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
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
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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL5705 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26940742 |
0.98 µM [IC50] | ||
Target ID: GO:0006927 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22105358 |
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Target ID: CHEMBL4261 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20473380 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | Pyrithione zinc shampoo Approved UsePyrithione 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 Date5.10796792E11 |
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Primary | Unknown Approved UseUnknown |
Cmax
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 |
T1/2
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: 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
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: 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 |
PubMed
Title | Date | PubMed |
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Intracellular zinc fluctuations modulate protein tyrosine phosphatase activity in insulin/insulin-like growth factor-1 signaling. | 2003 Dec 10 |
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Non-toxic antifouling activity of polymeric 3-alkylpyridinium salts from the Mediterranean sponge Reniera sarai (Pulitzer-Finali). | 2003 Feb |
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Effect of Zn2+ ions on ryanodine binding to sarcoplasmic reticulum of striated muscles in the presence of pyrithione. | 2004 Dec |
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Chromatographic behavior of pyrithiones. | 2004 Oct 15 |
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Evaluation of metal-conjugated compounds as inhibitors of 3CL protease of SARS-CoV. | 2004 Sep 10 |
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Activation of a calcium entry pathway by sodium pyrithione in the bag cell neurons of Aplysia. | 2004 Sep 15 |
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A comparison of hair quality and cosmetic acceptance following the use of two anti-dandruff shampoos. | 2005 Dec |
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Product pharmacology and medical actives in achieving therapeutic benefits. | 2005 Dec |
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S100A9 deficiency alters adenosine-5'-triphosphate induced calcium signalling but does not generally interfere with calcium and zinc homeostasis in murine neutrophils. | 2005 Jun |
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Reaction of hydroxyl radical with aromatic hydrocarbons in nonaqueous solutions: A laser flash photolysis study in acetonitrile. | 2005 Mar 24 |
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Endogenous zinc in neurological diseases. | 2005 Oct |
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3-Alkylpyridinium compounds as potential non-toxic antifouling agents. | 2006 |
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Unconventional neuroprotection against Ca2+ -dependent insults by metalloporphyrin catalytic antioxidants. | 2006 Aug |
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The interactive effects of binary mixtures of three antifouling biocides and three heavy metals against the marine algae Chaetoceros gracilis. | 2006 Aug |
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Toxicity reduction of metal pyrithiones by near ultraviolet irradiation. | 2006 Aug |
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Inhibition of presynaptic activity by zinc released from mossy fiber terminals during tetanic stimulation. | 2006 Jan |
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Flow cytometric measurement of labile zinc in peripheral blood mononuclear cells. | 2006 May 15 |
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Acute toxicity of pyrithione antifouling biocides and joint toxicity with copper to red sea bream (Pagrus major) and toy shrimp (Heptacarpus futilirostris). | 2006 Nov |
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Zinc induces ERK-dependent cell death through a specific Ras isoform. | 2006 Nov |
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Overexpression of DSCR1 blocks zinc-induced neuronal cell death through the formation of nuclear aggregates. | 2007 Aug |
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Automated laser scanning cytometry: a powerful tool for multi-parameter analysis of drug-induced apoptosis. | 2007 Feb |
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Chemical genetics suggests a critical role for lysyl oxidase in zebrafish notochord morphogenesis. | 2007 Jan |
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Protective role of intracellular zinc in myocardial ischemia/reperfusion is associated with preservation of protein kinase C isoforms. | 2007 May |
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Role of zinc influx via AMPA/kainate receptor activation in metabotropic glutamate receptor-mediated calcium release. | 2007 May 1 |
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Toxicity of four antifouling biocides and their mixtures on the brine shrimp Artemia salina. | 2007 Nov 15 |
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2-(Benzyl-sulfan-yl)pyridine N-oxide. | 2008 Apr 26 |
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Poly[ethano-lbis(μ(3)-2-thio-xo-1,2-dihydro-pyridin-1-olato)dilithium(I)]. | 2008 Feb 8 |
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Thioperoxy derivative generated by UV-induced transformation of N-hydroxypyridine-2(1H)-thione isolated in low-temperature matrixes. | 2008 Jan 17 |
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2,2'-[2,3,5,6-Tetra-methyl-p-phenyl-ene-bis(methyl-enethio)]bis-(pyridine N-oxide). | 2008 Jan 9 |
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Synthesis and anticancer properties of water-soluble zinc ionophores. | 2008 Jul 1 |
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Aryl-bridged 1-hydroxypyridin-2-one: sensitizer ligands for Eu(III). | 2008 Jul 21 |
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2-(Mesitylmethylsulfanyl)pyridine N-oxide monohydrate. | 2008 Sep 17 |
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2-(2,3,5,6-Tetra-methyl-benzyl-sulfan-yl)pyridine N-oxide. | 2008 Sep 20 |
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Molecular mechanism underlying Akt activation in zinc-induced cardioprotection. | 2009 Aug |
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Rising zinc: a significant cause of ischemic neuronal death in the CA1 region of rat hippocampus. | 2009 Aug |
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Electrospray ionization mass spectrometric observation of ligand exchange of zinc pyrithione with amino acids. | 2009 Jul |
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Clioquinol and pyrithione activate TRPA1 by increasing intracellular Zn2+. | 2009 May 19 |
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Metal ionophores - an emerging class of anticancer drugs. | 2009 Nov |
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Tracing of intracellular zinc(II) fluorescence flux to monitor cell apoptosis by using FluoZin-3AM. | 2009 Oct |
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Pyrithione and 8-hydroxyquinolines transport lead across erythrocyte membranes. | 2009 Sep |
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Dandruff: the most commercially exploited skin disease. | 2010 Apr-Jun |
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Activation of the orphan receptor tyrosine kinase ALK by zinc. | 2010 Aug 6 |
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The roles of iPLA2, TRPM8 and TRPA1 in chemically induced cold hypersensitivity. | 2010 Jan 21 |
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DNA microarray analysis suggests that zinc pyrithione causes iron starvation to the yeast Saccharomyces cerevisiae. | 2010 May |
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Cellular zinc homeostasis is a regulator in monocyte differentiation of HL-60 cells by 1 alpha,25-dihydroxyvitamin D3. | 2010 May |
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K+ channel openers restore verapamil-inhibited lung fluid resolution and transepithelial ion transport. | 2010 May 27 |
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Novel antifouling agent zinc pyrithione: determination, acute toxicity, and bioaccumulation in marine mussels (Mytilus galloprovincialis). | 2010 Nov |
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Zinc in innate and adaptive tumor immunity. | 2010 Nov 18 |
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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 |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3882533
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
Edited
Fri Dec 15 15:05:25 UTC 2023
by
admin
on
Fri Dec 15 15:05:25 UTC 2023
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Record UNII |
R953O2RHZ5
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C514
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CFR |
21 CFR 358.710
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EPA PESTICIDE CODE |
88002
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WHO-VATC |
QD11AX12
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Food Contact Sustance Notif, (FCN No.) |
FCN NO. 1169
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WHO-ATC |
D11AX12
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236-671-3
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R953O2RHZ5
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100000085496
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R953O2RHZ5
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4498
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m9377
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CHEMBL1356238
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39952
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C010423
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SUB10172MIG
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2295
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ZINC PYRITHIONE
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4248
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DBSALT002737
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32076
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C47698
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |