Niclosamide
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| Clinical data | |
|---|---|
| Trade names | Niclocide, Fenasal, Phenasal etc.[1] |
| AHFS/Drugs.com | Micromedex Detailed Consumer Information |
| ATC code | P02DA01 (WHO) QP52AG03 (WHO) |
| Identifiers | |
| |
| CAS Number |
50-65-7  |
| PubChem (CID) | 4477 |
| DrugBank |
DB06803  |
| ChemSpider |
4322 |
| UNII |
8KK8CQ2K8G |
| KEGG |
D00436 |
| ChEMBL |
CHEMBL1448 |
| Chemical and physical data | |
| Formula | C13H8Cl2N2O4 |
| Molar mass | 327.119 g/mol |
| 3D model (Jmol) | Interactive image |
| Melting point | 225 to 230 °C (437 to 446 °F) |
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Niclosamide (trade name Niclocide[1]) is a teniacide in the anthelmintic family especially effective against cestodes that infect humans and many other animals. It is a salicylanilide compound (5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydrobenzamide) also used as a piscicide. While antihelmintics are a drug family used to treat worm infections, niclosamide is used specifically to treat tapeworms and is not effective against other worms such as pinworms or roundworms. It is a chewable tablet taken orally, dosage depending on type of worm and patient's age and/or weight. It is not usually considered the drug of choice for treating cestode infection in humans or animals because of its side effects, though it remains highly effective and is generally inexpensive.[2]
It is on the World Health Organization's List of Essential Medicines, the most important medications needed in a basic health system.[3]
Side effects
The medication can have side effects such as abdominal pain, anorexia, diarrhea, and emesis. 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.[4]
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)".[5] A 2016 drug repurposing screening study suggested that niclosamide may inhibit Zika virus replication in vitro.[6]
References
- 1 2 CID 4477 from PubChem
- ↑ Jim E. Riviere; Mark G. Papich (13 May 2013). Veterinary Pharmacology and Therapeutics. John Wiley & Sons. p. 1096. ISBN 978-1-118-68590-7.
- ↑ "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.
- ↑ Weinbach EC, Garbus J (1969). "Mechanism of action of reagents that uncouple oxidative phosphorylation". Nature. 221 (5185): 1016–8. doi:10.1038/2211016a0. PMID 4180173.
- ↑ 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. doi:10.1038/nm.4184. ISSN 1078-8956.
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.