2,4-diazatetracyclo[12.4.0.0^{2,6}.0^{7,12}]octadeca-1(14),3,7(12),8,10,15,17-heptaen-3-amine

• ChemBase编号: 631
• 分子式: C16H15N3
• 平均质量: 249.3104
• 单一同位素质量: 249.1265975
• SMILES: N12C(c3c(Cc4c1cccc4)cccc3)CN=C2N
• Canonical SMILES: NC1=NCC2N1c1ccccc1Cc1c2cccc1
• InChI: InChI=1S/C16H15N3/c17-16-18-10-15-13-7-3-1-5-11(13)9-12-6-2-4-8-14(12)19(15)16/h1-8,15H,9-10H2,(H2,17,18)
• InChIKey: WHWZLSFABNNENI-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2,4-diazatetracyclo[12.4.0.0^{2,6}.0^{7,12}]octadeca-1(14),3,7(12),8,10,15,17-heptaen-3-amine
• IUPAC传统名: epinastine
• 商标名: Elestat
• 别名: Epinastina [Spanish]; Epinastinum [Latin]; epinastine; Epinastine

登记号

• CAS号: 80012-43-7
• PubChem SID: 160964094; 46509056
• PubChem CID: 3241

理论计算性质

JChem

• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 0.7146667
• LogD (pH = 7.4): 1.72546
• Log P: 3.073111
• 摩尔折射率: 76.9014 cm^3
• 极化性: 28.761738 Å^3
• 极化表面积: 41.62 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.53
• LOG S: -3.18
• 溶解度: 1.63e-01 g/l

分子性质

理化性质

• 疏水性(logP): 3.1

详细说明

DrugBank - DB00751

• Drug Groups: approved; investigational
• Description: Epinastine is used for the prevention of itching associated with allergic conjunctivitis. It has a multi-action 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 H2-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.
• Indication: For the prevention of itching associated with allergic conjunctivitis.
• Pharmacology: 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 H₁-receptor antagonist and an inhibitor of the release of histamine from the mast cell. Epinastine is selective for the histamine H₁-receptor and has affinity for the histamine H2 receptor. Epinastine also possesses affinity for the a1-, a2-, and 5-HT₂ -receptors. Epinastine does not penetrate the blood/brain barrier and, therefore, is not expected to induce side effects of the central nervous system.
• Affected Organisms: Humans and other mammals
• Biotransformation: Mainly excreted unchanged, less than 10% metabolized.
• Absorption: The absolute bioavailability of epinastine is about 40%.
• Half Life: 12 hours
• Protein Binding: 64%
• Elimination: Epinastine is mainly excreted unchanged. The renal elimination is mainly via active tubular secretion.
• Clearance: * 56 L/hr [patients with allergic conjunctivitis receiving one drop of ELESTAT? ophthalmic solution in each eye twice daily for seven days]
• References: Walther G, Daniel H, Bechtel WD, Brandt K: New tetracyclic guanidine derivatives with H1-antihistaminic properties. Chemistry of epinastine. Arzneimittelforschung. 1990 Apr;40(4):440-6. [Pubmed] ; Schilling JC, Adamus WS, Kuthan H: Antihistaminic activity and side effect profile of epinastine and terfenadine in healthy volunteers. Int J Clin Pharmacol Ther Toxicol. 1990 Dec;28(12):493-7. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

参考文献

• Walther G, Daniel H, Bechtel WD, Brandt K: New tetracyclic guanidine derivatives with H1-antihistaminic properties. Chemistry of epinastine. Arzneimittelforschung. 1990 Apr;40(4):440-6. Pubmed
• Schilling JC, Adamus WS, Kuthan H: Antihistaminic activity and side effect profile of epinastine and terfenadine in healthy volunteers. Int J Clin Pharmacol Ther Toxicol. 1990 Dec;28(12):493-7. Pubmed