Perampanel

Base Information

• Chemical Name: Perampanel
• CAS No.: 380917-97-5
• Molecular Formula: C23H15N3O
• Molecular Weight: 349.392
• European Community (EC) Number: 691-969-4
• UNII: H821664NPK
• DSSTox Substance ID: DTXSID80191501
• Nikkaji Number: J2.400.987D
• Wikipedia: Perampanel
• Wikidata: Q868658
• NCI Thesaurus Code: C75029
• RXCUI: 1356552
• Pharos Ligand ID: SVLH6GSG9Z77
• Metabolomics Workbench ID: 65399
• ChEMBL ID: CHEMBL1214124
• Mol file: 380917-97-5.mol

Synonyms:3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one;E-2007;E2007;ER-155055-90;Fycompa;perampanel;perampanel hydrate;perampanel hydrate (4:3)

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Chemical Property of Perampanel

Chemical Property:

• Boiling Point: 619.1±55.0 °C(Predicted)
• PKA: 4.73±0.19(Predicted)
• PSA: 58.68000
• Density: 1.31±0.1 g/cm3(Predicted)
• LogP: 4.43818
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 349.121512110
• Heavy Atom Count: 27
• Complexity: 664

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Anticonvulsants
• Canonical SMILES: C1=CC=C(C=C1)N2C=C(C=C(C2=O)C3=CC=CC=C3C#N)C4=CC=CC=N4
• Recent ClinicalTrials: Alpha-Amino-3-Hydroxy-5-Methyl-4- Isoxazole Propionic Acid Receptor Components of the Anti-Depressant Ketamine Response
• Recent EU Clinical Trials: A Multicentric, Drug-Repositioning, Self Controlled Case Series (SCCS) Clinical Trial to Evaluate the Efficacy and Safety of Perampanel in Improving Behavioral Symptoms and Increasing the Quality of Life in Patients with White-Sutton syndrome (POGZRelated Disorder)
• Recent NIPH Clinical Trials: Investigation of the Clinical Safety and Efficacy of Long-term Treatment With Fycompa Tablets in Adolescence Epilepsy Patients With Partial-onset Seizures (With or Without Secondary Generalized Seizures) or Primary Generalized Tonic-clonic Seizures
• Description: Perampanel (licensed in 2012) is a third- generation AED known with the proprietary brand name of Fycompa? (Eisai, Hatfield) in the UK and Banzel? (Eisai, Hatfield) in the USA. In October 2012, the US FDA approved perampanel for the treatment of partial onset seizures in epileptic patients who are at least 12 years old. Perampanel is the first AMPA receptor antagonist to receive FDA approval as an AED. AMPA glutamate receptors are found primarily on postsynaptic neurons in the brain. As a selective, noncompetitive antagonist of AMPA, parampanel prevents ion channel opening and reduces propagation of action potential. Parampanel was discovered through lead optimization of a commercially available compound, 2,4-diphenyl-4H-[1,3,4]oxadiazin-5-one, which was identified by high-throughput screening of a compound collection employing a rat cortical neuron AMPA-induced cell-death assay. Modifications of aromatic rings at positions 1, 3, and 5 while changing the core to pyridone led to parampanel which inhibited AMPA-induced calcium influx (IC50=60 nM). Parampanel had a minimum effective oral dose of 2 mg/kg in an AMPA-induced mouse seizure model. The synthesis of parampanel was accomplished via a 6-step route utilizing Suzuki–Miyaura couplings and modified Ullmann reactions for incorporation of aryl groups.
• Indications: Epilepsy: Adjunctive treatment of focal seizures with or without secondary generalization and primary generalized tonic- clonic seizures.
• Uses: Isotope labelled Perampanel (P285520), is an antiepileptic drug. It inhibits α-amino-3-hydroxy-5-methyl-4-isoxazole-propionic acid (AMPA)-induced increases in intracellular Ca2+ and selectively blocks AMPA receptor-mediated synaptic transmission, thus reducing neuronal excitation.
• Clinical Use: Selective AMPA-type glutamate receptor antagonist: Antiepileptic
• Drug interactions: Potentially hazardous interactions with other drugs Antidepressants: anticonvulsant effect antagonised; avoid with St John’s wort. Antiepileptics: concentration reduced by carbamazepine, fosphenytoin, oxcarbazepine and phenytoin. Antimalarials: anticonvulsant effect antagonised by mefloquine. Antipsychotics: anticonvulsant effect antagonised. Orlistat: possibly increased risk of convulsions. Progestogens: high-dose perampanel reduces plasma concentration of progestogens (possibly reduced contraceptive effect).

Technology Process of Perampanel

There total 39 articles about Perampanel which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 73.0%

3-bromo-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridine-2-one (381248-06-2) + o-cyanophenylboronic acid-1,3-propylene glycol ester (172732-52-4) → [14C]-Perampanel (380917-97-5)

Guidance literature:

With caesium carbonate; palladium dichloride; In N,N-dimethyl-formamide; at 80 ℃; for 6h; Inert atmosphere;

DOI:10.1021/jm301268u

Reference yield: 72.0%

N-phenyl-2-(2-cyanophenyl)acetamide + C12H18N3(1+)*F6P(1-) → [14C]-Perampanel (380917-97-5)

Guidance literature:

With sodium ethanolate; In ethanol; dimethyl sulfoxide; at 40 - 45 ℃; for 0.5h; Reagent/catalyst; Solvent;

Reference yield: 69.0%

3-bromo-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridine-2-one (381248-06-2) + 2-(1,3-dioxaborinan-2-yl)benzonitrile → [14C]-Perampanel (380917-97-5)

Guidance literature:

With copper(l) iodide; palladium diacetate; potassium carbonate; triphenylphosphine; In 1,2-dimethoxyethane; at 70 - 95 ℃; for 5.5h; Inert atmosphere;

DOI:10.1055/s-0031-1289587

upstream raw materials:

3-(2-cyanophenyl)-5-(2-pyridyl)-1,2-dihydropyridin-2-one

phenylboronic acid

3-bromo-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridine-2-one

o-cyanophenylboronic acid-1,3-propylene glycol ester

Downstream raw materials:

3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one hydrate