Chemistry:Nifuroxazide
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| AHFS/Drugs.com | International Drug Names |
| Routes of administration | Oral |
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| Formula | C12H9N3O5 |
| Molar mass | 275.220 g·mol−1 |
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Nifuroxazide (INN) is an oral nitrofuran antibiotic, patented since 1966[1] and used to treat colitis and diarrhea in humans and non-humans.[2] It is sold under the brand names Ambatrol, Antinal, Bacifurane, Diafuryl (Turkey), Benol (Pakistan), Pérabacticel (France), Antinal, Diax (Egypt), Nifrozid, Ercefuryl (Romania, Czech Republic, Russia), Erfuzide (Thailand), Endiex (Slovakia), Enterofuryl (Bosnia and Herzegovina, Russia), Pentofuryl (Germany), Nifuroksazyd Hasco, Nifuroksazyd Polpharma (Poland), Topron, Enterovid (Latin America), Eskapar (Mexico), Enterocolin, Terracolin (Bolivia), Apazid (Morocco), Nifroxid (Tunisia), Nifural (Indonesia) and Septidiaryl. It is sold in capsule form and also as a suspension.
History
Maurice Claude Ernest Carron patented the drug in the United States in 1966.[1] Subsequent patents issued to Germano Cagliero of Marxer S.p.A. describe the use of nifuroxazide as an antibiotic used to treat livestock.[2]
Effectiveness in humans
In 1997, in an Ivory Coast promotional leaflet, GlaxoSmithKline claimed that nifuroxazide (under the brand name "Ambatrol") is an anti-dehydration treatment, "neutralise[s] microbacterials" in diarrhoea, and has "a spectrum which covers most enteropathogenic microbacterials, Shigella, Escherichia coli, Salmonella, Staphylococci, Klebsiella, Yersinia".[3] The international non-profit organization Healthy Skepticism, at the time using their former name, Medical Lobby for Appropriate Marketing (MaLAM), disagreed, stating "We have not found any scientific evidence to support these claims."[3]
STAT3 inhibition
In addition to its antibiotic activity, nifuroxazide has been found to be a potent inhibitor of STAT3, and consequently has been proposed as a cancer treatment.[4]
ALDH1 cancer stem cells
High aldehyde dehydrogenase (ALDH) 1 enzymatic activity is a marker for cancer stem cell/tumour initiating cell populations in many cancers. Nifuroxazide was found to be bio-activated by ALDH1 enzymes, and shown to selectively kill ALDH1-High melanoma cells in experimental human cell systems and mouse models. ALDH1 is enriched in melanoma patient samples following BRAF and MEK inhibitor treatments, and it has been proposed that nifuroxazide may be useful as a cancer treatment in this context.[5]
References
- ↑ 1.0 1.1 Carron MC, "Antibacterial nitrofurfurylidene derivatives and methods of using same", US patent 3290213, issued 6 December 1966, assigned to Laboratories Robert et Carriere SA
- ↑ 2.0 2.1 Cagliero G, "Method of and fodder for rearing white-meat calves for slaughter", US patent 4093746, issued 6 June 1978, assigned to Marxer SpA
- ↑ 3.0 3.1 "SmithKline Beecham Ambatrol (nifuroxazide)". Healthy Skepticism. June 1997. http://www.healthyskepticism.org/global/malam/int/mi1997-05_06/.
- ↑ "Toward a repositioning of the antibacterial drug nifuroxazide for cancer treatment". Drug Discovery Today 24 (9): 1930–1936. September 2019. doi:10.1016/j.drudis.2019.06.017. PMID 31260646.
- ↑ "ALDH1 Bio-activates Nifuroxazide to Eradicate ALDH High Melanoma-Initiating Cells". Cell Chemical Biology 25 (12): 1456–1469. December 2018. doi:10.1016/j.chembiol.2018.09.005. PMID 30293938.
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