Chemistry:Niclosamide
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| Trade names | Niclocide, Fenasal, Phenasal, others[1] |
| AHFS/Drugs.com | Micromedex Detailed Consumer Information |
| Routes of administration | By mouth |
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| Formula | C13H8Cl2N2O4 |
| Molar mass | 327.12 g·mol−1 |
| 3D model (JSmol) | |
| Melting point | 225 to 230 °C (437 to 446 °F) |
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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.[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
- ↑ CID 4477 from PubChem
- ↑ "Niclosamide Advanced Patient Information - Drugs.com". https://www.drugs.com/cons/niclosamide.html.
- ↑ 3.0 3.1 3.2 WHO Model Formulary 2008. World Health Organization. 2009. pp. 81, 87, 591. ISBN 9789241547659.
- ↑ "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.
- ↑ 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.
- ↑ 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.
- ↑ "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.
- ↑ Remington's Pharmaceutical Sciences (16th ed.). Easton: Mack Pub. Co.. 1980. p. 1182. OCLC 925174053.
- ↑ The Merck Manual of Diagnosis and Therapy (14th ed.). Rahway: Merck Sharp & Dohme Research Laboratories. 1982. p. 176. ISBN 978-0-911910-03-2.
- ↑ "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.
- ↑ Boogaard, Michael A. Delivery Systems of Piscicides "Request Rejected". https://www.usbr.gov/lc/phoenix/biology/azfish/pdf/borfinalreport6t7.pdf.
- ↑ 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.
- ↑ 13.0 13.1 "WHO Specifications And Evaluations. For Public Health Pesticides. Niclosamide". https://www.who.int/whopes/quality/en/Niclosamide.pdf.
- ↑ "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.
- ↑ "Clinical Trials Using Niclosamide". https://www.cancer.gov/about-cancer/treatment/clinical-trials/intervention/niclosamide.
- ↑ "Repurposing salicylanilide anthelmintic drugs to combat drug resistant Staphylococcus aureus". PLOS ONE 10 (4): e0124595. April 2015. doi:10.1371/journal.pone.0124595. PMID 25897961. Bibcode: 2015PLoSO..1024595R.
- ↑ "Niclosamide inhibits hepatitis E virus through suppression of NF-kappaB signalling". Antiviral Research 197: 105228. January 2022. doi:10.1016/j.antiviral.2021.105228. PMID 34929248.
- ↑ "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.
- ↑ "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.
Further reading
- Taber's Cyclopedic Medical Cictionary (19th ed.). Philadelphia: F.A.Davis Co. 2001. ISBN 978-0-8036-0655-5.
- "Helminths: Cestode (tapeworm) infection: Niclosamide". WHO model prescribing information : drugs used in parasitic diseases (2nd ed.). World Health Organization (WHO). 1995. ISBN 9789241401043. http://apps.who.int/medicinedocs/en/d/Jh2922e/3.1.3.html.
External links
- "Niclosamide". Drug Information Portal. U.S. National Library of Medicine. https://druginfo.nlm.nih.gov/drugportal/name/niclosamide.
- Niclosamide in the Pesticide Properties DataBase (PPDB)
- "MedlinePlus Drug Information: Niclosamide (Oral)". U.S. National Library of Medicine. 1995-06-23. https://www.nlm.nih.gov/medlineplus/druginfo/uspdi/202406.html.
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