PYRITHIONE ZINC

US Approved OTC

First approved in 1961

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 Search

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	Zn
Molecular Weight	65.409
Charge	2
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15685130 | https://www.drugs.com/cdi/pyrithione-zinc-shampoo.html | https://www.dermaharmony.com/ingredients/pyrithionezinc.aspx | https://www.ncbi.nlm.nih.gov/pubmed/26885780

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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Egl nine homolog 3 13 Target ID: CHEMBL5705 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26940742	Inhibitor 8504	0.98 µM [IC50]
transformed cell apoptotic process 104 Target ID: GO:0006927 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22105358	Activator 1447
Hypoxia-inducible factor 1 alpha 17 Target ID: CHEMBL4261 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20473380	Activator 1447

Conditions

Condition	Modality	Targets	Highest Phase	Product
Seborrhea 11 Sources: https://www.drugs.com/cdi/pyrithione-zinc-shampoo.html https://www.ncbi.nlm.nih.gov/pubmed/26885780 https://www.ncbi.nlm.nih.gov/pubmed/22866664	Curative		Approved 8583	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
Acute myeloid leukemia 141 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22105358	Primary		Preclinical	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
0.2 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/730082/	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

Value	Dose	Co-administered	Analyte	Population
27.01 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/730082/	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
115 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/730082/	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

Dose	Population	Adverse events
1 % 2 times / week multiple, topical Recommended Dose: 1 %, 2 times / week Route: topical Route: multiple Dose: 1 %, 2 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/12476017	unhealthy, 17–64 Health Status: unhealthy Age Group: 17–64 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/12476017	Disc. AE: Erythema... AEs leading to discontinuation/dose reduction: Erythema (1.25%) Sources: https://pubmed.ncbi.nlm.nih.gov/12476017

AEs

AE	Significance	Dose	Population
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: https://pubmed.ncbi.nlm.nih.gov/12476017	unhealthy, 17–64 Health Status: unhealthy Age Group: 17–64 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/12476017

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/21362439/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:36578	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:36578
ChemicalBook	CB8889373	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8889373
MolPort	MolPort-006-148-004	https://www.molport.com/shop/molecule-link/MolPort-006-148-004
ZINC	ZINC000013524343	http://zinc15.docking.org/substances/ZINC000013524343

PubMed

Title	Date	PubMed
Flow injection analysis of zinc pyrithione in hair care products on a cobalt phthalocyanine modified screen-printed carbon electrode.	2004 Apr 19	18969379
A comparison of hair quality and cosmetic acceptance following the use of two anti-dandruff shampoos.	2005 Dec	16382664
Product pharmacology and medical actives in achieving therapeutic benefits.	2005 Dec	16382663
Reaction of hydroxyl radical with aromatic hydrocarbons in nonaqueous solutions: A laser flash photolysis study in acetonitrile.	2005 Mar 24	16833557
3-Alkylpyridinium compounds as potential non-toxic antifouling agents.	2006	16805440
Unconventional neuroprotection against Ca2+ -dependent insults by metalloporphyrin catalytic antioxidants.	2006 Aug	16895586
The interactive effects of binary mixtures of three antifouling biocides and three heavy metals against the marine algae Chaetoceros gracilis.	2006 Aug	16841316
Toxicity reduction of metal pyrithiones by near ultraviolet irradiation.	2006 Aug	16841307
Flow cytometric measurement of labile zinc in peripheral blood mononuclear cells.	2006 May 15	16545333
Acute toxicity of pyrithione antifouling biocides and joint toxicity with copper to red sea bream (Pagrus major) and toy shrimp (Heptacarpus futilirostris).	2006 Nov	17089732
Zinc induces ERK-dependent cell death through a specific Ras isoform.	2006 Nov	17013754
Overexpression of DSCR1 blocks zinc-induced neuronal cell death through the formation of nuclear aggregates.	2007 Aug	17596961
Automated laser scanning cytometry: a powerful tool for multi-parameter analysis of drug-induced apoptosis.	2007 Feb	17200953
Opposing effects of ERK and p38 MAP kinases on HeLa cell apoptosis induced by dipyrithione.	2007 Feb 28	17464209
Chemical genetics suggests a critical role for lysyl oxidase in zebrafish notochord morphogenesis.	2007 Jan	17216056
Zinc homeostasis and immunity.	2007 Jan	17126599
Zinc induces cell death in immortalized embryonic hippocampal cells via activation of Akt-GSK-3beta signaling.	2007 Jan 15	17098228
Protective role of intracellular zinc in myocardial ischemia/reperfusion is associated with preservation of protein kinase C isoforms.	2007 May	17322024
Role of zinc influx via AMPA/kainate receptor activation in metabotropic glutamate receptor-mediated calcium release.	2007 May 1	17304583
Time-dependent X-ray absorption spectroscopic (XAS) study on the transformation of zinc basic salt into bis(N-oxopyridine-2-thionato) zinc (II).	2007 Nov	18047076
Toxicity of four antifouling biocides and their mixtures on the brine shrimp Artemia salina.	2007 Nov 15	17765949
Preliminary evaluation of antimicrobial activity of some chemicals on in vitro apple shoots infected by 'Candidatus Phytoplasma mali'.	2008	19226772
NADPH-dependent coenzyme Q reductase is the main enzyme responsible for the reduction of non-mitochondrial CoQ in cells.	2008	19096101
Synergistic toxic effects of zinc pyrithione and copper to three marine species: Implications on setting appropriate water quality criteria.	2008	18495176
2-(Benzyl-sulfan-yl)pyridine N-oxide.	2008 Apr 26	21202409
Comparative effects of sodium pyrithione evoked intracellular calcium elevation in rodent and primate ventral horn motor neurons.	2008 Feb 1	18053804
Poly[ethano-lbis(μ(3)-2-thio-xo-1,2-dihydro-pyridin-1-olato)dilithium(I)].	2008 Feb 8	21201855
2,2'-[2,3,5,6-Tetra-methyl-p-phenyl-ene-bis(methyl-enethio)]bis-(pyridine N-oxide).	2008 Jan 9	21201437
Synthesis and anticancer properties of water-soluble zinc ionophores.	2008 Jul 1	18593933
Aryl-bridged 1-hydroxypyridin-2-one: sensitizer ligands for Eu(III).	2008 Jul 21	18553909
Exogenous zinc protects cardiac cells from reperfusion injury by targeting mitochondrial permeability transition pore through inactivation of glycogen synthase kinase-3beta.	2008 Sep	18660440
2-(Mesitylmethylsulfanyl)pyridine N-oxide monohydrate.	2008 Sep 17	21201156
2-(2,3,5,6-Tetra-methyl-benzyl-sulfan-yl)pyridine N-oxide.	2008 Sep 20	21201175
Trace metals in antifouling paint particles and their heterogeneous contamination of coastal sediments.	2009 Apr	19100584
Molecular mechanism underlying Akt activation in zinc-induced cardioprotection.	2009 Aug	19525380
Leaching of hydrophobic Cu and Zn from discarded marine antifouling paint residues: evidence for transchelation of metal pyrithiones.	2009 Dec	19616352
Pannexin-1-dependent caspase-1 activation and secretion of IL-1beta is regulated by zinc.	2009 Feb	19130485
Electrospray ionization mass spectrometric observation of ligand exchange of zinc pyrithione with amino acids.	2009 Jul	19517459
Biofouling growth in cold estuarine waters and evaluation of some chitosan and copper anti-fouling paints.	2009 Jul 14	19742133
Metal ionophores - an emerging class of anticancer drugs.	2009 Nov	19859983
Tracing of intracellular zinc(II) fluorescence flux to monitor cell apoptosis by using FluoZin-3AM.	2009 Oct	19784961
Pyrithione and 8-hydroxyquinolines transport lead across erythrocyte membranes.	2009 Sep	19665691
Insulin storage and glucose homeostasis in mice null for the granule zinc transporter ZnT8 and studies of the type 2 diabetes-associated variants.	2009 Sep	19542200
Zinc signals promote IL-2-dependent proliferation of T cells.	2010 May	20201035
Cellular zinc homeostasis is a regulator in monocyte differentiation of HL-60 cells by 1 alpha,25-dihydroxyvitamin D3.	2010 May	20089671
K+ channel openers restore verapamil-inhibited lung fluid resolution and transepithelial ion transport.	2010 May 27	20507598
Novel antifouling agent zinc pyrithione: determination, acute toxicity, and bioaccumulation in marine mussels (Mytilus galloprovincialis).	2010 Nov	20853456
Zinc in innate and adaptive tumor immunity.	2010 Nov 18	21087493
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	21079686
UVB radiation induces an increase in intracellular zinc in human epidermal keratinocytes.	2010 Oct	20818483

Patents

Sample Use Guides

In Vivo Use Guide

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 `Mon Mar 31 17:46:05 GMT 2025` Edited by `admin` on `Mon Mar 31 17:46:05 GMT 2025`
Record UNII	R953O2RHZ5
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ZINC PYRITHIONE

Preferred Name

English

PYRITHIONE ZINC

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

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

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