Taranabant
Based on 2 publication(s) in Google Scholar
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.
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- Pureza: 99.95%
- No. CAS: 701977-09-5
- Fòrmula: C27H25ClF3N3O2
- Peso molecular:515.95
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Almacenamiento:Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 2 years , -20°C, 1 year
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Actividad biológica
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Chemical Information
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Solvente y solubilidad
- Protocolo
- Pureza y Documentación
- Referencias
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Publications Citing Use of MedChemExpress (MCE) Taranabant
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Actividad biológica
IC50: 0.3 nM (hCB1R), 0.4 nM (rCB1R)[1]
Ki: 0.13 nM (hCB1R), 0.27 nM (rCB1R)[1]
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| CHO | EC50 |
2.4 nM
Compound: 48, MK-0364
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Inverse agonist activity at human recombinant CB1 receptor assessed as inhibition of forskolin-induced cAMP production in CHO cells
Inverse agonist activity at human recombinant CB1 receptor assessed as inhibition of forskolin-induced cAMP production in CHO cells
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[PMID: 17181138] |
| CHO | IC50 |
0.094 nM
Compound: taranabant,, MK-0364
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Displacement of [3H]SR-141716 from human wild type CB1R expressed in CHO cells
Displacement of [3H]SR-141716 from human wild type CB1R expressed in CHO cells
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[PMID: 18333607] |
| CHO | IC50 |
0.29 nM
Compound: 55
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Displacement of [3H]CP-55940 from human CB1 receptor expressed in CHO cells
Displacement of [3H]CP-55940 from human CB1 receptor expressed in CHO cells
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[PMID: 18570365] |
| CHO | IC50 |
0.3 nM
Compound: 63
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Inhibition of radiolabeled CP5549 binding to human Cannabinoid receptor 1 expressed in CHO cells by competition assay
Inhibition of radiolabeled CP5549 binding to human Cannabinoid receptor 1 expressed in CHO cells by competition assay
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[PMID: 31497963] |
| CHO | IC50 |
0.3 nM
Compound: 1
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Displacement of [3H]CP-55940 from human recombinant CB1R expressed in CHO cells
Displacement of [3H]CP-55940 from human recombinant CB1R expressed in CHO cells
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[PMID: 17608398] |
| CHO | IC50 |
0.3 nM
Compound: 2, MK-0634
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Displacement of [3H]CP-55940 from recombinant human CB1 receptor expressed in CHO cells
Displacement of [3H]CP-55940 from recombinant human CB1 receptor expressed in CHO cells
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[PMID: 19632830] |
| CHO | IC50 |
0.3 nM
Compound: 48, MK-0364
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Inhibition of [3H]CP-55940 binding to human recombinant CB1 receptor in CHO cells
Inhibition of [3H]CP-55940 binding to human recombinant CB1 receptor in CHO cells
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[PMID: 17181138] |
| CHO | IC50 |
0.74 nM
Compound: 1
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Displacement of [3H]CP55490 from human recombinant cannabinoid CB1 receptor expressed in CHO cells
Displacement of [3H]CP55490 from human recombinant cannabinoid CB1 receptor expressed in CHO cells
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[PMID: 20643546] |
| CHO | IC50 |
0.74 nM
Compound: taranabant,, MK-0364
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Displacement of [3H]CP-55940 from human wild type CB1R expressed in CHO cells
Displacement of [3H]CP-55940 from human wild type CB1R expressed in CHO cells
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[PMID: 18333607] |
| CHO | IC50 |
1.2 nM
Compound: taranabant,, MK-0364
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Displacement of [3H]CP-55940 from human CB1R K192L mutant expressed in CHO cells
Displacement of [3H]CP-55940 from human CB1R K192L mutant expressed in CHO cells
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[PMID: 18333607] |
| CHO | IC50 |
19 nM
Compound: taranabant,, MK-0364
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Displacement of [3H]SR-141716 from human CBR1 S383A mutant expressed in CHO cells
Displacement of [3H]SR-141716 from human CBR1 S383A mutant expressed in CHO cells
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[PMID: 18333607] |
| CHO | IC50 |
22 nM
Compound: taranabant,, MK-0364
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Displacement of [3H]CP-55940 from human CB1R F170L mutant expressed in CHO cells
Displacement of [3H]CP-55940 from human CB1R F170L mutant expressed in CHO cells
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[PMID: 18333607] |
| CHO | IC50 |
285 nM
Compound: 2, MK-0634
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Displacement of [3H]CP-55940 from recombinant human CB2 receptor expressed in CHO cell
Displacement of [3H]CP-55940 from recombinant human CB2 receptor expressed in CHO cell
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[PMID: 19632830] |
| CHO | IC50 |
290 nM
Compound: 48, MK-0364
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Inhibition of [3H]CP-55940 binding to human recombinant CB2 receptor in CHO cells
Inhibition of [3H]CP-55940 binding to human recombinant CB2 receptor in CHO cells
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[PMID: 17181138] |
| CHO | IC50 |
4.9 nM
Compound: taranabant,, MK-0364
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Displacement of [3H]CP-55940 from human CB1R W279A mutant expressed in CHO cells
Displacement of [3H]CP-55940 from human CB1R W279A mutant expressed in CHO cells
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[PMID: 18333607] |
| CHO | IC50 |
5 nM
Compound: taranabant,, MK-0364
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Displacement of [3H]CP-55940 from human CB1R F200L mutant expressed in CHO cells
Displacement of [3H]CP-55940 from human CB1R F200L mutant expressed in CHO cells
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[PMID: 18333607] |
| CHO-K1 | IC50 |
1170 nM
Compound: 3, MK-0364
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Displacement of [3H]WIN-55212-2 from human CB2 receptor expressed in CHOK1 cells by liquid scintillation spectrometry
Displacement of [3H]WIN-55212-2 from human CB2 receptor expressed in CHOK1 cells by liquid scintillation spectrometry
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[PMID: 18954042] |
| HEK293 | IC50 |
0.3 nM
Compound: 7, MK-0364
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Displacement of [3H]CP-55940 from human CB1R expressed in HEK293 cells
Displacement of [3H]CP-55940 from human CB1R expressed in HEK293 cells
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[PMID: 18335976] |
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].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
| NCT Number | Sponsor | Condition | Start Date |
Phase
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|---|---|---|---|---|
| NCT01329991 | Plexxikon| | 2011-05 | PHASE1 |
Chemical Information
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No. CAS 701977-09-5
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Appearance Solid
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Peso molecular 515.95
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Fòrmula C27H25ClF3N3O2
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Color White to off-white
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SMILES
ClC1=CC=C(C[C@@H](C2=CC=CC(C#N)=C2)[C@@H](NC(C(C)(OC3=CC=C(C=N3)C(F)(F)F)C)=O)C)C=C1
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Synonyms
MK-0364
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Envío
Room temperature in continental US; may vary elsewhere.
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Almacenamiento
Powder -20°C 3 years 4°C 2 years In solvent -80°C 2 years -20°C 1 year
Publications (2)
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Journal Impact Factor
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Most Recent
Solvente y solubilidad
DMSO : ≥ 50 mg/mL (96.91 mM; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
* "≥" means soluble, but saturation unknown.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Select the appropriate dissolution method based on your experimental animal and administration route.
- For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
- To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
- The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.
Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline
Solubility: ≥ 2.5 mg/mL (4.85 mM); Clear solution
This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.
Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
Please enter the basic information of animal experiments:
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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
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%DMSO +
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
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%+
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+%Tween-80 + +
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%Saline +
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Working solution concentration: 0.22 mg/mL
Method for preparing stock solution: mg drug dissolved in μL DMSO. Stock solution concentration: mg/mL.
1. Take μL DMSO stock solution;
2. Add μL .
μL , mix evenly;
3. Then add μL Tween 80, mix evenly;
4. Then add μL
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Protocolo
The binding assay is performed by incubating various concentrations of Taranabant (MK-0364) with 0.5 nM [3H]CP 55,940, 1.5 μg of recombinant human CB1R-CHO membranes (or 0.1 μg of human CB2R-CHO membranes) in 50 mM Tris-HCl, pH 7.4, 5 mM MgCl2, 2.5 mM EDTA, 0.5 mg/mL fatty acid-free bovine serum albumin (BSA), 1× proteinase inhibitor mix, and 1% DMSO. After 1-h incubation at 37°C, the reaction is stopped by filtration, and bound radioligand is separated from free radioligand by washing the filter plate. Total specifically bound radiolabel is approximately 10% of the total added radiolabel. Inhibitory IC50 values are calculated through nonlinear curve fitting, from which Ki values are then calculated. The CB1R density (Bmax=5 pmol/mg based on [3H]CP 55,940 binding) in the recombinant human CB1R-CHO membranes is close to that from rat brain membranes (3-5 pmol/mg)[1].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Mice[1]
Male C57BL/6N wild-type mice are used. MK-0364 is dissolved or dispersed (with sonication) as a fine homogeneous suspension in 0.225% methylcellulose/10% Tween 80 in water for subsequent oral dosing of mice. All mice are weighed, and vehicle (0.225% methylcellulose/10% Tween 80 in water) or Taranabant (1 or 3 mg/kg) is administered by oral gavage to male mice approximately 30 min before the onset of the dark phase of the light cycle (n=12 per group, age 23 weeks, mean body weight 34.14±0.53 g). Mice are fed ad libitum in the dark phase after dosing. A preweighed aliquot of a highly palatable medium-high fat diet (25% kcal from sucrose, 32% kcal from fat, 4.41 kcal/g) is provided in the food hopper of the cage 5 min before the onset of the dark phase of the light cycle and weighed 2 and 18 h after the onset of the dark phase of the light cycle. In addition, all mice are weighed 18 h after the onset of the dark phase of the light cycle. The study is of crossover design, i.e., vehicle and 1-mk/kg groups are dosed first. After a 4-day washout, the previous vehicle group is dosed with 3 mg/kg Taranabant, and the previous 1-mg/kg group is dosed with vehicle.
Rats[1]
For acute experiments, male Sprague-Dawley DIO rats are randomized into groups (n=6 rats/group) for compound and vehicle dosing. Rats are weighed 17 h after dosing to determine effects on overnight body weight gain. Taranabant is administered orally to DIO rats 1 h before the start of the dark cycle (3:00 PM) at 0.3, 1, and 3 mg/kg p.o. Vehicle is 10% Tween 80 in water, and dosing volume is 2 mL/kg. Powdered food is provided in food cups that are weighed continuously at 5-min intervals over 18 h, and the data are recorded using a computerized system.
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Pureza y Documentación
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Ficha de datos (279 KB)
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SDS (563 KB)
- English - EN (563 KB)
- Français - FR (563 KB)
- Deutsch - DE (563 KB)
- Norwegian - NO (563 KB)
- Español - ES (563 KB)
- Swedish - SV (563 KB)
- Italian - IT (563 KB)
- Korean - KR (563 KB)
- Portuguese - PT (563 KB)
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Instrucciones de manejo (2659 KB)
Referencias
[1]. Fong TM, et al. 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. J Pharmacol Exp T [Content Brief]
[2]. Lin LS, et al. Discovery of N-[(1S,2S)-3-(4-Chlorophenyl)-2- (3-cyanophenyl)-1-methylpropyl]-2-methyl-2- {[5-(trifluoromethyl)pyridin-2-yl]oxy}propanamide (MK-0364), a novel, acyclic cannabinoid-1 receptor inverse agonist for the treatment of obesity. J M [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 1.9382 mL | 9.6909 mL | 19.3817 mL | 48.4543 mL |
| 5 mM | 0.3876 mL | 1.9382 mL | 3.8763 mL | 9.6909 mL | |
| 10 mM | 0.1938 mL | 0.9691 mL | 1.9382 mL | 4.8454 mL | |
| 15 mM | 0.1292 mL | 0.6461 mL | 1.2921 mL | 3.2303 mL | |
| 20 mM | 0.0969 mL | 0.4845 mL | 0.9691 mL | 2.4227 mL | |
| 25 mM | 0.0775 mL | 0.3876 mL | 0.7753 mL | 1.9382 mL | |
| 30 mM | 0.0646 mL | 0.3230 mL | 0.6461 mL | 1.6151 mL | |
| 40 mM | 0.0485 mL | 0.2423 mL | 0.4845 mL | 1.2114 mL | |
| 50 mM | 0.0388 mL | 0.1938 mL | 0.3876 mL | 0.9691 mL | |
| 60 mM | 0.0323 mL | 0.1615 mL | 0.3230 mL | 0.8076 mL | |
| 80 mM | 0.0242 mL | 0.1211 mL | 0.2423 mL | 0.6057 mL |
Taranabant Related Classifications
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