U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula 2C5H4NOS.Zn
Molecular Weight 317.722
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PYRITHIONE ZINC

SMILES

[Zn++].[O-][N+]1=CC=CC=C1[S-].[O-][N+]2=CC=CC=C2[S-]

InChI

InChIKey=OTPSWLRZXRHDNX-UHFFFAOYSA-L
InChI=1S/2C5H5NOS.Zn/c2*7-6-4-2-1-3-5(6)8;/h2*1-4,8H;/q;;+2/p-2

HIDE SMILES / InChI

Molecular Formula C5H5NOS
Molecular Weight 127.164
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula Zn
Molecular Weight 65.409
Charge 2
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Pyrithione zinc is an antibacterial and antifungal agent developed by scientists in the 1930's. Since then it has been used to treat seborrheic dermatitis of the scalp and other skin conditions such as eczema, athlete's foot, and vitiligo, as well as psoriasis. Because of its antifungal properties, it is commonly found in dandruff shampoo. Products containing pyrithione zinc are available today with and without prescription, and it is the main ingredient in many over-the-counter creams, lotions, soaps, and shampoos. It also has antibacterial properties and is effective against many pathogens from the Streptococcus and Staphylococcus genera. Pyrithione zinc`s other medical applications include treatments of psoriasis, eczema, ringworm, fungus, athletes foot, dry skin, atopic dermatitis, tinea, and vitiligo. Its antifungal effect is thought to derive from its ability to disrupt membrane transport by blocking the proton pump that energizes the transport mechanism.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Pyrithione zinc shampoo

Approved Use

Pyrithione zinc shampoo is used for: Treating and preventing itching, flaking, and scaling of the scalp caused by dandruff or seborrhea (oily, crusting, or scaling skin). Pyrithione zinc shampoo is an antiseborrheic. It works by slowing the production of skin cells, which helps to reduce flakiness.

Launch Date

1986
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.2 μg/mL
0.5 mg/kg single, oral
dose: 0.5 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
PYRITHIONE plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
27.01 μg × h/mL
0.5 mg/kg single, oral
dose: 0.5 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
PYRITHIONE plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
115 h
0.5 mg/kg single, oral
dose: 0.5 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
PYRITHIONE plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
1 % 2 times / week multiple, topical
Recommended
Dose: 1 %, 2 times / week
Route: topical
Route: multiple
Dose: 1 %, 2 times / week
Sources: Page: p.436, 438
unhealthy, 17–64
n = 160
Health Status: unhealthy
Condition: Severe dandruff |Seborrheic dermatitis
Age Group: 17–64
Sex: M+F
Population Size: 160
Sources: Page: p.436, 438
Disc. AE: Erythema...
AEs leading to
discontinuation/dose reduction:
Erythema (1.25%)
Sources: Page: p.436, 438
AEs

AEs

AESignificanceDosePopulation
Erythema 1.25%
Disc. AE
1 % 2 times / week multiple, topical
Recommended
Dose: 1 %, 2 times / week
Route: topical
Route: multiple
Dose: 1 %, 2 times / week
Sources: Page: p.436, 438
unhealthy, 17–64
n = 160
Health Status: unhealthy
Condition: Severe dandruff |Seborrheic dermatitis
Age Group: 17–64
Sex: M+F
Population Size: 160
Sources: Page: p.436, 438
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Zinc induces apoptosis that can be suppressed by lanthanum in C6 rat glioma cells.
2001 Aug
Zn2+-induced ERK activation mediated by reactive oxygen species causes cell death in differentiated PC12 cells.
2001 Aug
Intramolecular homolytic substitution at selenium: synthesis of novel selenium-containing vitamin E analogues.
2001 Sep 21
Zinc is involved in the expression of a nuclear-encoded alternative oxidase gene in the yeast Hansenula anomala.
2002 Dec
The relationship between intracellular free iron and cell injury in cultured neurons, astrocytes, and oligodendrocytes.
2002 Jul 15
New triruthenium clusters as photoinduced DNA-binding and cleaving agents.
2002 May
One-electron oxidation of "photo-Fenton" reagents and inhibition of lipid peroxidation.
2002 Nov 22
Intracellular zinc fluxes associated with apoptosis in growth plate chondrocytes.
2003 Apr 1
Examination of novel zinc-binding groups for use in matrix metalloproteinase inhibitors.
2003 Jun 2
Blocking NF-kappaB activation may be an effective strategy in the fever therapy.
2003 Oct
Flow injection analysis of zinc pyrithione in hair care products on a cobalt phthalocyanine modified screen-printed carbon electrode.
2004 Apr 19
Effect of Zn2+ ions on ryanodine binding to sarcoplasmic reticulum of striated muscles in the presence of pyrithione.
2004 Dec
Pyruvate limits zinc-induced rat oligodendrocyte progenitor cell death.
2004 Jan
Fluctuations of cellular, available zinc modulate insulin signaling via inhibition of protein tyrosine phosphatases.
2005
Activation of caspase-3 in HL-60 cells treated with pyrithione and zinc.
2005 Apr
Inhibition of presynaptic activity by zinc released from mossy fiber terminals during tetanic stimulation.
2006 Jan
Opposing effects of ERK and p38 MAP kinases on HeLa cell apoptosis induced by dipyrithione.
2007 Feb 28
Zinc homeostasis and immunity.
2007 Jan
Zinc induces cell death in immortalized embryonic hippocampal cells via activation of Akt-GSK-3beta signaling.
2007 Jan 15
Protective role of intracellular zinc in myocardial ischemia/reperfusion is associated with preservation of protein kinase C isoforms.
2007 May
2-(Benzyl-sulfan-yl)pyridine N-oxide.
2008 Apr 26
Potent in vitro anti-Trypanosoma cruzi activity of pyridine-2-thiol N-oxide metal complexes having an inhibitory effect on parasite-specific fumarate reductase.
2008 Jun
Exogenous zinc protects cardiac cells from reperfusion injury by targeting mitochondrial permeability transition pore through inactivation of glycogen synthase kinase-3beta.
2008 Sep
Trace metals in antifouling paint particles and their heterogeneous contamination of coastal sediments.
2009 Apr
Leaching of hydrophobic Cu and Zn from discarded marine antifouling paint residues: evidence for transchelation of metal pyrithiones.
2009 Dec
Tracing of intracellular zinc(II) fluorescence flux to monitor cell apoptosis by using FluoZin-3AM.
2009 Oct
Dandruff: the most commercially exploited skin disease.
2010 Apr-Jun
Activation of the orphan receptor tyrosine kinase ALK by zinc.
2010 Aug 6
An integrated imaging approach to the study of oxidative stress generation by mitochondrial dysfunction in living cells.
2010 Jul
Novel antifouling agent zinc pyrithione: determination, acute toxicity, and bioaccumulation in marine mussels (Mytilus galloprovincialis).
2010 Nov
Zn(2+) inhibits coronavirus and arterivirus RNA polymerase activity in vitro and zinc ionophores block the replication of these viruses in cell culture.
2010 Nov 4
UVB radiation induces an increase in intracellular zinc in human epidermal keratinocytes.
2010 Oct
Loss of ErbB2-PI3K/Akt signaling prevents zinc pyrithione-induced cardioprotection during ischemia/reperfusion.
2017 Apr
Patents

Sample Use Guides

Shake well before each use. Wet hair thoroughly. Apply pyrithione zinc shampoo and work into a lather. Rinse thoroughly and repeat. For best results, use pyrithione zinc shampoo at least 2 times per week or as directed by your doctor. Do not use more often than once daily.
Route of Administration: Topical
In Vitro Use Guide
Pyrithione zinc had a reversible inhibitory effect on the growth of BHK 21 cells at 0.1 ug/ml, but had a rapid, irreversible inhibitory effect at 1 ug/ml associated with cell rounding and detachment.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:05:25 GMT 2023
Edited
by admin
on Fri Dec 15 15:05:25 GMT 2023
Record UNII
R953O2RHZ5
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PYRITHIONE ZINC
INN   MART.   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
ZINC PYRITHIONE
HSDB   INCI   JAN   VANDF  
INCI  
Official Name English
ZINC PYRITHONE [VANDF]
Common Name English
ZINC PYRIDINETHIONE
Common Name English
pyrithione zinc [INN]
Common Name English
PYRITHIONE ZINC DERIVATIVE [MI]
Common Name English
SEBULON SHAMPOO
Brand Name English
NSC-290409
Code English
PYRITHIONE ZINC DERIVATIVE
MI  
Common Name English
PYRITHIONE ZINC [MART.]
Common Name English
ZINC PYRITHIONE [JAN]
Common Name English
ZINC PYRITHIONE [VANDF]
Common Name English
PYRITHIONE ZINC [VANDF]
Common Name English
ZINC OMADINE
Common Name English
ZINC-2-PYRIDINETHIONE-1-OXIDE
Systematic Name English
Bis[1-hydroxy-2(1H)-pyridinethionato]zinc
Common Name English
ZINC PYRITHIONE [INCI]
Common Name English
HEAD & SHOULDERS CONDITIONER
Brand Name English
PYRITHIONE ZINC [USAN]
Common Name English
ZINC, BIS(1-(HYDROXY-.KAPPA.O)-2(1H)-PYRIDINETHIONATO-.KAPPA.S2)-, (T-4)-
Systematic Name English
ZINC PYRITHIONE [HSDB]
Common Name English
PYRITHIONE ZINC [ORANGE BOOK]
Common Name English
Pyrithione zinc [WHO-DD]
Common Name English
ZINCPOLYANEMINE
Common Name English
ZINC, BIS(1-HYDROXY-2(1H)-PYRIDINETHIONATO-O,S)-(T-4)-
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C514
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
CFR 21 CFR 358.710
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
EPA PESTICIDE CODE 88002
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
WHO-VATC QD11AX12
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
Food Contact Sustance Notif, (FCN No.) FCN NO. 1169
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
WHO-ATC D11AX12
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
236-671-3
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
PRIMARY
FDA UNII
R953O2RHZ5
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
PRIMARY
SMS_ID
100000085496
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
PRIMARY
NSC
290409
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
PRIMARY
CAS
13463-41-7
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
PRIMARY
PUBCHEM
26041
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
PRIMARY
DAILYMED
R953O2RHZ5
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
PRIMARY
HSDB
4498
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
PRIMARY
MERCK INDEX
m9377
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL1356238
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
PRIMARY
RXCUI
39952
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
PRIMARY RxNorm
MESH
C010423
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
PRIMARY
EVMPD
SUB10172MIG
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
PRIMARY
INN
2295
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
PRIMARY
WIKIPEDIA
ZINC PYRITHIONE
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
PRIMARY
DRUG CENTRAL
4248
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
PRIMARY
DRUG BANK
DBSALT002737
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
PRIMARY
CHEBI
32076
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
PRIMARY
NCI_THESAURUS
C47698
Created by admin on Fri Dec 15 15:05:25 GMT 2023 , Edited by admin on Fri Dec 15 15:05:25 GMT 2023
PRIMARY
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PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY