TaranabantCAS# 701977-09-5 |
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Quality Control & MSDS
3D structure
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| Cas No. | 701977-09-5 | SDF | Download SDF |
| PubChem ID | 11226090 | Appearance | Powder |
| Formula | C27H25ClF3N3O2 | M.Wt | 515.97 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Synonyms | MK-0364 | ||
| Solubility | DMSO : ≥ 42 mg/mL (81.40 mM) *"≥" means soluble, but saturation unknown. | ||
| Chemical Name | N-[(2S,3S)-4-(4-chlorophenyl)-3-(3-cyanophenyl)butan-2-yl]-2-methyl-2-[5-(trifluoromethyl)pyridin-2-yl]oxypropanamide | ||
| SMILES | CC(C(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 | ||
| Standard InChIKey | QLYKJCMUNUWAGO-GAJHUEQPSA-N | ||
| Standard InChI | 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 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Taranabant is a highly potent and selective cannabinoid 1 (CB1) receptor inverse agonist that inhibits the binding and functional activity of various agonists, with a binding Ki of 0.13 nM for the human CB1R in vitro.In Vitro:Taranabant (MK-0364) binds to human or rat CB1R with an IC50 of 0.3 and 0.4 nM, respectively, corresponding to a Ki value of 0.13 and 0.27 nM, respectively. Taranabant binds to the human or rat CB2R with an IC50 value of 290 and 470 nM, respectively, corresponding to a Ki value of 170 and 310 nM, respectively. The selectivity ratio of CB1R over CB2R is approximately 1000-fold[1]. Taranabant (MK-0364) is a novel, acyclic cannabinoid-1 receptor inverse agonist for the treatment of obesity. IC50s of Taranabant for CB1R and CB2R by substituted amides is 0.3±0.1 nM, and 290±60 nM, respectively. Taranabant is a CB1R inverse agonist with minimal potential for covalent protein binding. Taranabant is an exceptionally potent and selective (900-fold over CB2) CB1R inverse agonist with >500-fold improvement in affinity over the original lead. In a functional assay of cyclic-AMP production, Taranabant is determined to be an inverse agonist (EC50=2.4±1.4 nM)[2].In Vivo:Taranabant (MK-0364) dose-dependently inhibits 2 h and overnight food intake as well as overnight gains in body weight in C57BL/6N mice. At the 1- and 3-mg/kg doses (p.o.), Taranabant significantly inhibits 2-h food intake (36 and 69% reductions, respectively; P<0.05 and P<0.00001, respectively) and overnight food intake (13 and 40% reductions, respectively; P<0.05 and P<0.00001, respectively) as well as overnight gains in body weight (48 and 165% reductions, respectively; P<0.01 and P<0.00001, respectively). Taranabant dose-dependently inhibits food intake and weight gain, with an acute minimum effective dose of 1 mg/kg in diet-induced obese (DIO) rats[1]. Taranabant (MK-0364) has a good pharmacokinetic profile in three species (rat, 1 mg/kg iv, 2 mg/kg po, F=74%, t1/2=2.7 h; dog, 0.2 mg/kg iv, 0.4 mg/kg po, F=31%; t1/2=14 h; rhesus monkey, 0.2 mg/kg iv, 0.4 mg/kg po, F=31%, t1/2=3.6 h) and good brain exposure (1 mg/kg iv, brain and plasma concentrations of 0.11 and 0.18 μM at 1 h, respectively)[2]. References: | |||||
Taranabant Dilution Calculator
Taranabant Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 1.9381 mL | 9.6905 mL | 19.381 mL | 38.7619 mL | 48.4524 mL |
| 5 mM | 0.3876 mL | 1.9381 mL | 3.8762 mL | 7.7524 mL | 9.6905 mL |
| 10 mM | 0.1938 mL | 0.969 mL | 1.9381 mL | 3.8762 mL | 4.8452 mL |
| 50 mM | 0.0388 mL | 0.1938 mL | 0.3876 mL | 0.7752 mL | 0.969 mL |
| 100 mM | 0.0194 mL | 0.0969 mL | 0.1938 mL | 0.3876 mL | 0.4845 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Taranabant is a Novel, Acyclic Cannabinoid-1 Receptor Inverse Agonist （CB1 Antagonist）for the Treatment of Obesity.
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Synthesis and cannabinoid-1 receptor binding affinity of conformationally constrained analogs of taranabant.[Pubmed:20643546]
Bioorg Med Chem Lett. 2010 Aug 15;20(16):4757-61.
The design, synthesis, and binding activity of ring constrained analogs of the acyclic cannabinoid-1 receptor (CB1R) inverse agonist Taranabant 1 are described. The initial inspiration for these Taranabant derivatives was its conformation 1a, determined by (1)H NMR, X-ray, and molecular modeling. The constrained analogs were all much less potent than their acyclic parent structure. The results obtained are discussed in the context of a predicted binding of 1 to a homology model of CB1R.
The cannabinoid-1 receptor inverse agonist taranabant reduces abdominal pain and increases intestinal transit in mice.[Pubmed:23692073]
Neurogastroenterol Motil. 2013 Aug;25(8):e550-9.
BACKGROUND: Constipation-predominant irritable bowel syndrome (IBS-C) is a common functional gastrointestinal (GI) disorder with abdominal pain and decreased motility. Current treatments of IBS-C are insufficient. The aim of this study was to evaluate the potential application of Taranabant, a cannabinoid type 1 (CB1) inverse agonist using mouse models mimicking the symptoms of IBS-C. METHODS: Changes in intestinal contractile activity were studied in vitro, using isolated mouse ileum and colon and intracellular recordings. In vivo, whole gastrointestinal transit (WGT) and fecal pellet output (FPO) were measured under standard conditions and with pharmacologically delayed GI transit. The antinociceptive effect was evaluated in mustard oil- and acetic acid-induced models of visceral pain. Forced swimming and tail suspension tests were performed and locomotor activity was measured to evaluate potential central side effects. KEY RESULTS: In vitro, Taranabant (10(-10) -10(-7) mol L(-1)) increased contractile responses in mouse ileum and blocked the effect of the CB agonist WIN 55,212-2. Taranabant had no effect on the amplitude of electrical field stimulation (EFS)-evoked junction potentials. In vivo, Taranabant (0.1-3 mg kg(-1), i.p. and 3 mg kg(-1), p.o.) increased WGT and FPO in mice and reversed experimental constipation. The effect of Taranabant was absent in CB1(-/-) mice. Taranabant significantly decreased the number of pain-related behaviors in animal models. At the doses tested, Taranabant did not display mood-related adverse side effects typical for CB1 receptor inverse agonists. CONCLUSIONS & INFERENCES: Taranabant improved symptoms related to slow GI motility and abdominal pain and may become an attractive template in the development of novel therapeutics targeting IBS-C.
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.[Pubmed:22722508]
J Clin Psychopharmacol. 2012 Aug;32(4):492-502.
INTRODUCTION: Taranabant is a cannabinoid 1 receptor inverse agonist that was in development for treatment of obesity. Because of central nervous system effects, the study was performed to assess the abuse potential and cognitive effects of Taranabant in recreational polydrug users compared with phentermine, dronabinol, and placebo. METHODS: Stimulant- and cannabis-experienced polydrug users (N = 30) were randomized in a double-blind crossover study to receive Taranabant 2, 4, 10, and 20 mg; phentermine 45 and 90 mg; dronabinol 20 mg; and placebo. Subjective and neurocognitive measures were administered for 24 hours, and peak/peak change from baseline effects were analyzed using a linear mixed-effects model. RESULTS: Phentermine 45 and 90 mg showed abuse-related subjective effects versus placebo, including drug liking, overall drug liking, and other positive/stimulant effects, whereas dronabinol 20 mg showed abuse-related positive, cannabis-like, and sedative effects. Taranabant was not significantly different from placebo on most of the subjective measures other than negative/dysphoric effects at the highest dose, and its effects were significantly less pronounced relative to phentermine and dronabinol on most measures. Phentermine improved cognitive/motor performance and dronabinol impaired motor/cognitive performance on some measures, whereas Taranabant 4 and 20 mg had minor impairment effects on manual tracking. CONCLUSIONS: The phentermine and dronabinol results demonstrate the validity and sensitivity of the study. Taranabant did not consistently show stimulant/cannabis-like effects or abuse potential in recreational polydrug users, indicating that cannabinoid 1 receptor inverse agonists/antagonists are unlikely to be recreationally abused.
Metabolism and excretion of [14C]taranabant, a cannabinoid-1 inverse agonist, in humans.[Pubmed:20722472]
Xenobiotica. 2010 Oct;40(10):691-700.
Taranabant (N-[(1S,2S)-3-(4-chlorophenyl)-2-(3-cyanophenyl)-1-methylpropyl]-2-methyl-2-{[5-( trifluoromethyl)pyridin-2-yl]oxy}propanamide or MK-0364) is an orally active inverse agonist of the cannabinoid 1 (CB-1) receptor that was under development for the management of obesity. The metabolism and excretion of Taranabant were investigated following a single oral dose of 5 mg/201 muCi [14C]Taranabant to six healthy male subjects. The overall excretion recovery of the administered radioactivity was nearly quantitative ( approximately 92%), with the majority of the dose ( approximately 87%) excreted into faeces and a much smaller fraction ( approximately 5%) into urine. Taranabant was absorbed rapidly, with C(max) of radioactivity attained at 1-2-h postdose. The parent compound and its monohydroxylated metabolite, M1, were the major radioactive components circulating in plasma and comprised approximately 12-24% and 33-42%, respectively, of the plasma radioactivity for up to 48 h. A second monohydroxylated metabolite, designated as M1a, represented approximately 10-12% of the radioactivity in the 2- and 8-h postdose plasma profiles. Metabolite profiles of the faeces samples consisted mainly of the (unabsorbed) parent compound and multiple diastereomeric carboxylic acid derivatives derived from oxidation of the geminal methyl group of the parent compound and of the hydroxylated metabolite/s. These data suggest that, similar to rats and monkeys, Taranabant is primarily eliminated in humans via oxidative metabolism and excretion of metabolites via the biliary/faecal route.
