1289023-67-1
1289023-67-1 structure
- Name: BMS-927711
- Chemical Name: [(5S,6S,9R)-5-amino-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-yl] 4-(2-oxo-3H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate
- CAS Number: 1289023-67-1
- Molecular Formula: C28H28F2N6O3
- Molecular Weight: 534.557
- Catalog: Signaling Pathways GPCR/G Protein CGRP Receptor
- Create Date: 2016-03-31 01:32:59
- Modify Date: 2024-01-02 13:09:49
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Rimegepant (BMS-927711) is a highly potent, oral calcitonin gene-related peptide (CGRP) receptor antagonist with a Ki value of 0.027 nM.
| Name | [(5S,6S,9R)-5-amino-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-yl] 4-(2-oxo-3H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate |
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| Synonyms |
Rimegepant
1-Piperidinecarboxylic acid, 4-(2,3-dihydro-2-oxo-1H-imidazo[4,5-b]pyridin-1-yl)-, (5S,6S,9R)-5-amino-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-yl ester BMS-927711 (5S,6S,9R)-5-nitro-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-yl 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate (5S,6S,9R)-5-amino-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-yl 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate (5S,6S,9R)-5-Amino-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-yl 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)-1-piperidinecarboxylate BMS 927711 |
| Description | Rimegepant (BMS-927711) is a highly potent, oral calcitonin gene-related peptide (CGRP) receptor antagonist with a Ki value of 0.027 nM. |
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| Related Catalog | |
| Target |
Ki: 0.027 nM (CGRP receptor)[1] IC50: 0.14 nM (CGRP receptor)[1] |
| In Vitro | Rimegepant (BMS-927711) is a full, competitive CGRP receptor antagonist with IC50 of 0.14±0.01 nM[1]. |
| In Vivo | Rimegepant (BMS-927711) has good oral bioavailability in rat and cynomolgus monkey, attractive overall preclinical properties, and shows dose-dependent activity in a primate model of CGRP-induced facial blood flow[1]. The ratios of the mean AUC (0-24 h) values for Rimegepant (BMS-927711) (60, 100, and 300 mg/kg) in the DBS matrix, compare with plasma, are 0.5-0.6 across all doses in rats. Results from this study suggest a strong correlation of Rimegepant concentrations between rat plasma and rat blood (DBS)[2]. |
| Animal Admin | Rats[2] Rats are treated with drug-free vehicle (control) or Rimegepant (BMS-927711) in vehicle at 60, 100, and 300 mg/kg once daily via oral gavage. There are 6 rats in each treatment group. For each treatment group, blood is collected at 1, 6, and 24 h from first three rats, and at 3 and 8 h from the second three rats on Day 1 and Day 14 from the tail vein following daily oral dosing of Rimegepant (BMS-927711) for two weeks. The mean hematocrits in the blood are 50.2±1.8%, 49.8±2.2%, 46.4±5.2% corresponding to the animal groups of 60, 100, and 300 mg/kg doses, respectively. For DBS evaluation, four 15 μL blood samples are spotted onto DBS cards (4 spots per card), dried at room temperature for at least 2 h, and each card is packaged separately in a ziplock bag with desiccant prior to shipment. The remaining blood in each sample tube is processed to plasma within 1 h of collection and stored at -70°C until analysis. Plasma samples are shipped on dry ice, and DBS cards are shipped at ambient temperature. Rimegepant (BMS-927711) concentrations in rat plasma are analyzed. Rimegepant in rat DBS is analyzed using the DBS method. The toxicokinetic (TK) parameters are calculated from blood concentration and time data using non-compartmental methods using Kinetica. |
| References |
| Density | 1.5±0.1 g/cm3 |
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| Molecular Formula | C28H28F2N6O3 |
| Molecular Weight | 534.557 |
| Exact Mass | 534.219116 |
| PSA | 119.39000 |
| LogP | 1.73 |
| Index of Refraction | 1.676 |
|
~82%
1289023-67-1 |
| Literature: Luo, Guanglin; Chen, Ling; Conway, Charles M.; Denton, Rex; Keavy, Deborah; Signor, Laura; Kostich, Walter; Lentz, Kimberley A.; Santone, Kenneth S.; Schartman, Richard; Browning, Marc; Tong, Gary; Houston, John G.; Dubowchik, Gene M.; MacOr, John E. Journal of Medicinal Chemistry, 2012 , vol. 55, # 23 p. 10644 - 10651 |
| Precursor 1 | |
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| DownStream 0 | |