Pyrithione

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

MedKoo CAT#: 533192

CAS#: 1121-31-9

Description: 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

img
Pyrithione
CAS# 1121-31-9

Theoretical Analysis

MedKoo Cat#: 533192
Name: Pyrithione
CAS#: 1121-31-9
Chemical Formula: C5H5NOS
Exact Mass: 127.01
Molecular Weight: 127.160
Elemental Analysis: C, 47.23; H, 3.96; N, 11.02; O, 12.58; S, 25.21

Price and Availability

Size Price Availability Quantity
5g USD 350 2 Weeks
25g USD 500 2 Weeks
Bulk inquiry

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:
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.

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x