基本情報
- CAS
357336-20-0- 標準SMILES
CCC[C@@H]1CC(=O)N([C@@H](CC)C(N)=O)C1- InChIKey
MSYKRHVOOPPJKU-BDAKNGLRSA-N- 分子式
- C11H20N2O2
- 平均分子量
- 212.29 g/mol
- 単同位体質量
- 212.15247789
概要
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.
名称と識別子
- 優先名称
- Brivaracetam
- IUPAC
- (2S)-2-[(4R)-2-oxo-4-propylpyrrolidin-1-yl]butanamide
- 現地名
- ブリバラセタム
- 英語名
- Brivaracetam
- 分子式
- C11H20N2O2
- 分子量
- 212.29
名称と別名
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
名称をさらに表示
ブリバラセタムブリバラセタムブリーバラセタム(S)-2-(4β-プロピル-2-オキソ-1-ピロリジニル)ブタンアミド(2S)-2-[(4R)-2-オキソ-4-プロピルピロリジン-1-イル]ブタンアミド(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
データベース識別子
- CAS
物性
構造計算による物性
- XLogP
- 1
- 極性表面積
- 63.4 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 2
- 回転可能結合数
- 5
- 重原子数
- 15
- 形式電荷
- 0
- 複雑度
- 253
実験および物理化学的性質
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
物理化学的性質
- 融点
- 76.38 ° · 76.38°
- 比旋光度
- 25 · D25 -60.57° (c = 1 in methanol)
- 沸点
- 409.3 · 409.3±28.0 °C(Predicted)
- 比重(密度)
- 1.062 · 1.062
- 貯蔵温度
- Refrigerator
- 溶解性
- DMSO（微量）、メタノール（微量）
- 外見
- 個体
- 酸解離定数(Pka)
- 15.74 · 15.74±0.50(Predicted)
- 色
- ホワイトからオフホワイト
- 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
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
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.
危険有害性情報
Regulatory InformationDEA schedule V controlled substance
Hazard Classes and CategoriesAcute Tox. 4 (66.7%)
毒性情報
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
化学と産業
薬理情報
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.
関連反応
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化合物ノート
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