Furazolidone

Furazolidone
Structural formula of furazolidone
Space-filling model of the furazolidone model
Clinical data
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Routes of
administration		Oral-Local
ATC code
Identifiers
IUPAC name
  • 3-[(5-nitrofuran-2-yl)methylideneamino]-1,3-oxazolidin-2-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.594
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Chemical and physical data
FormulaC8H7N3O5
Molar mass225.16 g·mol−1
3D model (JSmol)
SMILES
  • [O-][N+](=O)c2oc(C=NN1C(=O)OCC1)cc2
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 checkY
  • Key:PLHJDBGFXBMTGZ-UHFFFAOYSA-N checkY
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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

Use in humans

In humans it has been used to treat diarrhoea and enteritis caused by bacteria or protozoan infections, including traveler's diarrhoea, cholera and bacteremic salmonellosis. Use in treating Helicobacter pylori infections has also been proposed.[2]

Furazolidone has also been used for giardiasis (due to Giardia lamblia), amoebiasis and shigellosis also though it is not a first line treatment.[3]

Use in animals

As a veterinary medicine, furazolidone has been used with some success to treat salmonids for Myxobolus cerebralis infections.

It has also been used in aquaculture.[4]

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.[5]

Furazolidone is no longer available in the US.

Use in laboratory

It is used to differentiate micrococci and staphylococci.

Mechanism of action

It is believed to work by crosslinking of DNA.[6]

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: tremors, convulsions, peripheral neuritis, gastrointestinal disturbances, depression of spermatogenesis. Nitrofurans are recognized by FDA as mutagens/carcinogens, and can no longer be used since 1991.[7]

See also

References

  1. 1 2 A.M. Timperio; H.A. Kuiper & L. Zolla (February 2003). "Identification of a furazolidone metabolite responsible for the inhibition of amino oxidases". Xenobiotica. 33 (2): 153–167. doi:10.1080/0049825021000038459. PMID 12623758. S2CID 35868007.
  2. ↑ 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): 160–5. doi:10.2223/JPED.1772. PMID 18372934.
  3. ↑ Petri WA (February 2005). "Treatment of Giardiasis". Curr Treat Options Gastroenterol. 8 (1): 13–17. doi:10.1007/s11938-005-0047-3. PMID 15625030. S2CID 22893579.
  4. ↑ Meng J, Mangat SS, Grudzinski IP, Law FC (1998). "Evidence of 14C-furazolidone metabolite binding to the hepatic DNA of trout". Drug Metabol Drug Interact. 14 (4): 209–19. doi:10.1515/DMDI.1998.14.4.209. PMID 10694929. S2CID 20792443.
  5. ↑ Bagley, Clell. "Drugs Prohibited from Extralabel Use in Animals". Retrieved 14 April 2014.
  6. ↑ "DrugBank: Showing Furazolidone (DB00614)". Retrieved 2008-12-19.
  7. ↑ http://caraga.da.gov.ph/services/banmed-Nitrofurans.htm Archived September 24, 2007, at the Wayback Machine
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