FURAZOLIDONE

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 278 Target ID: CHEMBL2364041 Sources: http://www.ncbi.nlm.nih.gov/pubmed/535918	Crosslinking Agent 81

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial or protozoal diarrhea 1 Sources: http://www.ncbi.nlm.nih.gov/pubmed/3514312	Curative		Approved 8429	FUROXONE Approved Use Unknown Launch Date 1961
Bacterial or protozoal enteritis 1 Sources: http://www.ncbi.nlm.nih.gov/pubmed/3514312	Curative		Approved 8429	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 Co-administed with:: amoxicillin, p.o(1000 mg, t.i.d) Sources: https://pubmed.ncbi.nlm.nih.gov/23376004 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: https://pubmed.ncbi.nlm.nih.gov/23376004 Page: p.2, p.7	Disc. AE: Allergic skin reaction... AEs leading to discontinuation/dose reduction: Allergic skin reaction (0.96%) Sources: https://pubmed.ncbi.nlm.nih.gov/23376004 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: https://pubmed.ncbi.nlm.nih.gov/23376004 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: https://pubmed.ncbi.nlm.nih.gov/23376004 Page: p.2, p.7	Disc. AE: Anaphylaxis... AEs leading to discontinuation/dose reduction: Anaphylaxis (0.96%) Sources: https://pubmed.ncbi.nlm.nih.gov/23376004 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: https://pubmed.ncbi.nlm.nih.gov/16127567 Page: p.113	unhealthy, 42 n = 52 Health Status: unhealthy Condition: Helicobacter pylori infections Age Group: 42 Sex: M+F Population Size: 52 Sources: https://pubmed.ncbi.nlm.nih.gov/16127567 Page: p.113	Disc. AE: Nausea... AEs leading to discontinuation/dose reduction: Nausea Sources: https://pubmed.ncbi.nlm.nih.gov/16127567 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: https://pubmed.ncbi.nlm.nih.gov/26157713 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: https://pubmed.ncbi.nlm.nih.gov/26157713 Page: p.5	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 Page: p.5

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 Co-administed with:: amoxicillin, p.o(1000 mg, t.i.d) Sources: https://pubmed.ncbi.nlm.nih.gov/23376004 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: https://pubmed.ncbi.nlm.nih.gov/23376004 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: https://pubmed.ncbi.nlm.nih.gov/23376004 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: https://pubmed.ncbi.nlm.nih.gov/23376004 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: https://pubmed.ncbi.nlm.nih.gov/16127567 Page: p.113	unhealthy, 42 n = 52 Health Status: unhealthy Condition: Helicobacter pylori infections Age Group: 42 Sex: M+F Population Size: 52 Sources: https://pubmed.ncbi.nlm.nih.gov/16127567 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: https://pubmed.ncbi.nlm.nih.gov/26157713 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: https://pubmed.ncbi.nlm.nih.gov/26157713 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: https://pubmed.ncbi.nlm.nih.gov/26157713 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: https://pubmed.ncbi.nlm.nih.gov/26157713 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: https://pubmed.ncbi.nlm.nih.gov/26157713 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: https://pubmed.ncbi.nlm.nih.gov/26157713 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: https://pubmed.ncbi.nlm.nih.gov/26157713 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: https://pubmed.ncbi.nlm.nih.gov/26157713 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: https://pubmed.ncbi.nlm.nih.gov/26157713 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: https://pubmed.ncbi.nlm.nih.gov/26157713 Page: p.5

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
UGT1A8 36 UGT1A10 32		CYP1A1 108

Drug as perpetrator

Target	Modality	Activity
UGT1A10 41	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25834030/	weak
UGT1A8 48	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25834030/	weak
CYP1A1 218	inducer 1573 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
MolPort	MolPort-006-110-177	https://www.molport.com/shop/molecule-link/MolPort-006-110-177
ZINC	ZINC000250090469	http://zinc15.docking.org/substances/ZINC000250090469
eMolecules	36495922	https://www.emolecules.com/cgi-bin/more?vid=36495922

PubMed

Title	Date	PubMed
Nitroheterocyclic antimicrobial agents. I. Nitrothiazolecarboxaldehyde derivatives.	1969 May	4892243
[Methods of treatment of puerperal endometritis in cows].	1975	1108409
[Peripheral neuropathy due to furazolidone].	1975 Aug 1	169188
Cholestatic hepatitis after administration of furan derivatives.	1975 May	150825
Some pharmacological and toxicological properties of furazolidone.	1983 Jan	6346666
Monoamine oxidase inhibition and furazolidone-induced cardiomyopathy in turkey poults.	1983 Sep	6634611
Cardiomyopathy in turkeys.	1984	6143637
Reduced lipid peroxidation in dilated hearts of cardiomyopathic turkeys.	1988 Nov	3256424
Furazolidone and nitrofurantoin in the treatment of experimental Pneumocystis carinii pneumonia.	1991 Jan	2014971
Generation of furazolidone radical anion and its inhibition by glutathione.	1992 Aug	1326300
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.	1992 Sep	1416885
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	8427473
[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
Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro.	1996 Dec	9039272
Furazolidone-induced mood disorder during the treatment of refractory giardiasis in a patient with AIDS.	1998 Apr	9564507
Antituberculosis activity of certain antifungal and antihelmintic drugs.	1999	10707260
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	11736729
Effects of furazolidone, PCB77, PCB126, Aroclor 1248, paraquat and p,p'-DDE on transketolase activity in embryonal chicken brain.	2002 May 1	11960673
Analysis of matrix-bound nitrofuran residues in worldwide-originated honeys by isotope dilution high-performance liquid chromatography-tandem mass spectrometry.	2004 Aug 25	15315362
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Nitroreductive metabolic activation of some carcinogenic nitro heterocyclic food contaminants in rat mammary tissue cellular fractions.	2009 Jan	19017535
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	22258563
Involvement of the p38 MAPK signaling pathway in S-phase cell-cycle arrest induced by Furazolidone in human hepatoma G2 cells.	2013 Dec	23112108
The Effect of GADD45a on Furazolidone-Induced S-Phase Cell-Cycle Arrest in Human Hepatoma G2 Cells.	2015 Oct	26095818
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	26687534

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 `Fri Dec 15 16:13:02 GMT 2023` Edited by `admin` on `Fri Dec 15 16:13:02 GMT 2023`
Record UNII	5J9CPU3RE0
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FURAZOLIDONE

Official 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

FUROXONE

Brand 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