Furazolidone Explained

Verifiedfields:changed
Watchedfields:changed
Verifiedrevid:461105422
Iupac Name:3-[(5-nitrofuran-2-yl)methylideneamino]-1,3-oxazolidin-2-one
Alt2:Space-filling model of the furazolidone model
Routes Of Administration:Oral-Local
Cas Number:67-45-8
Atc Prefix:G01
Atc Suffix:AX06
Pubchem:3435
Drugbank:DB00614
Chemspiderid:3317
Unii:5J9CPU3RE0
Kegg:C07999
Chembl:1103
C:8
H:7
N:3
O:5
Smiles:C1COC(=O)N1N=CC2=CC=C(O2)[N+](=O)[O-]
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:PLHJDBGFXBMTGZ-UHFFFAOYSA-N

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:

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, also though 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.

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.

Use in laboratory

It is used to differentiate micrococci and staphylococci.

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

Notes and References

  1. Timperio AM, Kuiper HA, Zolla L . 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 . February 2003 . 12623758 . 10.1080/0049825021000038459 . 35868007 .
  2. Book: Xiao SD . How we discovered in Cina in 1972 that antibiotics cure peptic ulcer. . Helicobacter Pioneers: Firsthand Accounts from the Scientists Who Discovered Helicobacters, 1893-1983. 2002 . 99–104 . Wiley . 978-0-86793-035-1 .
  3. Machado RS, Silva MR, Viriato A . Furazolidone, tetracycline and omeprazole: a low-cost alternative for Helicobacter pylori eradication in children . Jornal de Pediatria . 84 . 2 . 160–165 . 2008 . 18372934 . 10.2223/JPED.1772 . free .
  4. Petri WA . Treatment of Giardiasis . Current Treatment Options in Gastroenterology . 8 . 1 . 13–17 . February 2005 . 15625030 . 10.1007/s11938-005-0047-3 . 22893579 .
  5. Meng J, Mangat SS, Grudzinski IP, Law FC . Evidence of 14C-furazolidone metabolite binding to the hepatic DNA of trout . Drug Metabolism and Drug Interactions . 14 . 4 . 209–219 . 1998 . 10694929 . 10.1515/DMDI.1998.14.4.209 . 20792443 .
  6. Web site: Bagley C . Drugs Prohibited from Extralabel Use in Animals . Utah State University Extension . https://web.archive.org/web/20140416035403/http://extension.usu.edu/dairy/files/uploads/htms/drugs.htm . 16 April 2014 . 14 April 2014.
  7. Web site: Furazolidone (DB00614) . DrugBank . 2008-12-19.
  8. Web site: Declaring a Ban/Phase-Out of the Use of Nitrofurans in Food-Producing Animals. . 17 August 2000 . Republic of the Philippines . Department of Health, Department of Agriculture . https://web.archive.org/web/20070924183919/http://caraga.da.gov.ph/services/banmed-Nitrofurans.htm . September 24, 2007.