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{{drugbox |
{{Drugbox
| IUPAC_name = ''N''-benzyl-2-(2-nitroimidazol-1-yl)acetamide
| verifiedrevid = 414638558
| image = Benznidazole.svg
| IUPAC_name = ''N''-benzyl-2-(2-nitro-1''H''-imidazol-1-yl)acetamide
| image = Benznidazole Wiki Str.png
 
 
<!--Clinical data-->
| tradename = Rochagan, Radanil
| Drugs.com = {{drugs.com|CONS|benznidazole}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B            / C / D / X -->
| pregnancy_category = 
| legal_AU = <!-- Unscheduled / S2 / S3 / S4  / S8 -->
| legal_CA = <!--                            / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| legal_US = <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| legal_status = 
| routes_of_administration = Oral
 
<!--Pharmacokinetic data-->
| bioavailability = High
| protein_bound = 
| metabolism = [[Liver|Hepatic]]
| elimination_half-life = 12 hours
| excretion = [[Kidney|Renal]] and fecal
 
<!--Identifiers-->
| CASNo_Ref = {{cascite|correct|??}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 22994-85-0
| CAS_number = 22994-85-0
| ATC_prefix = P01
| ATC_prefix = P01
| ATC_suffix = CA02
| ATC_suffix = CA02
| PubChem = 31593
| PubChem = 31593
| DrugBank =  
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| C = 12 | H = 12 | N = 4 | O = 3
| DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 29299
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = YC42NRJ1ZD
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D02489
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 110
 
<!--Chemical data-->
| C=12 | H=12 | N=4 | O=3  
| molecular_weight = 260.249 g/mol
| molecular_weight = 260.249 g/mol
| bioavailability = High
| smiles = O=[N+]([O-])c1nccn1CC(=O)NCc2ccccc2
| protein_bound =
| InChI = 1/C12H12N4O3/c17-11(14-8-10-4-2-1-3-5-10)9-15-7-6-13-12(15)16(18)19/h1-7H,8-9H2,(H,14,17)
| metabolism = [[Liver|Hepatic]]
| InChIKey = CULUWZNBISUWAS-UHFFFAOYAD
| elimination_half-life = 12 hours
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| excretion = [[Kidney|Renal]] and fecal
| StdInChI = 1S/C12H12N4O3/c17-11(14-8-10-4-2-1-3-5-10)9-15-7-6-13-12(15)16(18)19/h1-7H,8-9H2,(H,14,17)
| pregnancy_AU =  <!-- A / B1 / B2 / B3 / C / D / X -->
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| pregnancy_US = <!-- A / B            / C / D / X -->
| StdInChIKey = CULUWZNBISUWAS-UHFFFAOYSA-N
| pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4  / S8 -->
| legal_CA =  <!--                             / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK =  <!-- GSL        / P      / POM / CD / Class A, B, C -->
| legal_US =  <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| legal_status =  
| routes_of_administration = Oral
}}
}}
'''Benznidazole''' ([[International Nonproprietary Name|INN]], marketed by [[Hoffman-La Roche]] under the trade names '''Rochagan''' and '''Radanil''') is an [[antiparasitic]] [[medication]] used in the treatment of [[Chagas disease]].
__NOTOC__
{{SI}}
{{CMG}}
== Overview ==
'''Benznidazole''' ([[International Nonproprietary Name|INN]], formerly marketed by [[Hoffman-La Roche]] under the trade names Rochagan and Radanil) is an [[antiparasitic]] [[medication]] used in the treatment of [[Chagas disease]]. Its mechanism of action is the production of [[Radical_(chemistry)|free radicals]], to which the ''[[Trypanosoma cruzi]]'' is particularly sensitive given its reduced detoxification capabilities.<ref name=urbina>{{cite web | url=http://www.fac.org.ar/fec/chagas2/llave/md5/md508/urbina.htm | title=Nuevas drogas para el tratamiento etiológico  de la Enfermedad de Chagas | accessdate=March 24, 2012 | author=Urbina, Julio A. | language=Spanish}}</ref> Roche donated the technology and rights to produce benznidazole to the Brazilian government.<ref>http://www.itg.be/evde/04_Chagas_diseasep12.htm</ref>
 
<!-- Society and culture -->
It is on the [[World Health Organization's List of Essential Medicines]], the most important medications needed in a basic [[health system]].<ref>{{cite web|title=WHO Model List of EssentialMedicines|url=http://apps.who.int/iris/bitstream/10665/93142/1/EML_18_eng.pdf?ua=1|work=World Health Organization|accessdate=22 April 2014|date=October 2013}}</ref>
 
==Medical uses==
Benznidazole has a significant activity during the acute phase of the disease, with a therapeutical success rate of up to 80%. Its curative capabilities during the chronic phase are, however, limited. Some studies have found parasitologic cure (a complete elimination of ''T. cruzi'' from the body) in pediatric and young patients during the early stage of the chronic phase, but overall failure rate in chronically infected individuals is typically above 80%.<ref name=urbina />
 
However, some studies indicate treatment with benznidazole in chronic patients, even if incapable of producing parasitologic cure, carries a significative reduction of occurrence of electrocardiographic changes and a delayed worsening of the clinical condition of the patient.<ref name=urbina />
 
Benznidazole has proven to be effective in the treatment of reactivated  ''T. cruzi''  infections caused by [[immunosuppression]], such as [[AIDS]] patients or those under immunosuppressive therapy related to organ transplants.<ref name=urbina />


==Side effects==
==Side effects==
The [[adverse drug reaction|side effect]]s most commonly associated with benznidazole therapy are [[rash]] and [[Gastrointestinal tract|gastrointestinal]] symptoms such as [[nausea]]. Rarely, [[peripheral neuropathy]] may present after prolonged treatment.
The [[adverse drug reaction|side effect]]s most commonly associated with benznidazole therapy are [[rash]] and [[Gastrointestinal tract|gastrointestinal]] symptoms such as [[nausea]]. Rarely, [[peripheral neuropathy]] may present after prolonged treatment.
==References==
<!--This article uses the Cite.php citation mechanism. If you would like more information on how to add references to this article, please see http://meta.wikimedia.org/wiki/Cite/Cite.php -->
{{Reflist|2}}


==External links==
==External links==
*{{pt icon}} {{cite web | title = Rochagan® <nowiki>[Patient Information]</nowiki> | url= http://www.roche.com.br/NR/rdonlyres/26F1D9BB-FE75-4CC4-8EFD-96CB85C374BD/603/Rochagan.pdf | format = [[PDF]] | publisher = [[Hoffmann-La Roche]] | accessdate = 2006-11-27}}
*{{cite web | title = Rochagan <nowiki>[Patient Information]</nowiki> | url= http://www.roche.com.br/NR/rdonlyres/26F1D9BB-FE75-4CC4-8EFD-96CB85C374BD/603/Rochagan.pdf | format = [[PDF]] | publisher = [[Hoffmann-La Roche]] | accessdate = 2006-11-27|language=pt}}
 
{{Excavata antiparasitics}}


[[Category:Drug]]
[[Category:Antiprotozoal agents]]
[[Category:Antiprotozoal agents]]
[[Category:Imidazoles]]
[[Category:Nitroimidazoles]]
[[Category:Nitro compounds]]
[[Category:Amides]]
[[Category:World Health Organization essential medicines]]


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Revision as of 15:11, 13 April 2015

Benznidazole
Clinical data
Trade namesRochagan, Radanil
AHFS/Drugs.comMicromedex Detailed Consumer Information
Routes of
administration		Oral
ATC code
Pharmacokinetic data
BioavailabilityHigh
MetabolismHepatic
Elimination half-life12 hours
ExcretionRenal and fecal
Identifiers
CAS Number
PubChem CID
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
FormulaC12H12N4O3
Molar mass260.249 g/mol
3D model (JSmol)
  (verify)

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

Overview

Benznidazole (INN, formerly marketed by Hoffman-La Roche under the trade names Rochagan and Radanil) is an antiparasitic medication used in the treatment of Chagas disease. Its mechanism of action is the production of free radicals, to which the Trypanosoma cruzi is particularly sensitive given its reduced detoxification capabilities.[1] Roche donated the technology and rights to produce benznidazole to the Brazilian government.[2]

It is on the World Health Organization's List of Essential Medicines, the most important medications needed in a basic health system.[3]

Medical uses

Benznidazole has a significant activity during the acute phase of the disease, with a therapeutical success rate of up to 80%. Its curative capabilities during the chronic phase are, however, limited. Some studies have found parasitologic cure (a complete elimination of T. cruzi from the body) in pediatric and young patients during the early stage of the chronic phase, but overall failure rate in chronically infected individuals is typically above 80%.[1]

However, some studies indicate treatment with benznidazole in chronic patients, even if incapable of producing parasitologic cure, carries a significative reduction of occurrence of electrocardiographic changes and a delayed worsening of the clinical condition of the patient.[1]

Benznidazole has proven to be effective in the treatment of reactivated T. cruzi infections caused by immunosuppression, such as AIDS patients or those under immunosuppressive therapy related to organ transplants.[1]

Side effects

The side effects most commonly associated with benznidazole therapy are rash and gastrointestinal symptoms such as nausea. Rarely, peripheral neuropathy may present after prolonged treatment.

References

  1. ↑ 1.0 1.1 1.2 1.3 Urbina, Julio A. "Nuevas drogas para el tratamiento etiológico de la Enfermedad de Chagas" (in Spanish). Retrieved March 24, 2012.
  2. ↑ http://www.itg.be/evde/04_Chagas_diseasep12.htm
  3. ↑ "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.

External links

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