From Wikipedia, the free encyclopedia
Chemical compound
Rosonabant
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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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PubChem
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CompTox Dashboard (
EPA) | |
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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]
See also
References
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^ 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.
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^ 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.
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^ 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.
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^ 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.
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^ 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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Hydrocarbons | |
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Indazole carboxamides | |
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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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Pyrrolobenzoxazines | |
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Quinolinyl esters | |
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Tetramethylcyclo- propanoylindazoles | |
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Tetramethylcyclo- propanoylindoles | |
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Tetramethylcyclo- propylindoles | |
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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 |
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2-AG
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2-AGE (noladin ether)
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3,3'-Diindolylmethane
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4-O-Methylhonokiol
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α-Amyrin · β-Amyrin
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A-796,260
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A-834,735
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A-836,339
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AM-1172
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AM-1221
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AM-1235
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AM-1241
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AM-2232
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Anandamide
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AZ-11713908
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Cannabinol
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Caryophyllene
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CB-13
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CBS-0550
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CP 55,940
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GW-405,833 (L-768,242)
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GW-842,166X
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HU-308
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JTE 7-31
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JWH-007
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JWH-015
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JWH-018
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JWH-73
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JWH-133
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L-759,633
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L-759,656
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Lenabasum (anabasum)
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Magnolol
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MDA-19
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Nabitan
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NADA
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Olorinab (APD-371)
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PF-03550096
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S-444,823
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SER-601
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Serinolamide A
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UR-144
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Tedalinab
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THC (dronabinol)
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THCV
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Tetrahydromagnolol
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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)
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ARN-272 (FAAH-like anandamide transporter inhibitor)
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