Nifuroxazide

Nifuroxazide (INN) is an oral nitrofuran antibiotic, patented since 1966[1] and used to treat colitis and diarrhoea in humans and non-humans.[2] It is sold under the brand names Ambatrol, Antinal, Bacifurane, Diafuryl (Turkey), Pérabacticel (France), Antinal, Diax (Egypt), Nifrozid, Ercefuryl (Romania, Czech Republic, Russia), Erfuzide (Thailand), Endiex (Slovakia), Enterofuryl (Russia), Pentofuryl (Germany), Topron, Enterovid (Latin America), Eskapar (Mexico), Enterocolin,TERRACOLIN 100Mg./200Mg.(Bolivia), Apazid (Morocco), Nifural (Indonesia) and Septidiaryl. It is sold in capsule form and also as a suspension.

Nifuroxazide

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	A07AX03 (WHO)
Identifiers
IUPAC name 4-hydroxy-N-[(E)-(5-nitrofuran-2-yl)methylideneamino]benzamide
CAS Number	965-52-6
PubChem CID	5337997
ChemSpider	4495115
UNII	PM5LI0P38J
KEGG	D07111
ChEMBL	ChEMBL244888
CompTox Dashboard (EPA)	DTXSID4045343
ECHA InfoCard	100.012.293
Chemical and physical data
Formula	C12H9N3O5
Molar mass	275.220 g·mol^−1
3D model (JSmol)	Interactive image
SMILES c1cc(O)ccc1C(=O)N/N=C/c2ccc(o2)[N+](=O)[O-]
InChI InChI=1S/C12H9N3O5/c16-9-3-1-8(2-4-9)12(17)14-13-7-10-5-6-11(20-10)15(18)19/h1-7,16H,(H,14,17)/b13-7+ Key:YCWSUKQGVSGXJO-NTUHNPAUSA-N
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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]

Notes

1. US 3290213, Carron MC, "Antibacterial nitrofurfurylidene derivatives and methods of using same", issued 6 December 1966, assigned to Laboratories Robert et Carriere SA
2. US 4093746, Cagliero G, "Method of and fodder for rearing white-meat calves for slaughter", issued 6 June 1978, assigned to Marxer SpA
3. "SmithKline Beecham Ambatrol (nifuroxazide)". Healthy Skepticism. June 1997. Archived from the original on 2010-12-21. Retrieved 2010-12-21.