Chemistry:Niclosamide

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

Side effects include nausea, vomiting, abdominal pain, and itchiness. It may be used during pregnancy.[2] It works by blocking glucose uptake and oxidative phosphorylation by the worm.[3]

Niclosamide was first synthesized in 1958.[4] It is on the World Health Organization's List of Essential Medicines.[5] Niclosamide is not available for human use in the United States.[6]

Side effects

Of note, niclosamide kills the pork tapeworm in such a way that causes a multitude of viable eggs to be released and may result in cysticercosis. So, a purge should be given one or two hours after treatment. CNS cysticercosis is a life-threatening condition and may require brain surgery.[7][8]

Mechanism of action

Niclosamide inhibits glucose uptake, oxidative phosphorylation, and anaerobic metabolism in the tapeworm.[9]

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,[10][11] as a molluscide,[12] 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.[12] Researchers have found that niclosamide is effective in killing invasive zebra mussels in cool freshwater aquatic environments.[13]

Medical research

Niclosamide is under investigation as a potential treatment for certain types of cancer,[14] bacterial infections,[15] and viral infections.[16][17]

In 2018, niclosamide was observed to be a potent activator of PTEN-induced kinase 1 in primary cortical neurons.[18]


It appears to show in-vitro antifungal effects against some forms of eumycetoma.[19]

References

  1. ↑ "Niclosamide Advanced Patient Information - Drugs.com". https://www.drugs.com/cons/niclosamide.html. 
  2. ↑ 2.0 2.1 WHO Model Formulary 2008. World Health Organization. 2009. pp. 81, 87, 591. ISBN 978-92-4-154765-9. 
  3. ↑ "Antinematodal Drugs". Veterinary Pharmacology and Therapeutics. John Wiley & Sons. 13 May 2013. p. 1096. ISBN 978-1-118-68590-7. https://books.google.com/books?id=xAPa4WDzAnQC&pg=PA1096. 
  4. ↑ Encyclopedia of Parasitology: A-M. Springer Science & Business Media. 2008. p. 483. ISBN 978-3-540-48994-8. https://books.google.com/books?id=Jpg1ysgVn-AC&pg=PA483. 
  5. ↑ World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. 2019. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO. 
  6. ↑ "Dipylidium – Resources for Health Professionals". U.S. Centers for Disease Control and Prevention (CDC). 21 May 2020. https://www.cdc.gov/parasites/dipylidium/health_professionals/index.html. 
  7. ↑ Remington's Pharmaceutical Sciences (16th ed.). Easton: Mack Pub. Co.. 1980. p. 1182. OCLC 925174053. 
  8. ↑ The Merck Manual of Diagnosis and Therapy (14th ed.). Rahway: Merck Sharp & Dohme Research Laboratories. 1982. p. 176. ISBN 978-0-911910-03-2. 
  9. ↑ "Mechanism of action of reagents that uncouple oxidative phosphorylation". Nature 221 (5185): 1016–1018. March 1969. doi:10.1038/2211016a0. PMID 4180173. Bibcode: 1969Natur.221.1016W. 
  10. ↑ "Chapter 6: Delivery Systems of Piscicides". Integrated management techniques to control nonnative fishes.. La Crosse, Wisconsin: US Geological Survey, Upper Midwest Environmental Sciences Center. 2003. pp. 39–50. https://www.usbr.gov/lc/phoenix/biology/azfish/pdf/borfinalreport6t7.pdf. Retrieved 2017-05-30. 
  11. ↑ 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. Bibcode: 2003JGLR...29..475D. 
  12. ↑ 12.0 12.1 "WHO Specifications And Evaluations. For Public Health Pesticides. Niclosamide". https://www.who.int/whopes/quality/en/Niclosamide.pdf. 
  13. ↑ "Researchers find new methods to combat invasive zebra mussels". The Minnesota Daily. 30 October 2018. http://www.mndaily.com/article/2018/10/n-researchers-find-new-methods-to-combat-invasive-zebra-mussels. 
  14. ↑ "Clinical Trials Using Niclosamide". https://www.cancer.gov/about-cancer/treatment/clinical-trials/intervention/niclosamide. 
  15. ↑ "Repurposing salicylanilide anthelmintic drugs to combat drug resistant Staphylococcus aureus". PLOS ONE 10 (4). April 2015. doi:10.1371/journal.pone.0124595. PMID 25897961. Bibcode: 2015PLoSO..1024595R. 
  16. ↑ "Niclosamide inhibits hepatitis E virus through suppression of NF-kappaB signalling". Antiviral Research 197. January 2022. doi:10.1016/j.antiviral.2021.105228. PMID 34929248. 
  17. ↑ "Drugs that inhibit TMEM16 proteins block SARS-CoV-2 spike-induced syncytia". Nature 594 (7861): 88–93. June 2021. doi:10.1038/s41586-021-03491-6. PMID 33827113. Bibcode: 2021Natur.594...88B. 
  18. ↑ "The Anthelmintic Drug Niclosamide and Its Analogues Activate the Parkinson's Disease Associated Protein Kinase PINK1". ChemBioChem 19 (5): 425–429. March 2018. doi:10.1002/cbic.201700500. PMID 29226533. 
  19. ↑ "Niclosamide Is Active In Vitro against Mycetoma Pathogens". Molecules 26 (13): 4005. June 2021. doi:10.3390/molecules26134005. PMID 34209118. 

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