Taranabant (MK-0364)

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 319568

CAS#: 701977-09-5

Description: Taranabant, aslo known as MK-0364, a cannabinoid receptor type 1 inverse agonist being investigated as a potential treatment for obesity due to its anorectic effects. Taranabant reduces abdominal pain and increases intestinal transit in mice. 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 side effects, mainly depression and anxiety.

Chemical Structure

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Taranabant (MK-0364)
CAS# 701977-09-5
Instruction

Theoretical Analysis

MedKoo Cat#: 319568
Name: Taranabant (MK-0364)
CAS#: 701977-09-5
Chemical Formula: C27H25ClF3N3O2
Exact Mass: 515.16
Molecular Weight: 515.960
Elemental Analysis: C, 62.85; H, 4.88; Cl, 6.87; F, 11.05; N, 8.14; O, 6.20

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Synonym: MK-0364, MK 0364, MK0364, Taranabant

IUPAC/Chemical Name: N-((2S,3S)-4-(4-chlorophenyl)-3-(3-cyanophenyl)butan-2-yl)-2-methyl-2-((5-(trifluoromethyl)pyridin-2-yl)oxy)propanamide

InChi Key: QLYKJCMUNUWAGO-GAJHUEQPSA-N

InChi Code: 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

SMILES Code: CC(OC1=NC=C(C(F)(F)F)C=C1)(C)C(N[C@H]([C@H](C2=CC=CC(C#N)=C2)CC3=CC=C(Cl)C=C3)C)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 515.96 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Fichna J, Sibaev A, Sałaga M, Sobczak M, Storr M. The cannabinoid-1 receptor inverse agonist taranabant reduces abdominal pain and increases intestinal transit in mice. Neurogastroenterol Motil. 2013 Aug;25(8):e550-9. doi: 10.1111/nmo.12158. Epub 2013 May 21. PubMed PMID: 23692073.

2: Schoedel KA, Addy C, Chakraborty B, Rosko K, Dunbar S, Maes A, Chen N, Stoch SA, Wagner J, Chodakewitz J, Sellers EM. Human abuse potential and cognitive effects of taranabant, a cannabinoid 1 receptor inverse agonist: a randomized, double-blind, placebo- and active-controlled, crossover study in recreational polydrug users. J Clin Psychopharmacol. 2012 Aug;32(4):492-502. doi: 10.1097/JCP.0b013e31825d380d. PubMed PMID: 22722508.

3: Karanam B, Addy C, Bateman T, Reddy VB, Li S, Dean D, Li H, Jones A, Schenk D, Zhang AS, Braun M, Freeman A, Flach S, Stoch A, Chodakewitz J, Wagner JA, Kumar S. Metabolism and excretion of [14C]taranabant, a cannabinoid-1 inverse agonist, in humans. Xenobiotica. 2010 Oct;40(10):691-700. doi: 10.3109/00498254.2010.509820. PubMed PMID: 20722472.

4: Kopka IE, Lin LS, Jewell JP, Lanza TJ, Fong TM, Shen CP, Lao ZJ, Ha S, Castonguay LG, Van der Ploeg L, Goulet MT, Hagmann WK. Synthesis and cannabinoid-1 receptor binding affinity of conformationally constrained analogs of taranabant. Bioorg Med Chem Lett. 2010 Aug 15;20(16):4757-61. doi: 10.1016/j.bmcl.2010.06.127. Epub 2010 Jul 1. PubMed PMID: 20643546.

5: Reddy VB, Doss GA, Karanam BV, Samuel K, Lanza TJ Jr, Lin LS, Yu NX, Zhang AS, Raab CE, Stearns RA, Kumar S. In vitro and in vivo metabolism of a novel cannabinoid-1 receptor inverse agonist, taranabant, in rats and monkeys. Xenobiotica. 2010 Sep;40(9):650-62. doi: 10.3109/00498254.2010.501117. PubMed PMID: 20608842.

6: Li XS, Nielsen J, Cirincione B, Li H, Addy C, Wagner J, Hartford A, Erondu N, Gantz I, Morgan J, Stone J. Development of a population pharmacokinetic model for taranabant, a cannibinoid-1 receptor inverse agonist. AAPS J. 2010 Dec;12(4):537-47. doi: 10.1208/s12248-010-9212-2. Epub 2010 Jun 26. PubMed PMID: 20582578; PubMed Central PMCID: PMC2976981.

7: 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. 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 Obes Metab. 2010 Jun;12(6):517-31. doi: 10.1111/j.1463-1326.2009.01188.x. PubMed PMID: 20518807.

8: Koch L. Obesity: Taranabant no longer developed as an antiobesity agent. Nat Rev Endocrinol. 2010 Jun;6(6):300. doi: 10.1038/nrendo.2010.56. PubMed PMID: 20518102.

9: Wadden TA, Fujioka K, Toubro S, Gantz I, Erondu NE, Chen M, Suryawanshi S, Carofano W, Johnson-Levonas AO, Shapiro DR, Kaufman KD, Heymsfield SB, Amatruda JM. A randomized trial of lifestyle modification and taranabant for maintaining weight loss achieved with a low-calorie diet. Obesity (Silver Spring). 2010 Dec;18(12):2301-10. doi: 10.1038/oby.2010.67. Epub 2010 Apr 8. PubMed PMID: 20379151.

10: Proietto J, Rissanen A, Harp JB, Erondu N, Yu Q, Suryawanshi S, Jones ME, Johnson-Levonas AO, Heymsfield SB, Kaufman KD, Amatruda JM. A clinical trial assessing the safety and efficacy of the CB1R inverse agonist taranabant in obese and overweight patients: low-dose study. Int J Obes (Lond). 2010 Aug;34(8):1243-54. doi: 10.1038/ijo.2010.38. Epub 2010 Mar 9. PubMed PMID: 20212496.

11: Morrison MF, Ceesay P, Gantz I, Kaufman KD, Lines CR. Randomized, controlled, double-blind trial of taranabant for smoking cessation. Psychopharmacology (Berl). 2010 Apr;209(3):245-53. doi: 10.1007/s00213-010-1790-2. Epub 2010 Feb 27. PubMed PMID: 20191360.

12: 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. A clinical trial assessing the safety and efficacy of taranabant, a CB1R inverse agonist, in obese and overweight patients: a high-dose study. Int J Obes (Lond). 2010 May;34(5):919-35. doi: 10.1038/ijo.2010.21. Epub 2010 Feb 16. PubMed PMID: 20157323.

13: Martín-García E, Burokas A, Martín M, Berrendero F, Rubí B, Kiesselbach C, Heyne A, Gispert JD, Millán O, Maldonado R. Central and peripheral consequences of the chronic blockade of CB1 cannabinoid receptor with rimonabant or taranabant. J Neurochem. 2010 Mar;112(5):1338-13351. doi: 10.1111/j.1471-4159.2009.06549.x. Epub 2009 Dec 17. PubMed PMID: 20028452.

14: Addy C, Jumes P, Rosko K, Li S, Li H, Maes A, Johnson-Levonas AO, Chodakewitz J, Stoch SA, Wagner JA. Pharmacokinetics, safety, and tolerability of phentermine in healthy participants receiving taranabant, a novel cannabinoid-1 receptor (CB1R) inverse agonist. J Clin Pharmacol. 2009 Oct;49(10):1228-38. doi: 10.1177/0091270009341651. PubMed PMID: 19783715.

15: Denker AE, Morelli G, Vessey LK, Li S, Yuan J, Dunbar S, Lewis NM, Taggart W, Wagner JA. Pharmacokinetics of digoxin in healthy subjects receiving taranabant, a novel cannabinoid-1 receptor inverse agonist. Adv Ther. 2009 Feb;26(2):230-40. doi: 10.1007/s12325-009-0003-z. Epub 2009 Feb 14. PubMed PMID: 19219408.

16: Chen YW, Liu Y, Novak T, Frey L, Campos K, Klapars A, Chen CY, Phenix B. Identification and structural elucidation of process impurities generated in the end-game synthesis of taranabant (MK-0364) via cyanuric chloride. J Pharm Biomed Anal. 2009 Apr 5;49(3):702-10. doi: 10.1016/j.jpba.2009.01.003. Epub 2009 Jan 9. PubMed PMID: 19188037.

17: Schwartz JI, Dunbar S, Yuan J, Li S, Gipson A, Rosko K, Johnson-Levonas AO, Lasseter KC, Addy C, Stoch AS, Wagner JA. Influence of taranabant, a cannabinoid-1 receptor inverse agonist, on pharmacokinetics and pharmacodynamics of warfarin. Adv Ther. 2008 Nov;25(11):1175-90. doi: 10.1007/s12325-008-0116-9. PubMed PMID: 18989636.

18: Schwartz JI, Dunbar S, Yuan J, Li S, Miller DL, Rosko K, Johnson-Levonas AO, Lasseter KC, Wagner JA. Influence of taranabant, an orally active, highly selective, potent cannabinoid-1 receptor (CB1R) inverse agonist, on ethinyl estradiol and norelgestromin plasma pharmacokinetics. J Clin Pharmacol. 2009 Jan;49(1):72-9. doi: 10.1177/0091270008325930. Epub 2008 Oct 20. PubMed PMID: 18936284.

19: Fremming BA, Boyd ST. Taranabant, a novel cannabinoid type 1 receptor inverse agonist. Curr Opin Investig Drugs. 2008 Oct;9(10):1116-29. Review. PubMed PMID: 18821475.

20: Hagmann WK. The discovery of taranabant, a selective cannabinoid-1 receptor inverse agonist for the treatment of obesity. Arch Pharm (Weinheim). 2008 Jul;341(7):405-11. doi: 10.1002/ardp.200700255. Review. PubMed PMID: 18574849.