FURAZOLIDONE

US Previously Marketed

First approved in 1957

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H7N3O5
Molecular Weight	225.1583
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[O-][N+](=O)C1=CC=C(O1)\C=N\N2CCOC2=O

InChI

InChIKey=PLHJDBGFXBMTGZ-WEVVVXLNSA-N

InChI=1S/C8H7N3O5/c12-8-10(3-4-15-8)9-5-6-1-2-7(16-6)11(13)14/h1-2,5H,3-4H2/b9-5+

HIDE SMILES / InChI

Molecular Formula	C8H7N3O5
Molecular Weight	225.1583
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Curator's Comment: http://www.ncbi.nlm.nih.gov/pubmed/8030368

Furazolidone is a nitrofuran derivarive with broad antibacterial, antiprotazoal properties. It was used for the treatment of bacterial or protozoal enteritis and diarrhea, but now the drug is no longer prescibed in the US. The mechanism of furazolidone action is supposed to be mediated by its binding to bacterial DNA.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA 282 Target ID: CHEMBL2364041 Sources: http://www.ncbi.nlm.nih.gov/pubmed/535918	Crosslinking Agent 83

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial or protozoal diarrhea 1 Sources: http://www.ncbi.nlm.nih.gov/pubmed/3514312	Curative		Approved 8583	FUROXONE Approved Use Unknown Launch Date 1961
Bacterial or protozoal enteritis 1 Sources: http://www.ncbi.nlm.nih.gov/pubmed/3514312	Curative		Approved 8583	FUROXONE Approved Use Unknown Launch Date 1961

C_max

Value	Dose	Co-administered	Analyte	Population
0.34 μg/mL EXPERIMENT https://bpspubs.onlinelibrary.wiley.com/doi/full/10.1046/j.0306-5251.2001.01435.x	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		FURAZOLIDONE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
0.89 μg × h/mL EXPERIMENT https://bpspubs.onlinelibrary.wiley.com/doi/full/10.1046/j.0306-5251.2001.01435.x	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		FURAZOLIDONE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
4.87 h EXPERIMENT https://bpspubs.onlinelibrary.wiley.com/doi/full/10.1046/j.0306-5251.2001.01435.x	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		FURAZOLIDONE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Doses

Dose	Population	Adverse events
100 mg 3 times / day multiple, oral Recommended Dose: 100 mg, 3 times / day Route: oral Route: multiple Dose: 100 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/23376004	unhealthy, 18-79 Health Status: unhealthy Age Group: 18-79 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/23376004	Disc. AE: Allergic skin reaction... AEs leading to discontinuation/dose reduction: Allergic skin reaction (0.96%) Sources: https://pubmed.ncbi.nlm.nih.gov/23376004
100 mg 3 times / day multiple, oral Recommended Dose: 100 mg, 3 times / day Route: oral Route: multiple Dose: 100 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/23376004	unhealthy, 21-79 Health Status: unhealthy Age Group: 21-79 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/23376004	Disc. AE: Anaphylaxis... AEs leading to discontinuation/dose reduction: Anaphylaxis (0.96%) Sources: https://pubmed.ncbi.nlm.nih.gov/23376004
200 mg 3 times / day multiple, oral Highest studied dose Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16127567	unhealthy, 42 Health Status: unhealthy Age Group: 42 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/16127567	Disc. AE: Nausea... AEs leading to discontinuation/dose reduction: Nausea Sources: https://pubmed.ncbi.nlm.nih.gov/16127567
200 mg 3 times / day multiple, oral Highest studied dose Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/26157713	unhealthy, 42.3 (± 14.31) Health Status: unhealthy Age Group: 42.3 (± 14.31) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/26157713	Disc. AE: Headache, Vomiting... AEs leading to discontinuation/dose reduction: Headache (severe) Vomiting Urticaria Fever Orthostatic dysregulation (severe) Sources: https://pubmed.ncbi.nlm.nih.gov/26157713

AEs

AE	Significance	Dose	Population
Allergic skin reaction	0.96% Disc. AE	100 mg 3 times / day multiple, oral Recommended Dose: 100 mg, 3 times / day Route: oral Route: multiple Dose: 100 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/23376004	unhealthy, 18-79 Health Status: unhealthy Age Group: 18-79 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/23376004
Anaphylaxis	0.96% Disc. AE	100 mg 3 times / day multiple, oral Recommended Dose: 100 mg, 3 times / day Route: oral Route: multiple Dose: 100 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/23376004	unhealthy, 21-79 Health Status: unhealthy Age Group: 21-79 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/23376004
Nausea	Disc. AE	200 mg 3 times / day multiple, oral Highest studied dose Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16127567	unhealthy, 42 Health Status: unhealthy Age Group: 42 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/16127567
Fever	Disc. AE	200 mg 3 times / day multiple, oral Highest studied dose Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/26157713	unhealthy, 42.3 (± 14.31) Health Status: unhealthy Age Group: 42.3 (± 14.31) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/26157713
Urticaria	Disc. AE	200 mg 3 times / day multiple, oral Highest studied dose Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/26157713	unhealthy, 42.3 (± 14.31) Health Status: unhealthy Age Group: 42.3 (± 14.31) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/26157713
Vomiting	Disc. AE	200 mg 3 times / day multiple, oral Highest studied dose Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/26157713	unhealthy, 42.3 (± 14.31) Health Status: unhealthy Age Group: 42.3 (± 14.31) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/26157713
Headache	severe Disc. AE	200 mg 3 times / day multiple, oral Highest studied dose Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/26157713	unhealthy, 42.3 (± 14.31) Health Status: unhealthy Age Group: 42.3 (± 14.31) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/26157713
Orthostatic dysregulation	severe Disc. AE	200 mg 3 times / day multiple, oral Highest studied dose Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/26157713	unhealthy, 42.3 (± 14.31) Health Status: unhealthy Age Group: 42.3 (± 14.31) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/26157713

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
UGT1A8 37 UGT1A10 37		CYP1A1 151

Drug as perpetrator

Target	Modality	Activity
UGT1A10 46	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25834030/	weak
UGT1A8 49	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25834030/	weak
CYP1A1 272	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/18388420/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:5195	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:5195
eMolecules	36495922	https://www.emolecules.com/cgi-bin/more?vid=36495922
MolPort	MolPort-006-110-177	https://www.molport.com/shop/molecule-link/MolPort-006-110-177
ZINC	ZINC000250090469	http://zinc15.docking.org/substances/ZINC000250090469

PubMed

Title	Date	PubMed
P21(Waf1/Cip1) plays a critical role in furazolidone-induced apoptosis in HepG2 cells through influencing the caspase-3 activation and ROS generation.	2016-02	26687534
The Effect of GADD45a on Furazolidone-Induced S-Phase Cell-Cycle Arrest in Human Hepatoma G2 Cells.	2015-10	26095818
Involvement of the p38 MAPK signaling pathway in S-phase cell-cycle arrest induced by Furazolidone in human hepatoma G2 cells.	2013-12	23112108
Characterization of primary human hepatocytes, HepG2 cells, and HepaRG cells at the mRNA level and CYP activity in response to inducers and their predictivity for the detection of human hepatotoxins.	2012-04	22258563
Nitroreductive metabolic activation of some carcinogenic nitro heterocyclic food contaminants in rat mammary tissue cellular fractions.	2009-01	19017535
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005-06	15962942
Analysis of matrix-bound nitrofuran residues in worldwide-originated honeys by isotope dilution high-performance liquid chromatography-tandem mass spectrometry.	2004-08-25	15315362
Effects of furazolidone, PCB77, PCB126, Aroclor 1248, paraquat and p,p'-DDE on transketolase activity in embryonal chicken brain.	2002-05-01	11960673
One-week regimens containing ranitidine bismuth citrate, furazolidone and either amoxicillin or tetracycline effectively eradicate Helicobacter pylori: a multicentre, randomized, double-blind study.	2001-12	11736729
Antituberculosis activity of certain antifungal and antihelmintic drugs.	1999	10707260
Furazolidone-induced mood disorder during the treatment of refractory giardiasis in a patient with AIDS.	1998-04	9564507
Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro.	1996-12	9039272
[The effect of nitrofurazone and furazolidone on induction of cytochrome P-450 in the CYPIA test].	1995	8619122
Experimental furazolidone toxicosis in broiler chicks: effect of dosage, duration and age upon clinical signs and some blood parameters.	1995	7491876
Clinical pathologic profiles of dogs and turkeys with congestive heart failure, either noninduced or induced by rapid ventricular pacing, and turkeys with furazolidone toxicosis.	1993-01	8427473
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.	1992-09	1416885
Generation of furazolidone radical anion and its inhibition by glutathione.	1992-08	1326300
Furazolidone and nitrofurantoin in the treatment of experimental Pneumocystis carinii pneumonia.	1991-01	2014971
Reduced lipid peroxidation in dilated hearts of cardiomyopathic turkeys.	1988-11	3256424
Cardiomyopathy in turkeys.	1984	6143637
Monoamine oxidase inhibition and furazolidone-induced cardiomyopathy in turkey poults.	1983-09	6634611
Some pharmacological and toxicological properties of furazolidone.	1983-01	6346666
[Peripheral neuropathy due to furazolidone].	1975-08-01	169188
Cholestatic hepatitis after administration of furan derivatives.	1975-05	150825
[Methods of treatment of puerperal endometritis in cows].	1975	1108409
Nitroheterocyclic antimicrobial agents. I. Nitrothiazolecarboxaldehyde derivatives.	1969-05	4892243

Sample Use Guides

In Vivo Use Guide

One 100-mg tablet four times daily (adults), 25 to 50 mg four times daily (children).

Route of Administration: Oral

In Vitro Use Guide

The in vitro susceptibilities of 50 strains of Salmonella spp., 80 strains of Shigella spp., and 50 enterotoxigenic Escherichia coli, 14 Yersinia enterocolitica, 6 Aeromonas hydrophila, 4 Plesiomonas shigelloides, 9 Vibrio parahaemolyticus, and 30 Campylobacter jejuni strains that were recently isolated from worldwide sources were determined for furazolidone. MICs values were about 0.5-2 ug/ml (Salmonella spp.), 0.5-4 ug/ml (Shigella spp.), 16-128 ug/ml (Y. enterocolitica), 0.5-1 ug/ml (A. hydrophila, V. parahaemolyticus),0.5 ug/ml (P. shigelloides, C. jejuni).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:22:11 GMT 2025` Edited by `admin` on `Mon Mar 31 18:22:11 GMT 2025`
Record UNII	5J9CPU3RE0
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FURAZOLIDONE

Official Name

English

FUROXONE

Preferred Name

English

FURAZOLIDONE [USP-RS]

Common Name

English

Furazolidone [WHO-DD]

Common Name

English

NIFURAZOLIDONE

Common Name

English

FURAZOLIDONE [HSDB]

Common Name

English

FURAZOLIDONE [ORANGE BOOK]

Common Name

English

FURAZOLIDONE [GREEN BOOK]

Common Name

English

3-[(5-Nitrofurfurylidene)amino]-2-oxazolidinone

Systematic Name

English

FURAZOLIDONE [MI]

Common Name

English

furazolidone [INN]

Common Name

English

2-OXAZOLIDINONE, 3-(((5-NITRO-2-FURANYL)METHYLENE)AMINO)-

Systematic Name

English

FURAZOLIDONE [USP MONOGRAPH]

Common Name

English

FURAZOLIDONE [IARC]

Common Name

English

FURAZOLIDONE [USP IMPURITY]

Common Name

English

FURAZOLIDONE [MART.]

Common Name

English

NSC-6469

Code

English

Classification Tree Code System Code

IARC

Furazolidone

CFR

21 CFR 524.1005