Niclosamide

Chemical compound From Wikipedia, the free encyclopedia

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.[2] It is taken by mouth.[3]

Trade namesNiclocide, Fenasal, Phenasal, others[1]
ATC code
Quick facts Clinical data, Trade names ...
Niclosamide
Clinical data
Trade namesNiclocide, Fenasal, Phenasal, others[1]
AHFS/Drugs.comMicromedex 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 InfoCard100.000.052 Edit this at Wikidata
Chemical and physical data
FormulaC13H8Cl2N2O4
Molar mass327.12 g·mol−1
3D model (JSmol)
Melting point225 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
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Side effects include nausea, vomiting, abdominal pain, and itchiness. It may be used during pregnancy.[3] It works by blocking glucose uptake and oxidative phosphorylation by the worm.[4]

Niclosamide was first synthesized in 1958.[5] It is on the World Health Organization's List of Essential Medicines.[6] Niclosamide is not available for human use in the United States.[7]

Side effects

Side effects include nausea, vomiting, abdominal pain, constipation, and itchiness.[3] 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.[citation needed]

Of note, niclosamide kills the pork tapeworm in a way that causes a multitude of viable eggs to be released and may result in cysticercosis. Neurocysticercosis is a life-threatening condition that may require brain surgery.[8][9]

Mechanism of action

Niclosamide inhibits glucose uptake, oxidative phosphorylation, and anaerobic metabolism in the tapeworm.[10]

Use as a pesticide

Niclosamide's metabolic effects are relevant to a 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,[11][12] as a molluscide,[13] 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 restocking within a few days of eradicating the previous population.[13] Researchers have found that niclosamide is effective in killing invasive zebra mussels in cool freshwater aquatic environments.[14]

Medical research

Niclosamide is under investigation as a potential treatment for certain types of cancer,[15] bacterial infections,[16] and viral infections.[17][18]

In 2018, niclosamide was observed to be a potent activator of PTEN-induced kinase 1 in primary cortical neurons.[19]

It appears to show in-vitro antifungal effects against some forms of eumycetoma.[20]

References

Further reading

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