Furazolidone

Furazolidone

Systematic (IUPAC) name
3-{[(5-nitro-2-furyl)methylene]amino}-1,3-oxazolidin-2-one
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Routes of administration	Oral-Local
Identifiers
CAS Number	67-45-8
ATC code	G01AX06 (WHO) QJ01XE90
PubChem	CID 3435
DrugBank	DB00614
ChemSpider	3317
UNII	5J9CPU3RE0
KEGG	C07999
ChEMBL	CHEMBL1103
Chemical data
Formula	C8H7N3O5
Molar mass	225.16
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 Key:PLHJDBGFXBMTGZ-UHFFFAOYSA-N
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Furazolidone is a nitrofuran antibacterial agent. It is marketed by Roberts Laboratories under the brand name Furoxone and by GlaxoSmithKline as Dependal-M. Diafuron, medaron

Uses

Furazolidone has been used in human and veterinary medicine. It has a broad spectrum of activity being active against

• Gram positive
  • Clostridium perfringens
  • Corynebacterium pyogenes
  • Streptococci
  • Staphylococci
• Gram negative
  • 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 bacteria or protozoan infections. It has been used to treat traveler's diarrhoea, cholera and bacteremic salmonellosis. Use in treating Helicobacter pylori infections has also been proposed.^[1]

Furazolidone is also used for giardiasis (due to Giardia lamblia), though it is not a first line treatment.^[2]

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.^[3]

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.^[4]

Use in laboratory

It is used to differentiate micrococci and staphylococci.

Mechanism

It is believed to work by crosslinking of DNA.^[5]

Side effects

Furazolidone is no longer available in the US. Though an effective antibiotic when all others fail, against extremely drug resistant infections, it has many side effects, 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.^[6]

See also

• Nitrofurazone
• Nitrofurantoin

References

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): 160–5. doi:10.2223/JPED.1772. PMID 18372934.
2. Petri WA (February 2005). "Treatment of Giardiasis". Curr Treat Options Gastroenterol 8 (1): 13–17. doi:10.1007/s11938-005-0047-3. PMID 15625030.
3. 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. PMID 10694929.
4. Bagley, Clell. "Drugs Prohibited from Extralabel Use in Animals". Retrieved 14 April 2014.
5. "DrugBank: Showing Furazolidone (DB00614)". Retrieved 2008-12-19.
6. http://caraga.da.gov.ph/services/banmed-Nitrofurans.htm Archived September 24, 2007, at the Wayback Machine.