Pyridoxine hydrochlorideProduct ingredient for Pyridoxine

Name
Pyridoxine hydrochloride
Drug Entry
Pyridoxine

Pyridoxine 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 1.

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) 2.

Pyridoxine is used medically for the treatment of vitamin B6 deficiency and for the prophylaxis of isoniazid-induced peripheral neuropathy (due to Isoniazid's mechanism of action which competitively inhibits the action of pyridoxine in the above-mentioned metabolic functions). It is also used in combination with Doxylamine (as the commercially available product Diclectin) for the treatment of nausea and vomiting in pregnancy.

Accession Number
DBSALT000151
Structure
Thumb
Synonyms
Pyridoxine HCl
UNII
68Y4CF58BV
CAS Number
58-56-0
Weight
Average: 205.639
Monoisotopic: 205.050570962
Chemical Formula
C8H12ClNO3
InChI Key
ZUFQODAHGAHPFQ-UHFFFAOYSA-N
InChI
InChI=1S/C8H11NO3.ClH/c1-5-8(12)7(4-11)6(3-10)2-9-5;/h2,10-12H,3-4H2,1H3;1H
IUPAC Name
4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol hydrochloride
SMILES
Cl.CC1=C(O)C(CO)=C(CO)C=N1
External Links
PubChem Compound
6019
ChemSpider
5797
ChEBI
30961
ChEMBL
CHEMBL1200756
Wikipedia
Pyridoxine
Predicted Properties
PropertyValueSource
logP-0.95ChemAxon
pKa (Strongest Acidic)9.4ChemAxon
pKa (Strongest Basic)5.58ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area73.58 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.11 m3·mol-1ChemAxon
Polarizability17.11 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon