CAS Number3696-28-4
Synonyms1-oxido-2-[(1-oxidopyridin-1-ium-2-yl)disulfanyl]pyridin-1-ium; 2,2'-disulfanediyldipyridine 1,1'-dioxide; 2,2'-dithiobis[pyridine] 1,1'-dioxide; di-2-pyridyl disulfide 1,1'-dioxide; 2,2'-Dithiobis(pyridine-N-oxide); EINECS 223-024-5
Molecular FormulaC10H8O2N2S2
Molecular Weight252.32
Purity98%%
Density1.38 g/cm3
Boiling Point582.8ºC at 760 mmHg
Melting Point205ºC
AppearanceBeige crystalline powder
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 3696-28-4 |
| Catalog No. | 2A-9059735 |
| Chinese Name | 2,2'-二硫代二(吡啶-1-氧化物) |
| Synonyms | 1-oxido-2-[(1-oxidopyridin-1-ium-2-yl)disulfanyl]pyridin-1-ium; 2,2'-disulfanediyldipyridine 1,1'-dioxide; 2,2'-dithiobis[pyridine] 1,1'-dioxide; di-2-pyridyl disulfide 1,1'-dioxide; 2,2'-Dithiobis(pyridine-N-oxide); EINECS 223-024-5 |
| Molecular Formula | C10H8O2N2S2 |
| Molecular Weight | 252.32 |
| Purity | 98% |
| Density | 1.38 g/cm3 |
| Boiling Point | 582.8ºC at 760 mmHg |
| Melting Point | 205ºC |
| Appearance | Beige crystalline powder |
| Storage Condition | room temperature, dry |
| Application | Bipyridylthione is an effective antibacterial agent. Dipyrithione has antifungal and antiproliferative activity. Dipyrithione induces apoptosis and cycle arrest in G1 phase. Dipyridinethione has anti- |
| HTC | 2933399090 |
| MDL Number | MFCD00006197 |
| SMILES | [O-][n+]1ccccc1SSc1cccc[n+]1[O-] |
| InChI | InChI=1S/C10H8N2O2S2/c13-11-7-3-1-5-9(11)15-16-10-6-2-4-8-12(10)14/h1-8H |
| InChI Key | ZHDBTKPXEJDTTQ-UHFFFAOYSA-N |
| MSDS | msds/59735_1_3696_28_4.pdf |
| Bioactivity | Dipyrithione is a potent antimicrobial agent. Dipyrithione shows antifungal activity and antiproliferative activity. Dipyrithione induces apoptosis and cycle arrest at G1 phase. Dipyrithione shows anti-inflammatory activity in vivo. Dipyrithione shows anti-tumor activity. Dipyrithione has the potential for the research of dermatophytosis[1][2][3]. Related Catalog Signaling Pathways >> Apoptosis >> Apoptosis Research Areas >> Cancer Research Areas >> Infection Signaling Pathways >> Anti-infection >> Fungal Research Areas >> Inflammation/Immunology Signaling Pathways >> Anti-infection >> Bacterial In Vitro Dipyrithione (20 μg/mL) shows antifungal activity with MIC values of 6.03 µM for Trichophyton rubrum[1]. Dipyrithione (72 h) shows cytotoxic activity against 293 T cells with an IC50 value of 0.22 µM[1]. Dipyrithione (1-5 µM; 8.5 h) inhibits LPS (100 ng/ml)-induced up-regulation of iNOS and COX-2 in RAW264.7 cells in a dose-dependent manner[2]. Dipyrithione (1 µM; 8.5 h) suppresses LPS-induced increase of iNOS but not COX-2 mRNA level, inhibits LPS-increased NO production[2]. Dipyrithione (3 µM; 2, 5 h) decreases phosphorylation of STAT1 induced by LPS and does not influence LPS-induced MAPK and NF-κB activation in RAW 246.7 cells[2]. Dipyrithione (0-5 μg/mL; 48 h) shows antiproliferative activity for KB, 231, U937 and K562 cells in a dose dependent manner[3]. Dipyrithione (2.5 μg/ml) induces apoptosis and cycle arrest at G1 phase[3]. Western Blot Analysis[2] Cell Line: RAW264.7 cells Concentration: 1-5 µM Incubation Time: 8.5 h Result: Inhibited the expression of LPS (100 ng/ml)-induced up-regulation of iNOS and COX-2 in a dose-dependent manner. Cell Proliferation Assay[2] Cell Line: KB, 231, U937, K562 cells Concentration: 2.5 μg/ml Incubation Time: 24 h Result: Induced cell cycle arrest at G1 phase with induced p21 accumulation, CyclinD1 and CyclinE1 expressions were downregulated. Apoptosis Analysis[3] Cell Line: KB, 231, U937, K562 cells Concentration: 2.5 μg/ml Incubation Time: 36 h Result: Induced apoptosis by induced cleavage of caspase-9, caspase-3 and PARP. Western Blot Analysis[3] Cell Line: RAW264.7 cells Concentration: 1-5 µM Incubation Time: 8.5 h Result: Inhibited the expression of LPS (100 ng/ml)-induced up-regulation of iNOS and COX-2 in a dose-dependent manner. In Vivo Dipyrithione (0.2 mg/cm2; externally once daily for 10 days) shows great anti-dermatophyte activity effects in guinea pig[1]. Dipyrithione (1, 2.5, 5 mg/kg; i.p.) shows anti-inflammatory activity in mouse[2].Dipyrithione (5 mg/kg; i.p.; daily for 10 days) shows anti-tumor acyivity in mouse[3]. Animal Model: Guinea pig (infected with Trichophyton rubrum)[1] Dosage: 0.2 mg/cm2 Administration: Externally once daily for 10 days Result: Showed normal hair growth, with no scaly skin. Animal Model: 18-22g male ICR mice2 Dosage: 1, 2.5, 5 mg/kg Administration: I.p. Result: Raised the survival rate from 10% to 30%, 60% and 90%, respectively. Animal Model: 6 weeks, 18-20 g male ICR mice (hepatoma 22 (H22) cells)[3] Dosage: 2.5 mg/kg Administration: I.p.; daily for 10 days Result: Inhibited the growth of tumor. References [1]. Song X, et al. In vivo antifungal activity of dipyrithione against Trichophyton rubrum on guinea pig dermatophytosis models. Biomed Pharmacother. 2018 Dec;108:558-564. [2]. Liu Z, et al. 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. [3]. Fan Y, et al. 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. Chemical & Physical Properties Density 1.38 g/cm3 Boiling Point 582.8ºC at 760 mmHg Melting Point 205ºC Molecular Formula C10H8N2O2S2 Molecular Weight 252.31300 Flash Point 306.2ºC Exact Mass 252.00300 PSA 101.52000 LogP 3.34300 Index of Refraction 1.681 InChIKey ZHDBTKPXEJDTTQ-UHFFFAOYSA-N SMILES [O-][n+]1ccccc1SSc1cccc[n+]1[O-] |
| Use of | Dipyrithione is a potent antimicrobial agent. Dipyrithione shows antifungal activity and antiproliferative activity. Dipyrithione induces apoptosis and cycle arrest at G1 phase. Dipyrithione shows anti-inflammatory activity in vivo. Dipyrithione shows anti-tumor activity. Dipyrithione has the potential for the research of dermatophytosis[1][2][3]. Properties Name dipyrithione Synonym More Synonyms 2,2'-Dithiobis(pyridine-N-oxide) Biological Activity Description Dipyrithione is a potent antimicrobial agent. Dipyrithione shows antifungal activity and antiproliferative activity. Dipyrithione induces apoptosis and cycle arrest at G1 phase. Dipyrithione shows anti-inflammatory activity in vivo. Dipyrithione shows anti-tumor activity. Dipyrithione has the potential for the research of dermatophytosis[1][2][3]. Related Catalog Signaling Pathways >> Apoptosis >> Apoptosis Research Areas >> Cancer Research Areas >> Infection Signaling Pathways >> Anti-infection >> Fungal Research Areas >> Inflammation/Immunology Signaling Pathways >> Anti-infection >> Bacterial References [1]. Song X, et al. In vivo antifungal activity of dipyrithione against Trichophyton rubrum on guinea pig dermatophytosis models. Biomed Pharmacother. 2018 Dec;108:558-564. [2]. Liu Z, et al. 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. [3]. Fan Y, et al. 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. Chemical & Physical Properties Molecular Formula C10H8N2O2S2 Exact Mass 252.00300 PSA 101.52000 LogP 3.34300 Index of Refraction 1.681 InChIKey ZHDBTKPXEJDTTQ-UHFFFAOYSA-N |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 20.0% |
| Transport Info | Product name: Summary 2933399090. other compounds containing an unfused pyridine ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0% |
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