Niclosamide
ニクロサミド;
| Formula |
C13H8Cl2N2O4
|
|---|---|
| cas |
50-65-7
|
| Mol weight |
327.1196
|
CAS Registry Number: 50-65-7
Niclosamide, sold under the brand name Niclocide among others, is a medication used to treat tapeworm infestations.[2] 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, and itchiness.[2] 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 by the worm.[4]
Niclosamide was discovered in 1958.[5] It is on the World Health Organization’s List of Essential Medicines, the safest and most effective 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.[citation needed]
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 such as Bayluscide for killing lamprey larvae,[9][10] as a molluscide,[11] 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.[11] Researchers have found that niclosamide is effective in killing invasive zebra mussels in cool waters.[12]
Research
Niclosamide is being studied in a number of types of cancer.[13] 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)”.[14]
syn
https://www.sciencedirect.com/science/article/pii/S0099542805320028
References
- ^ Jump up to:a b c d e f 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.
- ^ Jump up to:a b c “Niclosamide Advanced Patient Information – Drugs.com”. http://www.drugs.com. Archived from the original on 20 December 2016. Retrieved 8 December 2016.
- ^ Jump up to:a b Jim E. Riviere; Mark G. Papich (13 May 2013). Veterinary Pharmacology and Therapeutics. John Wiley & Sons. p. 1096. ISBN 978-1-118-68590-7. Archived from the original on 10 September 2017.
- ^ Mehlhorn, Heinz (2008). Encyclopedia of Parasitology: A-M. Springer Science & Business Media. p. 483. ISBN 9783540489948. Archived from the original on 2016-12-20.
- ^ 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.
- ^ “Niclosamide”. International Drug Price Indicator Guide. Archived from the original on 10 May 2017. Retrieved 1 December 2016.
- ^ 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.
- ^ Boogaard, Michael A. Delivery Systems of Piscicides “Request Rejected”(PDF). Archived (PDF) from the original on 2017-06-01. Retrieved 2017-05-30.
- ^ 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.
- ^ Jump up to:a b “WHO Specifications And Evaluations. For Public Health Pesticides. Niclosamide” (PDF).[dead link]
- ^ “Researchers find new methods to combat invasive zebra mussels”. The Minnesota Daily. Retrieved 2018-11-19.
- ^ “Clinical Trials Using Niclosamide”. NCI. Retrieved 20 March 2019.
- ^ Rajamuthiah R, Fuchs BB, Conery AL, Kim W, Jayamani E, Kwon B, Ausubel FM, Mylonakis E (April 2015). Planet PJ (ed.). “Repurposing Salicylanilide Anthelmintic Drugs to Combat Drug Resistant Staphylococcus aureus”. PLoS ONE. 10 (4): e0124595. doi:10.1371/journal.pone.0124595. ISSN 1932-6203. PMC 4405337. PMID 25897961.
External links
- “Niclosamide”. Drug Information Portal. U.S. National Library of Medicine.
- Taber, Clarence Wilbur; Venes, Donald; Thomas, Clayton L. (2001). Taber’s cyclopedic medical dictionary. Philadelphia: F.A.Davis Co.
- 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.
- World Health Organization (1995). “Helminths: Cestode (tapeworm) infection: Niclosamide”. WHO model prescribing information : drugs used in parasitic diseases (2nd ed.). World Health Organization (WHO). hdl:10665/41765.
Niclosamide
|
|
| Clinical data | |
|---|---|
| Trade names | Niclocide, Fenasal, Phenasal, others[1] |
| AHFS/Drugs.com | Micromedex Detailed Consumer Information |
| Routes of administration |
By mouth |
| ATC code | |
| Identifiers | |
| CAS Number | |
| PubChem CID | |
| DrugBank | |
| ChemSpider | |
| UNII | |
| KEGG | |
| ChEBI | |
| ChEMBL | |
| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.000.052  |
| Chemical and physical data | |
| Formula | C13H8Cl2N2O4 |
| Molar mass | 327.119 g/mol g·mol−1 |
| 3D model (JSmol) | |
| Melting point | 225 to 230 °C (437 to 446 °F) |
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