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 19 Target ID: CHEMBL5705 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26940742	Inhibitor 8297	0.98 µM [IC50]
transformed cell apoptotic process 108 Target ID: GO:0006927 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22105358	Activator 1430
Hypoxia-inducible factor 1 alpha 17 Target ID: CHEMBL4261 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20473380	Activator 1430

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 8429	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 136 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 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: https://pubmed.ncbi.nlm.nih.gov/12476017 Page: p.436, 438	Disc. AE: Erythema... AEs leading to discontinuation/dose reduction: Erythema (1.25%) Sources: https://pubmed.ncbi.nlm.nih.gov/12476017 Page: p.436, 438

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 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: https://pubmed.ncbi.nlm.nih.gov/12476017 Page: p.436, 438

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 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
Endogenous zinc in neurological diseases.	2005 Oct	20396459
Overexpression of DSCR1 blocks zinc-induced neuronal cell death through the formation of nuclear aggregates.	2007 Aug	17596961
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
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
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
Poly[ethano-lbis(μ(3)-2-thio-xo-1,2-dihydro-pyridin-1-olato)dilithium(I)].	2008 Feb 8	21201855
Thioperoxy derivative generated by UV-induced transformation of N-hydroxypyridine-2(1H)-thione isolated in low-temperature matrixes.	2008 Jan 17	18085761
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
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
Rising zinc: a significant cause of ischemic neuronal death in the CA1 region of rat hippocampus.	2009 Aug	19491923
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
Clioquinol and pyrithione activate TRPA1 by increasing intracellular Zn2+.	2009 May 19	19416844
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
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
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
Dandruff: the most commercially exploited skin disease.	2010 Apr-Jun	20606879
Activation of the orphan receptor tyrosine kinase ALK by zinc.	2010 Aug 6	20621063
The roles of iPLA2, TRPM8 and TRPA1 in chemically induced cold hypersensitivity.	2010 Jan 21	20092626
An integrated imaging approach to the study of oxidative stress generation by mitochondrial dysfunction in living cells.	2010 Jul	20413366
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
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 `Fri Dec 15 16:34:07 GMT 2023` Edited by `admin` on `Fri Dec 15 16:34:07 GMT 2023`
Record UNII	6GK82EC25D
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PYRITHIONE

Common Name

English

NSC-179790

Code

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