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Details

Stereochemistry RACEMIC
Molecular Formula C10H11N3O5S
Molecular Weight 285.276
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of NIFURATEL

SMILES

CSCC1CN(\N=C\C2=CC=C(O2)[N+]([O-])=O)C(=O)O1

InChI

InChIKey=SRQKTCXJCCHINN-NYYWCZLTSA-N
InChI=1S/C10H11N3O5S/c1-19-6-8-5-12(10(14)18-8)11-4-7-2-3-9(17-7)13(15)16/h2-4,8H,5-6H2,1H3/b11-4+

HIDE SMILES / InChI

Molecular Formula C10H11N3O5S
Molecular Weight 285.276
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry
Defined Stereocenters 0 / 1
E/Z Centers 1
Optical Activity ( + / - )

Description

Nifuratel is a furane-derivative provided with a strong trichomonicidal activity; it has a broad antibacterial spectrum of action, including both Gram-negative and Gram-positive organisms. It is active against Chlamydia trachomatis and Mycoplasma spp. and has also some degree of activity against Candida spp. and mycetes. The action mechanism of nitrofurans has not been fully elucidated, and it may be the inhibiting of acetyl coenzyme A interfere with the early stages of bacterial glucose metabolism. Nifuratel alone or in complex with nystatin is indicated for the treatment of vulvovaginal and urinary tract infections. The drug is not approved by FDA.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MACMIROR
Primary
MACMIROR
PubMed

PubMed

TitleDatePubMed
Microbiological and pharmaco-toxicological profile of nifuratel and its favourable risk/benefit ratio for the treatment of vulvo-vaginal infections. A review.
2002
Clinical effects of nifuratel in vulvovaginal infections. A meta-analysis of metronidazole-controlled trials.
2002
Clinical study on the dose-effect relationship of a nifuratel-nystatin combination in the treatment of vulvo-vaginal infections.
2003
In vitro activity of nifuratel on vaginal bacteria: could it be a good candidate for the treatment of bacterial vaginosis?
2011 May
High-dose nifuratel for simple and mixed aerobic vaginitis: A single-center prospective open-label cohort study.
2016 Oct
Patents

Patents

Sample Use Guides

In Vivo Use Guide
MACMIROR tablets (200 mg nifuratel) for the treatment of vaginal infections: 1 tablet 3 times daily after meals for 1 week, for both partners. Urinary tract infections: 3 to 6 tablets per day for 1-2 weeks, depending on the cause and severity of the infection. MACMIROR complex vaginal capsules (500 mg nifuratel / 200 000 nystatin): 1 vaginal capsule daily or as directed by your doctor.
Route of Administration: oral, vaginal
In Vitro Use Guide
In vitro, nifuratel is able to inhibit the growth of A. vaginae, with a MIC range of 0.125-1 μg/mL; it is active against G. vaginalis (MICs ranging from <0.125 to 4 μg/ml) and does not affect lactobacilli.
Substance Class Chemical
Created
by admin
on Tue Mar 06 14:56:56 UTC 2018
Edited
by admin
on Tue Mar 06 14:56:56 UTC 2018
Record UNII
U60U6P08SP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NIFURATEL
INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
5-(METHYLTHIOMETHYL)-3-(5-NITRO-2-FURFURYLIDENAMINO)OXAZOLIDIN-2-ONE
Common Name English
NIFURATEL [WHO-DD]
Common Name English
NF-113
Code English
NIFURATEL [MART.]
Common Name English
SAP-113
Code English
2-OXAZOLIDINONE, 5-((METHYLTHIO)METHYL)-3-(((5-NITRO-2-FURANYL)METHYLENE)AMINO)-
Systematic Name English
5-((METHYLTHIO)METHYL)-3-(((5-NITRO-2-FURANYL)METHYLENE)AMINO)-2-OXAZOLIDINONE
Systematic Name English
NIFURATEL [USAN]
Common Name English
OMNES
Brand Name English
METHYLMERCADONE
Common Name English
INIMUR
Brand Name English
5-((METHYLTHIO)METHYL)-3-((5-NITROFURFURYLIDENE)AMINO)-2-OXAZOLIDINONE
Systematic Name English
TYDANTIL
Common Name English
NIFURATEL [MI]
Common Name English
NIFURATEL [INN]
Common Name English
MAGMILOR
Brand Name English
POLMIROR
Brand Name English
5-(METHYLMERCAPTOMETHYL)-3-(5-NITRO-2-FURFURYLIDENAMINO)-2-OXAZOLIDINONE
Common Name English
MACMIROR
Brand Name English
3-((5-NITRO-2-FURFURYLIDENE)AMINO)-5-((METHYLTHIO)METHYL)-2-OXAZOLIDINONE
Common Name English
2-OXAZOLIDINONE, 5-((METHYLTHIO)METHYL)-3-((5-NITROFURFURYLIDENE)AMINO)-
Systematic Name English
Classification Tree Code System Code
WHO-ATC G01AX05
Created by admin on Tue Mar 06 14:56:56 UTC 2018 , Edited by admin on Tue Mar 06 14:56:56 UTC 2018
WHO-VATC QG01AX05
Created by admin on Tue Mar 06 14:56:56 UTC 2018 , Edited by admin on Tue Mar 06 14:56:56 UTC 2018
Code System Code Type Description
INN
2314
Created by admin on Tue Mar 06 14:56:56 UTC 2018 , Edited by admin on Tue Mar 06 14:56:56 UTC 2018
PRIMARY
MESH
D009545
Created by admin on Tue Mar 06 14:56:56 UTC 2018 , Edited by admin on Tue Mar 06 14:56:56 UTC 2018
PRIMARY
ChEMBL
CHEMBL514315
Created by admin on Tue Mar 06 14:56:56 UTC 2018 , Edited by admin on Tue Mar 06 14:56:56 UTC 2018
PRIMARY
MERCK INDEX
M7886
Created by admin on Tue Mar 06 14:56:56 UTC 2018 , Edited by admin on Tue Mar 06 14:56:56 UTC 2018
PRIMARY Merck Index
RXCUI
7419
Created by admin on Tue Mar 06 14:56:56 UTC 2018 , Edited by admin on Tue Mar 06 14:56:56 UTC 2018
PRIMARY RxNorm
PUBCHEM
6433427
Created by admin on Tue Mar 06 14:56:56 UTC 2018 , Edited by admin on Tue Mar 06 14:56:56 UTC 2018
PRIMARY SWITZERF
WIKIPEDIA
NIFURATEL
Created by admin on Tue Mar 06 14:56:56 UTC 2018 , Edited by admin on Tue Mar 06 14:56:56 UTC 2018
PRIMARY
EVMPD
SUB09261MIG
Created by admin on Tue Mar 06 14:56:56 UTC 2018 , Edited by admin on Tue Mar 06 14:56:56 UTC 2018
PRIMARY
ECHA (EC/EINECS)
225-576-2
Created by admin on Tue Mar 06 14:56:56 UTC 2018 , Edited by admin on Tue Mar 06 14:56:56 UTC 2018
PRIMARY
CAS
4936-47-4
Created by admin on Tue Mar 06 14:56:56 UTC 2018 , Edited by admin on Tue Mar 06 14:56:56 UTC 2018
PRIMARY
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