Bithionol (sulfoxide)

Names

[ CAS No. ]:
844-26-8

[ Name ]:
Bithionol (sulfoxide)

[Synonym ]:
Sulphene
bithionol sulfoxide
Bithionoloxide
4,6,4',6'-tetrachloro-2,2'-sulfinyl-di-phenol
Disto-5-cogla
Bitionoloxido [Spanish]
Bithionoloxide [INN]
2,2'-sulfinyl-bis(4,6-dichlorophenol)
Bitin S
Distobitin
Bis-(3,5-dichlor-2-hydroxyphenyl)sulfoxid
Bis-(3.5-dichlor-2-hydroxy-phenyl)-sulfoxyd
Bithionoloxidum [Latin]
4,6,4',6'-Tetrachlor-2,2'-sulfinyl-di-phenol
Bithionol (sulfoxide)

Biological Activity

[Description]:

Bithionol sulfoxide(Bitin-S) is a clinically approved anti-parasitic drug; has been shown to inhibit solid tumor growth in several preclinical cancer models.IC50 value:Target: anticaner agentBithionol caused dose dependent cytotoxicity against all ovarian cancer cell lines tested with IC50 values ranging from 19 μM - 60 μM. BT treatment resulted in cell cycle arrest at G1/M phase and increased ROS generation [1]. Both bithionol and bithionol sulphoxide demonstrated in vitro toxicity to Neoparamoeba spp. at all concentrations examined (0.1 to 10 mg l(-1) over 72 h), with a comparable toxicity to freshwater observed for both chemicals at concentrations > 5 mg l(-1) following a 72 h treatment [2].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Parasite

Research Areas >> Cancer

[References]

[1]. Ayyagari VN, et al. Bithionol inhibits ovarian cancer cell growth in vitro - studies on mechanism(s) of action. BMC Cancer. 2014 Feb 4;14:61.

[2]. Florent RL, et al. In vitro toxicity of bithionol and bithionol sulphoxide to Neoparamoeba spp., the causative agent of amoebic gill disease (AGD). Dis Aquat Organ. 2010 Sep 17;91(3):257-62.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.86 g/cm3

[ Boiling Point ]:
532.7ºC at 760 mmHg

[ Molecular Formula ]:
C₁₂H₆Cl₄O₃S

[ Molecular Weight ]:
372.05100

[ Flash Point ]:
276ºC

[ Exact Mass ]:
369.87900

[ PSA ]:
76.74000

[ LogP ]:
5.74380

[ Index of Refraction ]:
1.769

[ Storage condition ]:
2-8℃

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: SM8800000

CHEMICAL NAME :: Phenol, 2,2'-sulfinylbis(4,6-dichloro-

CAS REGISTRY NUMBER :: 844-26-8

BEILSTEIN REFERENCE NO. :: 2003972

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C12-H6-Cl4-O3-S

MOLECULAR WEIGHT :: 372.04

WISWESSER LINE NOTATION :: QR BG DG FSO&R BQ CG EG

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 56 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Mutation in microorganisms

TEST SYSTEM :: Bacteria - Salmonella typhimurium

DOSE/DURATION :: 10 ug/plate

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 188,53,1987

Safety Information

[ HS Code ]:
2930909090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2930909090

[ Summary ]:
2930909090. other organo-sulphur compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%