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MedKoo Cat#: 533192 | Name: Pyrithione

Description:

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

Pyrithione inhibits NADH-fumarate reductase purified from Trypanosoma cruzi. It is precursor to O-acyl thiohydroxamates. It ligates to metals to form biologically active complexes.

Chemical Structure

Pyrithione
Pyrithione
CAS#1121-31-9

Theoretical Analysis

MedKoo Cat#: 533192

Name: Pyrithione

CAS#: 1121-31-9

Chemical Formula: C5H5NOS

Exact Mass: 127.0092

Molecular Weight: 127.16

Elemental Analysis: C, 47.23; H, 3.96; N, 11.02; O, 12.58; S, 25.21

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
13463-41-7
Synonym
Pyrithione; 2-Mercaptopyridine N-oxide
IUPAC/Chemical Name
1-hydroxypyridine-2-thione
InChi Key
YBBJKCMMCRQZMA-UHFFFAOYSA-N
InChi Code
InChI=1S/C5H5NOS/c7-6-4-2-1-3-5(6)8/h1-4,7H
SMILES Code
C1=CC(=S)N(C=C1)O
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
>3 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 inhibits NADH-fumarate reductase purified from Trypanosoma cruzi.
In vitro activity:
This study explored pyrithione-containing cephalosporins as antimycobacterial agents against Mycobacterium tuberculosis (Mtb). These compounds displayed activity against Mtb in both replicating and non-replicating states, without requiring a β-lactamase inhibitor. Their efficacy relied on the in situ release of pyrithione, which independently eliminated non-replicating Mtb, which is distinct from the A β-lactamase class BlaC. Replicating Mtb was susceptible to both released pyrithione and β-lactam. Reference: ACS Infect Dis. 2019 Aug 9;5(8):1433-1445. https://pubmed.ncbi.nlm.nih.gov/31184461/
In vivo activity:
Pyrithione can be a lead compound for further drug development to overcome imatinib resistance in chronic myelogenous leukemia (CML) patients. Pyrithione induces apoptosis in Bcr-Abl wild-type and Bcr-Abl-T315I mutation cells, inhibits the growth of imatinib-resistant Bcr-Abl-T315I xenografts, downregulates Bcr-Abl levels, and decreases Bcr-Abl protein mediated by DUBs inhibition-induced caspase activation. Reference: Cell Death Dis. 2017 Jul 6;8(7):e2913. https://pubmed.ncbi.nlm.nih.gov/28682311/

Preparing Stock Solutions

The following data is based on the product molecular weight 127.16 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. Lopez Quezada L, Li K, McDonald SL, Nguyen Q, Perkowski AJ, Pharr CW, Gold B, Roberts J, McAulay K, Saito K, Somersan Karakaya S, Javidnia PE, Porras de Francisco E, Amieva MM, Dı Az SP, Mendoza Losana A, Zimmerman M, Liang HH, Zhang J, Dartois V, Sans S, Lagrange S, Goullieux L, Roubert C, Nathan C, Aubé J. Dual-Pharmacophore Pyrithione-Containing Cephalosporins Kill Both Replicating and Nonreplicating Mycobacterium tuberculosis. ACS Infect Dis. 2019 Aug 9;5(8):1433-1445. doi: 10.1021/acsinfecdis.9b00112. Epub 2019 Jun 11. Erratum in: ACS Infect Dis. 2019 Dec 13;5(12):2175. PMID: 31184461; PMCID: PMC7241432. 2. Krejčová P, Kučerová P, Stafford GI, Jäger AK, Kubec R. Antiinflammatory and neurological activity of pyrithione and related sulfur-containing pyridine N-oxides from Persian shallot (Allium stipitatum). J Ethnopharmacol. 2014 May 28;154(1):176-82. doi: 10.1016/j.jep.2014.03.066. Epub 2014 Apr 8. PMID: 24721027. 3. Lan X, Zhao C, Chen X, Zhang P, Zang D, Wu J, Chen J, Long H, Yang L, Huang H, Wang X, Shi X, Liu J. Platinum pyrithione induces apoptosis in chronic myeloid leukemia cells resistant to imatinib via DUB inhibition-dependent caspase activation and Bcr-Abl downregulation. Cell Death Dis. 2017 Jul 6;8(7):e2913. doi: 10.1038/cddis.2017.284. PMID: 28682311; PMCID: PMC5550844.
In vitro protocol:
1. Lopez Quezada L, Li K, McDonald SL, Nguyen Q, Perkowski AJ, Pharr CW, Gold B, Roberts J, McAulay K, Saito K, Somersan Karakaya S, Javidnia PE, Porras de Francisco E, Amieva MM, Dı Az SP, Mendoza Losana A, Zimmerman M, Liang HH, Zhang J, Dartois V, Sans S, Lagrange S, Goullieux L, Roubert C, Nathan C, Aubé J. Dual-Pharmacophore Pyrithione-Containing Cephalosporins Kill Both Replicating and Nonreplicating Mycobacterium tuberculosis. ACS Infect Dis. 2019 Aug 9;5(8):1433-1445. doi: 10.1021/acsinfecdis.9b00112. Epub 2019 Jun 11. Erratum in: ACS Infect Dis. 2019 Dec 13;5(12):2175. PMID: 31184461; PMCID: PMC7241432. 2. Krejčová P, Kučerová P, Stafford GI, Jäger AK, Kubec R. Antiinflammatory and neurological activity of pyrithione and related sulfur-containing pyridine N-oxides from Persian shallot (Allium stipitatum). J Ethnopharmacol. 2014 May 28;154(1):176-82. doi: 10.1016/j.jep.2014.03.066. Epub 2014 Apr 8. PMID: 24721027.
In vivo protocol:
1. Lan X, Zhao C, Chen X, Zhang P, Zang D, Wu J, Chen J, Long H, Yang L, Huang H, Wang X, Shi X, Liu J. Platinum pyrithione induces apoptosis in chronic myeloid leukemia cells resistant to imatinib via DUB inhibition-dependent caspase activation and Bcr-Abl downregulation. Cell Death Dis. 2017 Jul 6;8(7):e2913. doi: 10.1038/cddis.2017.284. PMID: 28682311; PMCID: PMC5550844.