CAS 3696-28-4|2,2'-Dithiobis(pyridine-N-oxide)

Introduction：Basic information about CAS 3696-28-4|2,2'-Dithiobis(pyridine-N-oxide), including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. 2,2'-Dithiobis(pyridine-N-oxide) BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Customs
7. Synonyms

Common Name	2,2'-Dithiobis(pyridine-N-oxide)
CAS Number	3696-28-4	Molecular Weight	252.31300
Density	1.38 g/cm3	Boiling Point	582.8ºC at 760 mmHg
Molecular Formula	C₁₀H₈N₂O₂S₂	Melting Point	205ºC
MSDS	/	Flash Point	306.2ºC

Names

Name	dipyrithione
Synonym	More Synonyms

2,2'-Dithiobis(pyridine-N-oxide) BiologicalActivity

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 >>ApoptosisResearch Areas >>CancerResearch Areas >>InfectionSignaling Pathways >>Anti-infection >>FungalResearch Areas >>Inflammation/ImmunologySignaling 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-]

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UT2965000

CHEMICAL NAME :: Pyridine, 2,2'-dithiodi-, 1,1'-dioxide

CAS REGISTRY NUMBER :: 3696-28-4

BEILSTEIN REFERENCE NO. :: 0217725

LAST UPDATED :: 199807

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C10-H8-N2-O2-S2

MOLECULAR WEIGHT :: 252.32

WISWESSER LINE NOTATION :: T6NJ AO BSS- BT6NJ AO

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration into the eye

SPECIES OBSERVED :: Rodent - rabbit

REFERENCE :: NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: OTS0535316 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 5280 ug/kg

SEX/DURATION :: female 16 day(s) pre-mating female 1-6 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - other measures of fertility

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 15,947,1978

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 1600 ug/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Effects on Newborn - behavioral

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 15,1169,1978

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 1344 ug/kg

SEX/DURATION :: female 15-21 day(s) after conception lactating female 21 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Newborn - behavioral Reproductive - Effects on Newborn - physical

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 16,131,1978

Safety Information

Safety Phrases	S24/25
HS Code	2933399090

Customs

HS Code	2933399090
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%

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

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