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
Product Name
Bithionol
CAS No.
97-18-7
Chemical Name
Bithionol
Synonyms
Bitin;d26;xl7;D 26;XL 7;tkhsd;Bithin;cp3438;CP 3438;tbp[qr]
CBNumber
CB5709001
Molecular Formula
C12H6Cl4O2S
Formula Weight
356.05
MOL File
97-18-7.mol
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Bithionol Property

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.
CAS DataBase Reference
97-18-7(CAS DataBase Reference)
NIST Chemistry Reference
Bis(2-hydroxy-3,5-dichlorophenyl)sulfide(97-18-7)
EPA Substance Registry System
Bithionol (97-18-7)
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Safety

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
Hazardous Substances Data
97-18-7(Hazardous Substances Data)
Toxicity
LD50 oral in rat: 7mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H300Fatal if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
31622
Product name
Bithionol
Purity
VETRANAL
Packaging
250mg
Price
$53.9
Updated
2024/03/01
TCI Chemical
Product number
T0865
Product name
2,2'-Thiobis(4,6-dichlorophenol)
Purity
>97.0%(GC)(T)
Packaging
25g
Price
$71
Updated
2024/03/01
TCI Chemical
Product number
T0865
Product name
2,2'-Thiobis(4,6-dichlorophenol)
Purity
>97.0%(GC)(T)
Packaging
500g
Price
$313
Updated
2024/03/01
Cayman Chemical
Product number
21844
Product name
Bithionol
Purity
≥98%
Packaging
25g
Price
$49
Updated
2024/03/01
Cayman Chemical
Product number
21844
Product name
Bithionol
Purity
≥98%
Packaging
50g
Price
$92
Updated
2024/03/01
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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.

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).

Chemical Properties

off-white crystalline powder

Chemical Properties

Bithionol is a white or grayish powder with a slight phenolic odor.

Physical properties

Bithionol is virtually insoluble in water, readily soluble in ethanol, diethyl ether, acetone, glacial acetic acid, and dilute alkalis.

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.

Production Methods

Bithionol is prepared by reaction of 2,4-dichlorophenol with sulfur dichloride and AlCl3 in carbon disulfide or tetrachloromethane. It is used as a microbicide to protect aqueous functional fluids from biodeterioration and to control algae and slime formation in process water systems.

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.

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.

First aid

If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.

storage

Color Code—Blue: Health Hazard/Poison: Storein a secure poison location. Store in a refrigerator or a cooldry place.

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.

References

1) Li?et al. (2009),?Novel inhibitors complexed with glutamate dehydrogenase: allosteric regulation by control of protein dynamics; J. Biol. Chem.,?284?22988 2) Zocher?et al. (2012),?Biochemical and structural characterization of Plasmodium falciparum glutamate dehydrogenase 2; Mol. Biochem. Parasitol.,?183?52

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Bithionol Suppliers

Shanghai Boyle Chemical Co., Ltd.
Tel
021-50182298 021-50180596
Fax
+86-21-57758967
Email
sales@boylechem.com
Country
China
ProdList
2208
Advantage
55
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
94657
Advantage
76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
021-61259108 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40228
Advantage
62
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24529
Advantage
81
Energy Chemical
Tel
021-021-58432009 400-005-6266
Fax
021-58436166
Email
sales8178@energy-chemical.com
Country
China
ProdList
44689
Advantage
61
Shanghai Hanhong Scientific Co.,Ltd.
Tel
021-54306202 13764082696
Email
info@hanhongsci.com
Country
China
ProdList
42958
Advantage
64
Syntechem Co.,Ltd
Tel
Fax
E-Mail Inquiry
Email
info@syntechem.com
Country
China
ProdList
12984
Advantage
57
Sichuan Kulinan Technology Co., Ltd
Tel
400-1166-196 18981987031
Fax
028-84555506 800101999
Email
cdhxsj@163.com
Country
China
ProdList
11707
Advantage
57
Maya High Purity Chemicals
Tel
+86 (573) 82222445 (0)18006601000 452520369
Fax
+86 (573) 82222643
Email
sales@maya-r.com
Country
China
ProdList
11707
Advantage
57
Chengdu Ai Keda Chemical Technology Co., Ltd.
Tel
4008-755-333 18080918076
Fax
028-86757656
Email
800078821@qq.com
Country
China
ProdList
9718
Advantage
55
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View Lastest Price from Bithionol manufacturers

HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
Bithionol 97-18-7
Price
US $99.00-80.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000
Release date
2024-08-21
Shaanxi Dideu Medichem Co. Ltd
Product
Bithionol 97-18-7
Price
US $0.00-0.00/Kg
Min. Order
1KG
Purity
99.0%
Supply Ability
500 tons
Release date
2020-04-27
Career Henan Chemical Co
Product
Bithionol 97-18-7
Price
US $3.00/KG
Min. Order
1KG
Purity
99
Supply Ability
100kg
Release date
2019-07-10

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