Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C5H4NOS.Na.H2O |
| Molecular Weight | 167.161 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.[Na+].[O-][N+]1=CC=CC=C1[S-]
InChI
InChIKey=HTJXGDXCIFMYMU-UHFFFAOYSA-M
InChI=1S/C5H5NOS.Na.H2O/c7-6-4-2-1-3-5(6)8;;/h1-4,8H;;1H2/q;+1;/p-1
| 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 | HO |
| Molecular Weight | 17.0073 |
| 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 |
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 |
0.98 µM [IC50] | ||
Target ID: GO:0006927 |
|||
Target ID: CHEMBL4261 |
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 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: |
unhealthy, 17–64 |
Disc. AE: Erythema... AEs leading to discontinuation/dose reduction: Erythema (1.25%) Sources: |
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: |
unhealthy, 17–64 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Zinc induces apoptosis that can be suppressed by lanthanum in C6 rat glioma cells. | 2001 Aug |
|
| Antimicrobial susceptibility changes and T-OMP shifts in pyrithione-passaged planktonic cultures of Pseudomonas aeruginosa PAO1. | 2002 |
|
| Experimental tinea unguium model to assess topical antifungal agents using the infected human nail with dermatophyte in vitro. | 2002 Dec |
|
| Requirement of caspase and p38MAPK activation in zinc-induced apoptosis in human leukemia HL-60 cells. | 2002 Dec |
|
| Intracellular zinc fluctuations modulate protein tyrosine phosphatase activity in insulin/insulin-like growth factor-1 signaling. | 2003 Dec 10 |
|
| Characterisation of zinc uptake into rat cultured cerebrocortical oligodendrocyte progenitor cells. | 2003 Dec 4 |
|
| Blocking NF-kappaB activation may be an effective strategy in the fever therapy. | 2003 Oct |
|
| Effect of Zn2+ ions on ryanodine binding to sarcoplasmic reticulum of striated muscles in the presence of pyrithione. | 2004 Dec |
|
| Pyruvate limits zinc-induced rat oligodendrocyte progenitor cell death. | 2004 Jan |
|
| Monitoring apoptosis with fluorescent Zn2+-indicators. | 2004 Mar 2 |
|
| Chromatographic behavior of pyrithiones. | 2004 Oct 15 |
|
| Evaluation of metal-conjugated compounds as inhibitors of 3CL protease of SARS-CoV. | 2004 Sep 10 |
|
| Activation of a calcium entry pathway by sodium pyrithione in the bag cell neurons of Aplysia. | 2004 Sep 15 |
|
| Fluctuations of cellular, available zinc modulate insulin signaling via inhibition of protein tyrosine phosphatases. | 2005 |
|
| Pyrithiones as antifoulants: environmental fate and loss of toxicity. | 2005 |
|
| Activation of caspase-3 in HL-60 cells treated with pyrithione and zinc. | 2005 Apr |
|
| A comparison of hair quality and cosmetic acceptance following the use of two anti-dandruff shampoos. | 2005 Dec |
|
| Product pharmacology and medical actives in achieving therapeutic benefits. | 2005 Dec |
|
| S100A9 deficiency alters adenosine-5'-triphosphate induced calcium signalling but does not generally interfere with calcium and zinc homeostasis in murine neutrophils. | 2005 Jun |
|
| Pustular psoriasis and the Kobner phenomenon caused by allergic contact dermatitis from zinc pyrithione-containing shampoo. | 2005 Mar |
|
| Reaction of hydroxyl radical with aromatic hydrocarbons in nonaqueous solutions: A laser flash photolysis study in acetonitrile. | 2005 Mar 24 |
|
| Endogenous zinc in neurological diseases. | 2005 Oct |
|
| 3-Alkylpyridinium compounds as potential non-toxic antifouling agents. | 2006 |
|
| Unconventional neuroprotection against Ca2+ -dependent insults by metalloporphyrin catalytic antioxidants. | 2006 Aug |
|
| The interactive effects of binary mixtures of three antifouling biocides and three heavy metals against the marine algae Chaetoceros gracilis. | 2006 Aug |
|
| Toxicity reduction of metal pyrithiones by near ultraviolet irradiation. | 2006 Aug |
|
| Inhibition of presynaptic activity by zinc released from mossy fiber terminals during tetanic stimulation. | 2006 Jan |
|
| Flow cytometric measurement of labile zinc in peripheral blood mononuclear cells. | 2006 May 15 |
|
| Opposing effects of ERK and p38 MAP kinases on HeLa cell apoptosis induced by dipyrithione. | 2007 Feb 28 |
|
| NADPH-dependent coenzyme Q reductase is the main enzyme responsible for the reduction of non-mitochondrial CoQ in cells. | 2008 |
|
| Synergistic toxic effects of zinc pyrithione and copper to three marine species: Implications on setting appropriate water quality criteria. | 2008 |
|
| Synthesis and anticancer properties of water-soluble zinc ionophores. | 2008 Jul 1 |
|
| Aryl-bridged 1-hydroxypyridin-2-one: sensitizer ligands for Eu(III). | 2008 Jul 21 |
|
| Insights into Zn2+ homeostasis in neurons from experimental and modeling studies. | 2008 Mar |
|
| 2-(Mesitylmethylsulfanyl)pyridine N-oxide monohydrate. | 2008 Sep 17 |
|
| Trace metals in antifouling paint particles and their heterogeneous contamination of coastal sediments. | 2009 Apr |
|
| Leaching of hydrophobic Cu and Zn from discarded marine antifouling paint residues: evidence for transchelation of metal pyrithiones. | 2009 Dec |
|
| Biofouling growth in cold estuarine waters and evaluation of some chitosan and copper anti-fouling paints. | 2009 Jul 14 |
|
| Metal ionophores - an emerging class of anticancer drugs. | 2009 Nov |
|
| Tracing of intracellular zinc(II) fluorescence flux to monitor cell apoptosis by using FluoZin-3AM. | 2009 Oct |
|
| Pyrithione and 8-hydroxyquinolines transport lead across erythrocyte membranes. | 2009 Sep |
|
| Activation of the orphan receptor tyrosine kinase ALK by zinc. | 2010 Aug 6 |
|
| The roles of iPLA2, TRPM8 and TRPA1 in chemically induced cold hypersensitivity. | 2010 Jan 21 |
|
| An integrated imaging approach to the study of oxidative stress generation by mitochondrial dysfunction in living cells. | 2010 Jul |
|
| DNA microarray analysis suggests that zinc pyrithione causes iron starvation to the yeast Saccharomyces cerevisiae. | 2010 May |
|
| Zinc signals promote IL-2-dependent proliferation of T cells. | 2010 May |
|
| Cellular zinc homeostasis is a regulator in monocyte differentiation of HL-60 cells by 1 alpha,25-dihydroxyvitamin D3. | 2010 May |
|
| Novel antifouling agent zinc pyrithione: determination, acute toxicity, and bioaccumulation in marine mussels (Mytilus galloprovincialis). | 2010 Nov |
|
| 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
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
TYX8368Q25
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| Record Status |
Validated (UNII)
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| Record Version |
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Preferred Name | English | ||
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| Code System | Code | Type | Description | ||
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43835086
Created by
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304675-78-3
Created by
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207511-13-5
Created by
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NON-SPECIFIC STOICHIOMETRY | |||
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TYX8368Q25
Created by
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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PARENT -> SALT/SOLVATE | |||
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ANHYDROUS->SOLVATE |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |