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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
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 2
Optical Activity NONE

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

Patents

Patents

Sample Use Guides

Single dose - 600 mg
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:27:33 UTC 2023
Edited
by admin
on Fri Dec 15 16:27:33 UTC 2023
Record UNII
Z35R6K4C26
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NIFURZIDE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
nifurzide [INN]
Common Name English
NIFURZIDE [MART.]
Common Name English
NIFURZIDE [MI]
Common Name English
5-NITRO-2-THIOPHENECARBOXYLIC ACID (3-(5-NITRO-2-FURYL)ALLYLIDENE)HYDRAZIDE
Common Name English
2-THIOPHENECARBOXYLIC ACID, 5-NITRO-, 2-(3-(5-NITRO-2-FURANYL)-2-PROPEN-1-YLIDENE)HYDRAZIDE
Systematic Name English
RICRIDENE
Brand Name English
Nifurzide [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC A07AX04
Created by admin on Fri Dec 15 16:27:33 UTC 2023 , Edited by admin on Fri Dec 15 16:27:33 UTC 2023
WHO-VATC QA07AX04
Created by admin on Fri Dec 15 16:27:33 UTC 2023 , Edited by admin on Fri Dec 15 16:27:33 UTC 2023
NCI_THESAURUS C28394
Created by admin on Fri Dec 15 16:27:33 UTC 2023 , Edited by admin on Fri Dec 15 16:27:33 UTC 2023
Code System Code Type Description
ECHA (EC/EINECS)
254-728-0
Created by admin on Fri Dec 15 16:27:33 UTC 2023 , Edited by admin on Fri Dec 15 16:27:33 UTC 2023
PRIMARY
ChEMBL
CHEMBL2106530
Created by admin on Fri Dec 15 16:27:33 UTC 2023 , Edited by admin on Fri Dec 15 16:27:33 UTC 2023
PRIMARY
SMS_ID
100000083899
Created by admin on Fri Dec 15 16:27:33 UTC 2023 , Edited by admin on Fri Dec 15 16:27:33 UTC 2023
PRIMARY
EPA CompTox
DTXSID30865982
Created by admin on Fri Dec 15 16:27:33 UTC 2023 , Edited by admin on Fri Dec 15 16:27:33 UTC 2023
PRIMARY
FDA UNII
Z35R6K4C26
Created by admin on Fri Dec 15 16:27:33 UTC 2023 , Edited by admin on Fri Dec 15 16:27:33 UTC 2023
PRIMARY
INN
4127
Created by admin on Fri Dec 15 16:27:33 UTC 2023 , Edited by admin on Fri Dec 15 16:27:33 UTC 2023
PRIMARY
CAS
39978-42-2
Created by admin on Fri Dec 15 16:27:33 UTC 2023 , Edited by admin on Fri Dec 15 16:27:33 UTC 2023
PRIMARY
RXCUI
31786
Created by admin on Fri Dec 15 16:27:33 UTC 2023 , Edited by admin on Fri Dec 15 16:27:33 UTC 2023
PRIMARY RxNorm
DRUG BANK
DB13325
Created by admin on Fri Dec 15 16:27:33 UTC 2023 , Edited by admin on Fri Dec 15 16:27:33 UTC 2023
PRIMARY
WIKIPEDIA
NIFURZIDE
Created by admin on Fri Dec 15 16:27:33 UTC 2023 , Edited by admin on Fri Dec 15 16:27:33 UTC 2023
PRIMARY
EVMPD
SUB09283MIG
Created by admin on Fri Dec 15 16:27:33 UTC 2023 , Edited by admin on Fri Dec 15 16:27:33 UTC 2023
PRIMARY
PUBCHEM
9571044
Created by admin on Fri Dec 15 16:27:33 UTC 2023 , Edited by admin on Fri Dec 15 16:27:33 UTC 2023
PRIMARY
MESH
C029924
Created by admin on Fri Dec 15 16:27:33 UTC 2023 , Edited by admin on Fri Dec 15 16:27:33 UTC 2023
PRIMARY
MERCK INDEX
m7894
Created by admin on Fri Dec 15 16:27:33 UTC 2023 , Edited by admin on Fri Dec 15 16:27:33 UTC 2023
PRIMARY Merck Index
NCI_THESAURUS
C90985
Created by admin on Fri Dec 15 16:27:33 UTC 2023 , Edited by admin on Fri Dec 15 16:27:33 UTC 2023
PRIMARY
DRUG CENTRAL
1931
Created by admin on Fri Dec 15 16:27:33 UTC 2023 , Edited by admin on Fri Dec 15 16:27:33 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY