Taranabant
Chemical compound
Taranabant Routes of administration Oral ATC code Legal status
N -[(2S ,3S )-4-(4-chlorophenyl)-3-(3-cyanophenyl)-2-butanyl]-2-methyl-2-{[5-(trifluoromethyl)-2-pyridinyl]oxy}propanamide
CAS Number PubChem CID ChemSpider UNII CompTox Dashboard (EPA ) ECHA InfoCard 100.207.983 Formula C 27 H 25 Cl F 3 N 3 O 2 Molar mass 515.96 g·mol−1 3D model (JSmol )
C[C@@H]([C@@H](CC1=CC=C(C=C1)Cl)C2=CC=CC(=C2)C#N)NC(=O)C(C)(C)OC3=NC=C(C=C3)C(F)(F)F
InChI=1S/C27H25ClF3N3O2/c1-17(34-25(35)26(2,3)36-24-12-9-21(16-33-24)27(29,30)31)23(14-18-7-10-22(28)11-8-18)20-6-4-5-19(13-20)15-32/h4-13,16-17,23H,14H2,1-3H3,(H,34,35)/t17-,23+/m0/s1
Key:QLYKJCMUNUWAGO-GAJHUEQPSA-N
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Taranabant (codenamed MK-0364 ) is a cannabinoid receptor type 1 (CB1 ) inverse agonist that was investigated as a potential treatment for obesity due to its anorectic effects.[1] [2] It was discovered by Merck & Co.
In October 2008, Merck has stopped its phase III clinical trials with the drugs due to high level of central nervous system side effects, mainly depression and anxiety .[3] [4] [5] [6]
See also
References
^ Armstrong HE, Galka A, Lin LS, Lanza TJ Jr, Jewell JP, Shah SK, et al. (2007). "Substituted acyclic sulfonamides as human cannabinoid-1 receptor inverse agonists". Bioorganic & Medicinal Chemistry Letters . 17 (8): 2184–7. doi :10.1016/j.bmcl.2007.01.087 . PMID 17293109 .
^ Fong TM, Guan XM, Marsh DJ, Shen CP, Stribling DS, Rosko KM, et al. (Jun 2007). "Antiobesity efficacy of a novel cannabinoid-1 receptor inverse agonist, N-[(1S,2S)-3-(4-chlorophenyl)-2-(3-cyanophenyl)-1-methylpropyl]-2-methyl-2-5-(trifluoromethyl)pyridin-2-yl]oxy]propanamide (MK-0364), in rodents". Journal of Pharmacology and Experimental Therapeutics . 321 (3): 1013–22. doi :10.1124/jpet.106.118737 . PMID 17327489 . S2CID 20001781 .
^ "Press release by Merck" . Retrieved 4 October 2008 .
^ Aronne LJ, Tonstad S, Moreno M, Gantz I, Erondu N, Suryawanshi S, Molony C, Sieberts S, Nayee J, Meehan AG, Shapiro D, Heymsfield SB, Kaufman KD, Amatruda JM (May 2010). "A clinical trial assessing the safety and efficacy of taranabant, a CB1R inverse agonist, in obese and overweight patients: a high-dose study". International Journal of Obesity . 34 (5): 919–35. doi :10.1038/ijo.2010.21 . PMID 20157323 . S2CID 6769554 .
^ Kipnes MS, Hollander P, Fujioka K, Gantz I, Seck T, Erondu N, Shentu Y, Lu K, Suryawanshi S, Chou M, Johnson-Levonas AO, Heymsfield SB, Shapiro D, Kaufman KD, Amatruda JM (June 2010). "A one-year study to assess the safety and efficacy of the CB1R inverse agonist taranabant in overweight and obese patients with type 2 diabetes". Diabetes, Obesity & Metabolism . 12 (6): 517–31. doi :10.1111/j.1463-1326.2009.01188.x . PMID 20518807 . S2CID 23886192 .
^ Proietto J, Rissanen A, Harp JB, Erondu N, Yu Q, Suryawanshi S, Jones ME, Johnson-Levonas AO, Heymsfield SB, Kaufman KD, Amatruda JM (August 2010). "A clinical trial assessing the safety and efficacy of the CB1R inverse agonist taranabant in obese and overweight patients: low-dose study". International Journal of Obesity . 34 (8): 1243–54. doi :10.1038/ijo.2010.38 . PMID 20212496 . S2CID 23352608 .
Phytocannabinoids (comparison )
Cannabibutols Cannabichromenes Cannabicyclols Cannabidiols Cannabielsoins Cannabigerols Cannabiphorols Cannabinols Cannabitriols Cannabivarins Delta-8-tetrahydrocannabinols Delta-9-tetrahydrocannabinols Delta-10-Tetrahydrocannabinols Miscellaneous cannabinoids Active metabolites
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Allosteric CBR Tooltip Cannabinoid receptor ligands Endocannabinoid enhancers (inactivation inhibitors) Anticannabinoids (antagonists/inverse agonists/antibodies)
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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)
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MDA-19
Nabitan
NADA
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PF-03550096
S-444,823
SER-601
Serinolamide A
UR-144
Tedalinab
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NAGly (GPR18 )
GPR55
GPR119
Transporter (modulators )
eCBTs Tooltip Endocannabinoid transporter
Enzyme (modulators )
Others
Others: 2-PG (directly potentiates activity of 2-AG at CB1 receptor)
ARN-272 (FAAH-like anandamide transporter inhibitor)