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페라엠패널

Perampanel

HCID 9924495
노트반응
기본 정보이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
380917-97-5
표준 SMILES
N#Cc1ccccc1-c1cc(-c2ccccn2)cn(-c2ccccc2)c1=O
InChIKey
PRMWGUBFXWROHD-UHFFFAOYSA-N
분자식
C23H15N3O
평균 분자량
349.4 g/mol
단동위원소 질량
349.12151211

이름 및 식별자

우선 이름
Perampanel
IUPAC
2-(2-oxo-1-phenyl-5-pyridin-2-yl-3-pyridinyl)benzonitrile
현지명
페라엠패널
영어명
PeraMpanel
분자식
C23H15N3O
분자량
349.38

이름 및 동의어

Perampanel380917-97-5FycompaE2007ER-155055-90E-2007perampanelumE 20073-(2-Cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one2-(2-oxo-1-phenyl-5-pyridin-2-ylpyridin-3-yl)benzonitrileCHEBI:71013H821664NPK
이름 더 보기
페라엠패널PerampanePeraMpanel-D5PERAMPANEL APIPerampanel Impurity3-(2-Cyanophenyl)-1-phenyl-5-(2-pyridyl)-1,2-dihydropyridin-2-one2-(2-oxo-1-phenyl-5-(pyridin-2-yl)-1,2-dihydropyridin-3-yl)benzonitrileCS-1116
Benzonitrile, 2-(1',6'-dihydro-6'-oxo-1'-phenyl[2,3'-bipyridin]-5'-yl)-DTXSID801915012-(6'-oxo-1'-phenyl-1',6'-dihydro-2,3'-bipyridin-5'-yl)benzonitrileBenzonitrile, 2-(1',6'-dihydro-6'-oxo-1'-phenyl(2,3'-bipyridin)-5'-yl)-RefChem:58336DTXCID50113992N03AX22Fycompa (TN)

데이터베이스 식별자

CAS
380917-97-5
PubChem CID
9924495
DTXSID
DTXSID80191501
ChEMBL
CHEMBL1214124
ChEBI
CHEBI:71013
UNII
H821664NPK
EC Number
691-969-4
Nikkaji
J2.400.987D

물성

구조 계산 물성

XLogP
3.4
극성 표면적
57 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
3
회전 가능 결합 수
3
무거운 원자 수
27
형식 전하
0
복잡도
664

실험 및 물리화학적 성질

SolubilityPractically insoluble in water.

물리화학적 성질

끓는 점
619.1 · 619.1±55.0 °C(Predicted)
밀도
1.31 · 1.31±0.1 g/cm3(Predicted)
용해도
DMSO에 용해됨
물리적 상태
가루
산도 계수 (pKa)
4.73 · 4.73±0.19(Predicted)

안전 및 규제

GHS 분류

GHS Classification · 5건

Warning

H302 (88.4%): Harmful if swallowed [Warning Acute toxicity, oral]；H413 (88.4%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]

P264, P270, P273, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 43 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

유해성 정보

Hazard Classes and CategoriesAcute Tox. 4 (88.4%)；Aquatic Chronic 4 (88.4%)

독성 정보

Hepatotoxicity · 1건

Limited data are available on the hepatotoxicity of perampanel. In clinical trials, therapy with perampanel was not associated with an increased frequency of serum aminotransferase elevations as compared to placebo treatment, and there were no reported instances of clinically apparent liver injury. No individual case reports of perampanel hepatotoxicity have been published since its general clinical availability. Perampanel has been implicated in rare instances of severe cutaneous hypersensitivity reactions including DRESS syndrome, which can be associated with variable degrees of liver injury. Thus, clinically apparent liver injury due to perampanel may occur, but must be very rare.；Likelihood score: E (unlikely cause of clinically apparent liver injury).

Drug Induced Liver Injury · 6건

Drug Induced Liver Injury Rank (DILIrank 2.0)

Perampanel

vNo-DILI-concern

0

화학 및 산업

약리 정보

ATC Code · 3건

N03AX22

N - Nervous system；N03 - Antiepileptics；N03A - Antiepileptics；N03AX - Other antiepileptics；N03AX22 - Perampanel

QN - Nervous system；QN03 - Antiepileptics；QN03A - Antiepileptics；QN03AX - Other antiepileptics；QN03AX22 - Perampanel

Protein BindingPerampanel is 95-96% plasma protein bound with most binding to the plasma proteins α1-acid glycoprotein and albumin.
PharmacodynamicsPerampanel is involved in inhibiting neuronal excitation in the central nervous system leading to such effects as decreased pyschomotor performance.
Mechanism of ActionThe exact mechanism of action of perampanel in seizures is not yet determined, but it is known that perampanel decreases neuronal excitation by non-competitive ihibition of the AMPA receptor.
Biological Half-LifePerampanel has a long elmination half-life of about 105 hours.
Metabolism/MetabolitesPerampanel is highly metabolized by CYP3A4 and/or CYP3A5 primary oxidation and by sequential glucuronidation.
FDA Pharmacological Classification · 6건

H821664NPK

PERAMPANEL

Established Pharmacologic Class [EPC] - Noncompetitive AMPA Glutamate Receptor Antagonist

Mechanisms of Action [MoA] - AMPA Receptor Antagonists

Mechanisms of Action [MoA] - UGT2B7 Inhibitors

Mechanisms of Action [MoA] - UGT1A9 Inhibitors

Absorption, Distribution and Excretion · 4건

After oral adminitration, perampanel is absorbed rapidly and completely.

Perampanel is eliminated mostely in the feces (48%) and to a lesser exten in the urine (22%).

The volume of distribution of perampanel was not quantified.

In healthy patients, perampanel has a clearance of about 12 mL/min.

관련 반응

15건
반응 기록 만들기
HRID 229658 반응식
HRID 229658생성물로uspto-grants-2009_07
HRID 229693 반응식
HRID 229693반응물로uspto-grants-2009_07
HRID 497821 반응식
HRID 497821생성물로uspto-grants-2005_09
HRID 497856 반응식
HRID 497856반응물로uspto-grants-2005_09
HRID 547690 반응식
HRID 547690생성물로uspto-grants-2011_05
HRID 547724 반응식
HRID 547724반응물로uspto-grants-2011_05
HRID 700944 반응식
HRID 700944생성물로반응물로Training data from https://doi.org/10.1039/C8SC04228D (3/10)
HRID 2159203 반응식
HRID 2159203생성물로Training data from https://doi.org/10.1039/C8SC04228D (4/10)
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DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation · 1건

◉ Summary of Use during Lactation；A minimal amount of information indicates that perampanel milk levels are quite low. If perampanel is required by the mother, it is not a reason to discontinue breastfeeding, but monitor the infant for drowsiness, agitation, adequate weight gain, and developmental milestones, especially in younger, exclusively breastfed infants and when using combinations of drugs.；◉ Effects in Breastfed Infants；An infant was exclusively breastfed by a mother taking perampanel, brivaracetam and lacosamide for 6 weeks, then partially breastfed. The infant did not exhibit reduced wakefulness or feeding problems. At one year of age, the mother reported normal development.[1]；◉ Effects on Lactation and Breastmilk；Relevant published information was not found as of the revision date.

안전 데이터

신호 어
Warning
유해·위험 문구
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드 H302
응용 분야 · 2건

개요In 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.

용도Isotope 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.

상·하류 제품 정보

상류 원료

380917-96-46'-메톡시-2,3'-비피리딘5'-broMo-1'-phenyl-[2,3'-bipyridin]-6'(1'H)-one5-(2-피리딜)-1,2-DIHYDROPYRIDIN-2-ONE2-(1,3,2-디옥사보롤란-2-YL)벤조니트릴2,5-Dibromopyridine5-Bromo-2-methoxypyridine
추가 설명 · 1건

정의ChEBI: A member of the class of bipyridines that is 2,3'-bipyridin-6'-one substituted at positions 1' and 5' by phenyl and 2-cyanophenyl groups respectively. Used as an adjunctive therapy for the treatment of partial-onset seizures in patients with epilepsy.