U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C8H7N3O5
Molecular Weight 225.1586
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of FURAZOLIDONE

SMILES

c1cc(N(=O)=O)oc1/C(/[H])=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

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL2364041
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
FUROXONE

Approved Use

Unknown

Launch Date

-2.77171208E11
Curative
FUROXONE

Approved Use

Unknown

Launch Date

-2.77171208E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.34 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
0.89 μg × h/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.87 h
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

Doses

DosePopulationAdverse 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
Co-administed with::
amoxicillin, p.o(1000 mg, t.i.d)
Sources: Page: p.2, p.7
unhealthy, 18-79
n = 108
Health Status: unhealthy
Condition: Helicobacter pylori infections
Age Group: 18-79
Sex: M+F
Population Size: 108
Sources: Page: p.2, p.7
Disc. AE: Allergic skin reaction...
AEs leading to
discontinuation/dose reduction:
Allergic skin reaction (0.96%)
Sources: Page: p.2, p.7
100 mg 3 times / day multiple, oral
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Co-administed with::
amoxicillin, p.o(1000 mg, t.i.d)
Sources: Page: p.2, p.7
unhealthy, 21-79
n = 104
Health Status: unhealthy
Condition: Helicobacter pylori infections
Age Group: 21-79
Sex: M+F
Population Size: 104
Sources: Page: p.2, p.7
Disc. AE: Anaphylaxis...
AEs leading to
discontinuation/dose reduction:
Anaphylaxis (0.96%)
Sources: Page: p.2, p.7
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
Co-administed with::
lansoprazole, p.o(30 mg, q.d.)
tetracycline, p.o(500 mg, q.i.d.)
Sources: Page: p.113
unhealthy, 42
n = 52
Health Status: unhealthy
Condition: Helicobacter pylori infections
Age Group: 42
Sex: M+F
Population Size: 52
Sources: Page: p.113
Disc. AE: Nausea...
AEs leading to
discontinuation/dose reduction:
Nausea
Sources: Page: p.113
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
Co-administed with::
amoxicillin, p.o(1000 mg, b.i.d)
Sources: Page: p.5
unhealthy, 42.3 (± 14.31)
n = 124
Health Status: unhealthy
Condition: Helicobacter pylori infections
Age Group: 42.3 (± 14.31)
Sex: M+F
Population Size: 124
Sources: Page: p.5
Disc. AE: Headache, Vomiting...
AEs leading to
discontinuation/dose reduction:
Headache (severe)
Vomiting
Urticaria
Fever
Orthostatic dysregulation (severe)
Sources: Page: p.5
AEs

AEs

AESignificanceDosePopulation
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
Co-administed with::
amoxicillin, p.o(1000 mg, t.i.d)
Sources: Page: p.2, p.7
unhealthy, 18-79
n = 108
Health Status: unhealthy
Condition: Helicobacter pylori infections
Age Group: 18-79
Sex: M+F
Population Size: 108
Sources: Page: p.2, p.7
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
Co-administed with::
amoxicillin, p.o(1000 mg, t.i.d)
Sources: Page: p.2, p.7
unhealthy, 21-79
n = 104
Health Status: unhealthy
Condition: Helicobacter pylori infections
Age Group: 21-79
Sex: M+F
Population Size: 104
Sources: Page: p.2, p.7
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
Co-administed with::
lansoprazole, p.o(30 mg, q.d.)
tetracycline, p.o(500 mg, q.i.d.)
Sources: Page: p.113
unhealthy, 42
n = 52
Health Status: unhealthy
Condition: Helicobacter pylori infections
Age Group: 42
Sex: M+F
Population Size: 52
Sources: Page: p.113
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
Co-administed with::
amoxicillin, p.o(1000 mg, b.i.d)
Sources: Page: p.5
unhealthy, 42.3 (± 14.31)
n = 124
Health Status: unhealthy
Condition: Helicobacter pylori infections
Age Group: 42.3 (± 14.31)
Sex: M+F
Population Size: 124
Sources: Page: p.5
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
Co-administed with::
amoxicillin, p.o(1000 mg, b.i.d)
Sources: Page: p.5
unhealthy, 42.3 (± 14.31)
n = 124
Health Status: unhealthy
Condition: Helicobacter pylori infections
Age Group: 42.3 (± 14.31)
Sex: M+F
Population Size: 124
Sources: Page: p.5
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
Co-administed with::
amoxicillin, p.o(1000 mg, b.i.d)
Sources: Page: p.5
unhealthy, 42.3 (± 14.31)
n = 124
Health Status: unhealthy
Condition: Helicobacter pylori infections
Age Group: 42.3 (± 14.31)
Sex: M+F
Population Size: 124
Sources: Page: p.5
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
Co-administed with::
amoxicillin, p.o(1000 mg, b.i.d)
Sources: Page: p.5
unhealthy, 42.3 (± 14.31)
n = 124
Health Status: unhealthy
Condition: Helicobacter pylori infections
Age Group: 42.3 (± 14.31)
Sex: M+F
Population Size: 124
Sources: Page: p.5
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
Co-administed with::
amoxicillin, p.o(1000 mg, b.i.d)
Sources: Page: p.5
unhealthy, 42.3 (± 14.31)
n = 124
Health Status: unhealthy
Condition: Helicobacter pylori infections
Age Group: 42.3 (± 14.31)
Sex: M+F
Population Size: 124
Sources: Page: p.5
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as perpetrator​

PubMed

PubMed

TitleDatePubMed
Nitroheterocyclic antimicrobial agents. I. Nitrothiazolecarboxaldehyde derivatives.
1969 May
[Methods of treatment of puerperal endometritis in cows].
1975
[Peripheral neuropathy due to furazolidone].
1975 Aug 1
Cholestatic hepatitis after administration of furan derivatives.
1975 May
Some pharmacological and toxicological properties of furazolidone.
1983 Jan
Monoamine oxidase inhibition and furazolidone-induced cardiomyopathy in turkey poults.
1983 Sep
Cardiomyopathy in turkeys.
1984
Reduced lipid peroxidation in dilated hearts of cardiomyopathic turkeys.
1988 Nov
Furazolidone and nitrofurantoin in the treatment of experimental Pneumocystis carinii pneumonia.
1991 Jan
Generation of furazolidone radical anion and its inhibition by glutathione.
1992 Aug
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.
1992 Sep
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 Jan
[The effect of nitrofurazone and furazolidone on induction of cytochrome P-450 in the CYPIA test].
1995
Experimental furazolidone toxicosis in broiler chicks: effect of dosage, duration and age upon clinical signs and some blood parameters.
1995
Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro.
1996 Dec
Furazolidone-induced mood disorder during the treatment of refractory giardiasis in a patient with AIDS.
1998 Apr
Antituberculosis activity of certain antifungal and antihelmintic drugs.
1999
One-week regimens containing ranitidine bismuth citrate, furazolidone and either amoxicillin or tetracycline effectively eradicate Helicobacter pylori: a multicentre, randomized, double-blind study.
2001 Dec
Effects of furazolidone, PCB77, PCB126, Aroclor 1248, paraquat and p,p'-DDE on transketolase activity in embryonal chicken brain.
2002 May 1
Analysis of matrix-bound nitrofuran residues in worldwide-originated honeys by isotope dilution high-performance liquid chromatography-tandem mass spectrometry.
2004 Aug 25
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Nitroreductive metabolic activation of some carcinogenic nitro heterocyclic food contaminants in rat mammary tissue cellular fractions.
2009 Jan
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 Apr
Involvement of the p38 MAPK signaling pathway in S-phase cell-cycle arrest induced by Furazolidone in human hepatoma G2 cells.
2013 Dec
The Effect of GADD45a on Furazolidone-Induced S-Phase Cell-Cycle Arrest in Human Hepatoma G2 Cells.
2015 Oct
P21(Waf1/Cip1) plays a critical role in furazolidone-induced apoptosis in HepG2 cells through influencing the caspase-3 activation and ROS generation.
2016 Feb

Sample Use Guides

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).
Name Type Language
FURAZOLIDONE
GREEN BOOK   HSDB   INN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
FURAZOLIDONE [USP]
Common Name English
FURAZOLIDONE [USP-RS]
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
FUROXONE
Brand Name English
FURAZOLIDONE [WHO-DD]
Common Name English
FURAZOLIDONE [USP MONOGRAPH]
Common Name English
FURAZOLIDONE [IARC]
Common Name English
FURAZOLIDONE [MART.]
Common Name English
NSC-6469
Code English
Classification Tree Code System Code
IARC Furazolidone
CFR 21 CFR 524.1005
Created by admin on Fri Jun 25 20:56:53 UTC 2021 , Edited by admin on Fri Jun 25 20:56:53 UTC 2021
WHO-ATC G01AX06
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WHO-VATC QG01AX06
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WHO-VATC QJ01XE90
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NCI_THESAURUS C254
Created by admin on Fri Jun 25 20:56:53 UTC 2021 , Edited by admin on Fri Jun 25 20:56:53 UTC 2021
CFR 21 CFR 530.41
Created by admin on Fri Jun 25 20:56:53 UTC 2021 , Edited by admin on Fri Jun 25 20:56:53 UTC 2021
Code System Code Type Description
PUBCHEM
5323714
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PRIMARY
MERCK INDEX
M5600
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PRIMARY Merck Index
EPA CompTox
67-45-8
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PRIMARY
EVMPD
SUB07834MIG
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PRIMARY
INN
273
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PRIMARY
ChEMBL
CHEMBL1103
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PRIMARY
NCI_THESAURUS
C65783
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PRIMARY
WIKIPEDIA
Furazolidone
Created by admin on Fri Jun 25 20:56:53 UTC 2021 , Edited by admin on Fri Jun 25 20:56:53 UTC 2021
PRIMARY
DRUG CENTRAL
1257
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PRIMARY
DRUG BANK
DB00614
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PRIMARY
FDA UNII
5J9CPU3RE0
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PRIMARY
MESH
D005664
Created by admin on Fri Jun 25 20:56:53 UTC 2021 , Edited by admin on Fri Jun 25 20:56:53 UTC 2021
PRIMARY
HSDB
7036
Created by admin on Fri Jun 25 20:56:53 UTC 2021 , Edited by admin on Fri Jun 25 20:56:53 UTC 2021
PRIMARY
RXCUI
4601
Created by admin on Fri Jun 25 20:56:53 UTC 2021 , Edited by admin on Fri Jun 25 20:56:53 UTC 2021
PRIMARY RxNorm
ECHA (EC/EINECS)
200-653-3
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PRIMARY
CAS
67-45-8
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PRIMARY
USP_CATALOG
1286800
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PRIMARY USP-RS