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

Modify Date: 2024-01-09 19:22:13

2,2'-Dithiobis(pyridine-N-oxide) Structure
2,2'-Dithiobis(pyridine-N-oxide) structure
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 N/A Flash Point 306.2ºC

 Use of 2,2'-Dithiobis(pyridine-N-oxide)


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].

 Names

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
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

 MSDS

Name: 2 2 -Dithiobis(Pyridine-N-Oxide) 97% Material Safety Data Sheet
Synonym: Pyridine, 2,2'-Dithiobis-, 1,1'-Dioxide; Omadine Disulfide
CAS: 3696-28-4
Section 1 - Chemical Product MSDS Name:2 2 -Dithiobis(Pyridine-N-Oxide) 97% Material Safety Data Sheet
Synonym:Pyridine, 2,2'-Dithiobis-, 1,1'-Dioxide; Omadine Disulfide

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS
CAS# Chemical Name content EINECS#
3696-28-4 Pyridine, 2,2'-Dithiobis-, 1,1'-Dioxid 97 223-024-5
Hazard Symbols: None Listed.
Risk Phrases: None Listed.

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Hygroscopic (absorbs moisture from the air).
Potential Health Effects
Eye:
Causes severe eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
Adverse reproductive effects have been reported in animals.

Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Store protected from moisture.

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 3696-28-4: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: beige
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 205 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C10H8N2O2S2
Molecular Weight: 252.31

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants, exposure to moist air or water.
Incompatibilities with Other Materials:
Moisture, strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, oxides of sulfur, irritating and toxic fumes and gases, carbon dioxide, hydrogen sulfide.
Hazardous Polymerization: Has not been reported

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 3696-28-4: UT2965000 LD50/LC50:
CAS# 3696-28-4: Draize test, rabbit, eye: 100 uL/24H Severe.
Carcinogenicity:
Pyridine, 2,2'-Dithiobis-, 1,1'-Dioxide - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

Section 12 - ECOLOGICAL INFORMATION


Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 3696-28-4: No information available.
Canada
CAS# 3696-28-4 is listed on Canada's NDSL List.
CAS# 3696-28-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 3696-28-4 is listed on the TSCA inventory.


SECTION 16 - ADDITIONAL INFORMATION
N/A

 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