A nitrofuran derivative with antiprotozoal and antibacterial activity. Furazolidone binds bacterial DNA which leads to the gradual inhibition of monoamine oxidase. (From Martindale, The Extra Pharmacopoeia, 30th ed, p514)

Structure

Similar Structures

Synonyms

3-(5'-Nitrofurfuralamino)-2-oxazolidone
3-[(5-Nitrofurfurylidene)amino]-2-oxazolidinone
3-[(5-Nitrofurfurylidene)amino]-2-oxazolidone
3-[(5-Nitrofurylidene)amino]-2-oxazolidone
3-{[(5-nitro-2-furanyl)methylene]amino}-2-oxazolidinone
5-Nitro-N-(2-oxo-3-oxazolidinyl)-2-furanmethanimine
Furazolidona
Furazolidonum
FZL
N-(5-Nitro-2-furfurylidene)-3-amino-2-oxazolidone
N-(5-Nitro-2-furfurylidene)-3-aminooxazolidine-2-one
Nitrofurazolidone
Nitrofurazolidonum

External IDs

USAF EA-1

International/Other Brands

Dependal-M (GlaxoSmithKline) / Furoxone (Roberts Laboratories)

Categories

UNII

5J9CPU3RE0

CAS number

67-45-8

Weight

Average: 225.1583
Monoisotopic: 225.038570349

Chemical Formula

C₈H₇N₃O₅

InChI Key

PLHJDBGFXBMTGZ-UHFFFAOYSA-N

InChI

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

IUPAC Name

3-{[(5-nitrofuran-2-yl)methylidene]amino}-1,3-oxazolidin-2-one

SMILES

[H]C(=NN1CCOC1=O)C1=CC=C(O1)[N+]([O-])=O

Pharmacology

Indication

For the specific and symptomatic treatment of bacterial or protozoal diarrhea and enteritis caused by susceptible organisms.

Pharmacodynamics

Furoxone has a broad antibacterial spectrum covering the majority of gastrointestinal tract pathogens including E. coli, staphylococci, Salmonella, Shigella, Proteus, Aerobacter aerogenes, Vibrio cholerae and Giardia lamblia. Its bactericidal activity is based upon its interference with DNA replication and protein production; this antimicrobial action minimizes the development of resistant organisms.

Mechanism of action

Furazolidone and its related free radical products are believed to bind DNA and induce cross-links. Bacterial DNA is particularly susceptible to this drug leading to high levels of mutations (transitions and transversions) in the bacterial chromosome.

Target	Actions	Organism
ADNA	cross-linking/alkylation	Humans

Absorption

Radiolabeled drug studies indicate that furazolidone is well absorbed following oral administration

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Furazolidone is rapidly and extensively metabolized; the primary metabolic pathway identified begins with nitro-reduction to the aminofuran derivative. Two major metabolites are produced: 3-amino-2-oxazolidone (AOZ) or beta-hydroxyethylhydrazine (HEH). AOZ is responsible for monoamine oxidase inhibition. Detoxification and elimination of the drug is done primarily by conjugation with glutathione.

Route of elimination

Not Available

Half life

10 minutes

Clearance

Not Available

Toxicity

Reactions to Furoxone have been reported including a fall in blood pressure, urticaria, fever, arthralgia, and a vesicular morbilliform rash. Other adverse effects can include a brown discoloration of the urine; hemolysis can occur in G6PDH-deficient patients. The drug has a monoamine oxidase (MAO) inhibitory effect and should never be given concurrently to individuals already taking MAO inhibitors.

Affected organisms

Microbes (bacteria, parasites)

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
Unlock Additional Data
(R)-warfarin	The risk or severity of bleeding and hemorrhage can be increased when Furazolidone is combined with (R)-warfarin.
(S)-Warfarin	The risk or severity of bleeding and hemorrhage can be increased when Furazolidone is combined with (S)-Warfarin.
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid	The risk or severity of hypertension can be increased when Furazolidone is combined with 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid.
1-benzylimidazole	The risk or severity of hypertension can be increased when Furazolidone is combined with 1-benzylimidazole.
2,4-thiazolidinedione	Furazolidone may increase the hypoglycemic activities of 2,4-thiazolidinedione.
2,5-Dimethoxy-4-ethylamphetamine	Furazolidone may increase the hypertensive activities of 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamine	Furazolidone may increase the hypertensive activities of 2,5-Dimethoxy-4-ethylthioamphetamine.
4-Bromo-2,5-dimethoxyamphetamine	Furazolidone may increase the hypertensive activities of 4-Bromo-2,5-dimethoxyamphetamine.
4-hydroxycoumarin	The risk or severity of bleeding and hemorrhage can be increased when Furazolidone is combined with 4-hydroxycoumarin.
4-Methoxyamphetamine	Furazolidone may increase the hypertensive activities of 4-Methoxyamphetamine.

Additional Data Available

Extended Description

Extended description of the mechanism of action and particular properties of each drug interaction.

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Severity

A severity rating for each drug interaction, from minor to major.

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Evidence Level

A rating for the strength of the evidence supporting each drug interaction.

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Action

An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions

Not Available

References

Synthesis Reference

Drake, G.D., Gever, G. and Hayes, K.J.; U.S. Patent 2,759,931; August 21, 1956; assigned to The Norwich Pharmacal Company. Gever, G. and O'Keefe, C.J.; U.S. Patent 2,927,l IO; March 1, 1960; assigned to The Norwich Pharmacal Company.

US2742462

General References

Not Available

External Links

Human Metabolome Database: HMDB0014752
KEGG Drug: D00830
KEGG Compound: C07999
PubChem Compound: 3435
PubChem Substance: 46507291
ChemSpider: 3317
ChEBI: 5195
ChEMBL: CHEMBL1374738
Therapeutic Targets Database: DAP000993
PharmGKB: PA164746760
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Furazolidone

ATC Codes

G01AX06 — Furazolidone

MSDS

Download (74.1 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Completed	Treatment	Bacterial Infection Due to Helicobacter Pylori (H. Pylori) / Gastric Ulcer / Gastritis / Gastritis Chronic / Malignant Neoplasm of Stomach	1
4	Completed	Treatment	Functional Dyspepsia / Scarred Peptic Ulcer	1
4	Not Yet Recruiting	Treatment	Antimicrobial Susceptibility Testing / Bacterial Infection Due to Helicobacter Pylori (H. Pylori)	1
4	Not Yet Recruiting	Treatment	Antimicrobial Susceptibility Testing / Triple Therapy	1
4	Not Yet Recruiting	Treatment	Bacterial Infection Due to Helicobacter Pylori (H. Pylori)	5
4	Recruiting	Treatment	Antimicrobial Susceptibility Testing / Bacterial Infection Due to Helicobacter Pylori (H. Pylori)	1
4	Recruiting	Treatment	Bacterial Infection Due to Helicobacter Pylori (H. Pylori)	1
4	Recruiting	Treatment	Duodenal Ulcer Due to Helicobacter Pylori	1
4	Recruiting	Treatment	Helicobacter Pylori	1
Not Available	Completed	Treatment	Treatment of Helicobacter Pylori	1

Pharmacoeconomics

Manufacturers

Shire development inc

Packagers

Professional Co.

Dosage forms

Not Available

Prices

Unit description	Cost	Unit
Furazolidone powder	2.04USD	g

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	254-256	Drake, G.D., Gever, G. and Hayes, K.J.; U.S. Patent 2,759,931; August 21, 1956; assigned to The Norwich Pharmacal Company. Gever, G. and O'Keefe, C.J.; U.S. Patent 2,927,l IO; March 1, 1960; assigned to The Norwich Pharmacal Company
water solubility	40 mg/L (at 25 °C)	MERCK INDEX (1996); pH 6
logP	-0.04	DEBNATH,AK ET AL. (1991)

Predicted Properties

Property	Value	Source
Water Solubility	0.364 mg/mL	ALOGPS
logP	0.15	ALOGPS
logP	0.87	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	98.18 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	50.08 m³·mol^-1	ChemAxon
Polarizability	19.78 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	0.9038
Blood Brain Barrier	+	0.9117
Caco-2 permeable	-	0.5736
P-glycoprotein substrate	Non-substrate	0.7829
P-glycoprotein inhibitor I	Non-inhibitor	0.7761
P-glycoprotein inhibitor II	Non-inhibitor	0.9597
Renal organic cation transporter	Non-inhibitor	0.8351
CYP450 2C9 substrate	Non-substrate	0.8117
CYP450 2D6 substrate	Non-substrate	0.8415
CYP450 3A4 substrate	Substrate	0.5984
CYP450 1A2 substrate	Inhibitor	0.9107
CYP450 2C9 inhibitor	Non-inhibitor	0.907
CYP450 2D6 inhibitor	Non-inhibitor	0.9134
CYP450 2C19 inhibitor	Non-inhibitor	0.9026
CYP450 3A4 inhibitor	Non-inhibitor	0.928
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.8828
Ames test	AMES toxic	0.9108
Carcinogenicity	Non-carcinogens	0.9097
Biodegradation	Ready biodegradable	0.8978
Rat acute toxicity	2.1639 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.7889
hERG inhibition (predictor II)	Non-inhibitor	0.9057

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Taxonomy

Description: This compound belongs to the class of organic compounds known as nitrofurans. These are compounds containing a furan ring which bears a nitro group.
Kingdom: Organic compounds
Super Class: Organoheterocyclic compounds
Class: Furans
Sub Class: Nitrofurans
Direct Parent: Nitrofurans
Alternative Parents: Nitroaromatic compounds / Oxazolidinones / Heteroaromatic compounds / Organic carbonic acids and derivatives / Propargyl-type 1,3-dipolar organic compounds / Oxacyclic compounds / Organic oxoazanium compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds
show 3 more
Substituents: Nitroaromatic compound / 2-nitrofuran / Oxazolidinone / Oxazolidine / Heteroaromatic compound / C-nitro compound / Carbonic acid derivative / Organic nitro compound / Organic oxoazanium / Allyl-type 1,3-dipolar organic compound
show 13 more
Molecular Framework: Aromatic heteromonocyclic compounds
External Descriptors: oxazolidines, nitrofuran antibiotic (CHEBI:5195)

Targets

Details1. DNA

Kind

Nucleotide

Organism

Humans

Pharmacological action

Yes

Actions

Cross-linking/alkylation

DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Meng J, Mangat SS, Grudzinski IP, Law FC: Evidence of 14C-furazolidone metabolite binding to the hepatic DNA of trout. Drug Metabol Drug Interact. 1998;14(4):209-19. [PubMed:10694929]

Enzymes

Details1. Amine oxidase [flavin-containing] B

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Primary amine oxidase activity
Specific Function: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
Gene Name: MAOB
Uniprot ID: P27338
Uniprot Name: Amine oxidase [flavin-containing] B
Molecular Weight: 58762.475 Da

References

Timperio AM, Kuiper HA, Zolla L: Identification of a furazolidone metabolite responsible for the inhibition of amino oxidases. Xenobiotica. 2003 Feb;33(2):153-67. [PubMed:12623758]
Ali BH: Pharmacological, therapeutic and toxicological properties of furazolidone: some recent research. Vet Res Commun. 1999 Oct;23(6):343-60. [PubMed:10543364]
Hoogenboom LA, Tomassini O, Oorsprong MB, Kuiper HA: Use of pig hepatocytes to study the inhibition of monoamine oxidase by furazolidone. Food Chem Toxicol. 1991 Mar;29(3):185-91. [PubMed:2032659]

Details2. Amine oxidase [flavin-containing] A

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Serotonin binding
Specific Function: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
Gene Name: MAOA
Uniprot ID: P21397
Uniprot Name: Amine oxidase [flavin-containing] A
Molecular Weight: 59681.27 Da

References

Timperio AM, Kuiper HA, Zolla L: Identification of a furazolidone metabolite responsible for the inhibition of amino oxidases. Xenobiotica. 2003 Feb;33(2):153-67. [PubMed:12623758]
Ali BH: Pharmacological, therapeutic and toxicological properties of furazolidone: some recent research. Vet Res Commun. 1999 Oct;23(6):343-60. [PubMed:10543364]
Hoogenboom LA, Tomassini O, Oorsprong MB, Kuiper HA: Use of pig hepatocytes to study the inhibition of monoamine oxidase by furazolidone. Food Chem Toxicol. 1991 Mar;29(3):185-91. [PubMed:2032659]

Drug created on June 13, 2005 07:24 / Updated on December 02, 2019 05:29

Furazolidone

Identification

Structure for Furazolidone (DB00614)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

References

Enzymes

References

References