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Chemical compound
Rosonabant![](//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/Rosonabant.svg/220px-Rosonabant.svg.png) |
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ATC code | |
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(±)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-(1-piperidinyl)-4,5-dihydro-1H-pyrazole-3-carboxamide
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Formula | C21H21Cl3N4O |
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Molar mass | 451.78 g·mol−1 |
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3D model (JSmol) | |
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O=C(NN1CCCCC1)\C4=N\N(c2ccc(Cl)cc2Cl)C(c3ccc(Cl)cc3)C4
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InChI=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) Key:WMMMJGKFKKBRQR-UHFFFAOYSA-N
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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.[1][2] Development of the drug for clinical use was apparently halted shortly after the related CB1 antagonist rimonabant was discontinued in November 2008,[when?] due to the reports of severe psychiatric adverse effects such as anxiety, depression, and suicidal ideation associated with it and with similarly acting agents.[3][4][5]
- ^ Janero DR, Makriyannis A (March 2009). "Cannabinoid receptor antagonists: pharmacological opportunities, clinical experience, and translational prognosis". Expert Opinion on Emerging Drugs. 14 (1): 43–65. doi:10.1517/14728210902736568. PMID 19249987. S2CID 74250986.
- ^ Vickers SP, Cheetham SC (2007). "Preclinical Developments in Antiobesity Drugs". In Kirkham TC, Cooper SJ (eds.). Appetite and Body Weight: Integrative Systems and the Development of Anti-Obesity Drugs. Academic Press. p. 325. ISBN 978-0-12-370633-1. Retrieved 12 May 2012.
- ^ Heal DJ, Gosden J, Smith SL (December 2009). "Regulatory challenges for new drugs to treat obesity and comorbid metabolic disorders". British Journal of Clinical Pharmacology. 68 (6): 861–874. doi:10.1111/j.1365-2125.2009.03549.x. PMC 2810797. PMID 20002080.
- ^ Lee HK, Choi EB, Pak CS (2009). "The current status and future perspectives of studies of cannabinoid receptor 1 antagonists as anti-obesity agents". Current Topics in Medicinal Chemistry. 9 (6): 482–503. doi:10.2174/156802609788897844. PMID 19689362. Archived from the original on 2013-05-22.
- ^ Moreira FA, Crippa JA (June 2009). "The psychiatric side-effects of rimonabant". Revista Brasileira de Psiquiatria. 31 (2): 145–153. doi:10.1590/S1516-44462009000200012. PMID 19578688.
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Phytocannabinoids (comparison) | Cannabibutols | |
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Cannabichromenes | |
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Cannabicyclols | |
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Cannabidiols | |
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Cannabielsoins | |
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Cannabigerols | |
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Cannabiphorols | |
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Cannabinols | |
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Cannabitriols | |
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Cannabivarins | |
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Delta-8-tetrahydrocannabinols | |
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Delta-9-tetrahydrocannabinols | |
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Delta-10-Tetrahydrocannabinols | |
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Miscellaneous cannabinoids | |
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Active metabolites | |
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Endocannabinoids | |
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Synthetic cannabinoid receptor agonists / neocannabinoids | Classical cannabinoids (dibenzopyrans) | |
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Non-classical cannabinoids | |
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Adamantoylindoles | |
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Benzimidazoles | |
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Benzoylindoles | |
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Cyclohexylphenols | |
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Eicosanoids | |
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Indazole-3- carboxamides | |
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Indole-3-carboxamides | |
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Indole-3-carboxylates | |
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Naphthoylindazoles | |
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Naphthoylindoles | |
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Naphthoylpyrroles | |
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Naphthylmethylindenes | |
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Naphthylmethylindoles | |
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Phenylacetylindoles | |
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Pyrazolecarboxamides | |
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Tetramethylcyclo- propanoylindazoles | |
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Tetramethylcyclo- propanoylindoles | |
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Others | |
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Allosteric CBRTooltip Cannabinoid receptor ligands | |
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Endocannabinoid enhancers (inactivation inhibitors) | |
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Anticannabinoids (antagonists/inverse agonists/antibodies) | |
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Receptor (ligands) | CB1Tooltip Cannabinoid receptor type 1 | Agonists (abridged, full list) | |
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Inverse agonists | |
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Antagonists | |
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CB2Tooltip Cannabinoid receptor type 2 | Agonists |
- 2-AG
- 2-AGE (noladin ether)
- 3,3'-Diindolylmethane
- 4-O-Methylhonokiol
- α-Amyrin · β-Amyrin
- A-796,260
- A-834,735
- A-836,339
- AM-1172
- AM-1221
- AM-1235
- AM-1241
- AM-2232
- Anandamide
- AZ-11713908
- Cannabinol
- Caryophyllene
- CB-13
- CBS-0550
- CP 55,940
- GW-405,833 (L-768,242)
- GW-842,166X
- HU-308
- JTE 7-31
- JWH-007
- JWH-015
- JWH-018
- JWH-73
- JWH-133
- L-759,633
- L-759,656
- Lenabasum (anabasum)
- Magnolol
- MDA-19
- Nabitan
- NADA
- Olorinab (APD-371)
- PF-03550096
- S-444,823
- SER-601
- Serinolamide A
- UR-144
- Tedalinab
- THC (dronabinol)
- THCV
- Tetrahydromagnolol
- Virodhamine
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Antagonists | |
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NAGly (GPR18) | |
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GPR55 | |
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GPR119 | |
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Transporter (modulators) | eCBTsTooltip Endocannabinoid transporter | |
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Enzyme (modulators) | |
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Others |
- Others: 2-PG (directly potentiates activity of 2-AG at CB1 receptor)
- ARN-272 (FAAH-like anandamide transporter inhibitor)
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