NIFURATEL

Possibly Marketed Outside US

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 8504
glucose homeostasis 1 Target ID: GO:0042593 Sources: https://www.chemicalbook.com/ProductCatalog_EN/142119.htm	Inhibitor 8504

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 8583	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 207 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 8583	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.

C_max

Value	Dose	Co-administered	Analyte	Population
44.89 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17702193/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:		NIFURATEL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
155.02 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17702193/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:		NIFURATEL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
3.58 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17702193/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:		NIFURATEL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
1 % single, vaginal Studied dose Dose: 1 % Route: vaginal Route: single Dose: 1 % Sources: https://pubmed.ncbi.nlm.nih.gov/6851539/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/6851539/	Other AEs: Contact dermatitis... Other AEs: Contact dermatitis Sources: https://pubmed.ncbi.nlm.nih.gov/6851539/
30 mg/kg 4 times / day multiple, oral Highest studied dose Dose: 30 mg/kg, 4 times / day Route: oral Route: multiple Dose: 30 mg/kg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17309749/	unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17309749/	Other AEs: Urine discoloration, Tongue discoloration... Other AEs: Urine discoloration (grade 1, 100%) Tongue discoloration (grade 1, 51%) Nausea (grade 1, 5.5%) Skin rash (grade 1, 2.7%) Anorexia (grade 1, 1.4%) Fatigue (grade 1, 1.4%) Sources: https://pubmed.ncbi.nlm.nih.gov/17309749/

AEs

AE	Significance	Dose	Population
Contact dermatitis		1 % single, vaginal Studied dose Dose: 1 % Route: vaginal Route: single Dose: 1 % Sources: https://pubmed.ncbi.nlm.nih.gov/6851539/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/6851539/
Anorexia	grade 1, 1.4%	30 mg/kg 4 times / day multiple, oral Highest studied dose Dose: 30 mg/kg, 4 times / day Route: oral Route: multiple Dose: 30 mg/kg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17309749/	unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17309749/
Fatigue	grade 1, 1.4%	30 mg/kg 4 times / day multiple, oral Highest studied dose Dose: 30 mg/kg, 4 times / day Route: oral Route: multiple Dose: 30 mg/kg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17309749/	unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17309749/
Urine discoloration	grade 1, 100%	30 mg/kg 4 times / day multiple, oral Highest studied dose Dose: 30 mg/kg, 4 times / day Route: oral Route: multiple Dose: 30 mg/kg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17309749/	unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17309749/
Skin rash	grade 1, 2.7%	30 mg/kg 4 times / day multiple, oral Highest studied dose Dose: 30 mg/kg, 4 times / day Route: oral Route: multiple Dose: 30 mg/kg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17309749/	unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17309749/
Nausea	grade 1, 5.5%	30 mg/kg 4 times / day multiple, oral Highest studied dose Dose: 30 mg/kg, 4 times / day Route: oral Route: multiple Dose: 30 mg/kg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17309749/	unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17309749/
Tongue discoloration	grade 1, 51%	30 mg/kg 4 times / day multiple, oral Highest studied dose Dose: 30 mg/kg, 4 times / day Route: oral Route: multiple Dose: 30 mg/kg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17309749/	unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17309749/

PubMed

Title	Date	PubMed
High-dose nifuratel for simple and mixed aerobic vaginitis: A single-center prospective open-label cohort study.	2016-10	27435791
In vitro activity of nifuratel on vaginal bacteria: could it be a good candidate for the treatment of bacterial vaginosis?	2011-05	21321147
Clinical study on the dose-effect relationship of a nifuratel-nystatin combination in the treatment of vulvo-vaginal infections.	2003	14650366
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

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 `Wed Apr 02 08:50:49 GMT 2025` Edited by `admin` on `Wed Apr 02 08:50:49 GMT 2025`
Record UNII	U60U6P08SP
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

NIFURATEL

Official Name

English

INIMUR

Preferred 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

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