Furazolidone: Difference between revisions

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{{Drugbox|
{{Drugbox
|IUPAC_name = 3-{[(5-nitro-2-furyl)methylene]amino}-1,3-oxazolidin-2-one
| Verifiedfields = changed
| CAS_number=67-45-8
| Watchedfields = changed
| ATC_prsdfh adf sdfh lf-life=  
| verifiedrevid = 461105422
| excretion =  
| IUPAC_name = 3-{[(5-nitro-2-furyl)methylene]amino}-1,3-oxazolidin-2-one
| pregnancy_category =  
| image =Furazolidone.png
| legal_status =  
| alt = Structural formula of furazolidone
| routes_of_administration=Oral-Local
| 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-->
| CASNo_Ref = {{cascite|correct|CAS}}
| 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 = [O-][N+](=O)c2oc(C=NN1C(=O)OCC1)cc2
| InChI = 1/C8H7N3O5/c12-8-10(3-4-15-8)9-5-6-1-2-7(16-6)11(13)14/h1-2,5H,3-4H2
| InChIKey = PLHJDBGFXBMTGZ-UHFFFAOYAA
| 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
}}
}}
__Notoc__
{{SI}}
{{SI}}
{{CMG}}
==Overview==
'''Furazolidone''' is a [[nitrofuran]] [[antibacterial]]. It is marketed by [[Roberts Laboratories]] under the brand name '''Furoxone''' and by [[GlaxoSmithKline]] as '''Dependal-M'''. Diafuron, medaron
== Uses ==
Furazolidone has been used in human and veterinary medicine. It has a broad spectrum of activity being active against
*Gram positive
**''[[Clostridium perfringens]]''
**''[[Corynebacterium pyogenes]]''
**[[Streptococcus|Streptococci]]
**[[Staphylococcus|Staphylococci]]
*Gram negative
**''[[Escherichia coli]]''
**''[[Salmonella dublin]]''
**''[[Salmonella typhimurium]]''
*Protozoa
**''[[Giardia lamblia]]''
**''[[Eimeria]]'' species
**''[[Histomonas meleagridis]]''
=== Use in humans ===
In humans it has used to treat [[diarrhoea]] and [[enteritis]] caused by [[bacteria]] or [[protozoa]]n infections. It has been used to treat traveler's diarrhoea, [[cholera]] and [[salmonella|bacteremic salmonellosis]].
Use in treating ''[[Helicobacter pylori]]'' infections has also been proposed.<ref name="pmid18372934">{{cite journal |author=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=160–5 |year=2008 |pmid=18372934 |doi=10.2223/JPED.1772}}</ref>
Furazolidone is also used for [[giardiasis]] (due to ''[[Giardia lamblia]]''), though it is not a first line treatment.<ref name="pmid15625030">{{cite journal |author=Petri WA |title=Treatment of Giardiasis |journal=Curr Treat Options Gastroenterol |volume=8 |issue=1 |pages=13–17 |date=February 2005 |pmid=15625030 |doi= 10.1007/s11938-005-0047-3|url=http://www.treatment-options.com/1092-8472/8/13 |format={{dead link|date=May 2010}}}}</ref>
As for all medicines the most recent local recommendations for its use should be always be followed. The usual dose is:
* Adult: 100 mg 4 times daily. Usual duration: 2-5 days, up to 7 days in some patients or 10 days for giardiasis.
* Child: 1.25 mg/kg 4 times daily, usually given for 2-5 days or up to 10 days for giardiasis.
===Use in animals===
As a [[veterinary medicine]], furazolidone has been used with some success to treat [[salmon]]ids for ''[[Myxobolus cerebralis]]'' infections.


It has also been used in [[aquaculture]].<ref name="pmid10694929">{{cite journal |author=Meng J, Mangat SS, Grudzinski IP, Law FC |title=Evidence of 14C-furazolidone metabolite binding to the hepatic DNA of trout |journal=Drug Metabol Drug Interact |volume=14 |issue=4 |pages=209–19 |year=1998 |pmid=10694929 |doi= |url=}}</ref>


==Overview==
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|last=Bagley|first=Clell|title=Drugs Prohibited from Extralabel Use in Animals|url=http://extension.usu.edu/dairy/files/uploads/htms/drugs.htm|accessdate=14 April 2014}}</ref>
'''Furazolidone''' is an [[antibiotic]] used to treat [[diarrhea]] and [[enteritis]] caused by [[bacteria]] or [[protozoa]]n infections. It is marketed by Roberts Laboratories under the brand name '''Furoxone''' and by [[GlaxoSmithKline]] as Dependal-M.


Furazolidone is also used in combination with fluids for treatment of acute infantile diarrhea. Furazolidone is also used to treat traveler's diarrhea, [[cholera]], and [[salmonella|bacteremic salmonellosis]].
===Use in laboratory===


As a [[veterinary medicine]], furazolidone has been used with some success to treat [[salmon]]ids for ''[[Myxobolus cerebralis]]'' infections. This drug is commonly prescribed to infants and children in oral suspension. The drug is the most common treatment of diarrhea caused by water borne diseases.  
It is used to differentiate [[micrococcus|micrococci]] and [[staphylococcus|staphylococci]].


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


==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 [[nitrofuran]]s generally, [[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>http://caraga.da.gov.ph/services/banmed-Nitrofurans.htm {{dead link|date=December 2013}}</ref>
==See also==
*[[Nitrofurazone]]
*[[Nitrofurantoin]]
==References==
{{reflist|2}}


{{Gynecological anti-infectives and antiseptics}}
{{Gynecological anti-infectives and antiseptics}}
{{Excavata antiparasitics}}
{{Nucleic acid inhibitors}}
[[Category:Drug]]
[[Category:Antibiotics]]
[[Category:Antibiotics]]
[[Category:Antiprotozoal agents]]
[[Category:Antiprotozoal agents]]
[[Category:Furans]]
[[Category:Monoamine oxidase inhibitors]]
[[Category:Nitro compounds]]
 
 
 
{{WH}}
{{WS}}

Latest revision as of 19:18, 8 April 2015

Furazolidone
Structural formula of furazolidone
Space-filling model of the furazolidone model
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
Routes of
administration		Oral-Local
ATC code
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC8H7N3O5
Molar mass225.16
3D model (JSmol)
 ☒N☑Y (what is this?)  (verify)

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Furazolidone is a nitrofuran antibacterial. It is marketed by Roberts Laboratories under the brand name Furoxone and by GlaxoSmithKline as Dependal-M. Diafuron, medaron

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 used to treat diarrhoea and enteritis caused by bacteria or protozoan infections. It has been used to treat traveler's diarrhoea, cholera and bacteremic salmonellosis. Use in treating Helicobacter pylori infections has also been proposed.[1]

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

As for all medicines the most recent local recommendations for its use should be always be followed. The usual dose is:

  • Adult: 100 mg 4 times daily. Usual duration: 2-5 days, up to 7 days in some patients or 10 days for giardiasis.
  • Child: 1.25 mg/kg 4 times daily, usually given for 2-5 days or up to 10 days for giardiasis.

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.[3]

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.[4]

Use in laboratory

It is used to differentiate micrococci and staphylococci.

Mechanism

It is believed to work by crosslinking of DNA.[5]

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.[6]

See also

References

  1. ↑ 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.
  2. ↑ 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.
  3. ↑ 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.
  4. ↑ Bagley, Clell. "Drugs Prohibited from Extralabel Use in Animals". Retrieved 14 April 2014.
  5. ↑ "DrugBank: Showing Furazolidone (DB00614)". Retrieved 2008-12-19.
  6. ↑ http://caraga.da.gov.ph/services/banmed-Nitrofurans.htm[dead link]

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