PYRITHIONE SODIUM

US Approved OTC

First approved in 1961

Details

Stereochemistry	ACHIRAL
Molecular Formula	C5H4NOS.Na
Molecular Weight	149.146
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].[O-][N+]1=CC=CC=C1[S-]

InChI

InChIKey=WNGMMIYXPIAYOB-UHFFFAOYSA-M

InChI=1S/C5H5NOS.Na/c7-6-4-2-1-3-5(6)8;/h1-4,8H;/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula	Na
Molecular Weight	22.98976928
Charge	1
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
Elevated intracellular zinc and altered proton homeostasis in forebrain neurons.	2002	12204213
The relationship between intracellular free iron and cell injury in cultured neurons, astrocytes, and oligodendrocytes.	2002 Jul 15	12122047
Studies on cytotoxic and genotoxic effects of N-hydroxypyridine-2-thione (Omadine) in L5178Y mouse lymphoma cells.	2002 Nov 15	12368059
Delayed diagnosis of occupational contact dermatitis from sodium pyrithione in a metalworking fluid.	2002 Oct	12492539
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
Intracellular zinc fluctuations modulate protein tyrosine phosphatase activity in insulin/insulin-like growth factor-1 signaling.	2003 Dec 10	14644152
Characterisation of zinc uptake into rat cultured cerebrocortical oligodendrocyte progenitor cells.	2003 Dec 4	14625036
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
Flow injection analysis of zinc pyrithione in hair care products on a cobalt phthalocyanine modified screen-printed carbon electrode.	2004 Apr 19	18969379
Pyruvate limits zinc-induced rat oligodendrocyte progenitor cell death.	2004 Jan	14725623
Monitoring apoptosis with fluorescent Zn2+-indicators.	2004 Mar 2	15010549
Evaluation of metal-conjugated compounds as inhibitors of 3CL protease of SARS-CoV.	2004 Sep 10	15358550
Fluctuations of cellular, available zinc modulate insulin signaling via inhibition of protein tyrosine phosphatases.	2005	16240670
Pyrithiones as antifoulants: environmental fate and loss of toxicity.	2005	16019389
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
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
Automated laser scanning cytometry: a powerful tool for multi-parameter analysis of drug-induced apoptosis.	2007 Feb	17200953
Zinc homeostasis and immunity.	2007 Jan	17126599
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
In vitro-refolding of a single-chain Fv fragment in the presence of heteroaromatic thiols.	2008 Apr 30	18321603
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
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	18322709
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
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
Electrospray ionization mass spectrometric observation of ligand exchange of zinc pyrithione with amino acids.	2009 Jul	19517459
Synthesis and characterization of a pyridine-2-thiol N-oxide gold(I) complex with potent antiproliferative effect against Trypanosoma cruzi and Leishmania sp. insight into its mechanism of action.	2009 Oct	19361864
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
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 18:10:46 GMT 2025` Edited by `admin` on `Mon Mar 31 18:10:46 GMT 2025`
Record UNII	6L3991491R
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

PYRITHIONE SODIUM

Official Name

English

SODIUM PYRITHIONE

Preferred Name

English

AL02725

Code

English

TOMICIDE S

Brand Name

English

TOPCIDE 280

Brand Name

English

1-Hydroxy-2(1H)-pyridinethione, sodium salt

Common Name

English

Pyrithione sodium [WHO-DD]

Common Name

English

OMACIDE 24

Brand Name

English

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

Common Name

English

SODIUM SALT OF 1-HYDROXY 2(1H)-PYRIDINE THIONE

Common Name

English

AL-02725

Code

English

2(1H)-PYRIDINETHIONE, 1-HYDROXY-, SODIUM SALT (1:1)

Systematic Name

English

SODIUM OMADINE

Brand Name

English

NSC-4483

Code

English

OMADINE SODIUM

Common Name

English

PYRITHIONE SODIUM [USAN]

Common Name

English

PYRITHIONE SODIUM SALT

Common Name

English

2-PYRIDINETHIOL, 1-OXIDE, SODIUM SALT (1:1)

Systematic Name

English

2-PYRIDINETHIOL-1-OXIDE, SODIUM SALT

Common Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

88004