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Details

Stereochemistry ACHIRAL
Molecular Formula C8H12N2O2
Molecular Weight 168.1931
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PYRIDOXAMINE

SMILES

CC1=C(O)C(CN)=C(CO)C=N1

InChI

InChIKey=NHZMQXZHNVQTQA-UHFFFAOYSA-N
InChI=1S/C8H12N2O2/c1-5-8(12)7(2-9)6(4-11)3-10-5/h3,11-12H,2,4,9H2,1H3

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
Determination of vitamin B6 vitamers and pyridoxic acid in biological samples.
1992 Jul 1
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
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
FT-IR study of pyridoxamine 5' phosphate.
2003 Apr 11
Structure and mechanism of Escherichia coli pyridoxine 5'-phosphate oxidase.
2003 Apr 11
Inhibition of diphenolase activity of tyrosinase by vitamin b(6) compounds.
2003 Apr 23
Noncovalent binding of a reaction intermediate by a designed helix-loop-helix motif-implications for catalyst design.
2003 Apr 4
LR-90 a new advanced glycation endproduct inhibitor prevents progression of diabetic nephropathy in streptozotocin-diabetic rats.
2003 Aug
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
Structure and properties of recombinant human pyridoxine 5'-phosphate oxidase.
2003 Jul
Inhibitory effect of pyridoxal 5'-phosphate on endothelial cell proliferation, replicative DNA polymerase and DNA topoisomerase.
2003 Jul
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
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
Expression of a Brassic napus glutamate 1-semialdehyde aminotransferase in Escherichia coli and characterization of the recombinant protein.
2003 Jun
The AGE inhibitor pyridoxamine inhibits lipemia and development of renal and vascular disease in Zucker obese rats.
2003 Jun
[The role of nonenzymatic glycation and glyco-oxidation in the development of diabetic vascular complications].
2003 May
The biosynthesis of GDP-L-colitose: C-3 deoxygenation is catalyzed by a unique coenzyme B6-dependent enzyme.
2003 May 14
Biosynthesis of Vitamin B(6) in yeast. Incorporation pattern of trioses.
2003 May 2
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
Stereochemistry of the reactions of glutamate-1-semialdehyde aminomutase with 4,5-diaminovalerate.
2003 Oct 17
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
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
Regulation of glomerular endothelial cell proteoglycans by glucose.
2004 Apr
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
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
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
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
Vitamin B6 deficient plants display increased sensitivity to high light and photo-oxidative stress.
2009 Nov 10
Crystal structure of glutamate-1-semialdehyde aminotransferase from Bacillus subtilis with bound pyridoxamine-5'-phosphate.
2010 Nov 12
Biochemical and Structural Insights into the Aminotransferase CrmG in Caerulomycin Biosynthesis.
2016 Apr 15
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Name Type Language
PYRIDOXAMINE
MI   WHO-DD  
Common Name English
PYRIDOXAMINE [MI]
Common Name English
PYRIDOXYLAMINE
Common Name English
Pyridoxamine [WHO-DD]
Common Name English
3-PYRIDINEMETHANOL, 4-(AMINOMETHYL)-5-HYDROXY-6-METHYL-
Systematic Name English
Classification Tree Code System Code
DSLD 4299 (Number of products:1)
Created by admin on Fri Dec 15 15:29:41 GMT 2023 , Edited by admin on Fri Dec 15 15:29:41 GMT 2023
Code System Code Type Description
CHEBI
16410
Created by admin on Fri Dec 15 15:29:41 GMT 2023 , Edited by admin on Fri Dec 15 15:29:41 GMT 2023
PRIMARY
DRUG BANK
DB11673
Created by admin on Fri Dec 15 15:29:41 GMT 2023 , Edited by admin on Fri Dec 15 15:29:41 GMT 2023
PRIMARY
PUBCHEM
1052
Created by admin on Fri Dec 15 15:29:41 GMT 2023 , Edited by admin on Fri Dec 15 15:29:41 GMT 2023
PRIMARY
MERCK INDEX
m9363
Created by admin on Fri Dec 15 15:29:41 GMT 2023 , Edited by admin on Fri Dec 15 15:29:41 GMT 2023
PRIMARY Merck Index
SMS_ID
100000166683
Created by admin on Fri Dec 15 15:29:41 GMT 2023 , Edited by admin on Fri Dec 15 15:29:41 GMT 2023
PRIMARY
FDA UNII
6466NM3W93
Created by admin on Fri Dec 15 15:29:41 GMT 2023 , Edited by admin on Fri Dec 15 15:29:41 GMT 2023
PRIMARY
ECHA (EC/EINECS)
201-640-5
Created by admin on Fri Dec 15 15:29:41 GMT 2023 , Edited by admin on Fri Dec 15 15:29:41 GMT 2023
PRIMARY
CAS
85-87-0
Created by admin on Fri Dec 15 15:29:41 GMT 2023 , Edited by admin on Fri Dec 15 15:29:41 GMT 2023
PRIMARY
EPA CompTox
DTXSID6046929
Created by admin on Fri Dec 15 15:29:41 GMT 2023 , Edited by admin on Fri Dec 15 15:29:41 GMT 2023
PRIMARY
WIKIPEDIA
PYRIDOXAMINE
Created by admin on Fri Dec 15 15:29:41 GMT 2023 , Edited by admin on Fri Dec 15 15:29:41 GMT 2023
PRIMARY
EVMPD
SUB180935
Created by admin on Fri Dec 15 15:29:41 GMT 2023 , Edited by admin on Fri Dec 15 15:29:41 GMT 2023
PRIMARY
CHEBI
57761
Created by admin on Fri Dec 15 15:29:41 GMT 2023 , Edited by admin on Fri Dec 15 15:29:41 GMT 2023
PRIMARY
MESH
D011733
Created by admin on Fri Dec 15 15:29:41 GMT 2023 , Edited by admin on Fri Dec 15 15:29:41 GMT 2023
PRIMARY