Nifurzide

Nifurzide
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	A07AX04 (WHO) ;
Identifiers
	IUPAC name 5-Nitro-N′-[(1E,2E)-3-(5-nitro-2-furyl)-2-propen-1-ylidene]-2-thiophenecarbohydrazide;
CAS Number	39978-42-2 ;
PubChem CID	9571044;
ChemSpider	7845510;
UNII	Z35R6K4C26;
KEGG	D07251 ;
ECHA InfoCard	100.049.735
Chemical and physical data
Formula	C12H8N4O6S
Molar mass	336.28 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES [O-][N+](=O)c1ccc(o1)/C=C/C=N/NC(=O)c2ccc(s2)[N+](=O)[O-];
	InChI InChI=1S/C12H8N4O6S/c17-12(9-4-6-11(23-9)16(20)21)14-13-7-1-2-8-3-5-10(22-8)15(18)19/h1-7H,(H,14,17)/b2-1+,13-7+; Key:IDUMOVRJNBNOTR-BIZLIJPVSA-N;
	(verify)

Nifurzide is a nitrofuran derivative and intestinal anti-infectious agent active against Escherichia coli.^[1]

Synthesis

Esterification of 5-nitrothiophene-2-carboxylic acid (1) with ethanol gives the ester (2). Treatment with hydrazine forms its hydrazide (3). Nifurzide is the hydrazone formed between (3) and 5-nitrofuran-2-acrylaldehyde (4).^[2]^[3]^[4]

References

^ Delsarte A, Faway M, Frère JM, Coyette J, Calberg-Bacq CM, Heinen E (March 1981). "Nifurzide, a nitrofuran antiinfectious agent: interaction with Escherichia coli cells". Antimicrobial Agents and Chemotherapy. 19 (3): 477–86. doi:10.1128/aac.19.3.477. PMC 181457. PMID 7018391.
^ US patent 3847911, Szarvasi E, Fontaine L, "Novel substituted(nitrofurylacrylidene)hydrazines with antibacterial properties", issued 1974-11-12
^ Szarvasi E, Fontaine L, Betbeder-Matibet A (March 1973). "Antimicrobials. New nitrofuran derivatives". Journal of Medicinal Chemistry. 16 (3): 281–287. doi:10.1021/jm00261a027. PMID 4200221.
^ "Nifurzide". Pharmaceutical Substances. Thieme. Retrieved 2024-07-02.

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[1] Delsarte A, Faway M, Frère JM, Coyette J, Calberg-Bacq CM, Heinen E (March 1981). "Nifurzide, a nitrofuran antiinfectious agent: interaction with Escherichia coli cells". Antimicrobial Agents and Chemotherapy. 19 (3): 477–86. doi:10.1128/aac.19.3.477. PMC 181457. PMID 7018391.

[2] US patent 3847911, Szarvasi E, Fontaine L, "Novel substituted(nitrofurylacrylidene)hydrazines with antibacterial properties", issued 1974-11-12

[3] Szarvasi E, Fontaine L, Betbeder-Matibet A (March 1973). "Antimicrobials. New nitrofuran derivatives". Journal of Medicinal Chemistry. 16 (3): 281–287. doi:10.1021/jm00261a027. PMID 4200221.

[4] "Nifurzide". Pharmaceutical Substances. Thieme. Retrieved 2024-07-02.

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v t e Antidiarrheals, intestinal anti-inflammatory and anti-infective agents (A07)
Rehydration	Oral rehydration therapy
Intestinal anti-infectives	Antibiotics Amphotericin B Colistin Fidaxomicin Kanamycin Natamycin Neomycin Nystatin Paromomycin Polymyxin B Rifaximin Streptomycin Vancomycin Sulfonamides Phthalylsulfathiazole Succinylsulfathiazole Sulfaguanidine Nitrofuran Nifuroxazide Nifurzide Imidazole Miconazole Arsenical Acetarsol Oxyquinoline Broxyquinoline
Intestinal adsorbents	Charcoal Bismuth (including bismuth subsalicylate, known as Pepto-Bismol) Pectin Kaolin Crospovidone Attapulgite Diosmectite
Antipropulsives (opioids)	Opium tincture (laudanum) Codeine Morphine Camphorated opium tincture (paregoric) crosses BBB: Diphenoxylate (+atropine) Difenoxin does not cross BBB: Eluxadoline Loperamide^# (+simethicone)
Intestinal anti-inflammatory agents	corticosteroids acting locally Prednisolone^# Hydrocortisone Prednisone Betamethasone^# Tixocortol Budesonide Beclometasone antiallergic agents, excluding corticosteroids Cromoglicic acid Aminosalicylates Sulfasalazine Mesalazine Olsalazine Balsalazide
Antidiarrheal micro-organisms	Escherichia coli Saccharomyces boulardii
Other antidiarrheals	Albumin tannate Bismuth subsalicylate Ceratonia Crofelemer Octreotide Racecadotril Kaopectate
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III