Niclosamide

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
Niclosamide
Niclosamide.svg
Clinical data
Trade namesNiclocide, Fenasal, Phenasal, others[1]
AHFS/Drugs.comMicromedex Detailed Consumer Information
ATC code
Identifiers
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 mass327.119 g/mol g·mol−1
3D model (JSmol)
Melting point225 to 230 °C (437 to 446 °F)
 ☒N☑Y (what is this?)  (verify)

Niclosamide, sold under the trade name Niclocide among others, is a medication used to treat tapeworm infestations.[2] This includes diphyllobothriasis, hymenolepiasis, and taeniasis.[2] It is not effective against other worms such as pinworms or roundworms.[3] It is taken by mouth.[2]

Side effects include nausea, vomiting, abdominal pain, constipation, and itchiness.[2] It may be used during pregnancy and appears to be safe for the baby.[2] Niclosamide is in the anthelmintic family of medications.[3] It works by blocking the uptake of sugar by the worm.[4]

Niclosamide was discovered in 1958.[5] It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.[6] The wholesale cost in the developing world is about 0.24 USD for a course of treatment.[7] It is not commercially available in the United States.[3] It is effective in a number of other animals.[4]

Side effects[edit]

Side effects include nausea, vomiting, abdominal pain, constipation, and itchiness.[2] 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]

Mechanism of action[edit]

Niclosamide inhibits glucose uptake, oxidative phosphorylation, and anaerobic metabolism in the tapeworm.[8]

Other applications[edit]

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,[9][10] as a molluscide,[11] 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.[11] Researchers have found that niclosamide is effective in killing invasive zebra mussels in cool waters.[12]

Research[edit]

Niclosamide is being studied in a number of types of cancer.[13] Niclosamide along with oxyclozanide, another anti-tapeworm drug, was found in a 2015 study to display "strong in vivo and in vitro activity against methicillin-resistant Staphylococcus aureus (MRSA)".[14]

References[edit]

  1. ^ CID 4477 from PubChem
  2. ^ a b c d e f WHO Model Formulary 2008 (PDF). World Health Organization. 2009. pp. 81, 87, 591. ISBN 9789241547659. Archived (PDF) from the original on 2016-12-13. Cite uses deprecated parameter |deadurl= (help)
  3. ^ a b c "Niclosamide Advanced Patient Information - Drugs.com". www.drugs.com. Archived from the original on 20 December 2016. Retrieved 8 December 2016. Cite uses deprecated parameter |deadurl= (help)
  4. ^ a b Jim E. Riviere; Mark G. Papich (13 May 2013). Veterinary Pharmacology and Therapeutics. John Wiley & Sons. p. 1096. ISBN 978-1-118-68590-7. Archived from the original on 10 September 2017. Cite uses deprecated parameter |deadurl= (help)
  5. ^ Mehlhorn, Heinz (2008). Encyclopedia of Parasitology: A-M. Springer Science & Business Media. p. 483. ISBN 9783540489948. Archived from the original on 2016-12-20. Cite uses deprecated parameter |deadurl= (help)
  6. ^ "WHO Model List of Essential Medicines (19th List)" (PDF). World Health Organization. April 2015. Archived (PDF) from the original on 13 December 2016. Retrieved 8 December 2016. Cite uses deprecated parameter |deadurl= (help)
  7. ^ "Niclosamide". International Drug Price Indicator Guide. Archived from the original on 10 May 2017. Retrieved 1 December 2016. Cite uses deprecated parameter |deadurl= (help)
  8. ^ Weinbach EC, Garbus J (1969). "Mechanism of action of reagents that uncouple oxidative phosphorylation". Nature. 221 (5185): 1016–8. doi:10.1038/2211016a0. PMID 4180173.
  9. ^ Boogaard, Michael A. Delivery Systems of Piscicides "Request Rejected" (PDF). Archived (PDF) from the original on 2017-06-01. Retrieved 2017-05-30. Cite uses deprecated parameter |deadurl= (help)
  10. ^ Verdel K.Dawson (2003). "Environmental Fate and Effects of the Lampricide Bayluscide: a Review". Journal of Great Lakes Research. 29 (Supplement 1): 475–492. doi:10.1016/S0380-1330(03)70509-7.
  11. ^ a b "WHO Specifications And Evaluations. For Public Health Pesticides. Niclosamide" (PDF).[dead link]
  12. ^ "Researchers find new methods to combat invasive zebra mussels". The Minnesota Daily. Retrieved 2018-11-19.
  13. ^ "Clinical Trials Using Niclosamide". NCI. Retrieved 20 March 2019.
  14. ^ Repurposing Salicylanilide Anthelmintic Drugs to Combat Drug Resistant Staphylococcus aureus Archived 2015-05-02 at the Wayback Machine at PLOS

External links[edit]