taranabant

{{Short description|Chemical compound}}

{{cs1 config|name-list-style=vanc}}

{{Drugbox

| Watchedfields = changed

| verifiedrevid = 448081332

| IUPAC_name = N-[(2S,3S)-4-(4-chlorophenyl)-3-(3-cyanophenyl)-2-butanyl]-2-methyl-2-{[5-(trifluoromethyl)-2-pyridinyl]oxy}propanamide

| image = Taranabant.svg

| alt = Skeletal formula of taranabant

| width = 250

| image2 = Taranabant 3D spacefill.png

| alt2 = Space-filling model of the taranabant molecule

| tradename =

| pregnancy_AU =

| pregnancy_US =

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| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_status = Investigational (failed)

| routes_of_administration = Oral

| bioavailability =

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 701977-09-5

| ATC_prefix = A08

| ATC_suffix = AX

| PubChem = 11226090

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = X9U622S114

| ChemSpiderID = 9401143

| chemical_formula =

| C=27 | H=25 | Cl=1 | F=3 | N=3 | O=2

| smiles = 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

| StdInChI = 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

| StdInChIKey = QLYKJCMUNUWAGO-GAJHUEQPSA-N

}}

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.{{cite journal | vauthors = Armstrong HE, Galka A, Lin LS, Lanza TJ Jr, Jewell JP, Shah SK | display-authors = etal | year = 2007 | title = Substituted acyclic sulfonamides as human cannabinoid-1 receptor inverse agonists | journal = Bioorganic & Medicinal Chemistry Letters | volume = 17 | issue = 8| pages = 2184–7 | doi = 10.1016/j.bmcl.2007.01.087 | pmid = 17293109 }}{{cite journal | vauthors = Fong TM, Guan XM, Marsh DJ, Shen CP, Stribling DS, Rosko KM | display-authors = etal | date = Jun 2007 | title = 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 = Journal of Pharmacology and Experimental Therapeutics | volume = 321 | issue = 3| pages = 1013–22 | doi = 10.1124/jpet.106.118737 | pmid = 17327489 | s2cid = 20001781 }} It was developed by Merck & Co.

In October 2008, Merck stopped its phase III clinical trials with the drug due to high level of central nervous system side effects, mainly depression and anxiety.{{cite web |url=http://www.merck.com/newsroom/press_releases/research_and_development/2008_1002.html |title=Press release by Merck |access-date=4 October 2008}}{{cite journal |vauthors=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 |title=A clinical trial assessing the safety and efficacy of taranabant, a CB1R inverse agonist, in obese and overweight patients: a high-dose study |journal=International Journal of Obesity |volume=34 |issue=5 |pages=919–35 |date=May 2010 |pmid=20157323 |doi=10.1038/ijo.2010.21 |doi-access= |s2cid=6769554 }}{{cite journal |vauthors=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 |title=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 |journal=Diabetes, Obesity & Metabolism |volume=12 |issue=6 |pages=517–31 |date=June 2010 |pmid=20518807 |doi=10.1111/j.1463-1326.2009.01188.x |s2cid=23886192 |doi-access= }}{{cite journal |vauthors=Proietto J, Rissanen A, Harp JB, Erondu N, Yu Q, Suryawanshi S, Jones ME, Johnson-Levonas AO, Heymsfield SB, Kaufman KD, Amatruda JM |title=A clinical trial assessing the safety and efficacy of the CB1R inverse agonist taranabant in obese and overweight patients: low-dose study |journal=International Journal of Obesity |volume=34 |issue=8 |pages=1243–54 |date=August 2010 |pmid=20212496 |doi=10.1038/ijo.2010.38 |doi-access= |s2cid=23352608 }}