Furazolidone

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 ;
PubChem CID	3435;
DrugBank	DB00614 ;
ChemSpider	3317 ;
UNII	5J9CPU3RE0;
KEGG	C07999 ;
ChEMBL	ChEMBL1103 ;
CompTox Dashboard (EPA)	DTXSID4041997 ;
ECHA InfoCard	100.000.594
Chemical and physical data
Formula	C8H7N3O5
Molar mass	225.16 g·mol−1
3D model (JSmol)	Interactive image;
	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 ;
	(what is this?) (verify)

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.

Medical uses

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

Gram positive
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, including traveler's diarrhoea, cholera and bacteremic salmonellosis. Use in treating Helicobacter pylori infections has also been proposed.^[2]

Furazolidone has also been used for giardiasis (due to Giardia lamblia), amoebiasis and shigellosis also though it is not a first line treatment.^[3]

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.^[4]

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.^[5]

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.^[6]

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: 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.^[7]

References

^ ^a ^b A.M. Timperio; H.A. Kuiper & L. Zolla (February 2003). "Identification of a furazolidone metabolite responsible for the inhibition of amino oxidases". Xenobiotica. 33 (2): 153–167. doi:10.1080/0049825021000038459. PMID 12623758.
^ 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.
^ Petri WA (February 2005). "Treatment of Giardiasis". Curr Treat Options Gastroenterol. 8 (1): 13–17. doi:10.1007/s11938-005-0047-3. PMID 15625030.
^ 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.
^ Bagley, Clell. "Drugs Prohibited from Extralabel Use in Animals". Retrieved 14 April 2014.
^ "DrugBank: Showing Furazolidone (DB00614)". Retrieved 2008-12-19.
^ http://caraga.da.gov.ph/services/banmed-Nitrofurans.htm Archived September 24, 2007, at the Wayback Machine

[PMID12623758-1] A.M. Timperio; H.A. Kuiper & L. Zolla (February 2003). "Identification of a furazolidone metabolite responsible for the inhibition of amino oxidases". Xenobiotica. 33 (2): 153–167. doi:10.1080/0049825021000038459. PMID 12623758.

[pmid18372934-2] 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.

[pmid15625030-3] Petri WA (February 2005). "Treatment of Giardiasis". Curr Treat Options Gastroenterol. 8 (1): 13–17. doi:10.1007/s11938-005-0047-3. PMID 15625030.

[pmid10694929-4] 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.

[5] Bagley, Clell. "Drugs Prohibited from Extralabel Use in Animals". Retrieved 14 April 2014.

[urlDrugBank:_Showing_Furazolidone_(DB00614)-6] "DrugBank: Showing Furazolidone (DB00614)". Retrieved 2008-12-19.

[7] ttp://caraga.da.gov.ph/services/banmed-Nitrofurans.htm Archived September 24, 2007, at the Wayback Machine

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