mavatrepTRPV1 antagonist CAS# 956274-94-5 |
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Quality Control & MSDS
3D structure
Package In Stock
Number of papers citing our products
| Cas No. | 956274-94-5 | SDF | Download SDF |
| PubChem ID | 17751090 | Appearance | Powder |
| Formula | C25H21F3N2O | M.Wt | 422.44 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | DMSO : ≥ 28 mg/mL (66.28 mM) H2O : < 0.1 mg/mL (insoluble) *"≥" means soluble, but saturation unknown. | ||
| Chemical Name | 2-[2-[2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-3H-benzimidazol-5-yl]phenyl]propan-2-ol | ||
| SMILES | CC(C)(C1=CC=CC=C1C2=CC3=C(C=C2)N=C(N3)C=CC4=CC=C(C=C4)C(F)(F)F)O | ||
| Standard InChIKey | ORDHXXHTBUZRCN-NTEUORMPSA-N | ||
| Standard InChI | InChI=1S/C25H21F3N2O/c1-24(2,31)20-6-4-3-5-19(20)17-10-13-21-22(15-17)30-23(29-21)14-9-16-7-11-18(12-8-16)25(26,27)28/h3-15,31H,1-2H3,(H,29,30)/b14-9+ | ||
| 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. | ||
mavatrep Dilution Calculator
mavatrep Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.3672 mL | 11.836 mL | 23.672 mL | 47.344 mL | 59.18 mL |
| 5 mM | 0.4734 mL | 2.3672 mL | 4.7344 mL | 9.4688 mL | 11.836 mL |
| 10 mM | 0.2367 mL | 1.1836 mL | 2.3672 mL | 4.7344 mL | 5.918 mL |
| 50 mM | 0.0473 mL | 0.2367 mL | 0.4734 mL | 0.9469 mL | 1.1836 mL |
| 100 mM | 0.0237 mL | 0.1184 mL | 0.2367 mL | 0.4734 mL | 0.5918 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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Mavatrep is a potent and orally bioavailable antagonist of TRPV1 with IC50 value of 4.6 nM [1][2].
Transient receptor potential vanilloid-1 (TRPV1) is a thermosensitive and nonselective cation channel, and is a member of the TRP channel superfamily. The channel is activated by acidic pH (<6.8), thermal stimuli (>43℃), and endogenous lipidic mediators (anandamide and oxidative metabolites of linoleic acid) [1].
Mavatrep is a potent and orally bioavailable TRPV1 antagonist. In HEK293 cells that stably express human or rat TRPV1 (rTRPV1) channels, mavatrep (1 μM) inhibited capsaicin-induced Ca2+ influx with IC50 values of 4.6 nM and 21 nM. In whole-cell patch clamp electrophysiology assay, mavatrep concentration-dependently inhibited the activation of hTRPV1 channels by pH (5.0) and capsaicin (1 μM) with IC50 values of 6.8 and 23 nM, respectively. Mavatrep (0.1 μM) also inhibited 74 ± 8.1% heat-evoked currents mediated by hTRPV1 [1].
In the CFA model of inflammatory of pain, mavatrep (10 mg/kg po) significantly reversed CFA-induced thermal hypersensitivity with ED50 and ED80 values of 1.8 and 7.8 mg/kg, respectively [1].
Reference:
[1]. Parsons WH, Calvo RR, Cheung W, et al. Benzo[d]imidazole Transient Receptor Potential Vanilloid 1 Antagonists for the Treatment of Pain: Discovery of trans-2-(2-{2-[2-(4-Trifluoromethyl-phenyl)-vinyl]-1H-benzimidazol-5-yl}-phenyl)-propan-2-ol (Mavatrep). J Med Chem, 2015, 58(9): 3859-3874.
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Benzo[d]imidazole Transient Receptor Potential Vanilloid 1 Antagonists for the Treatment of Pain: Discovery of trans-2-(2-{2-[2-(4-Trifluoromethyl-phenyl)-vinyl]-1H-benzimidazol-5-yl}-phenyl)- propan-2-ol (Mavatrep).[Pubmed:25850459]
J Med Chem. 2015 May 14;58(9):3859-74.
Reported herein is the design, synthesis, and pharmacologic characterization of a class of TRPV1 antagonists constructed on a benzo[d]imidazole platform that evolved from a biaryl amide lead. This design composes three sections: a 2-substituted 5-phenyl headgroup attached to the benzo[d]imidazole platform, which is tethered at the two position to a phenyl tail group. Optimization of this design led to the identification of 4 (mavatrep), comprising a trifluoromethyl-phenyl-vinyl tail. In a TRPV1 functional assay, using cells expressing recombinant human TRPV1 channels, 4 antagonized capsaicin-induced Ca(2+) influx, with an IC50 value of 4.6 nM. In the complete Freund's adjuvant- and carrageenan-induced thermal hypersensitivity models, 4 exhibited full efficacy, with ED80 values of 7.8 and 0.5 mg/kg, respectively, corresponding to plasma levels of 270.8 and 9.2 ng/mL, respectively. On the basis of its superior pharmacologic and safety profile, 4 (mavatrep) was selected for clinical development for the treatment of pain.
