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MedKoo Cat#: 314235 | Name: Perampanel

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Perampanel is discontinued (DEA controlled substance). Perampanel is a selective noncompetitive antagonist of AMPA receptors, the major subtype of ionotropic glutamate receptors. Perampanel was found to be effective in the treatment of refractory partial-onset seizures in clinical trials.

Chemical Structure

Perampanel
Perampanel
CAS#380917-97-5

Theoretical Analysis

MedKoo Cat#: 314235

Name: Perampanel

CAS#: 380917-97-5

Chemical Formula: C23H15N3O

Exact Mass: 349.1215

Molecular Weight: 349.38

Elemental Analysis: C, 79.07; H, 4.33; N, 12.03; O, 4.58

Price and Availability

This product was removed for the commercial reasons.
Related CAS #
No Data
Synonym
E 2007; E2007; E-2007; ER15505590; ER 15505590; Perampanel; Brand name: Fycompa
IUPAC/Chemical Name
5'-(2-cyanophenyl)-1'-phenyl-2,3'-bipyridinyl-6'(1'H)-one
InChi Key
PRMWGUBFXWROHD-UHFFFAOYSA-N
InChi Code
InChI=1S/C23H15N3O/c24-15-17-8-4-5-11-20(17)21-14-18(22-12-6-7-13-25-22)16-26(23(21)27)19-9-2-1-3-10-19/h1-14,16H
SMILES Code
O=C1C(C2=CC=CC=C2C#N)=CC(C3=NC=CC=C3)=CN1C4=CC=CC=C4
Appearance
Grey solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO.
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 349.38 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Trinka E, Steinhoff BJ, Nikanorova M, Brodie MJ. Perampanel for focal epilepsy: insights from early clinical experience. Acta Neurol Scand. 2016 Mar;133(3):160-72. doi: 10.1111/ane.12529. Review. PubMed PMID: 26506904; PubMed Central PMCID: PMC4738453. 2: Glauser T, Laurenza A, Yang H, Williams B, Ma T, Fain R. Efficacy and tolerability of adjunct perampanel based on number of antiepileptic drugs at baseline and baseline predictors of efficacy: A phase III post-hoc analysis. Epilepsy Res. 2016 Jan;119:34-40. doi: 10.1016/j.eplepsyres.2015.11.014. PubMed PMID: 26656783. 3: Kwan P, Brodie MJ, Laurenza A, FitzGibbon H, Gidal BE. Analysis of pooled phase III trials of adjunctive perampanel for epilepsy: Impact of mechanism of action and pharmacokinetics on clinical outcomes. Epilepsy Res. 2015 Nov;117:117-24. doi: 10.1016/j.eplepsyres.2015.09.002. PubMed PMID: 26448264. 4: Ettinger AB, LoPresti A, Yang H, Williams B, Zhou S, Fain R, Laurenza A. Psychiatric and behavioral adverse events in randomized clinical studies of the noncompetitive AMPA receptor antagonist perampanel. Epilepsia. 2015 Aug;56(8):1252-63. doi: 10.1111/epi.13054. PubMed PMID: 26140524; PubMed Central PMCID: PMC4758397. 5: Montouris G, Yang H, Williams B, Zhou S, Laurenza A, Fain R. Efficacy and safety of perampanel in patients with drug-resistant partial seizures after conversion from double-blind placebo to open-label perampanel. Epilepsy Res. 2015 Aug;114:131-40. doi: 10.1016/j.eplepsyres.2015.04.011. PubMed PMID: 26088896. 6: Meador KJ, Yang H, Piña-Garza JE, Laurenza A, Kumar D, Wesnes KA. Cognitive effects of adjunctive perampanel for partial-onset seizures: A randomized trial. Epilepsia. 2016 Feb;57(2):243-51. doi: 10.1111/epi.13279. PubMed PMID: 26724782; PubMed Central PMCID: PMC4785606. 7: Yang H, Laurenza A, Williams B, Patten A, Hussein Z, Ferry J. Lack of effect of perampanel on QT interval duration: Results from a thorough QT analysis and pooled partial seizure Phase III clinical trials. Epilepsy Res. 2015 Aug;114:122-30. doi: 10.1016/j.eplepsyres.2015.04.010. PubMed PMID: 26088895. 8: Chen T, Dai SH, Jiang ZQ, Luo P, Jiang XF, Fei Z, Gui SB, Qi YL. The AMPAR Antagonist Perampanel Attenuates Traumatic Brain Injury Through Anti-Oxidative and Anti-Inflammatory Activity. Cell Mol Neurobiol. 2017 Jan;37(1):43-52. doi: 10.1007/s10571-016-0341-8. PubMed PMID: 26883519. 9: Vazquez B, Yang H, Williams B, Zhou S, Laurenza A. Perampanel efficacy and safety by gender: Subanalysis of phase III randomized clinical studies in subjects with partial seizures. Epilepsia. 2015 Jul;56(7):e90-4. doi: 10.1111/epi.13019. PubMed PMID: 26096637; PubMed Central PMCID: PMC4744665. 10: Laurenza A, Yang H, Williams B, Zhou S, Ferry J. Absence of Liver Toxicity in Perampanel-Treated Subjects: Pooled results from partial seizure phase III perampanel clinical studies. Epilepsy Res. 2015 Jul;113:76-85. doi: 10.1016/j.eplepsyres.2015.03.005. PubMed PMID: 25986193. 11: Rosenfeld W, Conry J, Lagae L, Rozentals G, Yang H, Fain R, Williams B, Kumar D, Zhu J, Laurenza A. Efficacy and safety of perampanel in adolescent patients with drug-resistant partial seizures in three double-blind, placebo-controlled, phase III randomized clinical studies and a combined extension study. Eur J Paediatr Neurol. 2015 Jul;19(4):435-45. doi: 10.1016/j.ejpn.2015.02.008. PubMed PMID: 25823975. 12: Villanueva V, Majid O, Nabangchang C, Yang H, Laurenza A, Ferry J, Hussein Z. Pharmacokinetics, exposure-cognition, and exposure-efficacy relationships of perampanel in adolescents with inadequately controlled partial-onset seizures. Epilepsy Res. 2016 Nov;127:126-134. doi: 10.1016/j.eplepsyres.2016.08.025. PubMed PMID: 27595590. 13: French JA, Krauss GL, Wechsler RT, Wang XF, DiVentura B, Brandt C, Trinka E, O'Brien TJ, Laurenza A, Patten A, Bibbiani F. Perampanel for tonic-clonic seizures in idiopathic generalized epilepsy A randomized trial. Neurology. 2015 Sep 15;85(11):950-7. PubMed PMID: 26296511; PubMed Central PMCID: PMC4567458. 14: Singh K, Shah YD, Luciano D, Friedman D, Devinsky O, Kothare SV. Safety and efficacy of perampanel in children and adults with various epilepsy syndromes: A single-center postmarketing study. Epilepsy Behav. 2016 Aug;61:41-5. doi: 10.1016/j.yebeh.2016.05.007. PubMed PMID: 27300147. 15: Leppik IE, Yang H, Williams B, Zhou S, Fain R, Patten A, Bibbiani F, Laurenza A. Analysis of falls in patients with epilepsy enrolled in the perampanel phase III randomized double-blind studies. Epilepsia. 2017 Jan;58(1):51-59. doi: 10.1111/epi.13600. PubMed PMID: 27869305. 16: Gidal BE, Laurenza A, Hussein Z, Yang H, Fain R, Edelstein J, Kumar D, Ferry J. Perampanel efficacy and tolerability with enzyme-inducing AEDs in patients with epilepsy. Neurology. 2015 May 12;84(19):1972-80. doi: 10.1212/WNL.0000000000001558. PubMed PMID: 25878177; PubMed Central PMCID: PMC4433458. 17: Barygin OI. Inhibition of calcium-permeable and calcium-impermeable AMPA receptors by perampanel in rat brain neurons. Neurosci Lett. 2016 Oct 28;633:146-151. doi: 10.1016/j.neulet.2016.09.028. PubMed PMID: 27663136. 18: Frampton JE. Perampanel: A Review in Drug-Resistant Epilepsy. Drugs. 2015 Sep;75(14):1657-68. doi: 10.1007/s40265-015-0465-z. Review. PubMed PMID: 26370209. 19: Mano Y, Takenaka O, Kusano K. High-performance liquid chromatography-tandem mass spectrometry method for the determination of perampanel, a novel α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor antagonist in human plasma. J Pharm Biomed Anal. 2015 Mar 25;107:56-62. doi: 10.1016/j.jpba.2014.12.018. PubMed PMID: 25569285. 20: Lagae L, Villanueva V, Meador KJ, Bagul M, Laurenza A, Kumar D, Yang H. Adjunctive perampanel in adolescents with inadequately controlled partial-onset seizures: A randomized study evaluating behavior, efficacy, and safety. Epilepsia. 2016 Jul;57(7):1120-9. doi: 10.1111/epi.13417. PubMed PMID: 27221398.