AMG 517 (CAT: I004486) is a potent and selective antagonist of the transient receptor potential vanilloid 1 (TRPV1) channel. It acts by antagonizing the activation of TRPV1 by capsaicin, protons (acidic pH), and heat. TRPV1 is a receptor involved in pain sensation and the perception of heat. By inhibiting TRPV1 activation, AMG 517 has potential applications in the treatment of pain and related conditions. Its selectivity towards TRPV1 makes it a valuable tool in studying the physiological and pathological roles of TRPV1 channels.
| Catalog Number | I004486 |
| CAS Number | 659730-32-2 |
| Synonyms | N-[4-[6-[4-(trifluoromethyl)phenyl]pyrimidin-4-yl]oxy-1,3-benzothiazol-2-yl]acetamide |
| Molecular Formula | C20H13F3N4O2S |
| Purity | 95% |
| Target | TRPV1 |
| Solubility | in DMSO > 10 mM |
| Storage | 3 years -20C powder |
| IC50 | ~1 nM [1] |
| InChI | InChI=1S/C20H13F3N4O2S/c1-11(28)26-19-27-18-15(3-2-4-16(18)30-19)29-17-9-14(24-10-25-17)12-5-7-13(8-6-12)20(21,22)23/h2-10H,1H3,(H,26,27,28) |
| InChIKey | YUTIXVXZQIQWGY-UHFFFAOYSA-N |
| SMILES | CC(NC1=NC2=C(OC3=NC=NC(C4=CC=C(C(F)(F)F)C=C4)=C3)C=CC=C2S1)=O |
| Reference | </br>1:Investigation of Phase Mixing in Amorphous Solid Dispersions of AMG 517 in HPMC-AS Using DSC, Solid-State NMR, and Solution Calorimetry. Calahan JL, Azali SC, Munson EJ, Nagapudi K.Mol Pharm. 2015 Nov 2;12(11):4115-23. doi: 10.1021/acs.molpharmaceut.5b00556. Epub 2015 Oct 23. PMID: 26457879 </br>2:Application of twin screw extrusion to the manufacture of cocrystals: scale-up of AMG 517-sorbic acid cocrystal production. Daurio D, Nagapudi K, Li L, Quan P, Nunez FA.Faraday Discuss. 2014;170:235-49. doi: 10.1039/c3fd00153a. PMID: 25406487 </br>3:Isothermal microcalorimetry to investigate the phase separation for amorphous solid dispersions of AMG 517 with HPMC-AS. Calahan JL, Zanon RL, Alvarez-Nunez F, Munson EJ.Mol Pharm. 2013 May 6;10(5):1949-57. doi: 10.1021/mp300714g. Epub 2013 Apr 24. PMID: 23574401 </br>4:Application of automated dried blood spot sampling and LC-MS/MS for pharmacokinetic studies of AMG 517 in rats. Uyeda C, Pham R, Fide S, Henne K, Xu G, Soto M, James C, Wong P.Bioanalysis. 2011 Oct;3(20):2349-56. doi: 10.4155/bio.11.227. PMID: 22011182 </br>5:Improved pharmacokinetics of AMG 517 through co-crystallization part 2: analysis of 12 carboxylic acid co-crystals. Stanton MK, Kelly RC, Colletti A, Langley M, Munson EJ, Peterson ML, Roberts J, Wells M.J Pharm Sci. 2011 Jul;100(7):2734-43. doi: 10.1002/jps.22502. Epub 2011 Feb 1. PMID: 21287556 </br>6:Improved pharmacokinetics of AMG 517 through co-crystallization. Part 1: comparison of two acids with corresponding amide co-crystals. Stanton MK, Kelly RC, Colletti A, Kiang YH, Langley M, Munson EJ, Peterson ML, Roberts J, Wells M.J Pharm Sci. 2010 Sep;99(9):3769-78. doi: 10.1002/jps.22181. PMID: 20665842 </br>7:A Multidisciplinary Investigation to Determine the Structure and Source of Dimeric Impurities in AMG 517 Drug Substance. Silva Elipe MV, Tan ZJ, Ronk M, Bostick T.Int J Anal Chem. 2009;2009:768743. doi: 10.1155/2009/768743. Epub 2008 Dec 17. PMID: 20140079 Free PMC Article</br>8:Characterization and optimization of AMG 517 supersaturatable self-emulsifying drug delivery system (S-SEDDS) for improved oral absorption. Gao P, Akrami A, Alvarez F, Hu J, Li L, Ma C, Surapaneni S.J Pharm Sci. 2009 Feb;98(2):516-28. doi: 10.1002/jps.21451. PMID: 18543293 </br>9:The co-crystal approach to improve the exposure of a water-insoluble compound: AMG 517 sorbic acid co-crystal characterization and pharmacokinetics. Bak A, Gore A, Yanez E, Stanton M, Tufekcic S, Syed R, Akrami A, Rose M, Surapaneni S, Bostick T, King A, Neervannan S, Ostovic D, Koparkar A.J Pharm Sci. 2008 Sep;97(9):3942-56. doi: 10.1002/jps.21280. PMID: 18214948 |
