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Furazolidone
Chemical compound
Chemical compound
| Field | Value | |||
|---|---|---|---|---|
| Verifiedfields | changed | |||
| Watchedfields | changed | |||
| verifiedrevid | 461105422 | |||
| IUPAC_name | 3-[(5-nitrofuran-2-yl)methylideneamino]-1,3-oxazolidin-2-one | |||
| image | Furazolidone.svg | |||
| image_class | skin-invert-image | |||
| alt | Structural formula of furazolidone | |||
| image2 | Furazolidone 3D spacefill.png | |||
| image_class2 | bg-transparent | |||
| alt2 | Space-filling model of the furazolidone model | |||
| Drugs.com | ||||
| routes_of_administration | Oral-Local | |||
| CAS_number_Ref | ||||
| CAS_number | 67-45-8 | |||
| ATC_prefix | G01 | |||
| ATC_suffix | AX06 | |||
| ATC_supplemental | ||||
| PubChem | 3435 | |||
| DrugBank_Ref | ||||
| DrugBank | DB00614 | |||
| ChemSpiderID_Ref | ||||
| ChemSpiderID | 3317 | |||
| UNII_Ref | ||||
| UNII | 5J9CPU3RE0 | |||
| KEGG_Ref | ||||
| KEGG | C07999 | |||
| ChEMBL_Ref | ||||
| ChEMBL | 1103 | |||
| C | 8 | H=7 | N=3 | O=5 |
| smiles | C1COC(=O)N1N=CC2=CC=C(O2)N+[O-] | |||
| StdInChI_Ref | ||||
| StdInChI | 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 | |||
| StdInChIKey_Ref | ||||
| StdInChIKey | PLHJDBGFXBMTGZ-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
- (February 2003). "Identification of a furazolidone metabolite responsible for the inhibition of amino oxidases". Xenobiotica; the Fate of Foreign Compounds in Biological Systems.
- (2008). "Furazolidone, tetracycline and omeprazole: a low-cost alternative for Helicobacter pylori eradication in children". Jornal de Pediatria.
- (February 2005). "Treatment of Giardiasis". Current Treatment Options in Gastroenterology.
- (2002). "Helicobacter Pioneers: Firsthand Accounts from the Scientists Who Discovered Helicobacters, 1893-1983". Wiley.
- (1998). "Evidence of 14C-furazolidone metabolite binding to the hepatic DNA of trout". Drug Metabolism and Drug Interactions.
- "Drugs Prohibited from Extralabel Use in Animals". Utah State University Extension.
- "Furazolidone (DB00614)". DrugBank.
- (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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