PYRITHIONE

US Approved OTC

First approved in 1961

Details

Stereochemistry	ACHIRAL
Molecular Formula	C5H5NOS
Molecular Weight	127.164
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[O-][N+]1=CC=CC=C1S

InChI

InChIKey=FGVVTMRZYROCTH-UHFFFAOYSA-N

InChI=1S/C5H5NOS/c7-6-4-2-1-3-5(6)8/h1-4,8H

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

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
Zinc is involved in the expression of a nuclear-encoded alternative oxidase gene in the yeast Hansenula anomala.	2002 Dec	12596861
Experimental tinea unguium model to assess topical antifungal agents using the infected human nail with dermatophyte in vitro.	2002 Dec	12525893
Intracellular zinc fluxes associated with apoptosis in growth plate chondrocytes.	2003 Apr 1	12616534
CAN-296-P is effective against cutaneous candidiasis in guinea pigs.	2003 Aug	12927959
Role of lipid-soluble complexes in targeted tumor therapy.	2003 Aug	12902421
Nuclear factor-kappaB inhibitors abolish hypoxic vasoconstriction in sheep-isolated pulmonary arteries.	2003 Jan 1	12498922
The use of 0.25% zinc pyrithione spray does not enhance the efficacy of clobetasol propionate 0.05% foam in the treatment of psoriasis.	2003 Jul	12833013
Examination of novel zinc-binding groups for use in matrix metalloproteinase inhibitors.	2003 Jun 2	12767177
Blocking NF-kappaB activation may be an effective strategy in the fever therapy.	2003 Oct	14975183
Membrane-permeant chelators can attenuate Zn2+-induced cortical neuronal death.	2003 Sep	12871659
Flow injection analysis of zinc pyrithione in hair care products on a cobalt phthalocyanine modified screen-printed carbon electrode.	2004 Apr 19	18969379
Effect of Zn2+ ions on ryanodine binding to sarcoplasmic reticulum of striated muscles in the presence of pyrithione.	2004 Dec	15569410
Monitoring apoptosis with fluorescent Zn2+-indicators.	2004 Mar 2	15010549
Chromatographic behavior of pyrithiones.	2004 Oct 15	15527126
Activation of a calcium entry pathway by sodium pyrithione in the bag cell neurons of Aplysia.	2004 Sep 15	15307146
A comparison of hair quality and cosmetic acceptance following the use of two anti-dandruff shampoos.	2005 Dec	16382664
S100A9 deficiency alters adenosine-5'-triphosphate induced calcium signalling but does not generally interfere with calcium and zinc homeostasis in murine neutrophils.	2005 Jun	15778088
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
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
In vitro-refolding of a single-chain Fv fragment in the presence of heteroaromatic thiols.	2008 Apr 30	18321603
Comparative effects of sodium pyrithione evoked intracellular calcium elevation in rodent and primate ventral horn motor neurons.	2008 Feb 1	18053804
Thioperoxy derivative generated by UV-induced transformation of N-hydroxypyridine-2(1H)-thione isolated in low-temperature matrixes.	2008 Jan 17	18085761
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
Insights into Zn2+ homeostasis in neurons from experimental and modeling studies.	2008 Mar	18184873
Exogenous zinc protects cardiac cells from reperfusion injury by targeting mitochondrial permeability transition pore through inactivation of glycogen synthase kinase-3beta.	2008 Sep	18660440
Molecular mechanism underlying Akt activation in zinc-induced cardioprotection.	2009 Aug	19525380
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
The roles of iPLA2, TRPM8 and TRPA1 in chemically induced cold hypersensitivity.	2010 Jan 21	20092626
DNA microarray analysis suggests that zinc pyrithione causes iron starvation to the yeast Saccharomyces cerevisiae.	2010 May	20347771
Zinc signals promote IL-2-dependent proliferation of T cells.	2010 May	20201035
Novel antifouling agent zinc pyrithione: determination, acute toxicity, and bioaccumulation in marine mussels (Mytilus galloprovincialis).	2010 Nov	20853456

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 18:31:34 GMT 2025` Edited by `admin` on `Mon Mar 31 18:31:34 GMT 2025`
Record UNII	6GK82EC25D
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-179790

Preferred Name

English

PYRITHIONE

Common Name

English

PYRITHIONE [MI]

Common Name

English

2-PYRIDINETHIOL 1-OXIDE

Systematic Name

English

Pyrithione [WHO-DD]

Common Name

English

PYRIDINETHIOL N-OXIDE

Systematic Name

English

2(1H)-PYRIDINETHIONE, 1-HYDROXY-

Systematic Name

English

OMADINE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29708