Contents

Nifuroxazide

Chemical compound

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 N
PubChem CID	5337997
DrugBank	DB13855 Y
ChemSpider	4495115 Y
UNII	PM5LI0P38J
KEGG	D07111 Y
ChEMBL	ChEMBL244888 Y
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+ Y Key:YCWSUKQGVSGXJO-NTUHNPAUSA-N Y
NY (what is this?)  (verify)

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.

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]

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]

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]

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]

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