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Identification
Name Pyridoxine
Accession Number DB00165 (APRD00204, NUTR00002)
Type small molecule
Groups approved, nutraceutical
Description

Pyridoxine is the 4-methanol form of vitamin B6 and is converted to pyridoxal 5-phosphate in the body. Pyridoxal 5-phosphate is a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. Although pyridoxine and vitamin B6 are still frequently used as synonyms, especially by medical researchers, this practice is erroneous and sometimes misleading. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Pyridoxol
Vitamin B6
Salts
  • pyridoxine hydrochloride
Brand names
Name Company
Aderoxine
Alestrol
Becilan
Beesix
Benadon
Bonasanit
Campoviton 6
Gravidox
Hexa-Betalin
Hexavibex
Hexermin
Hexermine
Hexobion
Hydoxin
Nestrex
Pydox
Pyridipca
Pyridox
Rodex TD
Tex Six T.R.
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Brand mixtures Not Available
Categories
  • Essential Vitamin
  • Vitamins (Vitamin B Complex)
  • Anti-inflammatory Agents
  • Vitamin B Complex
CAS number 65-23-6
Weight Average: 169.1778
Monoisotopic: 169.073893223
Chemical Formula C8H11NO3
InChI Key InChIKey=LXNHXLLTXMVWPM-UHFFFAOYSA-N
InChI
InChI=1S/C8H11NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,10-12H,3-4H2,1H3
Plain Text
IUPAC Name
4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol
SMILES
CC1=NC=C(CO)C(CO)=C1O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Pyridoxals and Derivatives
Substructures
  • Pyridoxals and Derivatives
  • Hydroxy Compounds
  • Pyridines and Derivatives
  • Alcohols and Polyols
  • Heterocyclic compounds
  • Aromatic compounds
  • Imines
  • Phenols and Derivatives
Pharmacology
Indication For the treatment of vitamin B6 deficiency and for the prophylaxis of isoniazid-induced peripheral neuropathy.
Pharmacodynamics Vitamin B6 (pyridoxine) is a water-soluble vitamin used in the prophylaxis and treatment of vitamin B6 deficiency and peripheral neuropathy in those receiving isoniazid (isonicotinic acid hydrazide, INH). Vitamin B6 has been found to lower systolic and diastolic blood pressure in a small group of subjects with essential hypertension. Hypertension is another risk factor for atherosclerosis and coronary heart disease. Another study showed pyridoxine hydrochloride to inhibit ADP- or epinephrine-induced platelet aggregation and to lower total cholesterol levels and increase HDL-cholesterol levels, again in a small group of subjects. Vitamin B6, in the form of pyridoxal 5'-phosphate, was found to protect vascular endothelial cells in culture from injury by activated platelets. Endothelial injury and dysfunction are critical initiating events in the pathogenesis of atherosclerosis. Human studies have demonstrated that vitamin B6 deficiency affects cellular and humoral responses of the immune system. Vitamin B6 deficiency results in altered lymphocyte differentiation and maturation, reduced delayed-type hypersensitivity (DTH) responses, impaired antibody production, decreased lymphocyte proliferation and decreased interleukin (IL)-2 production, among other immunologic activities.
Mechanism of action Vitamin B6 is the collective term for a group of three related compounds, pyridoxine (PN), pyridoxal (PL) and pyridoxamine (PM), and their phosphorylated derivatives, pyridoxine 5'-phosphate (PNP), pyridoxal 5'-phosphate (PLP) and pyridoxamine 5'-phosphate (PMP). 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. 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).
Absorption The B vitamins are readily absorbed from the gastrointestinal tract, except in malabsorption syndromes. Pyridoxine is absorbed mainly in the jejunum.
Volume of distribution Not Available
Protein binding 22%
Metabolism Hepatic.
Route of elimination Not Available
Half life 15-20 days
Clearance Not Available
Toxicity Oral Rat LD50 = 4 gm/kg. Toxic effects include convulsions, dyspnea, hypermotility, diarrhea, ataxia and muscle weakness.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Eli lilly and co
  • Akorn inc
  • App pharmaceuticals llc
  • Bel mar laboratories inc
  • Dell laboratories inc
  • Elkins sinn div ah robins co inc
  • Luitpold pharmaceuticals inc
  • Watson laboratories inc
Packagers
Dosage forms
Form Route Strength
Liquid Intramuscular
Solution Intramuscular
Solution / drops Oral
Tablet Oral
Prices
Unit description Cost Unit
Pyridoxine HCl 100 50 mg tablet Bottle 12.99 USD bottle
Pyridoxine HCl 100 mg/ml vial 11.69 USD vial
Pyridoxine 100 mg/ml vial 10.79 USD ml
Pyridoxine hcl crystals 6.94 USD g
Pyridoxine 500 mg tablet 0.18 USD tablet
Pyridoxine 25 mg tablet 0.14 USD tablet
Neuro k 500 mg tablet 0.13 USD tablet
Pyridoxine 250 mg tablet 0.13 USD tablet
CVS Pharmacy vitamin b-6 200 mg tablet 0.07 USD tablet
Neuro-k 250 mg tablet 0.06 USD tablet
Pyridoxine 50 mg tablet 0.06 USD tablet
Vitamin b-6 100 mg tablet 0.04 USD tablet
CVS Pharmacy vitamin b-6 100 mg tablet 0.03 USD tablet
Pyridoxine 100 mg tablet 0.03 USD tablet
Vitamin b6 50 mg tablet 0.03 USD tablet
Vitamin b-6 50 mg tablet 0.03 USD tablet
CVS Pharmacy vitamin b-6 50 mg tablet 0.02 USD tablet
Vitamin b-6 25 mg tablet 0.02 USD tablet
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Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 159-162 °C PhysProp
water solubility 2.2E+005 mg/L Not Available
logP -0.77 SANGSTER (1993)
Predicted Properties
Property Value Source
water solubility 1.61e+01 g/l ALOGPS
logP -0.57 ALOGPS
logP -0.95 ChemAxon
logS -1 ALOGPS
pKa (strongest acidic) 9.4 ChemAxon
pKa (strongest basic) 5.58 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 4 ChemAxon
hydrogen donor count 3 ChemAxon
polar surface area 73.58 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 44.11 ChemAxon
polarizability 17.12 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C00314 Link_out
PubChem Compound 1054 Link_out
PubChem Substance 46508560 Link_out
ChemSpider 1025 Link_out
ChEBI 16709 Link_out
ChEMBL 16709 Link_out
Therapeutic Targets Database DAP000869 Link_out
PharmGKB PA451897 Link_out
Drug Product Database 2246275 Link_out
Drugs.com http://www.drugs.com/cdi/pyridoxine-vitamin-b6-extended-release-tablets.html Link_out
PDRhealth http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/vit_0215.shtml Link_out
Wikipedia http://en.wikipedia.org/wiki/Pyridoxine Link_out
ATC Codes
  • A11HA02
AHFS Codes
  • 92:02.00*
  • 88:08.00
PDB Entries
FDA label Not Available
MSDS show (51.5 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Pyridoxal kinase

Pharmacological action: yes
Actions: ligand

Required for synthesis of pyridoxal-5-phosphate from vitamin B6

Organism class: human
UniProt ID: O00764 Link_out
Gene: PDXK Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Adams JB, George F, Audhya T: Abnormally high plasma levels of vitamin B6 in children with autism not taking supplements compared to controls not taking supplements. J Altern Complement Med. 2006 Jan-Feb;12(1):59-63. Pubmed
  2. Newman JA, Das SK, Sedelnikova SE, Rice DW: The crystal structure of an ADP complex of Bacillus subtilis pyridoxal kinase provides evidence for the parallel emergence of enzyme activity during evolution. J Mol Biol. 2006 Oct 20;363(2):520-30. Epub 2006 Aug 12. Pubmed
  3. Kim SY, An JJ, Kim DW, Choi SH, Lee SH, Hwang SI, Kwon OS, Kang TC, Won MH, Cho SW, Park J, Eum WS, Lee KS, Choi SY: Tat-mediated protein transduction of human brain pyridoxine-5-P oxidase into PC12 cells. J Biochem Mol Biol. 2006 Jan 31;39(1):76-83. Pubmed
  4. Nagahashi Y, Tazoe M, Hoshino T: Cloning of the pyridoxine 5’-phosphate phosphatase gene (pdxP) and vitamin B6 production in pdxP recombinant Sinorhizobium meliloti. Biosci Biotechnol Biochem. 2008 Feb;72(2):421-7. Epub 2008 Feb 7. Pubmed
Enzymes

1. Cytochrome P450 1A1

Actions: inhibitor

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics

UniProt ID: P04798 Link_out
Gene: CYP1A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Tangjarukij C, Navasumrit P, Zelikoff JT, Ruchirawat M: The effects of pyridoxine deficiency and supplementation on hematological profiles, lymphocyte function, and hepatic cytochrome P450 in B6C3F1 mice. J Immunotoxicol. 2009 Sep;6(3):147-60. doi: 10.1080/15476910903083866. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19