Dipyrithione | CAS# 3696-28-4 | bactericide and fungicide

MedKoo Cat#: 413808 | Name: Dipyrithione

Featured

Description:

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

Dipyrithione is a pyrithione derivate used as bactericide and fungicide. The drug was marketed under the name Crimanex in the form of shampoo for the treatment of dandruff, however it is no longer available on the manufacturer website

Chemical Structure

Dipyrithione

CAS#3696-28-4

Theoretical Analysis

MedKoo Cat#: 413808

Name: Dipyrithione

CAS#: 3696-28-4

Chemical Formula: C10H8N2O2S2

Exact Mass: 252.0027

Molecular Weight: 252.31

Elemental Analysis: C, 47.60; H, 3.20; N, 11.10; O, 12.68; S, 25.41

Price and Availability

Size	Price	Availability	Quantity
5g	USD 250.00	2 Weeks
25g	USD 550.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Dipyrithione; Bispyrithione; Omadine disulfide; OMDS; Dipiritiona; pyrithione disulfide; NSC 84740; NSC84740; NSC-84740; NSC-241716; NSC241716; NSC 241716

IUPAC/Chemical Name

2,2'-disulfanediylbis(pyridine 1-oxide)

InChi Key

ZHDBTKPXEJDTTQ-UHFFFAOYSA-N

InChi Code

InChI=1S/C10H8N2O2S2/c13-11-7-3-1-5-9(11)15-16-10-6-2-4-8-12(10)14/h1-8H

SMILES Code

[O-][N+]1=CC=CC=C1SSC2=CC=CC=[N+]2[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

>2 years if stored properly

Drug Formulation

To be determined

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:

Dipyrithione is a potent antimicrobial agent.

In vitro activity:

Results showed that PTS2 significantly decreased cell numbers in all 4 cancer cell lines compared with controls, as assessed using trypan blue (Figure 2B). These data indicate that PTS2 can decrease cell viability or proliferation within a suitable concentration range. Reference: BMC Pharmacol Toxicol. 2013 Oct 21;14:54. https://pubmed.ncbi.nlm.nih.gov/24139500/

In vivo activity:

This study determined that dipyrithione could potently inhibit the growth of Trichophyton rubrum, which is the most common cause of dermatophytosis. The MIC50 value of dipyrithione against T. rubrum was measured as 6.03 μM, as compared with miconazole (MIC50: 1.38 μM). Reference: Biomed Pharmacother. 2018 Dec;108:558-564. https://pubmed.ncbi.nlm.nih.gov/30243089/

Preparing Stock Solutions

The following data is based on the product molecular weight 252.31 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.

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. Fan Y, Liu C, Huang Y, Zhang J, Cai L, Wang S, Zhang Y, Duan X, Yin Z. Dipyrithione induces cell-cycle arrest and apoptosis in four cancer cell lines in vitro and inhibits tumor growth in a mouse model. BMC Pharmacol Toxicol. 2013 Oct 21;14:54. doi: 10.1186/2050-6511-14-54. PMID: 24139500; PMCID: PMC4015681. 2. Liu Z, Fan Y, Wang Y, Han C, Pan Y, Huang H, Ye Y, Luo L, Yin Z. Dipyrithione inhibits lipopolysaccharide-induced iNOS and COX-2 up-regulation in macrophages and protects against endotoxic shock in mice. FEBS Lett. 2008 May 28;582(12):1643-50. doi: 10.1016/j.febslet.2008.04.016. Epub 2008 Apr 22. PMID: 18435922. 3. Song X, Wei YX, Lai KM, He ZD, Zhang HJ. In vivo antifungal activity of dipyrithione against Trichophyton rubrum on guinea pig dermatophytosis models. Biomed Pharmacother. 2018 Dec;108:558-564. doi: 10.1016/j.biopha.2018.09.045. Epub 2018 Sep 20. PMID: 30243089. 4. Huang H, Pan Y, Ye Y, Gao M, Yin Z, Luo L. Dipyrithione attenuates oleic acid-induced acute lung injury. Pulm Pharmacol Ther. 2011 Feb;24(1):74-80. doi: 10.1016/j.pupt.2010.09.008. Epub 2010 Oct 2. PMID: 20888423.

In vitro protocol:

In vivo protocol:

1. Song X, Wei YX, Lai KM, He ZD, Zhang HJ. In vivo antifungal activity of dipyrithione against Trichophyton rubrum on guinea pig dermatophytosis models. Biomed Pharmacother. 2018 Dec;108:558-564. doi: 10.1016/j.biopha.2018.09.045. Epub 2018 Sep 20. PMID: 30243089. 2. Huang H, Pan Y, Ye Y, Gao M, Yin Z, Luo L. Dipyrithione attenuates oleic acid-induced acute lung injury. Pulm Pharmacol Ther. 2011 Feb;24(1):74-80. doi: 10.1016/j.pupt.2010.09.008. Epub 2010 Oct 2. PMID: 20888423.

1: Huang H, Pan Y, Ye Y, Gao M, Yin Z, Luo L. Dipyrithione attenuates oleic acid-induced acute lung injury. Pulm Pharmacol Ther. 2011 Feb;24(1):74-80. doi: 10.1016/j.pupt.2010.09.008. Epub 2010 Oct 2. PMID: 20888423. 2: Han C, Fu J, Liu Z, Huang H, Luo L, Yin Z. Dipyrithione inhibits IFN-gamma- induced JAK/STAT1 signaling pathway activation and IP-10/CXCL10 expression in RAW264.7 cells. Inflamm Res. 2010 Oct;59(10):809-16. doi: 10.1007/s00011-010-0192-6. Epub 2010 Apr 7. PMID: 20372968; PMCID: PMC7079753. 3: Liu Z, Fan Y, Wang Y, Han C, Pan Y, Huang H, Ye Y, Luo L, Yin Z. Dipyrithione inhibits lipopolysaccharide-induced iNOS and COX-2 up-regulation in macrophages and protects against endotoxic shock in mice. FEBS Lett. 2008 May 28;582(12):1643-50. doi: 10.1016/j.febslet.2008.04.016. Epub 2008 Apr 22. PMID: 18435922. 4: Fan Y, Liu C, Huang Y, Zhang J, Cai L, Wang S, Zhang Y, Duan X, Yin Z. Dipyrithione induces cell-cycle arrest and apoptosis in four cancer cell lines in vitro and inhibits tumor growth in a mouse model. BMC Pharmacol Toxicol. 2013 Oct 21;14:54. doi: 10.1186/2050-6511-14-54. PMID: 24139500; PMCID: PMC4015681. 5: Song X, Wei YX, Lai KM, He ZD, Zhang HJ. In vivo antifungal activity of dipyrithione against Trichophyton rubrum on guinea pig dermatophytosis models. Biomed Pharmacother. 2018 Dec;108:558-564. doi: 10.1016/j.biopha.2018.09.045. Epub 2018 Sep 20. PMID: 30243089. 6: Wedig JH, Maibach HI. Percutaneous penetration of dipyrithione in man: effect of skin color (race). J Am Acad Dermatol. 1981 Oct;5(4):433-8. doi: 10.1016/s0190-9622(81)70105-1. PMID: 7287959. 7: Wedig JH, Feldmann RJ, Maibach HI. Percutaneous penetration of the magnesium sulfate adduct of dipyrithione in man. Toxicol Appl Pharmacol. 1977 Jul;41(1):1-6. doi: 10.1016/0041-008x(77)90049-7. PMID: 898185. 8: Fan Y, Chen H, Qiao B, Luo L, Ma H, Li H, Jiang J, Niu D, Yin Z. Opposing effects of ERK and p38 MAP kinases on HeLa cell apoptosis induced by dipyrithione. Mol Cells. 2007 Feb 28;23(1):30-8. PMID: 17464209. 9: Ren Y, Elkington BG, Henkin JM, Sydara K, Kinghorn AD, Soejarto DD. Bioactive small-molecule constituents of Lao plants. J Med Plant Res. 2021 Dec;15(12):540-559. doi: 10.5897/jmpr2021.7137. Epub 2021 Dec 31. PMID: 35178192; PMCID: PMC8849567. 10: Gurgul A, Nauman MC, Wu Z, Shetye G, Ma R, Youn I, Souliya O, Bisson J, Johnson JJ, Che CT. Chemical constituents of the stem of Marsypopetalum modestum and their bioactivities. Nat Prod Res. 2022 Jul 12:1-8. doi: 10.1080/14786419.2022.2097229. Epub ahead of print. PMID: 35819993; PMCID: PMC9834434. 11: Butler M, Cabrera GM. A mass spectrometry and DFT study of pyrithione complexes with transition metals in the gas phase. J Mass Spectrom. 2017 Nov;52(11):728-738. doi: 10.1002/jms.3976. PMID: 28741315. 12: Faßbender S, Döring AK, Meermann B. Development of complementary CE-MS methods for speciation analysis of pyrithione-based antifouling agents. Anal Bioanal Chem. 2019 Nov;411(27):7261-7272. doi: 10.1007/s00216-019-02094-5. Epub 2019 Sep 7. PMID: 31494688. 13: Elkington BG, Sydara K, Newsome A, Hwang CH, Lankin DC, Simmler C, Napolitano JG, Ree R, Graham JG, Gyllenhaal C, Bouamanivong S, Souliya O, Pauli GF, Franzblau SG, Soejarto DD. New finding of an anti-TB compound in the genus Marsypopetalum (Annonaceae) from a traditional herbal remedy of Laos. J Ethnopharmacol. 2014 Feb 3;151(2):903-11. doi: 10.1016/j.jep.2013.11.057. Epub 2013 Dec 11. PMID: 24333958; PMCID: PMC3933013. 14: Mitoma C, Steeger T, Rogers J, Thomas D, Wedig JH. Metabolic disposition of pyrithiones. Fundam Appl Toxicol. 1983 Jul-Aug;3(4):256-63. doi: 10.1016/s0272-0590(83)80137-7. PMID: 6628887. 15: Johnson DE, Schardein JL, Mitoma C, Wedig JH. Reproductive toxicological evaluation of Omadine MDS. Fundam Appl Toxicol. 1984 Feb;4(1):81-90. doi: 10.1016/0272-0590(84)90221-5. PMID: 6693004.