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 Y
ATC code	G01AX06 (WHO) QJ01XE90 (WHO)
PubChem	CID: 3435
DrugBank	DB00614 Y
ChemSpider	3317 Y
UNII	5J9CPU3RE0 Y
KEGG	C07999 N
ChEMBL	CHEMBL1103 N
Chemical data
Formula	C8H7N3O5
Molecular 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 Y Key:PLHJDBGFXBMTGZ-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

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
• 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.

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

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.

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.

Use in laboratory

It is used to differentiate micrococci and staphylococci.

Mechanism

It is believed to work by crosslinking of DNA.

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.

See also

• Nitrofurazone
• Nitrofurantoin