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Furazolidone

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Furazolidone
Structural formula of furazolidone
Space-filling model of the furazolidone model
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
Routes of
administration
Oral-Local
ATC code
Identifiers
  • 3-[(5-nitrofuran-2-yl)methylideneamino]-1,3-oxazolidin-2-one
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.000.594Edit this at Wikidata
Chemical and physical data
FormulaC8H7N3O5
Molar mass225.160 g·mol−1
3D model (JSmol)
  • C1COC(=O)N1N=CC2=CC=C(O2)[N+](=O)[O-]
  • 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 checkY
  • Key:PLHJDBGFXBMTGZ-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Furazolidone is anitrofuranantibacterial agent andmonoamine oxidase inhibitor (MAOI).[1] It is marketed byRoberts Laboratories under the brand nameFuroxone and byGlaxoSmithKline asDependal-M.

Medical uses

[edit]

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

Use in humans

[edit]

In humans, it has been used to treatdiarrhoea andenteritis caused bybacterial orprotozoan infections, including traveler's diarrhoea,cholera, andbacteremic salmonellosis.

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

Furazolidone has also been used forgiardiasis (due toGiardia lamblia), amoebiasis, and shigellosis, although it is not a first-line treatment.[4]

Use in animals

[edit]

As aveterinary medicine, furazolidone has been used with some success to treatsalmonids forMyxobolus cerebralis infections.[citation needed]

It has also been used inaquaculture.[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

[edit]

It is used to differentiatemicrococci andstaphylococci.[citation needed]

Mechanism of action

[edit]

It is believed to work bycrosslinking of DNA.[7]

Side effects

[edit]

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

See also

[edit]

References

[edit]
  1. ^abTimperio 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.
  2. ^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.
  3. ^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.
  4. ^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.
  5. ^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.
  6. ^Bagley C."Drugs Prohibited from Extralabel Use in Animals".Utah State University Extension. Archived fromthe original on 16 April 2014. Retrieved14 April 2014.
  7. ^"Furazolidone (DB00614)".DrugBank. Retrieved2008-12-19.
  8. ^"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 fromthe original on September 24, 2007.
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AAADTooltip Aromatic L-amino acid decarboxylase
MAOTooltip Monoamine oxidase
Phenethylamines
(dopamine,epinephrine,
norepinephrine)
PAHTooltip Phenylalanine hydroxylase
THTooltip Tyrosine hydroxylase
DBHTooltip Dopamine beta-hydroxylase
PNMTTooltip Phenylethanolamine N-methyltransferase
COMTTooltip Catechol-O-methyl transferase
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TPHTooltip Tryptophan hydroxylase
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HDCTooltip Histidine decarboxylase
HNMTTooltip Histamine N-methyltransferase
DAOTooltip Diamine oxidase
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