1-Hydroxypyridine-2-thione zinc salt
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| Category | Bioactive by-products |
| Catalog number | BBF-04634 |
| CAS | 13463-41-7 |
| Molecular Weight | 317.69 |
| Molecular Formula | C10H8N2O2S2Zn |
| Purity | > 98 % |
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Description
Zinc pyrithione is an antifungal and antibacterial agent disrupting membrane transport by blocking the proton pump.
Specification
| Synonyms | 2-Mercaptopyridine 1-oxide Zinc Salt; 2-Pyridinethiol 1-oxide Zinc Salt; 2-Pyridinethiol N-oxide Zinc Salt; 2-Pyridylthiol-1-oxide Zinc Salt; Biocut ZP; Bis(1-hydroxy-2(1H)-pyridinethionato)zinc; Bis(2-pyridinethiol 1-oxide)zinc; Danex; Marukacide YP-DP; NSC 290409; Niccanon SKT; Niccanon ZP; Pyrithione zinc; Zinc Omadine; Zinc bis(2-mercaptopyridine-N-oxide); Zinc bis(2-pyridylthio-1-oxide); Zinc pyrethion; Zinc pyridine-2-thione-N-oxide |
| Storage | Store at -20 ℃ |
| IUPAC Name | zinc;1-oxidopyridin-1-ium-2-thiolate |
| Canonical SMILES | C1=CC=[N+](C(=C1)[S-])[O-].C1=CC=[N+](C(=C1)[S-])[O-].[Zn+2] |
| InChI | InChI=1S/2C5H5NOS.Zn/c2*7-6-4-2-1-3-5(6)8;/h2*1-4,8H;/q;;+2/p-2 |
| InChI Key | OTPSWLRZXRHDNX-UHFFFAOYSA-L |
Properties
| Appearance | Off-white powder |
| Application | ZPT-50 is the most important antidandruf agent in the world, which used for more than 30 years in shampoo. ZPT-50 shows excellent inhibiting effect on pytyrosporum ovale that causes dandruff. ZPT has broad spectrum bactericide and marine antifouling material, and is well used for cosmetic, shampoo, skins medicine, adhesive and coating painting and so on. |
| Antibiotic Activity Spectrum | Fungi; Bacterial |
| Boiling Point | 253.8 ℃ at 760 mmHg |
| Melting Point | 262 ℃ |
| Density | 1.782 g/cm3 at 25 ℃ |
| Solubility | Soluble in DMF, DMSO |
| LogP | 3.34050 |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Anaemia results from the excessive absorption of zinc suppressing copper and iron absorption, most likely through competitive binding of intestinal mucosal cells. Unbalanced levels of copper and zinc binding to Cu,Zn-superoxide dismutase has been linked to amyotrophic lateral sclerosis (ALS). Stomach acid dissolves metallic zinc to give corrosive zinc chloride, which can cause damage to the stomach lining. Metal fume fever is thought to be an immune response to inhaled zinc. |
| Toxicity | LD50: 177 mg/kg (Oral, Rat); LD50: 100 mg/kg (Dermal, Rabbit); LC50: 140 mg/m3 over 4 hours (Inhalation, Rat). |
Reference Reading
1.Sensitive and simultaneous quantification of zinc pyrithione and climbazole deposition from anti-dandruff shampoos onto human scalp.
Chen G1, Miao M2, Hoptroff M2, Fei X2, Collins LZ3, Jones A3, Janssen HG4. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Oct 15;1003:22-6. doi: 10.1016/j.jchromb.2015.09.009. Epub 2015 Sep 11.
A sensitive ultrahigh performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS) method has been developed and validated for simultaneous quantification of zinc pyrithione (ZPT) and climbazole (CBZ) deposited onto human scalp from anti-dandruff (AD) shampoos. Scrubbing with a buffer solution was used as the sampling method for the extraction of ZPT and CBZ from scalp. Derivatization of ZPT was carried out prior to UHPLC-MS/MS analysis. The identification of ZPT and CBZ was performed by examining ratios of selected multiple reaction monitoring (MRM) transitions in combination with UHPLC retention times. The limit of detection for ZPT and CBZ was established to be 1 and 2ng/mL, respectively. This sensitivity enables the quantification of ZPT and CBZ at deposition levels in the low ng/cm(2) range. The method was successfully applied for the analysis of scalp buffer scrub samples from an in vivo study. The levels of ZPT and CBZ deposited on the scalp at different time points after application of the AD shampoo were measured.
2.Zinc Pyrithione: A Topical Antimicrobial With Complex Pharmaceutics.
Schwartz JR. J Drugs Dermatol. 2016 Feb 1;15(2):140-4.
Zinc pyrithione (ZPT) is an active material that has been used for over 50 years to effectively treat dandruff and seborrheic dermatitis (D/SD). It has become the most common material for that purpose, its use has expanded to include other skin benefits such as skin hygiene. However, there is much about ZPT that is unappreciated. It is a rationally developed molecule that was modeled after the naturally occurring antimicrobial aspergillic acid. The molecular basis for its antifungal activity has been elucidated. The efficacy of ZPT originates from two attributes. First, it has a very broad antimicrobial spectrum of activity, including fungi, gram-positive and -negative bacteria. Second, the material has very low solubility, resulting in formulation and delivery as a particulate material, which has distinct performance advantages. The particles are deposited and retained on the target skin surfaces even when delivered from rinse-off products.
3.Anticancer activity of pyrithione zinc in oral cancer cells identified in small molecule screens and xenograft model: Implications for oral cancer therapy.
Srivastava G1, Matta A1, Fu G1, Somasundaram RT1, Datti A2, Walfish PG3, Ralhan R4. Mol Oncol. 2015 Oct;9(8):1720-35. doi: 10.1016/j.molonc.2015.05.005. Epub 2015 May 21.
Oral squamous cell carcinoma (OSCC) patients diagnosed in late stages have limited chemotherapeutic options, underscoring the great need for development of new anticancer agents for more effective disease management. We aimed to identify novel anticancer agents for OSCC using quantitative high throughput assays for screening six chemical libraries consisting of 5170 small molecule inhibitors. In depth characterization resulted in identification of pyrithione zinc (PYZ) as the most effective cytotoxic agent inhibiting cell proliferation and inducing apoptosis in OSCC cells in vitro. Further, treatment with PYZ reduced colony forming, migration and invasion potential of oral cancer cells in a dose-dependent manner. PYZ treatment also led to altered expression of several key components of the major signaling pathways including PI3K/AKT/mTOR and WNT/β-catenin in OSCC cells. In addition, treatment with PYZ also reduced expression of 14-3-3ζ, 14-3-3σ, cyclin D1, c-Myc and pyruvate kinase M2 (PKM2), proteins identified in our earlier studies to be involved in development and progression of OSCCs.
Spectrum
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C10H8N2O2S2Zn
Molecular Weight (Monoisotopic Mass): 315.9319 Da
Molecular Weight (Avergae Mass): 317.722 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C10H8N2O2S2Zn
Molecular Weight (Monoisotopic Mass): 315.9319 Da
Molecular Weight (Avergae Mass): 317.722 Da
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
