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Details

Stereochemistry ACHIRAL
Molecular Formula C12H8N4O6S
Molecular Weight 336.28
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of NIFURZIDE

SMILES

[O-][N+](=O)C1=CC=C(O1)\C=C\C=N\NC(=O)C2=CC=C(S2)[N+]([O-])=O

InChI

InChIKey=IDUMOVRJNBNOTR-BIZLIJPVSA-N
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+

HIDE SMILES / InChI

Molecular Formula C12H8N4O6S
Molecular Weight 336.28
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 2
Optical Activity NONE

Description

Nifurzide, a synthetic antimicrobial agent of the nitrofuran group. The MICs were excellent for Campylobacter spp. (97 strains); slightly higher for Shigella spp. (50 strains) and Aeromonas spp. (22 strains); and highest for Salmonella spp. (100 strains) and Yersinia enterocolitica. At low concentrations of nifurzide, the growth rate of the Escherichia coli cultures decreased, and elongated, nonseptate cells appeared. At high concentrations, complete growth inhibition occurred, accompanied by a rather strong bactericidal effect, but the appearance of the cells was normal; in particular, no bacteriolytic effect was observed. A very large number of antibiotic molecules were bound per bacterial cell. After cell disruption, similar amounts of nifurzide were found in the cytoplasm, cytoplasmic membranes, and cell wall, respectively. Nifurzide had no effect on a general infection, but significantly decreased the number of colony-forming germs in the digestive tract. It was rather insoluble in aqueous media, did not cross the intestinal barrier, and was not substantially metabolized in the intestine. The obnoxious side effects of other nitrofurans (induction of vomiting and inhibition of monoamine oxidase) were not observed with nifurzide, which makes it an interesting therapeutic agent against enteric infections.

Approval Year

Sample Use Guides

In Vivo Use Guide
Single dose - 600 mg
Route of Administration: Oral
Substance Class Chemical
Record UNII
Z35R6K4C26
Record Status Validated (UNII)
Record Version