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Bithionol

Pharmacology and mechanism of action Indications Side effects Contraindications and precautions Interactions Preparations References
Bithionol
Bithionol structure
CAS No.
97-18-7
Chemical Name:
Bithionol
Synonyms
d26;xl7;D 26;XL 7;Bitin;tkhsd;Bithin;cp3438;CP 3438;tbp[qr]
CBNumber:
CB5709001
Molecular Formula:
C12H6Cl4O2S
Formula Weight:
356.05
MOL File:
97-18-7.mol

Bithionol Properties

Melting point:
188°C
Boiling point:
444.7±45.0 °C(Predicted)
Density 
1.61
storage temp. 
Keep in dark place,Inert atmosphere,Room temperature
solubility 
DMSO: soluble20mg/mL, clear
pka
4.82, 10.50(at 25℃)
form 
powder
color 
white to beige
Water Solubility 
<0.1 g/100 mL at 23 ºC
Merck 
14,1306
BRN 
2003535
Stability:
Stable. Incompatible with strong oxidizing agents.
FDA 21 CFR
310.545
CAS DataBase Reference
97-18-7(CAS DataBase Reference)
FDA UNII
AMT77LS62O
NIST Chemistry Reference
Bis(2-hydroxy-3,5-dichlorophenyl)sulfide(97-18-7)
EPA Substance Registry System
Bithionol (97-18-7)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P301+P312+P330
Hazard Codes  T+,Xn
Risk Statements  28-20/21/22
Safety Statements  28-36/37-45-36
RIDADR  UN 2811 6.1/PG 2
WGK Germany  3
RTECS  SN0525000
HazardClass  6.1(a)
PackingGroup  II
HS Code  29309090
Toxicity LD50 oral in rat: 7mg/kg

Bithionol price More Price(8)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 31622 Bithionol VETRANAL 97-18-7 250mg $42.9 2021-03-22 Buy
Sigma-Aldrich SML1440 Bithionol ≥98% (HPLC) 97-18-7 50mg $54 2020-08-18 Buy
TCI Chemical T0865 2,2'-Thiobis(4,6-dichlorophenol) >97.0%(GC)(T) 97-18-7 25g $59 2021-03-22 Buy
TCI Chemical T0865 2,2'-Thiobis(4,6-dichlorophenol) >97.0%(GC)(T) 97-18-7 500g $259 2021-03-22 Buy
Cayman Chemical 21844 Bithionol ≥98% 97-18-7 25g $39 2021-03-22 Buy

Bithionol Chemical Properties,Uses,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 The drug has been replaced by praziquantel, but it is still used in some areas of the world, particularly against Fasciola hepatica.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


Bithionol Suppliers

Global( 138)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 29961 58
Hubei Jusheng Technology Co.,Ltd.
86-18871470254
027-59599243 linda@hubeijusheng.com CHINA 28229 58
Chongqing Chemdad Co., Ltd
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CONIER CHEM AND PHARMA LIMITED
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Shaanxi Dideu Medichem Co. Ltd
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029-88380327 1015@dideu.com CHINA 4149 58
Zhengzhou Alfa Chemical Co.,Ltd
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sales5@alfachem.cn;sales9@alfachem.cn;sale1@alfachem.cn;sales7@alfachem.cn CHINA 11790 58
Target Molecule Corp
18019718960 781-999-5354
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Dideu Industries Group Limited
029-88380327
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BOC Sciences
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inquiry@bocsci.com United States 19674 58
CD Chemical Group Limited
+8613651442114
0086-13651442114 info@codchem.com China 20384 58

View Lastest Price from Bithionol manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-06-19 Bithionol USP/EP/BP
97-18-7
US $1.10 / g 1g 99.9% 100 Tons Min Dideu Industries Group Limited
2020-04-28 Bithionol
97-18-7
US $0.00-0.00 / Kg 1KG 99.0% 500 tons Shaanxi Dideu Medichem Co. Ltd
2019-07-11 Bithionol
97-18-7
US $3.00 / KG 1KG 99 100kg career henan chemical co

Bithionol Spectrum


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