Identification

Name
Dipyrithione
Accession Number
DB11327
Type
Small Molecule
Groups
Approved
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 6. It is currently used as a pesticide 3.

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 1.

Pyrithione derivatives, such as Pyrithione and sodium pyrithione, are widely used as cosmetic preservatives and as anti-dandruff agents in shampoos 1. It may be combined with other ingredients, such as triclosan to serve as antifungal and antibacterial skin treatments 9.

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 4.

Structure
Thumb
Synonyms
  • Bispyrithione
  • Dipiritiona
  • Dipyrithione
  • Dipyrithionum
  • Omadine disulfide
  • OMDS
  • Pyrithione disulfide
  • Pyrithione disulphide
External IDs
OSY 20
Product Ingredients
IngredientUNIICASInChI Key
Bispyrithione magsulfex48H0YX0NT467182-81-4FNJVKRQYEQVPLK-UHFFFAOYSA-L
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Feix FacialDipyrithione (0.5 mL/100mL) + Octasulfur (0.2 mL/100mL)LiquidTopicalSpai Sons Pharmaceutical International Cosmetics2012-06-30Not applicableUs
Polytar AF ShampooDipyrithione (1.0 %) + Coal tar (0.5 %) + Levomenthol (0.5 %) + Salicylic acid (2.0 %)ShampooTopicalGlaxosmithkline Inc1994-12-312012-12-10Canada
Categories
Not Available
UNII
9L87N86R9A
CAS number
3696-28-4
Weight
Average: 252.31
Monoisotopic: 252.002719854
Chemical Formula
C10H8N2O2S2
InChI Key
ZHDBTKPXEJDTTQ-UHFFFAOYSA-N
InChI
InChI=1S/C10H8N2O2S2/c13-11-7-3-1-5-9(11)15-16-10-6-2-4-8-12(10)14/h1-8H
IUPAC 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-]

Pharmacology

Indication

Scalp dandruff 5

Associated Conditions
Pharmacodynamics

This drug decreases or eliminates dandruff from the scalp, which is caused by various types of fungi 6, 9.

Mechanism of action

This drug is a fungicidal agent 6, 1.
Fungicide, also called antimycotic, any toxic substance used to kill or inhibit the growth of fungi 11.

TargetActionsOrganism
UNitric oxide synthase, inducible
antagonist
Humans
UProstaglandin G/H synthase 2Not AvailableHumans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

References

General References
  1. Fan Y, Liu C, Huang Y, Zhang J, Cai L, Wang S, Zhang Y, Duan X, Yin Z: Dipyrithione induces cell-cycle arrest and apoptosis in four cancer cell lines in vitro and inhibits tumor growth in a mouse model. BMC Pharmacol Toxicol. 2013 Oct 21;14:54. doi: 10.1186/2050-6511-14-54. [PubMed:24139500]
  2. Wedig JH, Maibach HI: Percutaneous penetration of dipyrithione in man: effect of skin color (race). J Am Acad Dermatol. 1981 Oct;5(4):433-8. [PubMed:7287959]
  3. Elkington BG, Sydara K, Newsome A, Hwang CH, Lankin DC, Simmler C, Napolitano JG, Ree R, Graham JG, Gyllenhaal C, Bouamanivong S, Souliya O, Pauli GF, Franzblau SG, Soejarto DD: New finding of an anti-TB compound in the genus Marsypopetalum (Annonaceae) from a traditional herbal remedy of Laos. J Ethnopharmacol. 2014 Feb 3;151(2):903-11. doi: 10.1016/j.jep.2013.11.057. Epub 2013 Dec 11. [PubMed:24333958]
  4. Reeder NL, Kaplan J, Xu J, Youngquist RS, Wallace J, Hu P, Juhlin KD, Schwartz JR, Grant RA, Fieno A, Nemeth S, Reichling T, Tiesman JP, Mills T, Steinke M, Wang SL, Saunders CW: Zinc pyrithione inhibits yeast growth through copper influx and inactivation of iron-sulfur proteins. Antimicrob Agents Chemother. 2011 Dec;55(12):5753-60. doi: 10.1128/AAC.00724-11. Epub 2011 Sep 26. [PubMed:21947398]
  5. Dipyrithione [Link]
  6. Dipyrithione [Link]
  7. PPBD: dipyrithione (Ref: OSY-20) [Link]
  8. Dipyrithione inhibits lipopolysaccharide-induced iNOS and COX-2 up-regulation in macrophages and protects against endotoxic shock in mice [Link]
  9. Feix-Sulfur Liquid [Link]
  10. Dandruff [Link]
  11. Fungicide [Link]
External Links
ChemSpider
2998
RxNav
1362743
ChEBI
136010
ChEMBL
CHEMBL549473
ZINC
ZINC000001751811
MSDS
Download (170 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
LiquidTopical
ShampooTopical
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
PropertyValueSource
melting point (°C)205MSDS
boiling point (°C)582.8MSDS
logP2.32https://comptox.epa.gov/dashboard/dsstoxdb/results?search=Dipyrithione
Predicted Properties
PropertyValueSource
Water Solubility0.0511 mg/mLALOGPS
logP0.5ALOGPS
logP0.83ChemAxon
logS-3.7ALOGPS
pKa (Strongest Basic)0.55ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area53.88 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity63.28 m3·mol-1ChemAxon
Polarizability23.24 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as pyridinium derivatives. These 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
Heteroaromatic compounds / Organic disulfides / Sulfenyl compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Pyridinium / Heteroaromatic compound / Organic disulfide / Azacycle / Sulfenyl compound / Organic nitrogen compound / Organic oxygen compound / Organopnictogen compound / Organic oxide / Hydrocarbon derivative
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Tetrahydrobiopterin binding
Specific Function
Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity ...
Gene Name
NOS2
Uniprot ID
P35228
Uniprot Name
Nitric oxide synthase, inducible
Molecular Weight
131116.3 Da
References
  1. Dipyrithione inhibits lipopolysaccharide-induced iNOS and COX-2 up-regulation in macrophages and protects against endotoxic shock in mice [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
Molecular Weight
68995.625 Da
References
  1. Dipyrithione inhibits lipopolysaccharide-induced iNOS and COX-2 up-regulation in macrophages and protects against endotoxic shock in mice [Link]

Drug created on December 03, 2015 09:52 / Updated on March 01, 2020 23:57

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