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
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
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 |
---|---|---|
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 |
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)