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Niclosamide

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Niclosamide
Niclosamide.svg
Niclosamide-from-xtal-Mercury-3D-sf.png
Clinical data
Trade names Niclocide, Fenasal, Phenasal, others
AHFS/Drugs.com Micromedex Detailed Consumer Information
Routes of
administration
By mouth
ATC code
Identifiers
  • 5-Chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.000.052
Chemical and physical data
Formula C13H8Cl2N2O4
Molar mass 327.12 g·mol−1
3D model (JSmol)
Melting point 225 to 230 °C (437 to 446 °F)
  • Clc2cc(ccc2NC(=O)c1cc(Cl)ccc1O)[N+]([O-])=O
  • InChI=1S/C13H8Cl2N2O4/c14-7-1-4-12(18)9(5-7)13(19)16-11-3-2-8(17(20)21)6-10(11)15/h1-6,18H,(H,16,19) checkY
  • Key:RJMUSRYZPJIFPJ-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Niclosamide, sold under the brand name Niclocide among others, is an anthelmintic medication used to treat tapeworm infestations, including diphyllobothriasis, hymenolepiasis, and taeniasis. It is not effective against other worms such as flukes or roundworms. It is taken by mouth.

Side effects include nausea, vomiting, abdominal pain, and itchiness. It may be used during pregnancy. It works by blocking glucose uptake and oxidative phosphorylation by the worm.

Niclosamide was first synthesized in 1958. It is on the World Health Organization's List of Essential Medicines. Niclosamide is not available for human use in the United States.

Side effects

Side effects include nausea, vomiting, abdominal pain, constipation, and itchiness. Rarely, dizziness, skin rash, drowsiness, perianal itching, or an unpleasant taste occur. For some of these reasons, praziquantel is a preferable and equally effective treatment for tapeworm infestation. Important Note: Niclosamide kills the pork tapeworm and results in its digestion. This then may cause a multitude of viable eggs to be released and may result in cysticercosis. Therefore, a purge should be given 1 or two hours after treatment. CNS cysticercosis is a life-threatening condition and may require brain surgery.

Mechanism of action

Niclosamide inhibits glucose uptake, oxidative phosphorylation, and anaerobic metabolism in the tapeworm.

Other applications

Niclosamide's metabolic effects are relevant to wide ranges of organisms, and accordingly it has been applied as a control measure to organisms other than tapeworms. For example, it is an active ingredient in some formulations such as Bayluscide for killing lamprey larvae, as a molluscide, and as a general purpose piscicide in aquaculture. Niclosamide has a short half-life in water in field conditions; this makes it valuable in ridding commercial fish ponds of unwanted fish; it loses its activity soon enough to permit re-stocking within a few days of eradicating the previous population. Researchers have found that niclosamide is effective in killing invasive zebra mussels in cool waters.

Research

Niclosamide is under investigation for applications against types of cancer, bacterial infections, or viral infections.

In 2018, niclosamide was observed to be a potent activator of PTEN-induced kinase 1 in primary cortical neurons.

External links


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