ContaminantDB: Dipyrithione

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 04:36:33 UTC

Update Date

2016-11-09 01:15:39 UTC

Accession Number

CHEM017757

Identification

Common Name

Dipyrithione

Class

Small Molecule

Description

Dipyrithione is a pyrithione derivate used as bactericide and fungicide. The drug was marketed under the name Crimanex in the form of shampoo for the treatment of dandruff, however it is no longer available on the manufacturer website (Drossa Pharm . It is currently used as a pesticide . Interestingly, dipyrithione has been studied and shown to have cytotoxic and potent broad-spectrum antitumor activity, which suggests a potential basis for an anticancer drug development . Pyrithione derivatives, such as and sodium pyrithione, are widely used as cosmetic preservatives and as anti-dandruff agents in shampoos . It may be combined with other ingredients, such as triclosan to serve as antifungal and antibacterial skin treatments . 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_ .

Contaminant Sources

STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Bis(2-pyridyl-1-oxide)disulfide magnesium sulfate	MeSH
Omadine disulfide	MeSH
2,2'-Dithio-bis-pyridine-1-oxide magnesium sulfate	MeSH
Omadine MDS	MeSH
Dipyrithione magnesium sulfate	MeSH
OMDS	ChEMBL
2-[(1-oxo-1Λ⁵-pyridin-2-yl)disulphanyl]-1λ⁵-pyridin-1-one	Generator

Chemical Formula

C₁₀H₈N₂O₂S₂

Average Molecular Mass

252.310 g/mol

Monoisotopic Mass

252.003 g/mol

CAS Registry Number

3696-28-4

IUPAC Name

2-[(1-oxidopyridin-1-ium-2-yl)disulfanyl]pyridin-1-ium-1-olate

Traditional Name

2-[(1-oxidopyridin-1-ium-2-yl)disulfanyl]pyridin-1-ium-1-olate

SMILES

[O-][N+]1=CC=CC=C1SSC1=CC=CC=[N+]1[O-]

InChI Identifier

InChI=1S/C10H8N2O2S2/c13-11-7-3-1-5-9(11)15-16-10-6-2-4-8-12(10)14/h1-8H

InChI Key

ZHDBTKPXEJDTTQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as pyridinium derivatives. Pyridinium derivatives are compounds containing a pyridinium ring, which is the cationic form of pyridine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyridinium derivatives

Direct Parent

Pyridinium derivatives

Alternative Parents

Substituents

Pyridinium
Heteroaromatic compound
Organic disulfide
Azacycle
Sulfenyl compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.051 g/L	ALOGPS
logP	0.5	ALOGPS
logP	-0.44	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	0.25	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	53.88 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	63.28 m³·mol⁻¹	ChemAxon
Polarizability	23.21 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0090000000-601dedf671efaf6999b9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udl-3290000000-f3e72fbcfbbe83ae7da1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9430000000-8112fbbb93210fcb2d48	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-d98ad4dd38c8ecdcccf1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0090000000-150ef8016f22c89093a4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f6t-2490000000-b2f0da9003a6fa2604a2	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB11327

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

3109

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Dipyrithione (CHEM017757)

Structure for CHEM017757: Dipyrithione