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MedKoo Cat#: 341605 | Name: Pyrithione zinc
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Pyrithione zinc is a dimer of two pyrithione molecules bound by zinc. It is commonly found as an ingredient of commercial anti-dandruff shampoos. This products acts as an antifungal and antibacterial.

Chemical Structure

Pyrithione zinc
Pyrithione zinc
CAS#13463-41-7

Theoretical Analysis

MedKoo Cat#: 341605

Name: Pyrithione zinc

CAS#: 13463-41-7

Chemical Formula: C10H8N2O2S2Zn

Exact Mass:

Molecular Weight: 317.69

Elemental Analysis: C, 37.81; H, 2.54; N, 8.82; O, 10.07; S, 20.18; Zn, 20.58

Price and Availability

Size Price Availability Quantity
10g USD 250.00
100g USD 785.00
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Related CAS #
1121-31-9
Synonym
AI3-62421, BC-J, Biocut ZP, Finecide ZPT, Pyrithione zinc; Zinc pyrithione; 1-hydroxypyridine-2-thione zinc salt; 1 hydroxypyridine 2 thione zinc salt; 1-hydroxypyridine-2-thione zinc; 1 hydroxypyridine 2 thione zinc
IUPAC/Chemical Name
zinc;1-oxidopyridin-1-ium-2-thiolate
InChi Key
OTPSWLRZXRHDNX-UHFFFAOYSA-L
InChi Code
InChI=1S/2C5H5NOS.Zn/c2*7-6-4-2-1-3-5(6)8;/h2*1-4,8H;/q;;+2/p-2
SMILES Code
C1=CC=[N+](C(=C1)[S-])[O-].C1=CC=[N+](C(=C1)[S-])[O-].[Zn+2]
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Pyrithione zinc acts as an antifungal and antibacterial.
In vitro activity:
Treatment of oral squamous cell carcinoma cells with pyrithione zinc reduced cell colony formation, migration and invasion potential. Pyrithione zinc treatment led to altered expression of several key components of the major signaling pathways including PI3K/ AKT/ mTOR and WNT/β-catenin. Pyrithione zinc treatment also reduced expression of 14-3-3ζ, 14-3-3σ, cyclin D1, c-Myc and PKM2. Reference: Mol Oncol. 2015 Oct;9(8):1720-35. https://pubmed.ncbi.nlm.nih.gov/26115765/
In vivo activity:
Pyrithione zinc has potential antitumor properties as a proteasomal DUB inhibitor. Pyrithione zinc targets proteasome-associated DUBs (USP14 and UCHL5) and inhibits their activities, resulting in a rapid accumulation of protein-ubiquitin conjugates without inhibiting the proteolytic activities of 20S proteasomes. Pyrithione zinc efficiently inhibits the growth of lung adenocarcinoma cancer cell xenografts in nude mice. Reference: Oncotarget. 2017 Feb 21;8(8):13942-13956. https://pubmed.ncbi.nlm.nih.gov/28086217/
Solvent mg/mL mM
Solubility
DMSO 30.0 94.43
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 317.69 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Figueroa EE, Denton JS. Zinc pyrithione activates the volume-regulated anion channel through an antioxidant-sensitive mechanism. Am J Physiol Cell Physiol. 2021 Jun 1;320(6):C1088-C1098. doi: 10.1152/ajpcell.00070.2021. Epub 2021 Apr 7. PMID: 33826406; PMCID: PMC8285639. 2. Srivastava G, Matta A, Fu G, Somasundaram RT, Datti A, Walfish PG, Ralhan R. Anticancer activity of pyrithione zinc in oral cancer cells identified in small molecule screens and xenograft model: Implications for oral cancer therapy. Mol Oncol. 2015 Oct;9(8):1720-35. doi: 10.1016/j.molonc.2015.05.005. Epub 2015 May 21. PMID: 26115765; PMCID: PMC5528795. 3. Zhao C, Chen X, Yang C, Zang D, Lan X, Liao S, Zhang P, Wu J, Li X, Liu N, Liao Y, Huang H, Shi X, Jiang L, Liu X, Dou QP, Wang X, Liu J. Repurposing an antidandruff agent to treating cancer: zinc pyrithione inhibits tumor growth via targeting proteasome-associated deubiquitinases. Oncotarget. 2017 Feb 21;8(8):13942-13956. doi: 10.18632/oncotarget.14572. PMID: 28086217; PMCID: PMC5355152. 4. Cho YS, Lee KH, Park JW. Pyrithione-zinc Prevents UVB-induced Epidermal Hyperplasia by Inducing HIF-1alpha. Korean J Physiol Pharmacol. 2010 Apr;14(2):91-7. doi: 10.4196/kjpp.2010.14.2.91. Epub 2010 Apr 30. PMID: 20473380; PMCID: PMC2869458.
In vitro protocol:
1. Figueroa EE, Denton JS. Zinc pyrithione activates the volume-regulated anion channel through an antioxidant-sensitive mechanism. Am J Physiol Cell Physiol. 2021 Jun 1;320(6):C1088-C1098. doi: 10.1152/ajpcell.00070.2021. Epub 2021 Apr 7. PMID: 33826406; PMCID: PMC8285639. 2. Srivastava G, Matta A, Fu G, Somasundaram RT, Datti A, Walfish PG, Ralhan R. Anticancer activity of pyrithione zinc in oral cancer cells identified in small molecule screens and xenograft model: Implications for oral cancer therapy. Mol Oncol. 2015 Oct;9(8):1720-35. doi: 10.1016/j.molonc.2015.05.005. Epub 2015 May 21. PMID: 26115765; PMCID: PMC5528795.
In vivo protocol:
1. Zhao C, Chen X, Yang C, Zang D, Lan X, Liao S, Zhang P, Wu J, Li X, Liu N, Liao Y, Huang H, Shi X, Jiang L, Liu X, Dou QP, Wang X, Liu J. Repurposing an antidandruff agent to treating cancer: zinc pyrithione inhibits tumor growth via targeting proteasome-associated deubiquitinases. Oncotarget. 2017 Feb 21;8(8):13942-13956. doi: 10.18632/oncotarget.14572. PMID: 28086217; PMCID: PMC5355152. 2. Cho YS, Lee KH, Park JW. Pyrithione-zinc Prevents UVB-induced Epidermal Hyperplasia by Inducing HIF-1alpha. Korean J Physiol Pharmacol. 2010 Apr;14(2):91-7. doi: 10.4196/kjpp.2010.14.2.91. Epub 2010 Apr 30. PMID: 20473380; PMCID: PMC2869458.
1: Eid BG, Gurney AM. Zinc pyrithione activates K+ channels and hyperpolarizes the membrane of rat pulmonary artery smooth muscle cells. PLoS One. 2018 Feb 23;13(2):e0192699. doi: 10.1371/journal.pone.0192699. eCollection 2018. PubMed PMID: 29474372; PubMed Central PMCID: PMC5824988. 2: Ijaz N, Fitzgerald D. Seborrhoeic dermatitis. Br J Hosp Med (Lond). 2017 Jun 2;78(6):C88-C91. doi: 10.12968/hmed.2017.78.6.C88. PubMed PMID: 28614013. 3: Jones N, Carvalho M, Branvold-Herr A. Management of Psoriasis with a XemaTop Topical Compounded Formula: A Case Report. Int J Pharm Compd. 2017 May-Jun;21(3):205-211. PubMed PMID: 28557781. 4: Chen G, Ji C, Miao M, Yang K, Luo Y, Hoptroff M, Collins LZ, Janssen HG. Ex-vivo measurement of scalp follicular infundibulum delivery of zinc pyrithione and climbazole from an anti-dandruff shampoo. J Pharm Biomed Anal. 2017 Sep 5;143:26-31. doi: 10.1016/j.jpba.2017.05.031. Epub 2017 May 17. PubMed PMID: 28550716. 5: Bhattacharyya A, Jain N, Prasad S, Jain S, Yadav V, Ghosh S, Sengupta S. Evaluation of therapeutic potential of VB-001, a leave-on formulation, for the treatment of moderate adherent dandruff. BMC Dermatol. 2017 May 3;17(1):5. doi: 10.1186/s12895-017-0058-5. PubMed PMID: 28468620; PubMed Central PMCID: PMC5415814. 6: Thokala S, Inapurapu S, Bodiga VL, Vemuri PK, Bodiga S. Loss of ErbB2-PI3K/Akt signaling prevents zinc pyrithione-induced cardioprotection during ischemia/reperfusion. Biomed Pharmacother. 2017 Apr;88:309-324. doi: 10.1016/j.biopha.2017.01.065. Epub 2017 Jan 21. PubMed PMID: 28119233. 7: Zhao C, Chen X, Yang C, Zang D, Lan X, Liao S, Zhang P, Wu J, Li X, Liu N, Liao Y, Huang H, Shi X, Jiang L, Liu X, Dou QP, Wang X, Liu J. Repurposing an antidandruff agent to treating cancer: zinc pyrithione inhibits tumor growth via targeting proteasome-associated deubiquitinases. Oncotarget. 2017 Feb 21;8(8):13942-13956. doi: 10.18632/oncotarget.14572. PubMed PMID: 28086217; PubMed Central PMCID: PMC5355152. 8: Schwartz JR. Zinc Pyrithione: A Topical Antimicrobial With Complex Pharmaceutics. J Drugs Dermatol. 2016 Feb;15(2):140-4. Review. PubMed PMID: 26885780. 9: Danesh MJ, Kimball AB. Pyrithione zinc as a general management strategy for hidradenitis suppurativa. J Am Acad Dermatol. 2015 Nov;73(5):e175. doi: 10.1016/j.jaad.2015.07.026. PubMed PMID: 26475559. 10: Bodiga VL, Thokala S, Vemuri PK, Bodiga S. Zinc pyrithione inhibits caspase-3 activity, promotes ErbB1-ErbB2 heterodimerization and suppresses ErbB2 downregulation in cardiomyocytes subjected to ischemia/reperfusion. J Inorg Biochem. 2015 Dec;153:49-59. doi: 10.1016/j.jinorgbio.2015.09.010. Epub 2015 Sep 26. PubMed PMID: 26436560.

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