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 |
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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 Date1986 |
|||
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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Elevated intracellular zinc and altered proton homeostasis in forebrain neurons. | 2002 |
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Antimicrobial susceptibility changes and T-OMP shifts in pyrithione-passaged planktonic cultures of Pseudomonas aeruginosa PAO1. | 2002 |
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Zinc is involved in the expression of a nuclear-encoded alternative oxidase gene in the yeast Hansenula anomala. | 2002 Dec |
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Experimental tinea unguium model to assess topical antifungal agents using the infected human nail with dermatophyte in vitro. | 2002 Dec |
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The relationship between intracellular free iron and cell injury in cultured neurons, astrocytes, and oligodendrocytes. | 2002 Jul 15 |
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Delayed diagnosis of occupational contact dermatitis from sodium pyrithione in a metalworking fluid. | 2002 Oct |
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Intracellular zinc fluxes associated with apoptosis in growth plate chondrocytes. | 2003 Apr 1 |
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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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Nuclear factor-kappaB inhibitors abolish hypoxic vasoconstriction in sheep-isolated pulmonary arteries. | 2003 Jan 1 |
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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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Monitoring apoptosis with fluorescent Zn2+-indicators. | 2004 Mar 2 |
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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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Activation of caspase-3 in HL-60 cells treated with pyrithione and zinc. | 2005 Apr |
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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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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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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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Zinc homeostasis and immunity. | 2007 Jan |
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Zinc induces cell death in immortalized embryonic hippocampal cells via activation of Akt-GSK-3beta signaling. | 2007 Jan 15 |
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Preliminary evaluation of antimicrobial activity of some chemicals on in vitro apple shoots infected by 'Candidatus Phytoplasma mali'. | 2008 |
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Exogenous zinc protects cardiac cells from reperfusion injury by targeting mitochondrial permeability transition pore through inactivation of glycogen synthase kinase-3beta. | 2008 Sep |
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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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Activation of the orphan receptor tyrosine kinase ALK by zinc. | 2010 Aug 6 |
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Intracellular Zn(2+) Increase in Cardiomyocytes Induces both Electrical and Mechanical Dysfunction in Heart via Endogenous Generation of Reactive Nitrogen Species. | 2016 Feb |
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
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on
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Fri Dec 15 15:05:25 GMT 2023
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Record UNII |
R953O2RHZ5
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Record Status |
Validated (UNII)
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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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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 |