Pyridoxine

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Cat Number

API0232256

CAS Number

65-23-6

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CAS Number

65-23-6

EINECS

200-603-0

Storage

Store at room temperature

Synonyms

Pyridoxol; 3-hydroxy-4,5-bis(hydroxymethyl)-2-methylpyridine; Pyridoxin; Adermine; Gravidox; Hydoxin; Pyridoxolum

Molecular Formula

C8H11NO3

Molecular Weight

169.18

Smiles

CC1=NC=C(C(=C1O)CO)CO

Appearance

White to off-white solid powder

Melting Point

159-162°C

Boiling Point

491.9±40.0°C at 760 mmHg

Relative Density

1.4±0.1

General Description

Pyridoxine is a water-soluble vitamin B6 compound with a pyridine ring, a hydroxymethyl group, and a methyl group. Its chemical structure is 2-methyl-3-hydroxy-4,5-bis(hydroxymethyl)pyridine. Pyridoxine is a white crystalline powder, readily soluble in water. The molecule is the alcohol form of vitamin B6, and is converted to the active coenzyme pyridoxal 5'-phosphate (PLP).

Mechanism of Action

Pyridoxine is converted to pyridoxal 5'-phosphate (PLP), which serves as a cofactor for over 140 enzymatic reactions, primarily in amino acid metabolism, including transamination, decarboxylation, and deamination. It is also involved in the synthesis of neurotransmitters (serotonin, dopamine, GABA), heme synthesis, and glycogenolysis.

Application

Pyridoxine is indicated for the treatment and prevention of vitamin B6 deficiency, which can occur in patients with malabsorption, alcoholism, or isoniazid therapy. It is also used for the treatment of sideroblastic anemia, pyridoxine-dependent seizures in neonates, and as an adjunct for the management of nausea and vomiting during pregnancy.

A series of symmetric pyridoxine derivatives linked by sulfur‑containing connectors were synthesized as glucokinase activators. Two lead compounds activated glucokinase by ~150% and ~130% at 100 μM, comparable to the reference PF‑04937319. They showed low cytotoxicity and high oral safety (LD₅₀ >2000 mg/kg). Docking studies suggested binding modes. These compounds are viable preclinical candidates for type 2 diabetes.

Fig. 1 Comparison of GK activity and docking energy of compounds 5–8 and PF-04937139. (Dzyurkevich MS, et al., 2017)

References

Dzyurkevich MS, et al. Pyridoxine dipharmacophore derivatives as potent glucokinase activators for the treatment of type 2 diabetes mellitus. Sci Rep. 2017;7(1):16072.

Quaternary ammonium salt of pyridoxine (compound 3) demonstrated high biocidal activity against both planktonic and biofilm-embedded Staphylococcus aureus and Staphylococcus epidermidis, with complete death of biofilm-embedded cells at 64 and 16 µg/mL, respectively. Other pyridoxine derivatives were ineffective against biofilms despite low MICs against planktonic cells. This compound is a promising candidate for designing new antibiotics and disinfectants against biofilm-embedded bacteria.

Fig. 2 The effect of pyridoxine derivatives on the thickness of preformed biofilms of (a) S. aureus and (b) S. epidermidis. (Kayumov AR, et al., 2015)

References

Kayumov AR, et al. New Derivatives of Pyridoxine Exhibit High Antibacterial Activity against Biofilm-Embedded Staphylococcus Cells. Biomed Res Int. 2015;2015:890968.

Does Pyridoxine require protection from light during long-term storage?

Yes, it is photosensitive. UV exposure can cause photodegradation and discoloration of the pyridine ring. Store in light-resistant containers, preferably amber glass.

What is the recommended storage temperature for Pyridoxine?

Store at controlled room temperature (15-25°C). Avoid excessive heat above 30°C, which can accelerate degradation to 4-pyridoxic acid.

Is Pyridoxine stable in solution for injection or oral use?

Aqueous solutions are stable when protected from light and stored at room temperature.

How is the impurity 4-pyridoxic acid (an oxidation product) monitored?

This degradation product is quantified using a stability-indicating HPLC method with fluorescence detection, ensuring it remains within pharmacopoeial limits.