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
Pregnancy cat.	?
Legal status	?
Routes	Oral-Local
Identifiers
CAS number	67-45-8
ATC code	G01AX06
PubChem	CID 3435
DrugBank	DB00614
ChemSpider	3317
UNII	5J9CPU3RE0
KEGG	C07999
ChEMBL	CHEMBL1103
Chemical data
Formula	C8H7N3O5
Mol. mass	225.16
SMILES	eMolecules & PubChem
	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 ;
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Furazolidone is a nitrofuran antibacterial. It is marketed by Roberts Laboratories under the brand name Furoxone and by GlaxoSmithKline as Dependal-M.

Uses

It is used to treat diarrhoea and enteritis caused by bacteria or protozoan infections.

It has also been used in aquaculture.¹

Protozoan

Furazolidone is also used for giardiasis (due to Giardia lamblia), though it is not a first line treatment.²

Bacterial

Furazolidone is also used to treat traveler's diarrhoea, cholera, and bacteremic salmonellosis.

As a veterinary medicine, furazolidone has been used with some success to treat salmonids for Myxobolus cerebralis infections.

Use in treating Helicobacter pylori infections has been proposed.³

Mechanism

It is believed to work by crosslinking of DNA.⁴

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 1991.⁵

References

^ 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.
^ Petri WA (February 2005). "Treatment of Giardiasis" (^{dead link}). Curr Treat Options Gastroenterol 8 (1): 13–17. doi:10.1007/s11938-005-0047-3. PMID 15625030. http://www.treatment-options.com/1092-8472/8/13.
^ 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.
^ "DrugBank: Showing Furazolidone (DB00614)". http://www.drugbank.ca/drugs/DB00614. Retrieved 2008-12-19.
^ http://caraga.da.gov.ph/services/banmed-Nitrofurans.htm

[pmid10694929-0] 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.

[pmid15625030-1] Petri WA (February 2005). "Treatment of Giardiasis" (^{dead link}). Curr Treat Options Gastroenterol 8 (1): 13–17. doi:10.1007/s11938-005-0047-3. PMID 15625030. http://www.treatment-options.com/1092-8472/8/13.

[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.

[urlDrugBank:_Showing_Furazolidone_.28DB00614.29-3] "DrugBank: Showing Furazolidone (DB00614)". http://www.drugbank.ca/drugs/DB00614. Retrieved 2008-12-19.

[4] ttp://caraga.da.gov.ph/services/banmed-Nitrofurans.htm

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