fbpx
Wikipedia

Nifuroxazide

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.

Nifuroxazide
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration
Oral
ATC code
Identifiers
  • 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 InfoCard100.012.293
Chemical and physical data
FormulaC12H9N3O5
Molar mass275.220 g·mol−1
3D model (JSmol)
  • Interactive image
  • c1cc(O)ccc1C(=O)N/N=C/c2ccc(o2)[N+](=O)[O-]
  • 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)

History edit

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 edit

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 edit

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 edit

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 edit

  1. ^ a b US 3290213, Carron MC, "Antibacterial nitrofurfurylidene derivatives and methods of using same", issued 6 December 1966, assigned to Laboratories Robert et Carriere SA 
  2. ^ a b US 4093746, Cagliero G, "Method of and fodder for rearing white-meat calves for slaughter", issued 6 June 1978, assigned to Marxer SpA 
  3. ^ a b "SmithKline Beecham Ambatrol (nifuroxazide)". Healthy Skepticism. June 1997. from the original on 2010-12-31. Retrieved 2010-12-21.
  4. ^ Bailly C (September 2019). "Toward a repositioning of the antibacterial drug nifuroxazide for cancer treatment". Drug Discovery Today. 24 (9): 1930–1936. doi:10.1016/j.drudis.2019.06.017. PMID 31260646. S2CID 195771445.
  5. ^ Sarvi S (December 2018). "ALDH1 Bio-activates Nifuroxazide to Eradicate ALDH High Melanoma-Initiating Cells". Cell Chemical Biology. 25 (12): 1456–1469. doi:10.1016/j.chembiol.2018.09.005. PMC 6309505. PMID 30293938.


nifuroxazide, oral, nitrofuran, antibiotic, patented, since, 1966, used, treat, colitis, diarrhea, humans, humans, sold, under, brand, names, ambatrol, antinal, bacifurane, diafuryl, turkey, benol, pakistan, pérabacticel, france, antinal, diax, egypt, nifrozid. 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 Perabacticel 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 NifuroxazideClinical dataAHFS Drugs comInternational Drug NamesRoutes ofadministrationOralATC codeA07AX03 WHO IdentifiersIUPAC name 4 hydroxy N E 5 nitrofuran 2 yl methylideneamino benzamideCAS Number965 52 6 NPubChem CID5337997DrugBankDB13855 YChemSpider4495115 YUNIIPM5LI0P38JKEGGD07111 YChEMBLChEMBL244888 YCompTox Dashboard EPA DTXSID4045343ECHA InfoCard100 012 293Chemical and physical dataFormulaC 12H 9N 3O 5Molar mass275 220 g mol 13D model JSmol Interactive imageSMILES 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 YKey YCWSUKQGVSGXJO NTUHNPAUSA N Y N Y what is this verify Contents 1 History 2 Effectiveness in humans 3 STAT3 inhibition 4 ALDH1 cancer stem cells 5 ReferencesHistory editMaurice 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 editIn 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 editIn 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 editHigh 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 edit a b US 3290213 Carron MC Antibacterial nitrofurfurylidene derivatives and methods of using same issued 6 December 1966 assigned to Laboratories Robert et Carriere SA a b US 4093746 Cagliero G Method of and fodder for rearing white meat calves for slaughter issued 6 June 1978 assigned to Marxer SpA a b SmithKline Beecham Ambatrol nifuroxazide Healthy Skepticism June 1997 Archived from the original on 2010 12 31 Retrieved 2010 12 21 Bailly C September 2019 Toward a repositioning of the antibacterial drug nifuroxazide for cancer treatment Drug Discovery Today 24 9 1930 1936 doi 10 1016 j drudis 2019 06 017 PMID 31260646 S2CID 195771445 Sarvi S December 2018 ALDH1 Bio activates Nifuroxazide to Eradicate ALDH High Melanoma Initiating Cells Cell Chemical Biology 25 12 1456 1469 doi 10 1016 j chembiol 2018 09 005 PMC 6309505 PMID 30293938 nbsp This drug article relating to the gastrointestinal system is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Nifuroxazide amp oldid 1216338696, wikipedia, wiki, book, books, library,

article

, read, download, free, free download, mp3, video, mp4, 3gp, jpg, jpeg, gif, png, picture, music, song, movie, book, game, games.