View source for Biology:Furazolidone

{{Short description|Chemical compound}}
{{Infobox drug
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 461105422
| IUPAC_name = 3-[(5-nitrofuran-2-yl)methylideneamino]-1,3-oxazolidin-2-one
| image = Furazolidone.svg
| alt = Structural formula of furazolidone
| image2 = Furazolidone 3D spacefill.png
| alt2 = Space-filling model of the furazolidone model
<!--Clinical data-->
| tradename =
| Drugs.com = {{drugs.com|CONS|furazolidone}}
| pregnancy_category =
| legal_status =
| routes_of_administration = Oral-Local
<!--Pharmacokinetic data-->
| bioavailability =
| metabolism =
| elimination_half-life =
| excretion =
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 67-45-8
| ATC_prefix = G01
| ATC_suffix = AX06
| ATC_supplemental = {{ATCvet|J01|XE90}}
| PubChem = 3435
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00614
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 3317
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 5J9CPU3RE0
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C07999
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1103
<!--Chemical data-->
| C=8 | H=7 | N=3 | O=5
| molecular_weight = 225.16
| smiles = C1COC(=O)N1N=CC2=CC=C(O2)[N+](=O)[O-]
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| 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_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = PLHJDBGFXBMTGZ-UHFFFAOYSA-N
}}

'''Furazolidone''' is a nitrofuran antibacterial agent and [[Biology:Monoamine oxidase inhibitor|monoamine oxidase inhibitor]] (MAOI).<ref name="PMID12623758">{{cite journal | vauthors = Timperio AM, Kuiper HA, Zolla L | title = Identification of a furazolidone metabolite responsible for the inhibition of amino oxidases | journal = Xenobiotica; the Fate of Foreign Compounds in Biological Systems | volume = 33 | issue = 2 | pages = 153–167 | date = February 2003 | pmid = 12623758 | doi = 10.1080/0049825021000038459 | s2cid = 35868007 }}</ref> It is marketed by Roberts Laboratories under the brand name '''Furoxone''' and by [[Company:GlaxoSmithKline|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{{citation needed|date=December 2022}}
* Gram positivei
** ''[[Biology:Clostridium perfringens|Clostridium perfringens]]''
** ''Corynebacterium pyogenes''
** [[Biology:Streptococcus|Streptococci]]
** [[Biology:Staphylococcus|Staphylococci]]
* Gram negative
** ''[[Biology:Escherichia coli|Escherichia coli]]''
** ''Salmonella dublin''
** ''Salmonella typhimurium''
** ''Shigella''
* Protozoa
** ''[[Biology:Giardia lamblia|Giardia lamblia]]''
** ''[[Biology:Eimeria|Eimeria]]'' species
** ''Histomonas meleagridis''

===Use in humans===
In humans it has been used to treat diarrhoea and [[Medicine:Enteritis|enteritis]] caused by [[Biology:Bacteria|bacteria]] or [[Biology:Protozoa|protozoa]]n infections, including traveler's diarrhoea, [[Medicine:Cholera|cholera]] and [[Biology:Salmonella|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.<ref>{{cite book | vauthors = Xiao SD | chapter = How we discovered in Cina in 1972 that antibiotics cure peptic ulcer. | title = Helicobacter Pioneers: Firsthand Accounts from the Scientists Who Discovered Helicobacters, 1893-1983| date = 2002 | pages = 99–104 | publisher = Wiley | isbn = 978-0-86793-035-1 }}</ref> In 2002, a journal article suggested its use in treatment of helicobacter pylori infections in children.<ref name="pmid18372934">{{cite journal | vauthors = Machado RS, Silva MR, Viriato A | title = Furazolidone, tetracycline and omeprazole: a low-cost alternative for Helicobacter pylori eradication in children | journal = Jornal de Pediatria | volume = 84 | issue = 2 | pages = 160–165 | year = 2008 | pmid = 18372934 | doi = 10.2223/JPED.1772 | doi-access = free }}</ref>

Furazolidone has also been used for [[Medicine:Giardiasis|giardiasis]] (due to ''[[Biology:Giardia lamblia|Giardia lamblia]]''), amoebiasis and shigellosis also though it is not a first line treatment.<ref name="pmid15625030">{{cite journal | vauthors = Petri WA | title = Treatment of Giardiasis | journal = Current Treatment Options in Gastroenterology | volume = 8 | issue = 1 | pages = 13–17 | date = February 2005 | pmid = 15625030 | doi = 10.1007/s11938-005-0047-3 | s2cid = 22893579 }}</ref>

===Use in animals===
As a [[Medicine:Veterinary medicine|veterinary medicine]], furazolidone has been used with some success to treat salmonids for ''[[Biology:Myxobolus cerebralis|Myxobolus cerebralis]]'' infections.{{citation needed|date=February 2023}}

It has also been used in aquaculture.<ref name="pmid10694929">{{cite journal | vauthors = Meng J, Mangat SS, Grudzinski IP, Law FC | title = Evidence of 14C-furazolidone metabolite binding to the hepatic DNA of trout | journal = Drug Metabolism and Drug Interactions | volume = 14 | issue = 4 | pages = 209–219 | year = 1998 | pmid = 10694929 | doi = 10.1515/DMDI.1998.14.4.209 | s2cid = 20792443 }}</ref>

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.<ref>{{cite web| vauthors = Bagley C |title=Drugs Prohibited from Extralabel Use in Animals | work = Utah State University Extension |url= http://extension.usu.edu/dairy/files/uploads/htms/drugs.htm | archive-url = https://web.archive.org/web/20140416035403/http://extension.usu.edu/dairy/files/uploads/htms/drugs.htm | archive-date = 16 April 2014 |access-date=14 April 2014}}</ref>

Furazolidone is no longer available in the US.{{citation needed|date=June 2021}}

===Use in laboratory===
It is used to differentiate [[Biology:Micrococcus|micrococci]] and [[Biology:Staphylococcus|staphylococci]].{{citation needed|date=December 2022}}

==Mechanism of action==
It is believed to work by [[Biology:Crosslinking of DNA|crosslinking of DNA]].<ref name="urlDrugBank: Showing Furazolidone (DB00614)">{{cite web |url=http://www.drugbank.ca/drugs/DB00614 | work = DrugBank | title = Furazolidone (DB00614) |access-date=2008-12-19}}</ref>

==Side effects==
Though an effective antibiotic when all others fail, against extremely drug resistant infections, it has many side effects. including [[Biology:Monoamine oxidase inhibitor|inhibition of monoamine oxidase]],<ref name="PMID12623758"/> and as with other nitrofurans generally, [[Biology:Minimum inhibitory concentration|minimum inhibitory concentration]]s 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.<ref>{{cite web |url=http://caraga.da.gov.ph/services/banmed-Nitrofurans.htm |title= Declaring a Ban/Phase-Out of the Use of Nitrofurans in Food-Producing Animals. | date = 17 August 2000 | publisher = Republic of the Philippines | work = Department of Health, Department of Agriculture |archive-url=https://web.archive.org/web/20070924183919/http://caraga.da.gov.ph/services/banmed-Nitrofurans.htm |archive-date=September 24, 2007}}</ref>

== See also ==
* [[Chemistry:Nitrofurazone|Nitrofurazone]]
* [[Chemistry:Nitrofurantoin|Nitrofurantoin]]
* ''Norwich Pharmacal Co. & Others v Customs and Excise Commissioners''
* Peptic ulcers and Helicobacter pylori

== References ==
{{reflist|2}}

{{Gynecological anti-infectives and antiseptics}}
{{Excavata antiparasitics}}
{{Nucleic acid inhibitors}}
{{Monoamine metabolism modulators}}

[[Category:Acetaldehyde dehydrogenase inhibitors]]
[[Category:Antibiotics]]
[[Category:Antiprotozoal agents]]
[[Category:Monoamine oxidase inhibitors]]
[[Category:Hydrazones]]

{{Sourceattribution|Furazolidone}}