UEG

4,5-bis(hydroxymethyl)-2-methyl-pyridin-3-ol


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Chemical Component Summary

Name4,5-bis(hydroxymethyl)-2-methyl-pyridin-3-ol
Identifiers4,5-bis(hydroxymethyl)-2-methyl-pyridin-3-ol
FormulaC8 H11 N O3
Molecular Weight169.178
TypeNON-POLYMER
Isomeric SMILESCc1c(c(c(cn1)CO)CO)O
InChIInChI=1S/C8H11NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,10-12H,3-4H2,1H3
InChIKeyLXNHXLLTXMVWPM-UHFFFAOYSA-N

Chemical Details

Formal Charge0
Atom Count23
Chiral Atom Count0
Bond Count23
Aromatic Bond Count6

Drug Info: DrugBank

DrugBank IDDB00165 
NamePyridoxine
Groups
  • vet_approved
  • approved
  • nutraceutical
  • investigational
DescriptionPyridoxine is the 4-methanol form of vitamin B6, an important water-soluble vitamin that is naturally present in many foods. As its classification as a vitamin implies, Vitamin B6 (and pyridoxine) are essential nutrients required for normal functioning of many biological systems within the body. While many plants and microorganisms are able to synthesize pyridoxine through endogenous biological processes, animals must obtain it through their diet. More specifically, pyridoxine is converted to pyridoxal 5-phosphate in the body, which is an important coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, and aminolevulinic acid. It's important to note that Vitamin B6 is the collective term for a group of three related compounds, pyridoxine, pyridoxal, and pyridoxamine, and their phosphorylated derivatives, pyridoxine 5'-phosphate, pyridoxal 5'-phosphate and pyridoxamine 5'-phosphate. Although all six of these compounds should technically be referred to as vitamin B6, the term vitamin B6 is commonly used interchangeably with just one of them, pyridoxine [A32836]. Vitamin B6, principally in its biologically active coenzyme form pyridoxal 5'-phosphate, is involved in a wide range of biochemical reactions, including the metabolism of amino acids and glycogen, the synthesis of nucleic acids, hemogloblin, sphingomyelin and other sphingolipids, and the synthesis of the neurotransmitters serotonin, dopamine, norepinephrine and gamma-aminobutyric acid (GABA) [A32837]. Pyridoxine is used medically for the treatment of vitamin B6 deficiency and for the prophylaxis of isoniazid-induced peripheral neuropathy (due to [DB00951]'s mechanism of action which competitively inhibits the action of pyridoxine in the above-mentioned metabolic functions). It is also used in combination with [DB00366] (as the commercially available product Diclectin) for the treatment of nausea and vomiting in pregnancy.
Synonyms
  • 5-hydroxy-6-methyl-3,4-pyridinedimethanol
  • Pyridoxol
  • 3-hydroxy-4,5-dimethylol-α-picoline
  • 3-hydroxy-4,5-bis(hydroxymethyl)-2-methylpyridine
  • 2-methyl-3-hydroxy-4,5-dihydroxymethylpyridine
Brand Names
  • Innersource Tab
  • Mvc
  • Preplus
  • Folivane-OB
  • PureFe OB Plus
IndicationPyridoxine is indicated for the treatment of vitamin B6 deficiency and for the prophylaxis of [DB00951]-induced peripheral neuropathy. It is also approved by Health Canada for the treatment of nausea and vomiting in pregnancy in a combination product with [DB00366] (as the commercially available product Diclectin).
Categories
  • Alimentary Tract and Metabolism
  • Analogs/Derivatives
  • Antiinfectives for Systemic Use
  • Antimycobacterials
  • Diet, Food, and Nutrition
ATC-Code
  • J04AM08
  • A11HA02
CAS number65-23-6

Drug Targets

NameTarget SequencePharmacological ActionActions
Pyridoxal kinaseMEEECRVLSIQSHVIRGYVGNRAATFPLQVLGFEIDAVNSVQFSNHTGYA...unknownligand
Cytochrome P450 1A1MLFPISMSATEFLLASVIFCLVFWVIRASRPQVPKGLKNPPGPWGWPLIG...unknowninhibitor
Pyridoxal kinaseMEEECRVLSIQSHVIRGYVGNRAATFPLQVLGFEIDAVNSVQFSNHTGYA...unknownsubstrate
Pyridoxal phosphate phosphataseMARCERLRGAALRDVLGRAQGVLFDCDGVLWNGERAVPGAPELLERLARA...unknownsubstrate
Alkaline phosphatase, tissue-nonspecific isozymeMISPFLVLAIGTCLTNSLVPEKEKDPKYWRDQAQETLKYALELQKLNTNV...unknownsubstrate
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 1054
ChEMBL CHEMBL1364
ChEBI CHEBI:16709
CCDC/CSD BITZAF