Niclosamide

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Niclosamide
QP52AG03 (WHO
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Identifiers
  • 5-Chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide
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
 ☒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.[2] It is taken by mouth.[3]

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] 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.[8][9]

Mechanism of action

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

Other applications

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 re-stocking within a few days of eradicating the previous population.[13] Researchers have found that niclosamide is effective in killing invasive zebra mussels in cool waters.[14]

Research

Niclosamide is under investigation for applications against types of cancer,[15] bacterial infections,[16] or viral infections.[17][18]

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

References

  1. ^ CID 4477 from PubChem
  2. ^ "Niclosamide Advanced Patient Information - Drugs.com". www.drugs.com. Archived from the original on 20 December 2016. Retrieved 8 December 2016.
  3. ^
    ISBN 9789241547659
    .
  4. ISBN 978-1-118-68590-7. Archived
    from the original on 10 September 2017.
  5. ISBN 978-3-540-48994-8. Archived
    from the original on 2016-12-20.
  6. hdl:10665/325771
    . WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  7. ^ "Dipylidium - Resources for Health Professionals". U.S. Centers for Disease Control and Prevention (CDC). 21 May 2020.
  8. OCLC 925174053
    .
  9. ISBN 978-0-911910-03-2
    .
  10. S2CID 4209497
    .
  11. ^ Boogaard, Michael A. Delivery Systems of Piscicides "Request Rejected" (PDF). Archived (PDF) from the original on 2017-06-01. Retrieved 2017-05-30.
  12. doi:10.1016/S0380-1330(03)70509-7
    .
  13. ^ a b "WHO Specifications And Evaluations. For Public Health Pesticides. Niclosamide" (PDF). Archived from the original (PDF) on 2017-01-10. Retrieved 2019-08-07.
  14. ^ Blank L (30 October 2018). "Researchers find new methods to combat invasive zebra mussels". The Minnesota Daily. Archived from the original on 2018-11-21. Retrieved 2018-11-19.
  15. ^ "Clinical Trials Using Niclosamide". NCI. Retrieved 20 March 2019.
  16. PMID 25897961
    .
  17. PMID 34929248
    .
  18. PMID 33827113
    .
  19. PMID 29226533
    .

Further reading

External links
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