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Furazolidone

Chemical compound


Chemical compound

FieldValue
Verifiedfieldschanged
Watchedfieldschanged
verifiedrevid461105422
IUPAC_name3-[(5-nitrofuran-2-yl)methylideneamino]-1,3-oxazolidin-2-one
imageFurazolidone.svg
image_classskin-invert-image
altStructural formula of furazolidone
image2Furazolidone 3D spacefill.png
image_class2bg-transparent
alt2Space-filling model of the furazolidone model
Drugs.com
routes_of_administrationOral-Local
CAS_number_Ref
CAS_number67-45-8
ATC_prefixG01
ATC_suffixAX06
ATC_supplemental
PubChem3435
DrugBank_Ref
DrugBankDB00614
ChemSpiderID_Ref
ChemSpiderID3317
UNII_Ref
UNII5J9CPU3RE0
KEGG_Ref
KEGGC07999
ChEMBL_Ref
ChEMBL1103
C8H=7N=3O=5
smilesC1COC(=O)N1N=CC2=CC=C(O2)N+[O-]
StdInChI_Ref
StdInChI1S/C8H7N3O5/c12-8-10(3-4-15-8)9-5-6-1-2-7(16-6)11(13)14/h1-2,5H,3-4H2
StdInChIKey_Ref
StdInChIKeyPLHJDBGFXBMTGZ-UHFFFAOYSA-N

| Drugs.com = | elimination_half-life =

Furazolidone is a nitrofuran antibacterial agent and monoamine oxidase inhibitor (MAOI). 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:

  • Gram-positive bacteria
    • Clostridium perfringens
    • Corynebacterium pyogenes
    • Streptococci
    • Staphylococci
  • 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.

In 2002, a journal article suggested its use in treatment of H. pylori infections in children.

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

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.

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.

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.

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, 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 in food-producing animals in the United States as of 1991.

References

References

  1. (February 2003). "Identification of a furazolidone metabolite responsible for the inhibition of amino oxidases". Xenobiotica; the Fate of Foreign Compounds in Biological Systems.
  2. (2008). "Furazolidone, tetracycline and omeprazole: a low-cost alternative for Helicobacter pylori eradication in children". Jornal de Pediatria.
  3. (February 2005). "Treatment of Giardiasis". Current Treatment Options in Gastroenterology.
  4. (2002). "Helicobacter Pioneers: Firsthand Accounts from the Scientists Who Discovered Helicobacters, 1893-1983". Wiley.
  5. (1998). "Evidence of 14C-furazolidone metabolite binding to the hepatic DNA of trout". Drug Metabolism and Drug Interactions.
  6. "Drugs Prohibited from Extralabel Use in Animals". Utah State University Extension.
  7. "Furazolidone (DB00614)". DrugBank.
  8. (17 August 2000). "Declaring a Ban/Phase-Out of the Use of Nitrofurans in Food-Producing Animals.". Republic of the Philippines.
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