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Furazolidone - Wikipedia

From Wikipedia, the free encyclopedia

Furazolidone
Clinical data


AHFS/Drugs.com	Micromedex Detailed Consumer Information
Routes of administration	Oral-Local
ATC code	G01AX06 (WHO) QJ01XE90 (WHO)
Identifiers
IUPAC name 3-[(5-nitrofuran-2-yl)methylideneamino]-1,3-oxazolidin-2-one
CAS Number	67-45-8^Y
PubChem CID	3435
DrugBank	DB00614^Y
ChemSpider	3317^Y
UNII	5J9CPU3RE0
KEGG	C07999^N
ChEMBL	ChEMBL1103^N
CompTox Dashboard (EPA)	DTXSID4041997
ECHA InfoCard	100.000.594
Chemical and physical data
Formula	C₈H₇N₃O₅
Molar mass	225.160 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C1COC(=O)N1N=CC2=CC=C(O2)[N+](=O)[O-]
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^Y Key:PLHJDBGFXBMTGZ-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

Furazolidone is a nitrofuran antibacterial agent and monoamine oxidase inhibitor (MAOI).^[1] It is marketed by Roberts Laboratories under the brand name Furoxone and by GlaxoSmithKline as Dependal-M.

Medical uses

Furazolidone has been used in human and veterinary medicine. It has a broad spectrum of activity, being active against:^{[citation needed]}

Gram-positive bacteria
Gram-negative bacteria
- Escherichia coli
- Salmonella dublin
- Salmonella typhimurium
- Shigella
Protozoa
- Giardia lamblia
- Eimeria species
- Histomonas meleagridis

Use in humans

In humans, it has been used to treat diarrhoea and enteritis caused by bacterial or protozoan infections, including traveler's diarrhoea, cholera, and bacteremic salmonellosis.

From the early 1970s, it has been used in China to treat peptic ulcers, where the mechanism is treatment of the causative Helicobacter pylori infection.^[2] In 2002, a journal article suggested its use in treatment of H. pylori infections in children.^[3]

Furazolidone has also been used for giardiasis (due to Giardia lamblia), amoebiasis, and shigellosis, although it is not a first-line treatment.^[4]

Use in animals

As a veterinary medicine, furazolidone has been used with some success to treat salmonids for Myxobolus cerebralis infections.^{[citation needed]}

It has also been used in aquaculture.^[5]

Since furazolidone is a nitrofuran antibiotic, its use in food animals is currently prohibited by the FDA under the Animal Medicinal Drug Use Clarification Act, 1994.^[6]

Furazolidone is no longer available in the US.^{[citation needed]}

Use in laboratory

It is used to differentiate micrococci and staphylococci.^{[citation needed]}

Mechanism of action

It is believed to work by crosslinking of DNA.^[7]

Side effects

Though an effective antibiotic when all others fail, against extremely drug resistant infections, it has many side effects. including inhibition of monoamine oxidase,^[1] and as with other nitrofurans generally, minimum inhibitory concentrations also produce systemic toxicity, resulting in tremors, convulsions, peripheral neuritis, gastrointestinal disturbances, and depression of spermatogenesis. Nitrofurans are recognized by FDA as mutagens/carcinogens, and can no longer be used as of 1991.^[8]

References

^ ^a ^b Timperio AM, Kuiper HA, Zolla L (February 2003). "Identification of a furazolidone metabolite responsible for the inhibition of amino oxidases". Xenobiotica; the Fate of Foreign Compounds in Biological Systems. 33 (2): 153–167. doi:10.1080/0049825021000038459. PMID 12623758. S2CID 35868007.
^ Xiao SD (2002). "How we discovered in Cina in 1972 that antibiotics cure peptic ulcer.". Helicobacter Pioneers: Firsthand Accounts from the Scientists Who Discovered Helicobacters, 1893-1983. Wiley. pp. 99–104. ISBN 978-0-86793-035-1.
^ Machado RS, Silva MR, Viriato A (2008). "Furazolidone, tetracycline and omeprazole: a low-cost alternative for Helicobacter pylori eradication in children". Jornal de Pediatria. 84 (2): 160–165. doi:10.2223/JPED.1772. PMID 18372934.
^ Petri WA (February 2005). "Treatment of Giardiasis". Current Treatment Options in Gastroenterology. 8 (1): 13–17. doi:10.1007/s11938-005-0047-3. PMID 15625030. S2CID 22893579.
^ Meng J, Mangat SS, Grudzinski IP, Law FC (1998). "Evidence of 14C-furazolidone metabolite binding to the hepatic DNA of trout". Drug Metabolism and Drug Interactions. 14 (4): 209–219. doi:10.1515/DMDI.1998.14.4.209. PMID 10694929. S2CID 20792443.
^ Bagley C. "Drugs Prohibited from Extralabel Use in Animals". Utah State University Extension. Archived from the original on 16 April 2014. Retrieved 14 April 2014.
^ "Furazolidone (DB00614)". DrugBank. Retrieved 2008-12-19.
^ "Declaring a Ban/Phase-Out of the Use of Nitrofurans in Food-Producing Animals". Department of Health, Department of Agriculture. Republic of the Philippines. 17 August 2000. Archived from the original on September 24, 2007.

Gynecological anti-infectives and antiseptics (G01)

Antibiotics

Arsenic compounds

Acetarsol

Quinoline derivatives

Organic acids

Sulfonamides

Sulfatolamide

Antifungals

Imidazoles	Metronidazole Clotrimazole Miconazole Econazole Ornidazole Isoconazole Tioconazole Ketoconazole Fenticonazole Azanidazole Propenidazole Butoconazole Omoconazole Oxiconazole Flutrimazole
Triazoles	Terconazole
Polyenes	Nystatin Natamycin Amphotericin B
Other	Ciclopirox Methylrosaniline

Other

Antiparasitics directed at excavata parasites (P01)

Discicristata

Trypanosomiasis

African trypanosomiasis	ornithine (Eflornithine^#) arsenical (Atoxyl, Melarsoprol^#, Tryparsamide) benzamidine (Pentamidine^#) naphthalenesulfonate (Suramin^#) nitroimidazole (Fexinidazole^†)
Chagas disease	nitroimidazole (Benznidazole^#) nitrofuran (Nifurtimox^#)

Leishmaniasis

polyene (Amphotericin B^#)

Pentavalent antimonials (Meglumine antimoniate^#, Sodium stibogluconate)

PAM

polyene (Amphotericin B)

Trichozoa

Giardiasis	nitroimidazole (Metronidazole^#, Tinidazole) benzimidazole (Albendazole) thiazolide (Nitazoxanide) nitrofuran (Furazolidone) aminoacridine (Quinacrine)
Trichomoniasis	nitroimidazole (Carnidazole, Metronidazole^#, Tinidazole)
Dientamoebiasis	nitroimidazole (Metronidazole Secnidazole) oxyquinoline (Iodoquinol) tetracycline (Doxycycline) neomycin (Paromomycin)

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

v t e Antibacterials: others (J01X, D06AX)
Glycopeptides Lipoglycopeptides	Avoparcin Corbomycin Dalbavancin Oritavancin Ristocetin Teicoplanin Telavancin Vancomycin
Polymyxins	Colistin Polymyxin B
Steroid antibacterials	Fusidic acid
Imidazole derivatives	Metronidazole Ornidazole Tinidazole
Pleuromutilins	Azamulin Lefamulin Retapamulin Tiamulin Valnemulin
Nitrofuran derivatives	Furazolidone Nifuroxazide Nifurtoinol Nifurzide Nitrofurantoin Nitrofurazone
Other antibacterials	Bacitracin Clofoctol Daptomycin Fosfomycin Furaltadone Lefamulin Linezolid Mandelic acid Methenamine Nitroxoline Novobiocin Spectinomycin Tedizolid Xibornol

Monoamine metabolism modulators

Non-specific

AAAD

Substrates→Products: L-DOPA (levodopa)→Dopamine
5-HTP→Serotonin
L-Histidine→Histamine
Phenylalanine→Phenethylamine
L-Tyrosine→Tyramine
Tryptophan→Tryptamine

MAO

Substrates→Products (with ALDHTooltip Aldehyde dehydrogenase/ALRTooltip ALR): Epinephrine (adrenaline)→DHMA Metanephrine→MHPG/VMA Norepinephrine (noradrenaline)→DHMA Normetanephrine→MHPG/VMA Dopamine→DOPAC 3-Methoxytyramine→HVA Serotonin→5-HIAA Inhibitors: Non-selective: Benmoxin Caroxazone Echinopsidine Furazolidone Guineesine Hydralazine Indantadol Iproclozide Iproniazid Isocarboxazid Isoniazid Linezolid Mebanazine Metfendrazine Nialamide Octamoxin Paraxazone Phenelzine Pheniprazine Phenoxypropazine Pivhydrazine Procarbazine Safrazine Tranylcypromine
Inhibitors: MAO-A-selective: Amiflamine Bazinaprine Befloxatone Brofaromine Cimoxatone Clorgiline CX157 (Tyrima) Eprobemide Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine) Methylene blue Metralindole Minaprine Moclobemide Pirlindole Sercloremine Tetrindole Toloxatone
Inhibitors: MAO-B selective: Adarigiline Almoxatone D-Deprenyl Desmethylselegiline Ethanol Ladostigil Lazabemide Milacemide Mofegiline Nicotine Pargyline^‡ Rasagiline Safinamide Selegiline (L-Deprenyl) Sembragiline Tisolagiline Vafidemstat

Phenethylamines
(dopamine, epinephrine,
norepinephrine)

PAHTooltip Phenylalanine hydroxylase	Substrates→Products: Phenylalanine→Tyrosine Inhibitors: 3,4-Dihydroxystyrene α-Methylphenylalanine
THTooltip Tyrosine hydroxylase	Substrates→Products: Tyrosine→L-DOPA (levodopa) Inhibitors: 2-Hydroxyestradiol 2-Hydroxyestrone 3-Iodotyrosine α-Methyl-5-hydroxytryptophan (α-Me-5-HTP) α-Methylphenylalanine Aquayamycin Bulbocapnine Methyldopa (α-methyl-L-DOPA) Metirosine (α-methyl-p-tyrosine) Oudenone
DBHTooltip Dopamine beta-hydroxylase	Substrates→Products: Dopamine→Norepinephrine (Noradrenaline) Inhibitors: Bupicomide Disulfiram Dopastin Etamicastat Fusaric acid Nepicastat Phenopicolinic acid Tropolone Zamicastat
PNMTTooltip Phenylethanolamine N-methyltransferase	Substrates→Products: Norepinephrine (noradrenaline)→Epinephrine (adrenaline) Inhibitors: CGS-19281A SKF-64139 SKF-7698
COMTTooltip Catechol-O-methyl transferase	Substrates→Products: Dopamine→3-Methoxytyramine DOPAC→Homovanillic acid Norepinephrine→Normetanephrine Epinephrine→Metanephrine DOPEG→MOPEG DOMA→VMA 2-Hydroxyestradiol→2-Methoxyestradiol 2-Hydroxyestrone→2-Methoxyestrone 4-Hydroxyestradiol→4-Methoxyestradiol 4-Hydroxyestrone→4-Methoxyestrone Inhibitors: 2-Hydroxyestradiol 2-Hydroxyestrone Entacapone Nebicapone Neluxicapone Nitecapone Opicapone Quinalizarin Tolcapone

Tryptamines
(serotonin, melatonin)

TPHTooltip Tryptophan hydroxylase	Substrates→Products: Tryptophan→5-HTP Inhibitors: AGN-2979 Fenclonine (PCPA) Telotristat ethyl
AANATTooltip Serotonin N-acetyl transferase	Substrates→Products: Serotonin→N-Acetylserotonin
ASMTTooltip Acetylserotonin O-methyltransferase	Substrates→Products: N-Acetylserotonin→Melatonin

Histamine

HDCTooltip Histidine decarboxylase	Substrates→Products: L-Histidine→Histamine Inhibitors: Catechin Alpha-Fluoromethylhistidine Histidine methyl ester Meciadanol Naringenin Tritoqualine
HNMTTooltip Histamine N-methyltransferase	Substrates→Products: Histamine→N-Methylhistamine Inhibitors: Amodiaquine Diphenhydramine Harmaline Metoprine Quinacrine SKF-91488 Tacrine
DAOTooltip Diamine oxidase	Substrates→Products: Histamine→Imidazole acetic acid Inhibitors: Pimagedine (aminoguanidine)

See also: Receptor/signaling modulators • Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake inhibitors • Monoamine releasing agents • Monoamine neurotoxins