Niclosamide

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Niclosamide
Niclosamide.svg
Niclosamide-from-xtal-Mercury-3D-sf.png
Clinical data
Trade names Niclocide, Fenasal, Phenasal, others [1]
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 OOjs UI icon edit-ltr-progressive.svg
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) Yes check.svgY
  • Key:RJMUSRYZPJIFPJ-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (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]

Contents

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 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. [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

  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. 1 2 3 World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. pp. 81, 87, 591. hdl: 10665/44053 . ISBN   9789241547659.
  4. ↑ Lanusse CE, Alvarez LI, Sallovitz JM, Mottier ML, Sanchez Bruni SF (13 May 2013). "Antinematodal Drugs". In Riviere JE, Papich MG (eds.). Veterinary Pharmacology and Therapeutics. John Wiley & Sons. p. 1096. ISBN   978-1-118-68590-7. Archived from the original on 10 September 2017.
  5. ↑ Mehlhorn H (2008). Encyclopedia of Parasitology: A-M. Springer Science & Business Media. p. 483. ISBN   978-3-540-48994-8. Archived from the original on 2016-12-20.
  6. ↑ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. 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. ↑ Remington JP, Osol A, eds. (1980). Remington's Pharmaceutical Sciences (16th ed.). Easton: Mack Pub. Co. p. 1182. OCLC   925174053.
  9. ↑ The Merck Manual of Diagnosis and Therapy (14th ed.). Rahway: Merck Sharp & Dohme Research Laboratories. 1982. p. 176. ISBN   978-0-911910-03-2.
  10. ↑ Weinbach EC, Garbus J (March 1969). "Mechanism of action of reagents that uncouple oxidative phosphorylation". Nature. 221 (5185): 1016–1018. Bibcode:1969Natur.221.1016W. doi:10.1038/2211016a0. PMID   4180173. S2CID   4209497.
  11. ↑ Boogaard MA (2003). "Chapter 6: Delivery Systems of Piscicides" (PDF). Integrated management techniques to control nonnative fishes. La Crosse, Wisconsin: US Geological Survey, Upper Midwest Environmental Sciences Center. pp. 39–50. Archived from the original (PDF) on 2017-06-01. Retrieved 2017-05-30.
  12. ↑ Verdel K.Dawson (2003). "Environmental Fate and Effects of the Lampricide Bayluscide: a Review". Journal of Great Lakes Research. 29 (Supplement 1): 475–492. Bibcode:2003JGLR...29..475D. doi:10.1016/S0380-1330(03)70509-7.
  13. 1 2 "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. ↑ Rajamuthiah R, Fuchs BB, Conery AL, Kim W, Jayamani E, Kwon B, et al. (April 2015). Planet PJ (ed.). "Repurposing salicylanilide anthelmintic drugs to combat drug resistant Staphylococcus aureus". PLOS ONE. 10 (4): e0124595. Bibcode:2015PLoSO..1024595R. doi: 10.1371/journal.pone.0124595 . PMC   4405337 . PMID   25897961.
  17. ↑ Li Y, Li P, He Q, Zhang R, Li Y, Kamar N, et al. (January 2022). "Niclosamide inhibits hepatitis E virus through suppression of NF-kappaB signalling". Antiviral Research. 197: 105228. doi: 10.1016/j.antiviral.2021.105228 . PMID   34929248.
  18. ↑ Braga L, Ali H, Secco I, Chiavacci E, Neves G, Goldhill D, et al. (June 2021). "Drugs that inhibit TMEM16 proteins block SARS-CoV-2 spike-induced syncytia". Nature. 594 (7861): 88–93. Bibcode:2021Natur.594...88B. doi:10.1038/s41586-021-03491-6. PMC   7611055 . PMID   33827113.
  19. ↑ Barini E, Miccoli A, Tinarelli F, Mulholland K, Kadri H, Khanim F, et al. (March 2018). "The Anthelmintic Drug Niclosamide and Its Analogues Activate the Parkinson's Disease Associated Protein Kinase PINK1". ChemBioChem. 19 (5): 425–429. doi:10.1002/cbic.201700500. PMC   5901409 . PMID   29226533.
  20. ↑ Mahmoud AB, Abd Algaffar S, van de Sande W, Khalid S, Kaiser M, Mäser P (June 2021). "Niclosamide Is Active In Vitro against Mycetoma Pathogens". Molecules. 26 (13): 4005. doi: 10.3390/molecules26134005 . PMC   8271592 . PMID   34209118.

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