Niclosamide
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| Trade names | Niclocide, Fenasal, Phenasal, others[1] |
| AHFS/Drugs.com | Micromedex Detailed Consumer Information |
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| ECHA InfoCard | 100.000.052 |
| Chemical and physical data | |
| Formula | C13H8Cl2N2O4 |
| Molar mass | 327.119 g/mol |
| 3D model (JSmol) | |
| Melting point | 225 to 230 °C (437 to 446 °F) |
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Niclosamide, sold under the trade name Niclocide among others, is a medication used to treat tapeworm infestations. 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. 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.[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
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.
Mechanism of action
Niclosamide inhibits glucose uptake, oxidative phosphorylation, and anaerobic metabolism in the tapeworm.[8]
Other applications
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 for killing lamprey larvae,[9] as a molluscide,[10] 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.[10]
Research
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)".[11] A 2016 drug repurposing screening study suggested that niclosamide may inhibit Zika virus replication in vitro.[12]
References
- ↑ CID 4477 from PubChem
- 1 2 3 4 WHO Model Formulary 2008 (PDF). World Health Organization. 2009. pp. 81, 87, 591. ISBN 9789241547659.
- 1 2 3 "Niclosamide Advanced Patient Information - Drugs.com". www.drugs.com. Retrieved 8 December 2016.
- 1 2 Jim E. Riviere; Mark G. Papich (13 May 2013). Veterinary Pharmacology and Therapeutics. John Wiley & Sons. p. 1096. ISBN 978-1-118-68590-7.
- ↑ Mehlhorn, Heinz (2008). Encyclopedia of Parasitology: A-M. Springer Science & Business Media. p. 483. ISBN 9783540489948.
- ↑ "WHO Model List of Essential Medicines (19th List)" (PDF). World Health Organization. April 2015. Retrieved 8 December 2016.
- ↑ "Niclosamide". International Drug Price Indicator Guide. Retrieved 1 December 2016.
- ↑ Weinbach EC, Garbus J (1969). "Mechanism of action of reagents that uncouple oxidative phosphorylation". Nature. 221 (5185): 1016–8. PMID 4180173. doi:10.1038/2211016a0.
- ↑ Boogaard, Michael A. Delivery Systems of Piscicides
- 1 2 Who Specifications And Evaluations. For Public Health Pesticides. Niclosamide [www.who.int/whopes/quality/en/Niclosamide.pdf]
- ↑ Repurposing Salicylanilide Anthelmintic Drugs to Combat Drug Resistant Staphylococcus aureus at PLOS
- ↑ Xu, Miao; Lee, Emily M; Wen, Zhexing; Cheng, Yichen; Huang, Wei-Kai; Qian, Xuyu; TCW, Julia; Kouznetsova, Jennifer; Ogden, Sarah C; Hammack, Christy; Jacob, Fadi; Nguyen, Ha Nam; Itkin, Misha; Hanna, Catherine; Shinn, Paul; Allen, Chase; Michael, Samuel G; Simeonov, Anton; Huang, Wenwei; Christian, Kimberly M; Goate, Alison; Brennand, Kristen J; Huang, Ruili; Xia, Menghang; Ming, Guo-li; Zheng, Wei; Song, Hongjun; Tang, Hengli (2016). "Identification of small-molecule inhibitors of Zika virus infection and induced neural cell death via a drug repurposing screen". Nature Medicine. 22: 1101–1107. ISSN 1078-8956. PMID 27571349. doi:10.1038/nm.4184.
Further reading
- Taber, Clarence Wilbur; Venes, Donald; Thomas, Clayton L. (2001). Taber's cyclopedic medical dictionary. Philadelphia: F.A.Davis Co.
External links
- Niclosamide in the Pesticide Properties DataBase (PPDB)
- "MedlinePlus Drug Information: Niclosamide (Oral)". MedlinePlus. U.S. National Library of Medicine. 1995-06-23. Archived from the original on 2006-12-16.
- "Helminths: Cestode (tapeworm) infection: Niclosamide". WHO Model Prescribing Information: Drugs Used in Parasitic Diseases - Second Edition. WHO. 1995. Retrieved 2015-11-01.