Bithionol

Base Information

• Chemical Name: Bithionol
• CAS No.: 97-18-7
• Molecular Formula: C12H6Cl4O2S
• Molecular Weight: 356.056
• Hs Code.: 29309090
• European Community (EC) Number: 202-565-0
• NSC Number: 47129,9872
• UN Number: 2811
• UNII: AMT77LS62O
• DSSTox Substance ID: DTXSID9021342
• Nikkaji Number: J4.438E
• Wikipedia: Bithionol
• Wikidata: Q4918862
• NCI Thesaurus Code: C77030
• Pharos Ligand ID: X95TNKPL4S1A
• Metabolomics Workbench ID: 53014
• ChEMBL ID: CHEMBL290106
• Mol file: 97-18-7.mol

Synonyms:Bithionol;Bitin

Chemical Property of Bithionol

Chemical Property:

• Appearance/Colour: off-white crystalline powder
• Melting Point: 188°C
• Boiling Point: 444.7 °C at 760 mmHg
• PKA: 4.82, 10.50(at 25℃)
• Flash Point: 222.8 °C
• PSA: 65.76000
• Density: 1.75 g/cm³
• LogP: 5.86260
• Storage Temp.: 0-6°C
• Solubility.: DMSO: soluble20mg/mL, clear
• Water Solubility.: <0.1 g/100 mL at 23 oC
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 355.881311
• Heavy Atom Count: 19
• Complexity: 282
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

Bithionol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+,Xn
• Hazard Codes: T+,Xn
• Statements: 28-20/21/22
• Safety Statements: 28-36/37-45-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Biocides/Disinfectants
• Canonical SMILES: C1=C(C=C(C(=C1SC2=C(C(=CC(=C2)Cl)Cl)O)O)Cl)Cl
• Indications: Infections with Parogonimus westermani (lung fluke) and Fasciola hepatica (liver fluke). Bithionol should only be used as a second-line drug in the treatment of paragonimiasis for those patients who fail to respond to full course therapy with praziquantel. Triclabendazole, which is a new drug still under clinical evaluation, will most probably become the drug of choice against fascioliasis in the near future. Bithionol (Actamer) is a phenolic derivative whose mode of action is related to uncoupling of parasitespecific fumarate reductase–mediated oxidative phosphorylation. The drug is administered orally and is absorbed from the intestinal tract. Peak blood levels are achieved in 4 to 8 hours. Excretion is mainly by the kidneys. Bithionol is used in treatment of F. hepatica infections and as an alternative to praziquantel in the treatment of infestation by P. westermani. It is highly active against the adult worm but exerts no action against the migratory stages. A second course of treatment is required for complete cure in 20 to 30% of patients. Side effects are generally mild and transient; they include nausea, vomiting, diarrhea, headache, dizziness, urticaria, and other skin rashes in 50% of patients.
• Description: Bithionol (97-18-7) is an antihelmintic drug with bacteriostatic and fungicidal properties. Bithionol has also been found to be an inhibitor of glutamate dehydrogenase1,2?(IC50?= 4.8 μM bovine GDH1).
• Uses: bactericide; antihelmintic; algicide; proposed as agricultural fungicide; food additive in feed and drinking water for foodproducing animals; permitted in food for human consumption; deodorant; in germicide pharmaceuticals, antibacterial agent in soaps, cosmetics, veterinary antiseptic and antihelminthic products, industrial cleansers, etc. anthelmintic, antiseptic
• Clinical Use: 2,2’-Thiobis(4,6-dichlorophenol), or bis(2-hydroxy-3,5-dichlorophenyl)sulfide (Lorothidol, Bithin), a chlorinatedbisphenol, was formerly used in soaps and cosmetics for itsantimicrobial properties but was removed from the marketfor topical use because of reports of contact photodermatitis.Bithionol has useful anthelmintic properties and hasbeen used as a fasciolicide and taeniacide. It is still consideredthe agent of choice for the treatment of infestationscaused by the liver fluke Fasciola hepatica and the lungfluke Paragonimus westermani. Niclosamide is believed tobe superior to it for the treatment of tapeworm infestations.

Technology Process of Bithionol

There total 6 articles about Bithionol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

bithionol sulfoxide (844-26-8) → bithionol (97-18-7)

Guidance literature:

With acetic acid; zinc; at 100 ℃; for 4h;

DOI:10.1073/pnas.1904700116

Reference yield:

2,4-dichlorophenol (120-83-2,40477-79-0) → bithionol (97-18-7)

Guidance literature:

With tetrachloromethane; aluminium trichloride; sulfur dichloride;

Reference yield:

carbon disulfide (75-15-0,12122-00-8) + aluminium trichloride (7446-70-0) + 2,4-dichlorophenol (120-83-2,40477-79-0) → bithionol (97-18-7)

Guidance literature:

upstream raw materials:

2,4-dichlorophenol

carbon disulfide

aluminium trichloride

tetrachloromethane

Downstream raw materials:

Ni⁽²⁺⁾*C₁₂H₄Cl₄O₂S^(2-)={NiC₁₂H₄Cl₄O₂S}

bis-(2-acetoxy-3,5-dichloro-phenyl)-sulfoxide

bis-(2-acetoxy-3,5-dichloro-phenyl)-sulfide

4,6,4',6'-tetrachloro-2,2'-sulfonyl-di-phenol

Refernces

• 1、 Kim, Wooseong,Zou, Guijin,Hari, Taylor P. A.,Wilt, Ingrid K.,Zhu, Wenpeng,Galle, Nicolas,Faizi, Hammad A.,Hendricks, Gabriel L.,Tori, Katerina,Pan, Wen,Huang, Xiaowen,Steele, Andrew D.,Csatary, Erika E.,Dekarske, Madeline M.,Rosen, Jake L.,De Queiroz Ribeiro, Noelly,Lee, Kiho,Port, Jenna,Fuchs, Beth Burgwyn,Vlahovska, Petia M.,Wuest, William M.,Gao, Huajian,Ausubel, Frederick M.,Mylonakis, Eleftherios. "A selective membrane-targeting repurposed antibiotic with activity against persistent methicillin-resistant Staphylococcus aureus". . p. 16529 - 16534. Retrieved 2019/08/20.
• 2、 -. "Carbonates of acetylenic alcohols". . . Retrieved 2008/06/13.