Furazolidone

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Furazolidone
Furazolidone.svg
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Clinical data
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Routes of
administration
Oral-Local
ATC code
Identifiers
  • 3-[(5-nitrofuran-2-yl)methylideneamino]-1,3-oxazolidin-2-one
CAS Number
PubChem CID
DrugBank
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UNII
KEGG
ChEMBL
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ECHA InfoCard 100.000.594 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C8H7N3O5
Molar mass 225.160 g·mol−1
3D model (JSmol)
  • C1COC(=O)N1N=CC2=CC=C(O2)[N+](=O)[O-]
  • 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 Yes check.svgY
  • Key:PLHJDBGFXBMTGZ-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (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.

Contents

Medical uses

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

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.[ 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

Related Research Articles

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References

  1. 1 2 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.