View source for Chemistry:Rosonabant

{{Short description|Chemical compound}}
{{Drugbox
| IUPAC_name               = (±)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-''N''-(1-piperidinyl)-4,5-dihydro-1''H''-pyrazole-3-carboxamide
| image                    = Rosonabant.svg
| CAS_number               = 861151-12-4
| CAS_supplemental         = 
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7X5RY2T485
| ATC_prefix               = None
| ATC_suffix               = 
| PubChem                  = 11316914
| ChemSpiderID             = 9491881
| C=21 | H=21 | Cl=3 | N=4 | O=1
| smiles                   = O=C(NN1CCCCC1)\C4=N\N(c2ccc(Cl)cc2Cl)C(c3ccc(Cl)cc3)C4
| StdInChI                 = 1S/C21H21Cl3N4O/c22-15-6-4-14(5-7-15)20-13-18(21(29)26-27-10-2-1-3-11-27)25-28(20)19-9-8-16(23)12-17(19)24/h4-9,12,20H,1-3,10-11,13H2,(H,26,29)
| StdInChIKey              = WMMMJGKFKKBRQR-UHFFFAOYSA-N
| bioavailability          = 
| protein_bound            = 
| metabolism               = 
| elimination_half-life    = 
| excretion                = 
| pregnancy_category       = 
| legal_status             = 
| routes_of_administration = 
}}

'''Rosonabant''' (INN; '''E-6776''') is a drug acting as a CB<sub>1</sub> receptor [[Biology:Receptor antagonist|antagonist]]/[[Chemistry:Inverse agonist|inverse agonist]] that was under investigation by Esteve as an appetite suppressant for the treatment of obesity.<ref name="pmid19249987">{{cite journal | vauthors = Janero DR, Makriyannis A | title = Cannabinoid receptor antagonists: pharmacological opportunities, clinical experience, and translational prognosis | journal = Expert Opinion on Emerging Drugs | volume = 14 | issue = 1 | pages = 43–65 | date = March 2009 | pmid = 19249987 | doi = 10.1517/14728210902736568 |  s2cid = 74250986 }}</ref><ref name="KirkhamCooper2007">{{cite book | vauthors = Vickers SP, Cheetham SC | chapter = Preclinical Developments in Antiobesity Drugs | veditors = Kirkham TC, Cooper SJ | title = Appetite and Body Weight: Integrative Systems and the Development of Anti-Obesity Drugs | chapter-url = https://books.google.com/books?id=YO3BUp3nicMC&pg=PA325 | access-date = 12 May 2012 | year = 2007 | publisher = Academic Press | isbn = 978-0-12-370633-1 | page = 325}}</ref> Development of the drug for clinical use was apparently halted shortly after the related CB<sub>1</sub> antagonist [[Chemistry:Rimonabant|rimonabant]] was discontinued in November 2008,{{when|date=October 2019}} due to the reports of severe psychiatric [[Medicine:Adverse effect|adverse effect]]s such as [[Medicine:Anxiety|anxiety]], depression, and [[Medicine:Suicidal ideation|suicidal ideation]] associated with it and with similarly acting agents.<ref name="pmid20002080">{{cite journal | vauthors = Heal DJ, Gosden J, Smith SL | title = Regulatory challenges for new drugs to treat obesity and comorbid metabolic disorders | journal = British Journal of Clinical Pharmacology | volume = 68 | issue = 6 | pages = 861–874 | date = December 2009 | pmid = 20002080 | pmc = 2810797 | doi = 10.1111/j.1365-2125.2009.03549.x }}</ref><ref name="pmid19689362">{{cite journal | vauthors = Lee HK, Choi EB, Pak CS | title = The current status and future perspectives of studies of cannabinoid receptor 1 antagonists as anti-obesity agents | journal = Current Topics in Medicinal Chemistry | volume = 9 | issue = 6 | pages = 482–503 | year = 2009 | pmid = 19689362 | doi = 10.2174/156802609788897844 | url = http://www.benthamdirect.org/pages/content.php?CTMC/2009/00000009/00000006/0003R.SGM | url-status = dead | archive-url = https://web.archive.org/web/20130522160822/http://www.benthamdirect.org/pages/content.php?CTMC%2F2009%2F00000009%2F00000006%2F0003R.SGM | archive-date = 2013-05-22 }}</ref><ref>{{cite journal | vauthors = Moreira FA, Crippa JA | title = The psychiatric side-effects of rimonabant | journal = Revista Brasileira de Psiquiatria | volume = 31 | issue = 2 | pages = 145–153 | date = June 2009 | pmid = 19578688 | doi = 10.1590/S1516-44462009000200012 | doi-access = free }}</ref>

==See also==
*[[Chemistry:Cannabinoid receptor antagonist|Cannabinoid receptor antagonist]]

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

{{Anorectics}}
{{Cannabinoids}}
{{Cannabinoidergics}}

[[Category:Anorectics]]
[[Category:Cannabinoids]]
[[Category:Carboxamides]]
[[Category:CB1 receptor antagonists]]
[[Category:Chlorobenzenes]]
[[Category:Piperidines]]
[[Category:Pyrazolines]]



{{Sourceattribution|Rosonabant}}