| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 50mg |
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| 100mg | |||
| 250mg | |||
| Other Sizes |
| Targets |
CB1 receptor (cannabinoid receptor type 1). The racemate binds to CB1 with moderate affinity, but the (1R,2R) enantiomer is the primary active component; the (1S,2S) form has greatly reduced activity.
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|---|---|
| ln Vitro |
In vitro, taranabant racemate binds to CB1 receptors and inhibits agonist‑induced signaling. It reduces cAMP accumulation in CB1‑expressing cells, showing antagonist/inverse agonist properties. The racemate's potency is lower than that of the pure (1R,2R) enantiomer because only half of the mixture is active. It does not show significant activity at CB2 or other common GPCRs. In functional assays, the racemate blocks CP‑55,940‑stimulated [3⁵S]GTPgammaS binding with an IC₅0 approximately twofold higher than the active enantiomer.
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| ln Vivo |
In vivo, the racemate produces dose‑dependent suppression of food intake and body weight gain in rodent models, but with reduced potency compared to the pure enantiomer on a molar basis. Oral administration at 1-10 mg/kg reduces acute feeding and chronic weight gain. The effects are mediated through CB1 receptor blockade, as they are reversed by CB1 agonists and absent in CB1‑knockout animals. Clinical studies with the racemate were not pursued; instead, the active enantiomer was developed, but both were eventually abandoned due to psychiatric side effects.
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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 varying concentrations of taranabant racemate (0.01-10,000 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 determined with 10 microM unlabeled CP‑55,940. Bound ligand is separated by filtration through GF/B filters presoaked in 0.3% PEI, and counted. Competitive binding curves are analyzed to obtain Ki values. For functional antagonism, [3⁵S]GTPgammaS binding is measured in the presence of a fixed concentration of CP‑55,940 (agonist) and increasing concentrations of racemate.
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| Cell Assay |
Cells stably expressing human CB1 are seeded in 96‑well plates. The racemate is added at concentrations ranging from 0.01 to 10,000 nM, with or without forskolin (1-5 microM) to stimulate cAMP production. After 15-30 min incubation, cAMP levels are measured by HTRF or ELISA. The compound's ability to inhibit forskolin‑stimulated cAMP is determined, and IC₅0 values are calculated. For inverse agonism, basal cAMP (without forskolin) is measured; a reduction indicates inverse agonist activity. The racemate's effects are compared to those of the pure (1R,2R) enantiomer to assess the contribution of the inactive enantiomer.
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| Animal Protocol |
In vivo studies are performed in diet‑induced obese (DIO) mice or rats. The racemate is administered orally by gavage at doses of 1, 3, and 10 mg/kg, once daily for 7-14 days. Food intake and body weight are monitored. Blood samples are collected for pharmacokinetic analysis. The racemate's efficacy is compared to that of the active enantiomer at equimolar doses. To confirm CB1 specificity, a CB1 antagonist (e.g., rimonabant) may be used as a positive control, and the effects of the racemate are evaluated in CB1‑knockout animals to verify target engagement.
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| ADME/Pharmacokinetics |
Taranabant racemate has molecular formula C2₇H2₅ClF3N3O2 and molecular weight 515.95. It is a lipophilic compound with good oral bioavailability. Following oral administration, the racemate is absorbed rapidly, with Tmax ~1-2 h. The two enantiomers may have different pharmacokinetic profiles due to stereoselective metabolism. The compound is extensively metabolized by CYP3A4 and eliminated via urine and feces. Plasma protein binding is high (>95%). The half‑life in rodents is approximately 4-8 h.
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| Toxicity/Toxicokinetics |
The racemate shares the same toxicity profile as the active enantiomer. In preclinical studies, it was generally well‑tolerated at effective doses, but clinical development was halted due to psychiatric adverse events (anxiety, depression, irritability) and gastrointestinal effects (nausea, vomiting). No specific organ toxicity was reported at therapeutic doses. The compound is for research use only and is not intended for human consumption.
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| References | |
| Additional Infomation |
Taraban is a stilbene compound.
Drug Indications It has been studied for the treatment of obesity.Obesity Taranabant racemate is a racemic mixture of the CB1 inverse agonist taranabant. It is used as a research tool to study enantioselective pharmacology of CB1 receptor ligands and to compare the activity of the racemate versus the pure (1R,2R) enantiomer. The racemate was originally developed by Merck as an anti‑obesity candidate, but the program was discontinued. It remains available for laboratory research to investigate the endocannabinoid system, appetite regulation, and metabolic disorders. The compound is supplied as a powder for reconstitution in appropriate solvents. |
| Molecular Formula |
C27H25CLF3N3O2
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|---|---|
| Molecular Weight |
515.954516172409
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| Exact Mass |
515.158
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| CAS # |
701977-00-6
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| Related CAS # |
Taranabant;701977-09-5;Taranabant ((1R,2R)stereoisomer);701977-08-4
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| PubChem CID |
11226090
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| Appearance |
White to off-white solid powder
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| LogP |
6.5
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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 |
ClC1C=CC(=CC=1)C[C@H](C1C=CC=C(C#N)C=1)[C@@H](C)NC(C(C)(C)OC1C=CC(C(F)(F)F)=CN=1)=O
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| InChi Key |
QLYKJCMUNUWAGO-GAJHUEQPSA-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+/m0/s1
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| Chemical Name |
N-[(2S,3S)-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: 2.5 mg/mL (4.85 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 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: ≥ 2.5 mg/mL (4.85 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 25.0 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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