Furazolidone

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.

Furazolidone

Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Routes of administration	Oral-Local
ATC code	G01AX06 (WHO) QJ01XE90 (WHO)
Identifiers
IUPAC name 3-[(5-nitrofuran-2-yl)methylideneamino]-1,3-oxazolidin-2-one
CAS Number	67-45-8 Y
PubChem CID	3435
DrugBank	DB00614 Y
ChemSpider	3317 Y
UNII	5J9CPU3RE0
KEGG	C07999 N
ChEMBL	ChEMBL1103 N
CompTox Dashboard (EPA)	DTXSID4041997
ECHA InfoCard	100.000.594
Chemical and physical data
Formula	C8H7N3O5
Molar mass	225.160 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1COC(=O)N1N=CC2=CC=C(O2)[N+](=O)[O-]
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)

Medical uses

Furazolidone has been used in human and veterinary medicine. It has a broad spectrum of activity, being active against:^{[citation needed]}

• 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.

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.^[2] In 2002, a journal article suggested its use in treatment of H. pylori infections in children.^[3]

Furazolidone has also been used for giardiasis (due to Giardia lamblia), amoebiasis, and shigellosis, although it is not a first-line treatment.^[4]

Use in animals

As a veterinary medicine, furazolidone has been used with some success to treat salmonids for Myxobolus cerebralis infections.^{[citation needed]}

It has also been used in aquaculture.^[5]

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.^[6]

Furazolidone is no longer available in the US.^{[citation needed]}

Use in laboratory

It is used to differentiate micrococci and staphylococci.^{[citation needed]}

Mechanism of action

It is believed to work by crosslinking of DNA.^[7]

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, 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 as of 1991.^[8]

See also

• Nitrofurazone
• Nitrofurantoin
• Norwich Pharmacal Co. & Others v Customs and Excise Commissioners
• Peptic ulcers and Helicobacter pylori

References

1. Timperio AM, Kuiper HA, Zolla L (February 2003). "Identification of a furazolidone metabolite responsible for the inhibition of amino oxidases". Xenobiotica; the Fate of Foreign Compounds in Biological Systems. 33 (2): 153–167. doi:10.1080/0049825021000038459. PMID 12623758. S2CID 35868007.
2. Xiao SD (2002). "How we discovered in Cina in 1972 that antibiotics cure peptic ulcer.". Helicobacter Pioneers: Firsthand Accounts from the Scientists Who Discovered Helicobacters, 1893-1983. Wiley. pp. 99–104. ISBN 978-0-86793-035-1.
3. 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): 160–165. doi:10.2223/JPED.1772. PMID 18372934.
4. Petri WA (February 2005). "Treatment of Giardiasis". Current Treatment Options in Gastroenterology. 8 (1): 13–17. doi:10.1007/s11938-005-0047-3. PMID 15625030. S2CID 22893579.
5. Meng J, Mangat SS, Grudzinski IP, Law FC (1998). "Evidence of 14C-furazolidone metabolite binding to the hepatic DNA of trout". Drug Metabolism and Drug Interactions. 14 (4): 209–219. doi:10.1515/DMDI.1998.14.4.209. PMID 10694929. S2CID 20792443.
6. Bagley C. "Drugs Prohibited from Extralabel Use in Animals". Utah State University Extension. Archived from the original on 16 April 2014. Retrieved 14 April 2014.
7. "Furazolidone (DB00614)". DrugBank. Retrieved 2008-12-19.
8. "Declaring a Ban/Phase-Out of the Use of Nitrofurans in Food-Producing Animals". Department of Health, Department of Agriculture. Republic of the Philippines. 17 August 2000. Archived from the original on September 24, 2007.