rosonabant

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = (±)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-(1-piperidinyl)-4,5-dihydro-1H-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 =

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| pregnancy_category =

| legal_status =

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}}

Rosonabant (INN; E-6776) is a drug acting as a CB₁ receptor antagonist/inverse agonist that was under investigation by Esteve as an appetite suppressant for the treatment of obesity.{{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 | author-link2 = Alexandros Makriyannis | s2cid = 74250986 }}{{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}} Development of the drug for clinical use was apparently halted shortly after the related CB₁ antagonist rimonabant was discontinued in November 2008,{{when|date=October 2019}} due to the reports of severe psychiatric adverse effects such as anxiety, depression, and suicidal ideation associated with it and with similarly acting agents.{{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 }}{{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 | url-access = subscription }}{{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 }}