| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 100mg | |||
| Other Sizes |
| Targets |
CB1 receptor (cannabinoid receptor type 1). Taranabant acts as an inverse agonist, binding with high affinity and selectivity to CB1 over CB2 and other related receptors.
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|---|---|
| ln Vitro |
In vitro, taranabant (1R,2R) binds to CB1 receptors with sub‑nanomolar affinity and potently inhibits agonist‑induced signaling. It reduces forskolin‑stimulated cAMP accumulation in CB1‑expressing cells, demonstrating functional inverse agonism. The compound shows high selectivity for CB1 over CB2 and other G‑protein‑coupled receptors, with minimal off‑target activity at concentrations up to 10 microM. Its inverse agonist activity distinguishes it from neutral antagonists, as it suppresses basal receptor activity in addition to blocking agonist effects.
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| ln Vivo |
In vivo, taranabant produces dose‑dependent reduction in food intake and body weight in rodent models of obesity. Oral administration at 0.1-3 mg/kg suppresses acute feeding and chronic weight gain. The compound also improves metabolic parameters such as insulin sensitivity and lipid profiles. However, in clinical trials, it caused dose‑related psychiatric side effects (anxiety, depression, irritability) and gastrointestinal disturbances, leading to termination of development. The (1R,2R) enantiomer is responsible for the majority of the pharmacological activity.
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| Enzyme Assay |
CB1 receptor binding assays are performed using membranes from cells expressing recombinant human CB1. Membranes are incubated with 0.5-1 nM [3H]‑CP‑55,940 and increasing concentrations of taranabant (0.001-1000 nM) in binding buffer (50 mM Tris‑HCl, pH 7.4, 5 mM MgCl2, 2.5 mM EDTA, 0.1% BSA) at 30 degC for 60 min. Non‑specific binding is defined with 10 microM unlabeled CP‑55,940. Bound radioactivity is separated by rapid filtration through GF/B filters presoaked in 0.3% PEI, and counted by scintillation. Ki values are calculated from competitive binding curves using nonlinear regression. For inverse agonism, [3⁵S]GTPgammaS binding assays are performed in the absence of agonist to measure basal G‑protein activation.
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| Cell Assay |
Functional assays are conducted in CHO or HEK‑293 cells stably expressing human CB1. Cells are seeded in 96‑well plates and treated with taranabant (0.001-1000 nM) for 15-30 min. cAMP levels are measured using a homogeneous time‑resolved fluorescence (HTRF) or ELISA‑based assay after stimulation with forskolin (1-5 microM). Inhibition of forskolin‑induced cAMP accumulation is expressed as percent of control. EC₅0 values are derived from sigmoidal dose‑response curves. To confirm inverse agonism, basal cAMP levels (without forskolin) are also measured; a reduction in basal cAMP indicates inverse agonist activity. Selectivity is verified by counter‑screening against CB2 and a panel of related GPCRs.
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| Animal Protocol |
In vivo efficacy is evaluated in diet‑induced obese (DIO) mice or rats. Taranabant is formulated in 0.5% methylcellulose or similar vehicle and administered orally by gavage at doses of 0.1, 0.3, 1, and 3 mg/kg, once daily for 7-28 days. Food intake is measured daily, and body weight is recorded every 2-3 days. For acute studies, food consumption is measured at 2, 4, 6, and 24 h post‑dose. Metabolic parameters (glucose, insulin, triglycerides) are measured in serum at study termination. To confirm CB1‑mediated effects, a separate group may be treated with a CB1 antagonist or compared to CB1 knockout animals. Pharmacokinetic blood samples are collected at various time points for LC‑MS/MS analysis.
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| ADME/Pharmacokinetics |
Taranabant has a molecular formula of C2₇H2₅ClF3N3O2 and molecular weight ~516. It is a lipophilic small molecule with high oral bioavailability in preclinical species. Following oral administration, Tmax is typically 1-2 h, and the terminal half‑life ranges from 4-8 h in rodents. The compound is extensively metabolized by hepatic CYP450 enzymes, primarily CYP3A4, and eliminated via both renal and biliary routes. Plasma protein binding is high (>95%). The (1R,2R) enantiomer shows linear pharmacokinetics over the dose range studied.
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| Toxicity/Toxicokinetics |
In preclinical toxicology studies, taranabant showed a margin of safety, but in human trials, it produced dose‑dependent adverse events including nausea, vomiting, dizziness, and neuropsychiatric effects such as anxiety, depression, and suicidal ideation. The therapeutic index was considered narrow, leading to discontinuation of development. At high doses, it may cause hepatotoxicity, though this was not a primary concern. The compound is not approved for human use and is strictly a research chemical.
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| References | |
| Additional Infomation |
Taranabant ((1R,2R) stereoisomer) is a research‑grade CB1 inverse agonist originally developed by Merck for obesity. It is one of the most potent and selective CB1 ligands available, with an IC₅0 for food intake suppression in the low nanomolar range after oral dosing. The compound is used extensively in academic and industrial labs to probe CB1 receptor function, distinguish inverse agonism from neutral antagonism, and investigate the role of the endocannabinoid system in energy homeostasis and behavior. It is not a marketed drug and is supplied only for laboratory research.
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| Molecular Formula |
C27H25CLF3N3O2
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|---|---|
| Molecular Weight |
515.954516172409
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| Exact Mass |
515.158
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| CAS # |
701977-08-4
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| Related CAS # |
Taranabant;701977-09-5;Taranabant racemate;701977-00-6
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| PubChem CID |
92979965
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
634.2±55.0 °C at 760 mmHg
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| Flash Point |
337.4±31.5 °C
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| Vapour Pressure |
0.0±1.9 mmHg at 25°C
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| Index of Refraction |
1.575
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| LogP |
7.13
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
8
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| Heavy Atom Count |
36
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| Complexity |
776
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| Defined Atom Stereocenter Count |
2
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| 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
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| InChi Key |
QLYKJCMUNUWAGO-HXOBKFHXSA-N
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| 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+/m1/s1
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| Chemical Name |
N-[(2R,3R)-4-(4-chlorophenyl)-3-(3-cyanophenyl)butan-2-yl]-2-methyl-2-[5-(trifluoromethyl)pyridin-2-yl]oxypropanamide
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~193.82 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.75 mg/mL (5.33 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 27.5 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.75 mg/mL (5.33 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 27.5 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.9382 mL | 9.6909 mL | 19.3817 mL | |
| 5 mM | 0.3876 mL | 1.9382 mL | 3.8763 mL | |
| 10 mM | 0.1938 mL | 0.9691 mL | 1.9382 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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