Pharmacology and mechanism of action Indications Side effects Contraindications and precautions Interactions Preparations References
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Bithionol

Pharmacology and mechanism of action Indications Side effects Contraindications and precautions Interactions Preparations References
Bithionol Structure
Bithionol
  • CAS No.97-18-7
  • Chemical Name:Bithionol
  • CBNumber:CB5709001
  • Molecular Formula:C12H6Cl4O2S
  • Formula Weight:356.05
  • MOL File:97-18-7.mol
Bithionol Property
Safety
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordWarning
  • Hazard statements H302
  • Precautionary statements P301+P312+P330
Bithionol Price More Price(8)
  • Brand: Sigma-Aldrich
  • Product number: 31622
  • Product name : Bithionol
  • Purity: VETRANAL
  • Packaging: 250mg
  • Price: $42.9
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: SML1440
  • Product name : Bithionol
  • Purity: ≥98% (HPLC)
  • Packaging: 50mg
  • Price: $54
  • Updated: 2020/08/18
  • Buy: Buy
  • Brand: TCI Chemical
  • Product number: T0865
  • Product name : 2,2'-Thiobis(4,6-dichlorophenol)
  • Purity: >97.0%(GC)(T)
  • Packaging: 25g
  • Price: $59
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: TCI Chemical
  • Product number: T0865
  • Product name : 2,2'-Thiobis(4,6-dichlorophenol)
  • Purity: >97.0%(GC)(T)
  • Packaging: 500g
  • Price: $259
  • Updated: 2021/03/22
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  • Brand: Cayman Chemical
  • Product number: 21844
  • Product name : Bithionol
  • Purity: ≥98%
  • Packaging: 25g
  • Price: $39
  • Updated: 2021/03/22
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Bithionol Chemical Properties,Usage,Production

  • Pharmacology and mechanism of action Bithionol is a dichlorophenol which is structurally related to hexachlorophene and niclosamide. It was introduced into clinical medicine three decades ago. The drug has been replaced by praziquantel, but it is still used in some areas of the world, particularly against Fasciola hepatica.
    The mechanism of action of bithionol is not well known. It inhibits oxidative phosphorylation of Paragonimus westermani and causes morphological alterations in Fasciola hepatica[1,2,3].
     
  • 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.
     
  • Side effects Side effects are common, but minor. About one third of the patients may experience diarrhoea that may be accompanied by anorexia, nausea and vomiting. Skin rashes or urticaria usually together with itching may be seen. Phototoxic reactions can occur[1,4,5,6].
     
  • Contraindications and precautions Efficacy and safety of the drug has not been established in children under 8 years of age.
     
  • Interactions There have been no reports.
     
  • Preparations • Bitin® (Tanabe Seiyaky) Tablets 500 mg.
  • References 1. Barret-Connor E (1982). Drugs for the treatment of parasitic infection. Med Clin North Am, 66, 245–255.
    2. Dawes B. Some apparent effects of Bithionol (Actamer) on Fasciola hepatica. Nature. 209, 424– 425.
    3. Yokogawa M, Muneo I (1965). Paragonimiasis. Adv Parasitol, 3, 99–158.
    4. Chung HL, Ho LY, Hsu CP, Ts’ao WJ (1981). Recent progress in studies of Paragonimus and paragonimiasis control in China. Chin Med J, 94, 493–494.
    5. Kim JS (1970). Treatment of Paragonimus westermani: infections with Bithionol. Am J Trop Med Hyg, 19, 940–942.
    6. O’Quinn SE, Kennedy CB, Isbell KH (1967). Contact photodermatitis due to bithionol and related compounds. J Am Med Ass, 199, 89–92.
  • Chemical Properties off-white crystalline powder
  • Chemical Properties Bithionol is a white or grayish powder with a slight phenolic odor.
  • 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.
  • Uses anthelmintic, antiseptic
  • Definition ChEBI: An aryl sulfide that is diphenyl sulfide in which each phenyl group is substituted at position 2 by hydroxy and at positions 3 and 5 by chlorine. A fungicide and anthelmintic, it was used in various topical drug products for the treatment of liver flukes, ut withdrawn after being shown to be a potent photosensitizer with the potential to cause serious skin disorders.
  • Indications 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.
  • brand name Lorothidol (Sterling Winthrop);Anafogene;Bacteriostat cs-1;Bidiphen;Lorothiodol;Neopellis;Nobacter;Prevenol;Tbp;Vancide bl.
  • World Health Organization (WHO) Bithionol, which has bactericidal and anthelminthic activity, was formerly available in soaps. By the late 1960s use of such preparations had been associated with a risk of photosensitivity reactions and cross-sensitivity with other halogenated disinfectants. This resulted in their withdrawal in the USA. Oral preparations of bithionol remain available for the treatment of paragonimiasis and fascioliasis.
  • General Description White or grayish white crystalline powder with a very faint aromatic or phenolic odor.
  • Air & Water Reactions Insoluble in water.
  • Reactivity Profile Bithionol is incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials may generate heat and toxic or flammable gases.
  • Hazard Toxic by ingestion.
  • Health Hazard ACUTE/CHRONIC HAZARDS: Bithionol is a skin irritant. When heated to decomposition or upon contact with acid or acid fumes, toxic fumes are evolved.
  • Fire Hazard Flash point data is not available for Bithionol, but Bithionol is probably combustible.
  • Mechanism of action Biothionol is bis-dichlorophenol, and it is structurally similar to hexachlorophene. It is the antihelmintic drug of choice for treating humans infected with Fasciola hepatica. It is an alternative drug to praziquantel that is used for treating pulmonary and cerebral paragonimiasis. The exact mechanism of action is not known, although it seems likely that it inhibits oxidative phosphorylation in Paeagonumus westermani. Synonyms of this drug are actamer, bitin, prevenol, and others.
  • 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.
  • Chemical Synthesis Bithionol, 2,2-thiobis(4,6-dichlorophenol) (38.1.38), is made by reacting a solution of 2,4-dichlorophenol in carbon tetrachloride with sulfur chloride in the presence of aluminum chloride.

  • Potential Exposure It is used as a surfactant-formulated antimicrobial against bacteria, molds and yeast. It is proposed as an agricultural fungicide. Other uses include deodorant, germicide, fungistat, and in the manufacture of pharmaceuticals. It is no longer allowed to be used in cosmetics. A food additive in feed and drinking water of animals. Also a food additive permitted in food for human consumption.
  • Shipping UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1—Poisonous materials, Technical Name Required.
  • Incompatibilities Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides.
Bithionol Preparation Products And Raw materials
Raw materials
Preparation Products
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