U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of PYRIDOXAMINE PHOSPHATE

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

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
Inhibition of gp120-CD4 interaction and human immunodeficiency virus type 1 infection in vitro by pyridoxal 5'-phosphate.
1994 Oct
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
Seizures induced by intracerebral administration of pyridoxal-5'-phosphate: effect of GABAergic drugs and glutamate receptor antagonists.
2001 Oct
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
Antioxidant activity of a Schiff base of pyridoxal and aminoguanidine.
2003 Dec 1
The nature of the rate-limiting steps in the refolding of the cofactor-dependent protein aspartate aminotransferase.
2003 Dec 12
Pyridoxal 5'-phosphate is a selective inhibitor in vivo of DNA polymerase alpha and epsilon.
2003 Dec 26
Pyridoxamine, an inhibitor of advanced glycation and lipoxidation reactions: a novel therapy for treatment of diabetic complications.
2003 Nov 1
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
Treponema denticola cystalysin catalyzes beta-desulfination of L-cysteine sulfinic acid and beta-decarboxylation of L-aspartate and oxalacetate.
2003 Nov 20
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
Catalytic enantioselective transamination of alpha-keto esters: an organic approach to enzymatic reactions.
2003 Oct 21
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
Dendrimeric pyridoxamine enzyme mimics.
2003 Oct 8
Antioxidant activities of chitobiose and chitotriose.
2003 Sep
Advanced glycation end-products and the progress of diabetic vascular complications.
2004
Advanced glycation end products in clinical nephrology.
2004
Regulation of glomerular endothelial cell proteoglycans by glucose.
2004 Apr
Conformational changes in the reaction of pyridoxal kinase.
2004 Apr 23
Expression, purification, and kinetic constants for human and Escherichia coli pyridoxal kinases.
2004 Aug
Vigabatrin inhibits pyridoxine-5'-phosphate oxidase, not pyridoxal kinase in the hippocampus of seizure prone gerbils.
2004 Feb
Disruption of the plr1+ gene encoding pyridoxal reductase of Schizosaccharomyces pombe.
2004 Feb
Effect of vitamin B6 on oxygen radicals, mitochondrial membrane potential, and lipid peroxidation in H2O2-treated U937 monocytes.
2004 Feb 15
American society of nephrology-36th annual meeting and renal week 2003.
2004 Jan
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
Gateways to clinical trials.
2004 Jan-Feb
A molecularly imprinted polymer-based synthetic transaminase.
2004 Jul 14
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
Transamination reactions with multiple turnovers catalyzed by hydrophobic pyridoxamine cofactors in the presence of polyethylenimine polymers.
2004 Jul 7
Genomic organization, tissue distribution and deletion mutation of human pyridoxine 5'-phosphate oxidase.
2004 Jun
Integrative annotation of 21,037 human genes validated by full-length cDNA clones.
2004 Jun
Pyridoxamine: an extremely potent scavenger of 1,4-dicarbonyls.
2004 Mar
[Carbonyl stress inhibitor towards new therapeutic interventions in diabetic nephropathy].
2004 May
Structural studies of the catalytic reaction pathway of a hyperthermophilic histidinol-phosphate aminotransferase.
2004 May 14
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
Amelioration of the beta-cell dysfunction in diabetic APA hamsters by antioxidants and AGE inhibitor treatments.
2004 May-Jun
Identification of a pyridoxine (pyridoxamine) 5'-phosphate oxidase from Arabidopsis thaliana.
2007 Feb 6
Metabolic profiling of an Echinostoma caproni infection in the mouse for biomarker discovery.
2008 Jul 2
Molecular evolution of B6 enzymes: binding of pyridoxal-5'-phosphate and Lys41Arg substitution turn ribonuclease A into a model B6 protoenzyme.
2008 Jun 19
Poisoning pyridoxal 5-phosphate-dependent enzymes: a new strategy to target the malaria parasite Plasmodium falciparum.
2009
Vitamin B6 deficient plants display increased sensitivity to high light and photo-oxidative stress.
2009 Nov 10
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
Vitamin B6 metabolism in chronic kidney disease--relation to transsulfuration, advanced glycation and cardiovascular disease.
2010
Crystal structure of glutamate-1-semialdehyde aminotransferase from Bacillus subtilis with bound pyridoxamine-5'-phosphate.
2010 Nov 12
Identification of novel thermostable taurine-pyruvate transaminase from Geobacillus thermodenitrificans for chiral amine synthesis.
2016 Apr
Biochemical and Structural Insights into the Aminotransferase CrmG in Caerulomycin Biosynthesis.
2016 Apr 15
Molecular dynamics simulations of apo, holo, and inactivator bound GABA-at reveal the role of active site residues in PLP dependent enzymes.
2016 Jul
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Name Type Language
PYRIDOXAMINE PHOSPHATE
JAN  
Common Name English
4-AMINOMETHYL-3-HYDROXY-2-METHYL-5-((PHOSPHONOOXY)METHYL)PYRIDINE DIHYDRATE
Systematic Name English
PYRIDOXAMINE PHOSPHATE [JAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C45812
Created by admin on Fri Dec 15 16:11:44 GMT 2023 , Edited by admin on Fri Dec 15 16:11:44 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C81633
Created by admin on Fri Dec 15 16:11:44 GMT 2023 , Edited by admin on Fri Dec 15 16:11:44 GMT 2023
PRIMARY
EPA CompTox
DTXSID001005188
Created by admin on Fri Dec 15 16:11:44 GMT 2023 , Edited by admin on Fri Dec 15 16:11:44 GMT 2023
PRIMARY
CHEBI
18335
Created by admin on Fri Dec 15 16:11:44 GMT 2023 , Edited by admin on Fri Dec 15 16:11:44 GMT 2023
PRIMARY
CAS
84878-64-8
Created by admin on Fri Dec 15 16:11:44 GMT 2023 , Edited by admin on Fri Dec 15 16:11:44 GMT 2023
PRIMARY
PUBCHEM
5282366
Created by admin on Fri Dec 15 16:11:44 GMT 2023 , Edited by admin on Fri Dec 15 16:11:44 GMT 2023
PRIMARY
SMS_ID
300000008628
Created by admin on Fri Dec 15 16:11:44 GMT 2023 , Edited by admin on Fri Dec 15 16:11:44 GMT 2023
PRIMARY
MESH
C010627
Created by admin on Fri Dec 15 16:11:44 GMT 2023 , Edited by admin on Fri Dec 15 16:11:44 GMT 2023
PRIMARY
FDA UNII
QWW7V29814
Created by admin on Fri Dec 15 16:11:44 GMT 2023 , Edited by admin on Fri Dec 15 16:11:44 GMT 2023
PRIMARY
DRUG BANK
DBSALT002045
Created by admin on Fri Dec 15 16:11:44 GMT 2023 , Edited by admin on Fri Dec 15 16:11:44 GMT 2023
PRIMARY
ChEMBL
CHEMBL1235353
Created by admin on Fri Dec 15 16:11:44 GMT 2023 , Edited by admin on Fri Dec 15 16:11:44 GMT 2023
PRIMARY