NIFURATEL

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 Search

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	No
Defined Stereocenters	0 / 1
E/Z Centers	1
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11838277/ | https://www.chemicalbook.com/ProductCatalog_EN/142119.htm | http://pharmacy-new.org/macmiror-12-vaginal-suppositories | http://pharmacy-new.org/macmiror-200-mg-20-tablets | https://www.drugs.com/international/nifuratel.html

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

Primary Target	Pharmacology	Condition	Potency
CHEBI:15351 1 Target ID: CHEBI:15351 Sources: https://www.chemicalbook.com/ProductCatalog_EN/142119.htm	Inhibitor 8297
glucose homeostasis 1 Target ID: GO:0042593 Sources: https://www.chemicalbook.com/ProductCatalog_EN/142119.htm	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Vulvovaginal infection 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11838277/ https://www.ncbi.nlm.nih.gov/pubmed/12442634 https://www.ncbi.nlm.nih.gov/pubmed/14650366 https://www.ncbi.nlm.nih.gov/pubmed/27435791	Curative		Approved 8429	MACMIROR Approved Use MACMIROR (nifuratel ) is indicated for the treatment of vulvovaginal infections and vaginal discharge caused by pathogenic microorganisms: Trichomonas, Monilia, micelles. Urinary tract infections.
Urinary tract infections 205 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4891333 https://www.ncbi.nlm.nih.gov/pubmed/974657 https://www.ncbi.nlm.nih.gov/pubmed/4550718	Curative		Approved 8429	MACMIROR Approved Use MACMIROR (nifuratel ) is indicated for the treatment of vulvovaginal infections and vaginal discharge caused by pathogenic microorganisms: Trichomonas, Monilia, micelles. Urinary tract infections.

PubMed

Title	Date	PubMed
Clinical effects of nifuratel in vulvovaginal infections. A meta-analysis of metronidazole-controlled trials.	2002	12442634
Microbiological and pharmaco-toxicological profile of nifuratel and its favourable risk/benefit ratio for the treatment of vulvo-vaginal infections. A review.	2002	11838277
Clinical study on the dose-effect relationship of a nifuratel-nystatin combination in the treatment of vulvo-vaginal infections.	2003	14650366
In vitro activity of nifuratel on vaginal bacteria: could it be a good candidate for the treatment of bacterial vaginosis?	2011 May	21321147
High-dose nifuratel for simple and mixed aerobic vaginitis: A single-center prospective open-label cohort study.	2016 Oct	27435791

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: Other

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 `Sat Dec 16 17:13:21 GMT 2023` Edited by `admin` on `Sat Dec 16 17:13:21 GMT 2023`
Record UNII	U60U6P08SP
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

NIFURATEL

Official Name

English

5-(METHYLTHIOMETHYL)-3-(5-NITRO-2-FURFURYLIDENAMINO)OXAZOLIDIN-2-ONE

Common Name

English

NF-113

Code

English

NIFURATEL [MART.]

Common Name

English

Nifuratel [WHO-DD]

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