N2O2 |
| Molecular Weight | 168.1931 |
| 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 |
|---|---|---|
| Molecular dynamics simulations of apo, holo, and inactivator bound GABA-at reveal the role of active site residues in PLP dependent enzymes. | 2016-07 |
|
| Biochemical and Structural Insights into the Aminotransferase CrmG in Caerulomycin Biosynthesis. | 2016-04-15 |
|
| Identification of novel thermostable taurine-pyruvate transaminase from Geobacillus thermodenitrificans for chiral amine synthesis. | 2016-04 |
|
| Crystal structure of glutamate-1-semialdehyde aminotransferase from Bacillus subtilis with bound pyridoxamine-5'-phosphate. | 2010-11-12 |
|
| Vitamin B6 metabolism in chronic kidney disease--relation to transsulfuration, advanced glycation and cardiovascular disease. | 2010 |
|
| Vitamin B6 deficient plants display increased sensitivity to high light and photo-oxidative stress. | 2009-11-10 |
|
| Application of the high-performance liquid chromatography method with coulometric detection for determination of vitamin B(6) in human plasma and serum. | 2009-10-01 |
|
| Poisoning pyridoxal 5-phosphate-dependent enzymes: a new strategy to target the malaria parasite Plasmodium falciparum. | 2009 |
|
| Metabolic profiling of an Echinostoma caproni infection in the mouse for biomarker discovery. | 2008-07-02 |
|
| Molecular evolution of B6 enzymes: binding of pyridoxal-5'-phosphate and Lys41Arg substitution turn ribonuclease A into a model B6 protoenzyme. | 2008-06-19 |
|
| Identification of a pyridoxine (pyridoxamine) 5'-phosphate oxidase from Arabidopsis thaliana. | 2007-02-06 |
|
| Expression, purification, and kinetic constants for human and Escherichia coli pyridoxal kinases. | 2004-08 |
|
| Bacillus subtilis GabR, a protein with DNA-binding and aminotransferase domains, is a PLP-dependent transcriptional regulator. | 2004-07-16 |
|
| 3-hydroxypyridine chromophores are endogenous sensitizers of photooxidative stress in human skin cells. | 2004-07-16 |
|
| A molecularly imprinted polymer-based synthetic transaminase. | 2004-07-14 |
|
| Transamination reactions with multiple turnovers catalyzed by hydrophobic pyridoxamine cofactors in the presence of polyethylenimine polymers. | 2004-07-07 |
|
| Genomic organization, tissue distribution and deletion mutation of human pyridoxine 5'-phosphate oxidase. | 2004-06 |
|
| Integrative annotation of 21,037 human genes validated by full-length cDNA clones. | 2004-06 |
|
| Structural studies of the catalytic reaction pathway of a hyperthermophilic histidinol-phosphate aminotransferase. | 2004-05-14 |
|
| Amelioration of the beta-cell dysfunction in diabetic APA hamsters by antioxidants and AGE inhibitor treatments. | 2004-05-11 |
|
| N,N'-ethylenebis(pyridoxylideneiminato) and N,N'-ethylenebis(pyridoxylaminato): synthesis, characterization, potentiometric, spectroscopic, and DFT studies of their vanadium(IV) and vanadium(V) complexes. | 2004-05-03 |
|
| [Carbonyl stress inhibitor towards new therapeutic interventions in diabetic nephropathy]. | 2004-05 |
|
| Conformational changes in the reaction of pyridoxal kinase. | 2004-04-23 |
|
| Regulation of glomerular endothelial cell proteoglycans by glucose. | 2004-04 |
|
| Pyridoxamine: an extremely potent scavenger of 1,4-dicarbonyls. | 2004-03 |
|
| Gateways to clinical trials. | 2004-02-28 |
|
| Effect of vitamin B6 on oxygen radicals, mitochondrial membrane potential, and lipid peroxidation in H2O2-treated U937 monocytes. | 2004-02-15 |
|
| Vigabatrin inhibits pyridoxine-5'-phosphate oxidase, not pyridoxal kinase in the hippocampus of seizure prone gerbils. | 2004-02 |
|
| Disruption of the plr1+ gene encoding pyridoxal reductase of Schizosaccharomyces pombe. | 2004-02 |
|
| Inactivation of gamma-aminobutyric acid aminotransferase by (S)-4-amino-4,5-dihydro-2-furancarboxylic acid does not proceed by the expected aromatization mechanism. | 2004-01-05 |
|
| American society of nephrology-36th annual meeting and renal week 2003. | 2004-01 |
|
| Advanced glycation end-products and the progress of diabetic vascular complications. | 2004 |
|
| Advanced glycation end products in clinical nephrology. | 2004 |
|
| Pyridoxal 5'-phosphate is a selective inhibitor in vivo of DNA polymerase alpha and epsilon. | 2003-12-26 |
|
| The nature of the rate-limiting steps in the refolding of the cofactor-dependent protein aspartate aminotransferase. | 2003-12-12 |
|
| Antioxidant activity of a Schiff base of pyridoxal and aminoguanidine. | 2003-12-01 |
|
| 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. | 2003-11-21 |
|
| Treponema denticola cystalysin catalyzes beta-desulfination of L-cysteine sulfinic acid and beta-decarboxylation of L-aspartate and oxalacetate. | 2003-11-20 |
|
| Involvement of advanced lipooxidation end products (ALEs) and protein oxidation in the apoptotic actions of nitric oxide in insulin secreting RINm5F cells. | 2003-11-15 |
|
| Pyridoxamine, an inhibitor of advanced glycation and lipoxidation reactions: a novel therapy for treatment of diabetic complications. | 2003-11-01 |
|
| Catalytic enantioselective transamination of alpha-keto esters: an organic approach to enzymatic reactions. | 2003-10-21 |
|
| Dendrimeric pyridoxamine enzyme mimics. | 2003-10-08 |
|
| Antioxidant activities of chitobiose and chitotriose. | 2003-09 |
|
| Tryptophan metabolism via transamination. In vitro aminotransferase assay using dinitrophenylhydrazine method. | 2003 |
|
| Clinical potential of advanced glycation end-product inhibitors in diabetes mellitus. | 2003 |
|
| The effect of vitamin B6 on cognition. | 2003 |
|
| Seizures induced by intracerebral administration of pyridoxal-5'-phosphate: effect of GABAergic drugs and glutamate receptor antagonists. | 2001-10 |
|
| Crystal structure of histidinol phosphate aminotransferase (HisC) from Escherichia coli, and its covalent complex with pyridoxal-5'-phosphate and l-histidinol phosphate. | 2001-08-24 |
|
| Inhibition of gp120-CD4 interaction and human immunodeficiency virus type 1 infection in vitro by pyridoxal 5'-phosphate. | 1994-10 |
|
| Determination of vitamin B6 vitamers and pyridoxic acid in biological samples. | 1992-07-01 |
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
YQ8NCR7V0O
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| Record Status |
Validated (UNII)
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| Record Version |
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |