基本情報
- CAS
80012-43-7- 標準SMILES
NC1=NCC2c3ccccc3Cc3ccccc3N12- InChIKey
WHWZLSFABNNENI-UHFFFAOYSA-N- 分子式
- C16H15N3
- 平均分子量
- 249.31 g/mol
- 単同位体質量
- 249.12659749
概要
Epinastine is a benzazepine that is 6,11-dihydro-5H-dibenzo[b,e]azepine in which the azepine ring is fused to the e side of 4,5-dihydro-1H-imidazol-2-amine. It has a role as a H1-receptor antagonist, a histamine antagonist, an anti-allergic agent and an ophthalmology drug. It is a member of guanidines and a benzazepine.
名称と識別子
- 優先名称
- Epinastine
- IUPAC
- 2,4-diazatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),3,7,9,11,14,16-heptaen-3-amine
- 現地名
- エピナスチン
- 英語名
- Epinastine
- 分子式
- C16H15N3
- 分子量
- 249.31
名称と別名
epinastine80012-43-7EpinastinaEpinastinum(+-)-EpinastinePurivist3-Amino-9,13b-dihydro-1H-dibenz(c,f)imidazo(1,5-a)azepine3-Amino-9,13b-dihydro-1H-dibenz[c,f]imidazo[1,5-a]azepineQ13WX941EFCHEBI:51032WAL-8013-amino-9,13b-dihydro-1H-benz(c,f)imidazo(1,5a)azepine
名称をさらに表示
9,13b-ジヒドロ-1H-ジベンゾ[c,f]イミダゾ[1,5-a]アゼピン-3-アミン(±)-3-アミノ-9,13b-ジヒドロ-1H-ジベンズ[c,f]イミダゾ[1,5-a]アゼピン9,13b-ジヒドロ-1H-ジベンゾ[c,f]イミダゾ[1,5-a]アゼピン-3-イルアミン3-アミノ-9,13b-ジヒドロ-1H-ジベンゾ[c,f]イミダゾ[1,5-a]アゼピンエピナスチン2,4-ジアザテトラシクロ[12.4.0.02,6.07,12]オクタデカ-1(18),3,7,9,11,14,16-ヘプタエン-3-アミンWAL801CS-1366EpastineELESTATWAL801Apinastine BaseEPINASTINE BASEEpinastine (WAL801)Epinastine USP/EP/BPEpinastine in methanol
DTXSID2048371R06AX241H-Dibenz(c,f)imidazo(1,5-a)azepin-3-amino, 9,13b-dihydro-RefChem:56561DTXCID8028345S01GX102,4-diazatetracyclo(12.4.0.02,?.0?,12)octadeca-1(18),3,7,9,11,14,16-heptaen-3-amine616-785-3
物性
構造計算による物性
- XLogP
- 3.5
- 極性表面積
- 41.6 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 1
- 回転可能結合数
- 0
- 重原子数
- 19
- 形式電荷
- 0
- 複雑度
- 378
実験および物理化学的性質
LogP3.1
Solubility1.63e-01 g/L
Human DrugsBreast Feeding; Lactation; Milk, Human; Antihistamines
Melting Point
205-208 °C
205 - 208 °C
Physical DescriptionSolid
物理化学的性質
- 融点
- 205 · 205-208°
- 沸点
- 428 · 428.0±55.0 °C(Predicted)
- 比重(密度)
- 1.32 · 1.32±0.1 g/cm3(Predicted)
- 貯蔵温度
- Keep in dark place,Inert atmosphere,Room temperature
- 溶解性
- 50 mg/mL · DMSO : ≥ 50 mg/mL (200.55 mM);Water : < 0.1 mg/mL (insoluble)
- 酸解離定数(Pka)
- 11.2 · 11.2(at 25℃)
- 外見
- Solid
- 色
- White to off-white
- CAS データベース
- 80012 · 80012-43-7(CAS DataBase Reference)
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 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 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 InformationREACH registered substance: 2,4-diazatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),3,7,9,11,14,16-heptaen-3-amine (EC: 616-785-3)
Hazard Classes and CategoriesAcute Tox. 4 (100%)
毒性情報
Adverse Effects
Epinastine is a safe and well-tolerated drug. It is used topically as an eye drop, and it does not cause any systemic side effects. However, it can cause a burning sensation in the eyes, hyperemia, increased lacrimation, folliculitis, and pruritus.
Toxicity SummaryThere are no reported cases of overdose with epinastine to date. However, in case of an overdose, the institution and health care providers must act promptly to ensure airway patency and that there is no circulatory collapse.
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Epinastine
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
安全データ
化学と産業
薬理情報
ATC Code
S01GX10
S - Sensory organs
R - Respiratory system
QR - Respiratory system
QS - Sensory organs
Protein Binding64%
Pharmacodynamics
Epinastine is an antihistamine and an inhibitor of histamine release from the mast cell for topical administration to the eyes. Epinastine is indicated for the prevention of itching associated with allergic conjunctivitis. Epinastine is a topically active, direct H<sub>1</sub>-receptor antagonist and an inhibitor of the release of histamine from the mast cell. Epinastine is selective for the histamine H<sub>1</sub>-receptor and has affinity for the histamine H2 receptor. Epinastine also possesses affinity for the a1-, a2-, and 5-HT<sub>2</sub> -receptors. Epinastine does not penetrate the blood/brain barrier and, therefore, is not expected to induce side effects of the central nervous system.
Mechanism of Action
Epinastine has a multiaction effect that inhibits the allergic response in 3 ways: 1. stabilizes mast cells by preventing mast cell degranulation to control the allergic response, 2. prevents histamine binding to both the H1- and H<sub>2</sub>-receptors to stop itching and provide lasting protection, and 3. prevents the release of proinflammatory chemical mediators from the blood vessel to halt progression of the allergic response.
Biological Half-Life12 hours
Metabolism/MetabolitesMainly excreted unchanged, less than 10% metabolized.
FDA Pharmacological Classification
Q13WX941EF
EPINASTINE
Mechanisms of Action [MoA] - Adrenergic Agonists
Established Pharmacologic Class [EPC] - Adrenergic Receptor Agonist
Physiologic Effects [PE] - Decreased Histamine Release
Mechanisms of Action [MoA] - Histamine H1 Receptor Antagonists
関連反応
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