기본 정보
- CAS
357336-20-0- 표준 SMILES
CCC[C@@H]1CC(=O)N([C@@H](CC)C(N)=O)C1- InChIKey
MSYKRHVOOPPJKU-BDAKNGLRSA-N- 분자식
- C11H20N2O2
- 평균 분자량
- 212.29 g/mol
- 단동위원소 질량
- 212.15247789
개요
Brivaracetam is a non-proteinogenic amino acid derivative that is butanamide in which the pro-S hydrogen at position 2 is replaced by a (4R)-2-oxo-4-propylpyrrolidin-1-yl. Used for treatment of partial onset seizures related to epilepsy. It has a role as an anticonvulsant. It is a gamma-lactam and a non-proteinogenic amino acid derivative. It is functionally related to a L-alpha-aminobutyric acid.
이름 및 식별자
- 우선 이름
- Brivaracetam
- IUPAC
- (2S)-2-[(4R)-2-oxo-4-propylpyrrolidin-1-yl]butanamide
- 현지명
- 브리바라세탐
- 영어명
- Brivaracetam
- 분자식
- C11H20N2O2
- 분자량
- 212.29
이름 및 동의어
Brivaracetam357336-20-0BriviactUCB 34714UCB-34714(2s)-2-[(4r)-2-oxo-4-propylpyrrolidin-1-yl]butanamideUCB34714brivaracetamum1-Pyrrolidineacetamide, alpha-ethyl-2-oxo-4-propyl-, (alphaS,4R)-U863JGG2IACHEBI:133013DTXSID00905081
이름 더 보기
브리바라세탐(S)-2-((R)-2-oxo-4-propylpyrrolidin-1-yl)butanaMide1-PyrrolidineacetaMide, α-ethyl-2-oxo-4-propyl-, (αS,4R)-(alphaS,4R)-alpha-Ethyl-2-oxo-4-propyl-1-pyrrolidineacetamide(alphaSBoisitanBoisetan
(2S)-2-((4R)-2-Oxo-4-propylpyrrolidin-1-yl)butanamide(2S)-2-((4R)-2-OXO-4-PROPYLTETRAHYDRO-1H-PYRROL-1-YL) BUTANAMIDERefChem:57048N03AX23DTXCID601334183Rikelta2-(2-oxo-4-propylpyrrolidin-1-yl)butanamideMFCD25976668
데이터베이스 식별자
- CAS
357336-20-0- PubChem CID
- 9837243
- DTXSID
DTXSID00905081
물성
구조 계산 물성
- XLogP
- 1
- 극성 표면적
- 63.4 Ų
- 수소 결합 공여자 수
- 1
- 수소 결합 수용자 수
- 2
- 회전 가능 결합 수
- 5
- 무거운 원자 수
- 15
- 형식 전하
- 0
- 복잡도
- 253
실험 및 물리화학적 성질
Drugs
DEA Schedule V Controlled Substance -> Depressants
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antiepileptics
LogP1.0
Human Drugs
Breast Feeding; Lactation; Milk, Human; Anticonvulsants
FDA approved drugs -> Active ingredient
EMA approved medicines: Human medicine
FDA approved drugs -> Active ingredient
물리화학적 성질
- 녹는점
- 76.38 ° · 76.38°
- 끓는 점
- 409.3 · 409.3±28.0 °C(Predicted)
- 밀도
- 1.062 · 1.062
- 저장 조건
- Refrigerator
- 용해도
- DMSO(약간 용해됨), 메탄올(약간 용해됨)
- 물리적 상태
- 고체
- 산도 계수 (pKa)
- 15.74 · 15.74±0.50(Predicted)
- 색상
- 흰색에서 황백색까지
- InChI
- InChI=1/C11H20N2O2/c1-3-5-8-6-10(14)13(7-8)9(4-2)11(12)15/h8-9H,3-7H2,1-2H3,(H2,12,15)/t8-,9+/s3
- InChIKey
- MSYKRHVOOPPJKU-MASDURLHNA-N
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
GHS Classification
Warning
H302 (66.7%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P271, P301+P317, P304+P340, P319, P330, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 3 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
유해성 정보
Regulatory InformationDEA schedule V controlled substance
Hazard Classes and CategoriesAcute Tox. 4 (66.7%)
독성 정보
Hepatotoxicity
Prospective studies reported that chronic brivaracetam therapy was not accompanied by significant elevations in serum aminotransferase levels and clinically apparent liver injury was not observed. Brivaracetam has had limited general use, but has not been linked to instances of clinically apparent liver injury. Levetiracetam, an anticonvulsant with similar structure and mechanism of action, has been linked to rare instances of acute liver injury, generally arising within 1 to 20 weeks and presenting with a hepatocellular pattern of injury without immunoallergic or autoimmune features. Whether similar cases will be linked to brivaracetam is not known.
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Brivaracetam
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
화학 및 산업
약리 정보
ATC Code
N03AX23
N - Nervous system
QN - Nervous system
Protein Binding<20% bound to plasma proteins.
Pharmacodynamics
Brivaracetam binds SV2A with high affinity. SV2A is known to play a role in epileptogenesis through modulation of synaptic GABA release. It is thought that brivaracetam exerts its anti-epileptogenic effects through its binding to SV2A. Brivaracetam is also known to inhibit Na+ channels which may also contribute to its anti-epileptogenic action.
Mechanism of ActionThe precise mechanism of brivaracetam's anti-epileptogenic activity is unknown.
Biological Half-Life7-8h.
Metabolism/Metabolites
Primarily metabolized by hydrolysis of the acetamide moeity to form a carboxylic acid metabolite. Another metabolite is created via oxidation of the propyl side chain by CYP2C8 as well as CYP3A4, CYP2C19, and CYP2B6. Some conjugation with glucuronic acid and taurine account for a small amount of metabolism.
FDA Pharmacological Classification
U863JGG2IA
BRIVARACETAM
Mechanisms of Action [MoA] - Epoxide Hydrolase Inhibitors
The mechanism of action of brivaracetam is as an Epoxide Hydrolase Inhibitor.
BRIVARACETAM
Epoxide Hydrolase Inhibitors [MoA]
MeSH Pharmacological ClassificationDrugs used to prevent SEIZURES or reduce their severity.
Absorption, Distribution and Excretion
Nearly 100% oral bioavailability.
\>95% excreted in urine with <10% of the parent compound unchanged. <1% excreted in feces.
0.5L/kg.
CL/F of 0.7-1.07 mL/min kg. Clearance is primarily metabolic with less than 10% of the parent drug excreted unchanged.
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