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QuickView for Furazolidone (compound)

Summary
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PubChem

PubChem Compound 3435

PubChem Compound 3435

Name:	Furazolidone
PubChem Compound ID:	3435
Description:	A nitrofuran derivative with antiprotozoal and antibacterial activity. Furazolidone acts by gradual inhibition of monoamine oxidase. (From Martindale, The Extra Pharmacopoeia, 30th ed, p514)
Molecular formula:	C₈H₇N₃O₅
Molecular weight:	225.158 g/mol
Synonyms:	2-Oxazolidinone, 3-[[ (5-nitro-2-furanyl)methylene]amino]-; NF 180; Ortazol; Furozolidine; 67-45-8; Tricoron; DivK1c_000085; Spectrum3_000436; NSC6469; Furidon. show more » 2-Oxazolidinone, 3-[[ (5-nitro-2-furanyl)methylene]amino]-; NF 180; Ortazol; Furozolidine; 67-45-8; Tricoron; DivK1c_000085; Spectrum3_000436; NSC6469; Furidon; Neftin; Spectrum4_000559; Giarlam; Prestwick0_000808; Prestwick1_000808; Topazone; Tikofuran; Furoxal; component of Topazone; Spectrum_001098; Furaxone; Spectrum2_001015; SMR000058228; component of Tricofuron; KBio2_001578; Furazon; Medaron; Furaxon; Furazol; KBio3_001272; Prestwick_1067; SPBio_002596; Furoxone swine mix; KBioSS_001578; KBioGR_001257; 2-Oxazolidinone, 3-[ (5-nitrofurfurylidene)amino]-; Nitrofurazolidone; Furall; ZINC00113418; Nifulidone; KBio2_006714; Optazol; Nicolen; Roptazol; N-(5-Nitro-2-furfurylidene)-3-amino-2-oxazolidone; Furazolidon; MLS000069727; 2-Furanmethanimine, 5-nitro-N-(2-oxo-3-oxazolidinyl)-; Diafuron; NINDS_000085; 3-[(5-Nitrofurylidene)amino]-2-oxazolidone; Furoxane; Giardil; Trichofuron; 3-[(5-Nitrofurfurylidene)amino]-2-oxazolidinone; Trifurox; Furazolidine; 3-[(5-Nitrofurfurylidene)amino]-2-oxazolidone; SPBio_001169; Furazolidone; KBio1_000085; Furoxone; 3-(5'-Nitrofurfuralamino)-2-oxazolidone; KBio2_004146; 2-Oxazolidinone, 3-[(5-nitrofurfurylidine)amino]-; Coryzium; Puradin; USAF EA-1; Nitrofuroxon; Furoxon; Tricofuron show less «

DrugBank

Identification

Name:	Furazolidone
Name (isomeric):	DB00614
Drug Type:	small molecule
Description:	A nitrofuran derivative with antiprotozoal and antibacterial activity. Furazolidone acts by gradual inhibition of monoamine oxidase. (From Martindale, The Extra Pharmacopoeia, 30th ed, p514)
Synonyms:	Nitrofurazolidone; USAF EA-1; Nitrofurazolidonum
Brand:	Ortazol, Coryzium, Furoxone Liquid, Sclaventerol, Tikofuran, Furidon, Trichofuron, Furox, Furazolidon, Diafuron, Giardil, Nifuran, Nifurazolidone, Furaxone, Furovag, Furozolidine, Roptazol, Giarlam, Furaxon, Furazolidine, Trifurox, Furall, Fiurox aerosol powder, Medaron, Puradin, Furoxal, Optazol, Enterotoxon, Furoxon, Neftin, Viofuragyn, Furoxane, Furoxone Swine Mix, Nicolen, Tricoron, Corizium, Furoxone, Topazone, Tricofuron, Nitrofuroxon, Nifulidone, Bifuron, Furazon, Furazol
Category:	Anti-Infective Agents, Local, Monoamine Oxidase Inhibitors, Anti-Infective Agents, Urinary, Antitrichomonal Agents
CAS number:	67-45-8

Pharmacology

Indication:	For the specific and symptomatic treatment of bacterial or protozoal diarrhea and enteritis caused by susceptible organisms.
Pharmacology:	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 act... show more » 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. show less «
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.
Absorption:	Radiolabeled drug studies indicate that furazolidone is well absorbed following oral administration
Biotransformation:	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.
Half Life:	10 minutes
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)

Interactions

Drug interaction:

Zolmitriptan	The MAO inhibitor, furazolidine, may increase the serum concentration of zolmitriptan by decreasing its metabolism. Concomitant therapy and use of zolmitriptan within two weeks of discontinuing furazolidine are contraindicated.
Trimipramine	Increased risk of serotonin syndrome. Ensure adequate washout period between therapies to avoid toxicity. Avoid combination or monitor for symptoms of serotonin syndrome and/or hypertensive crisis.
Tranylcypromine	Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Tramadol	Tramadol increases the risk of serotonin syndrome and seizure induction by the MAO inhibitor, Furazolidone.
Tolcapone	Tolcapone and Furazolidone decrease the metabolism of endogenous catecholamines. Concomitant therapy may result in increased catecholamine effects. Consider alternate therapy or use cautiously and monitor for increased catecholamine effects.

Targets

Enzymes

Amine oxidase [flavin-containing] B

Amine oxidase [flavin-containing] A