Bithionol

Names

[ CAS No. ]:
97-18-7

[ Name ]:
Bithionol

[Synonym ]:
Phenol, 2,2'-thiobis(4,6-dichloro)-
Phenol, 2,2'-thiobis[4,6-dichloro-
Bitin
2-Hydroxy-3,5-dichlorophenyl sulfide
Bithionolate
2,2'-Thiobis[4,6-dichlorophenol]
2,2-DIMETHYL-7-ETHOXY-6-METHOXY-4-CHROMANONE
MFCD00055727
2,2'-Sulfanediylbis(4,6-dichlorophenol)
Bidiphen
2,2'-Thiobis- (4,6-dichlorophenol)
2,2’-thiobis[4,6-dichlorophenol]
Bithionol sulfide
Bithin
EINECS 202-565-0
2,2'-Thio-bis(4,6-dichlorophenol)
2,2'-Thiobis(4,6-dichlorophenol)
Bithionol
2,2'-Sulfanediylbis(4,6-dichlorphenol)
2,2’-sulfanediylbis(4,6-dichlorophenol)
Bitionol
Bis(2-hydroxy-3,5-dichlorophenyl)sulfide
2-Hydroxy-3,5-dichlorophenyl sulphide
2,4-dichloro-6-(3,5-dichloro-2-hydroxyphenyl)sulfanylphenol
bis (2-hydroxy-3,5-dichlorophenyl)-sulphide
bis(3,5-dichloro-2-hydroxy phenyl)-sulfide
Phenol, 2,2'-thiobis 4,6-dichloro-
2,2’-thiobis(4,6-dichlorophenol)
Lorothidol
Actamer

Biological Activity

[Description]:

Bithionol 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]:
1.8±0.1 g/cm3

[ Boiling Point ]:
444.7±45.0 °C at 760 mmHg

[ Melting Point ]:
188°C

[ Molecular Formula ]:
C₁₂H₆Cl₄O₂S

[ Molecular Weight ]:
356.052

[ Flash Point ]:
222.8±28.7 °C

[ Exact Mass ]:
353.884247

[ PSA ]:
65.76000

[ LogP ]:
5.51

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.741

[ Storage condition ]:
0-6°C

[ Stability ]:
Stable. Incompatible with strong oxidizing agents.

[ Water Solubility ]:
<0.1 g/100 mL at 23 ºC

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: SN0525000

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

CAS REGISTRY NUMBER :: 97-18-7

BEILSTEIN REFERENCE NO. :: 2003535

LAST UPDATED :: 199710

DATA ITEMS CITED :: 8

MOLECULAR FORMULA :: C12-H6-Cl4-O2-S

MOLECULAR WEIGHT :: 356.04

WISWESSER LINE NOTATION :: QR BG DG FSR BQ CG EG

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 7 mg/kg

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

REFERENCE :: CLDND* Compilation of LD50 Values of New Drugs. (J.R. MacDougal, Dept. of National Health and Welfare, Food and Drug Divisions, 35 John St., Ottawa, Ont., Canada)

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 760 mg/kg

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

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,612,1982

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 100 mg/kg

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

REFERENCE :: NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: AD277-689

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 18 mg/kg

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

REFERENCE :: CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) Volume(issue)/page/year: NX#01763 ** TUMORIGENIC DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 12 gm/kg/78W-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Lungs, Thorax, or Respiration - tumors Blood - tumors

REFERENCE :: NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: PB223-159

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Precautionary Statements ]:
P301 + P312 + P330

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R20/21/22

[ Safety Phrases ]:
S28-S36/37-S45-S36

[ RIDADR ]:
UN 2811 6.1/PG 2

[ WGK Germany ]:
3

[ RTECS ]:
SN0525000

[ Packaging Group ]:
II

[ Hazard Class ]:
6.1(a)

[ 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%

Articles

An improved thyroid hormone reporter assay to determine the thyroid hormone-like activity of amiodarone, bithionol, closantel and rafoxanide.

Toxicol. Lett. 208(1) , 30-5, (2012)

A number of environmental chemicals have been reported to exhibit thyroid hormone-like activity. Since thyroid hormones play a crucial role in development, it is important to identify chemicals in the...

Determination of bithionol, bromophen, nitroxynil, oxyclozanide, and tribromsalan in milk with liquid chromatography coupled with tandem mass spectrometry.

J. AOAC Int. 93(4) , 1340-6, (2010)

LC/MS/MS was developed to determine the residues of bithionol (BTN), bromofen (BMF), nitroxynil (NTX), oxyclozanide (OCZ), and tribromsalan (TBS) in milk. Samples were extracted with ethyl acetate and...

Novel therapeutic strategy for neurodegeneration by blocking Aβ seeding mediated aggregation in models of Alzheimer's disease.

Neurobiol. Dis. 74 , 144-57, (2015)

Aβ accumulation plays a central role in the pathogenesis of Alzheimer's disease (AD). Recent studies suggest that the process of Aβ nucleated polymerization is essential for Aβ fibril formation, patho...

Related Compounds

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