- Pyridoxine hydrochloride
- Drug Entry
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
- Pyridoxine HCl
- CAS Number
- Average: 205.639
- Chemical Formula
- InChI Key
- IUPAC Name
- 4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol hydrochloride
- Predicted Properties
Property Value Source Water Solubility 16.1 mg/mL 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 Å2 ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 44.11 m3·mol-1 ChemAxon Polarizability 17.12 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon