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Details

Stereochemistry ACHIRAL
Molecular Formula C8H13N2O5P
Molecular Weight 248.173
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PYRIDOXAMINE PHOSPHATE ANHYDROUS

SMILES

CC1=NC=C(COP(O)(O)=O)C(CN)=C1O

InChI

InChIKey=ZMJGSOSNSPKHNH-UHFFFAOYSA-N
InChI=1S/C8H13N2O5P/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)

HIDE SMILES / InChI

Description
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

Curator's Comment: Pyridoxamine (PM) crosses the blood-brain barrier in mice

Originator

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

PubMed

PubMed

TitleDatePubMed
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
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Name Type Language
PYRIDOXAMINE 5'-PHOSPHATE [MI]
Preferred Name English
PYRIDOXAMINE PHOSPHATE ANHYDROUS
Common Name English
4-AMINOMETHYL-3-HYDROXY-2-METHYL-5-((PHOSPHONOOXY)METHYL)PYRIDINE
Systematic Name English
Pyridoxamine phosphate [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C45812
Created by admin on Mon Mar 31 18:23:37 GMT 2025 , Edited by admin on Mon Mar 31 18:23:37 GMT 2025
Code System Code Type Description
PUBCHEM
1053
Created by admin on Mon Mar 31 18:23:37 GMT 2025 , Edited by admin on Mon Mar 31 18:23:37 GMT 2025
PRIMARY
ECHA (EC/EINECS)
208-471-6
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PRIMARY
DRUG BANK
DB02142
Created by admin on Mon Mar 31 18:23:37 GMT 2025 , Edited by admin on Mon Mar 31 18:23:37 GMT 2025
PRIMARY
CAS
529-96-4
Created by admin on Mon Mar 31 18:23:37 GMT 2025 , Edited by admin on Mon Mar 31 18:23:37 GMT 2025
PRIMARY
MERCK INDEX
m9363
Created by admin on Mon Mar 31 18:23:37 GMT 2025 , Edited by admin on Mon Mar 31 18:23:37 GMT 2025
PRIMARY Merck Index
EPA CompTox
DTXSID3046825
Created by admin on Mon Mar 31 18:23:37 GMT 2025 , Edited by admin on Mon Mar 31 18:23:37 GMT 2025
PRIMARY
FDA UNII
Q05R77UO7P
Created by admin on Mon Mar 31 18:23:37 GMT 2025 , Edited by admin on Mon Mar 31 18:23:37 GMT 2025
PRIMARY
NCI_THESAURUS
C81631
Created by admin on Mon Mar 31 18:23:37 GMT 2025 , Edited by admin on Mon Mar 31 18:23:37 GMT 2025
PRIMARY
SMS_ID
300000008626
Created by admin on Mon Mar 31 18:23:37 GMT 2025 , Edited by admin on Mon Mar 31 18:23:37 GMT 2025
PRIMARY