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Identification
NamePyridoxine
Accession NumberDB00165  (APRD00204, NUTR00002)
Typesmall molecule
Groupsapproved, 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
Synonyms
SynonymLanguageCode
2-Methyl-3-hydroxy-4,5-dihydroxymethylpyridineNot AvailableNot Available
3-hydroxy-4,5-bis(hydroxymethyl)-2-methylpyridineNot AvailableNot Available
3-Hydroxy-4,5-dimethylol-alpha-picolineNot AvailableNot Available
5-Hydroxy-6-methyl-3,4-pyridinedimethanolNot AvailableNot Available
PyridoxineNot AvailableNot Available
PyridoxolNot AvailableNot Available
Vitamin B6Not AvailableNot Available
Salts
Name/CAS Structure Properties
Pyridoxine hydrochloride
58-56-0
Thumb
  • InChI Key: ZUFQODAHGAHPFQ-UHFFFAOYSA-N
  • Monoisotopic Mass: 205.050570962
  • Average Mass: 205.639
DBSALT000151
Brand names
NameCompany
BecilanNot Available
BeesixNot Available
BenadonNot Available
BonasanitNot Available
Hexa-BetalinNot Available
HexobionNot Available
NestrexNot Available
Brand mixtures
Brand NameIngredients
DICLEGISPyridoxine + Doxylamine
Categories
CAS number65-23-6
WeightAverage: 169.1778
Monoisotopic: 169.073893223
Chemical FormulaC8H11NO3
InChI KeyLXNHXLLTXMVWPM-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
IUPAC Name
4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol
SMILES
CC1=C(O)C(CO)=C(CO)C=N1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassPyridines and Derivatives
SubclassPyridoxines
Direct parentPyridoxines
Alternative parentsPolyols; Primary Alcohols; Polyamines
Substituentspolyol; polyamine; primary alcohol; alcohol; organonitrogen compound
Classification descriptionThis compound belongs to the pyridoxines. These are pyridoxal derivatives in which the carbaldehyde group at position 2 of the pyridoxal moiety is replaced by an hydroxymethyl group.
Pharmacology
IndicationFor the treatment of vitamin B6 deficiency and for the prophylaxis of isoniazid-induced peripheral neuropathy.
PharmacodynamicsVitamin 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 actionVitamin 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).
AbsorptionThe B vitamins are readily absorbed from the gastrointestinal tract, except in malabsorption syndromes. Pyridoxine is absorbed mainly in the jejunum.
Volume of distributionNot Available
Protein binding22%
Metabolism

Hepatic.

Route of eliminationNot Available
Half life15-20 days
ClearanceNot Available
ToxicityOral Rat LD50 = 4 gm/kg. Toxic effects include convulsions, dyspnea, hypermotility, diarrhea, ataxia and muscle weakness.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9728
Blood Brain Barrier + 0.6889
Caco-2 permeable - 0.8958
P-glycoprotein substrate Non-substrate 0.5579
P-glycoprotein inhibitor I Non-inhibitor 0.9723
P-glycoprotein inhibitor II Non-inhibitor 0.9221
Renal organic cation transporter Non-inhibitor 0.8177
CYP450 2C9 substrate Non-substrate 0.7386
CYP450 2D6 substrate Non-substrate 0.781
CYP450 3A4 substrate Non-substrate 0.7104
CYP450 1A2 substrate Non-inhibitor 0.9046
CYP450 2C9 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Non-inhibitor 0.923
CYP450 2C19 substrate Non-inhibitor 0.9025
CYP450 3A4 substrate Non-inhibitor 0.8648
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.695
Ames test Non AMES toxic 0.9133
Carcinogenicity Non-carcinogens 0.9418
Biodegradation Not ready biodegradable 0.5678
Rat acute toxicity 1.6573 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8454
hERG inhibition (predictor II) Non-inhibitor 0.8734
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
FormRouteStrength
LiquidIntramuscular
SolutionIntramuscular
Solution / dropsOral
TabletOral
Prices
Unit descriptionCostUnit
Pyridoxine HCl 100 50 mg tablet Bottle12.99USDbottle
Pyridoxine HCl 100 mg/ml vial11.69USDvial
Pyridoxine 100 mg/ml vial10.79USDml
Pyridoxine hcl crystals6.94USDg
Pyridoxine 500 mg tablet0.18USDtablet
Pyridoxine 25 mg tablet0.14USDtablet
Neuro k 500 mg tablet0.13USDtablet
Pyridoxine 250 mg tablet0.13USDtablet
CVS Pharmacy vitamin b-6 200 mg tablet0.07USDtablet
Neuro-k 250 mg tablet0.06USDtablet
Pyridoxine 50 mg tablet0.06USDtablet
Vitamin b-6 100 mg tablet0.04USDtablet
CVS Pharmacy vitamin b-6 100 mg tablet0.03USDtablet
Pyridoxine 100 mg tablet0.03USDtablet
Vitamin b6 50 mg tablet0.03USDtablet
Vitamin b-6 50 mg tablet0.03USDtablet
CVS Pharmacy vitamin b-6 50 mg tablet0.02USDtablet
Vitamin b-6 25 mg tablet0.02USDtablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point159-162 °CPhysProp
water solubility2.2E+005 mg/LNot Available
logP-0.77SANGSTER (1993)
Predicted Properties
PropertyValueSource
water solubility1.61e+01 g/lALOGPS
logP-0.57ALOGPS
logP-0.95ChemAxon
logS-1ALOGPS
pKa (strongest acidic)9.4ChemAxon
pKa (strongest basic)5.58ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count3ChemAxon
polar surface area73.58ChemAxon
rotatable bond count2ChemAxon
refractivity44.11ChemAxon
polarizability17.11ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
References
Synthesis Reference

Harumi Kita, “Production of pyridoxine.” U.S. Patent US4339586, issued October, 1972.

US4339586
General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC00314
ChEBI16709
ChEMBLCHEMBL1364
Therapeutic Targets DatabaseDAP000869
PharmGKBPA451897
Drug Product Database2246275
Drugs.comhttp://www.drugs.com/cdi/pyridoxine-vitamin-b6-extended-release-tablets.html
PDRhealthhttp://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/vit_0215.shtml
WikipediaPyridoxine
ATC CodesNot Available
AHFS Codes
  • 92:02.00*
  • 88:08.00
PDB Entries
FDA labelNot Available
MSDSshow(51.5 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Pyridoxal kinase

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: ligand

Components

Name UniProt ID Details
Pyridoxal kinase O00764 Details

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

Kind: protein

Organism: Human

Pharmacological action: no

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 1A1 P04798 Details

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

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Drug created on June 13, 2005 07:24 / Updated on September 24, 2013 13:55