Niclosamide

Structural formula
General
Non-proprietary name	Niclosamide
other names	5-chloro- N - (2-chloro-4-nitrophenyl) -2-hydroxybenzamide ( IUPAC ) ; 5,2′-dichloro-4′-nitrosalicylanilidethanolamine (ethanolamine salt);
Molecular formula	C 13 H 8 Cl 2 N 2 O 4
Brief description	yellowish white to yellowish, fine crystals
External identifiers / databases
EC number	200-056-8
ECHA InfoCard	100,000,052
PubChem	4477
ChemSpider	4322
DrugBank	DB06803
Wikidata	Q418523
Drug information
ATC code	P02 DA01
Drug class	Anthelmintic
properties
Molar mass	327.12 g · mol -1
Physical state	firmly
Melting point	230 ° C
solubility	practically insoluble in water, slightly soluble in acetone , sparingly soluble in ethanol
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 400
	P: 273
Toxicological data	2500 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Niclosamide was introduced by Bayer as a molluscicide in 1959 . In the form of the salt with 2-aminoethanol , it is used under the names Clonitralid and Bayluscid to combat the water snails that transmit schistosomiasis . Similarly, it is used in the Great Lakes of North America against sea lamprey in an environmentally harmful way . Niclosamide is also a drug that is considered to be the drug of choice for people infected with tapeworms . It is also effective against pinworms as an anthelmintic and prevents cercariae from penetrating human skin.

From a chemical point of view, it is a derivative of salicylic acid and p-nitroaniline , which are linked to one another as an amide (salicylanilide).

Spectrum of activity

Niclosamide works against the types:

Taenia saginata ( beef tapeworm )
Taenia solium ( pork tapeworm )

Diphyllobothrium latum ( fish tapeworm )

Enterobius vermicularis ( pinworm )

Trichobilharzia szidati and Schistosoma mansoni ( Pärchenegel )

Pharmacokinetics

The substance is practically not absorbed from the gastrointestinal tract and therefore has no systemic effects on the host's organism .

Mechanism of action

Niclosamide inhibits the uptake of glucose and glycolysis in the worms.

Clinical note

If the pork tapeworm ( Taenia solium ) is infested , a laxative should also be administered two hours after the drug has been applied to prevent cysticercosis .

Use in animals used for food production is banned in the EU.

Trade names

Yomesan (D)

literature

C.-J. Estler (Ed.): Pharmacology and Toxicology . 5th edition. Schattauer, Stuttgart a. New York 2000. pp. 664f.

Individual evidence

↑ ^a ^b Data sheet ANHYDROUS NICLOSAMIDE CRS (PDF) at EDQM , accessed on June 5, 2010.
↑ ^a ^b ^c ^d ^e entry on niclosamide. In: Römpp Online . Georg Thieme Verlag, accessed on June 1, 2014.
↑ ^a ^b Entry on niclosamide in the GESTIS substance database of the IFA , accessed on February 14, 2017(JavaScript required) .
↑ C. Wulff, S. Haeberlein, W. Haas: Cream formulations protecting against cercarial dermatitis by Trichobilharzia. In: Parasitology research. Volume 101, Number 1, June 2007, pp. 91-97, doi : 10.1007 / s00436-006-0431-5 . PMID 17252275 .

[Ph._Eur.-1] Data sheet ANHYDROUS NICLOSAMIDE CRS (PDF) at EDQM , accessed on June 5, 2010.

[RÖMPP-2] ↑ ^a ^b ^c ^d ^e entry on niclosamide. In: Römpp Online . Georg Thieme Verlag, accessed on June 1, 2014.

[GESTIS-3] Entry on niclosamide in the GESTIS substance database of the IFA , accessed on February 14, 2017(JavaScript required) .

[4] C. Wulff, S. Haeberlein, W. Haas: Cream formulations protecting against cercarial dermatitis by Trichobilharzia. In: Parasitology research. Volume 101, Number 1, June 2007, pp. 91-97, doi : 10.1007 / s00436-006-0431-5 . PMID 17252275 .