Pyrithione sodiumProduct ingredient for Pyrithione

Name
Pyrithione sodium
Drug Entry
Pyrithione

Pyrithione zinc, or zinc pyrithione or zinc pyridinethione, is a coordination complex consisted of pyrithione ligands chelated to zinc (2+) ions via oxygen and sulfur centers. In the crystalline state, it exists as a centrosymmetric dimer. Due to its dynamic fungistatic and bacteriostatic properties, pyrithione zinc is used to treat dandruff and seborrheic dermatitis. Dandruff is a common scalp disease affecting >40% of the world's adult population, and may be caused by fungi such as Malassezia globosa and M. restricta 3.

Pyrithione zinc is commonly found as an active ingredient in OTC antidandruff topical treatments such as shampoos. It mediates its action by increasing the cellular levels of copper, and damaging iron-sulfur clusters of proteins essential for fungal metabolism and growth 1. Due to low solubility, pyrithione zinc released from the topical formulations is deposited and retained relatively well onto the target skin surfaces 2. Other uses of pyrithione zinc include additive in antifouling outdoor paints and algaecide. While its use has been approved in the early 1960's by the FDA 4, safety and effectiveness of pyrithione zinc has been reported for decades. It is not shown to have any significant estrogenic activity according to the in vivo and in vitro assays 4.

Accession Number
DBSALT002738
Structure
Synonyms
2-pyridinethiol-1-oxide, sodium salt / Omadine sodium / Pyrithione sodium salt / Sodium omadine / Sodium pyrithione
External IDs
AL-02725 / AL02725
UNII
6L3991491R
CAS Number
3811-73-2
Weight
Average: 149.14
Monoisotopic: 148.99112921
Chemical Formula
C5H4NNaOS
InChI Key
WNGMMIYXPIAYOB-UHFFFAOYSA-M
InChI
InChI=1S/C5H5NOS.Na/c7-6-4-2-1-3-5(6)8;/h1-4,8H;/q;+1/p-1
IUPAC Name
sodium (1-oxidopyridin-1-ium-2-yl)sulfanide
SMILES
[Na+].[O-][N+]1=C([S-])C=CC=C1
ChemSpider
1513
ChEMBL
CHEMBL2364542
Predicted Properties
PropertyValueSource
Water Solubility6.45 mg/mLALOGPS
logP-0.28ALOGPS
logP0.2Chemaxon
logS-1.4ALOGPS
pKa (Strongest Acidic)6.84Chemaxon
pKa (Strongest Basic)0.66Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area26.94 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity31.64 m3·mol-1Chemaxon
Polarizability11.91 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon