5-[2-(benzenesulfonyl)ethyl]-3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-1H-indole

• ChemBase编号: 101
• 分子式: C22H26N2O2S
• 平均质量: 382.51904
• 单一同位素质量: 382.17149908
• SMILES: S(=O)(=O)(CCc1cc2c(C[C@@H]3N(CCC3)C)c[nH]c2cc1)c1ccccc1
• Canonical SMILES: CN1CCC[C@@H]1Cc1c[nH]c2c1cc(cc2)CCS(=O)(=O)c1ccccc1
• InChI: InChI=1S/C22H26N2O2S/c1-24-12-5-6-19(24)15-18-16-23-22-10-9-17(14-21(18)22)11-13-27(25,26)20-7-3-2-4-8-20/h2-4,7-10,14,16,19,23H,5-6,11-13,15H2,1H3/t19-/m1/s1
• InChIKey: PWVXXGRKLHYWKM-LJQANCHMSA-N

名称和登记号

名称

• IUPAC标准名: 5-[2-(benzenesulfonyl)ethyl]-3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-1H-indole
• IUPAC传统名: eletriptan; relpax
• 商标名: Relpax
• 别名: 3-[[(2R)-1-Methyl-2-pyrrolidinyl]methyl]-5-[2-(phenylsulfonyl)ethyl]-1H-indole; (R)-5-[2-(Benzenesulfonyl)ethyl]-3-[(N-methylpyrrolidin-2-yl)methyl]-1H-indole; UK-116044; Relpax free amine; EletriptanAlso see: R143400; eletriptan; Eletriptan

登记号

• CAS号: 143322-58-1
• PubChem SID: 46506380; 160963564
• PubChem CID: 77993

理论计算性质

JChem

• Acid pKa: 17.110289
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 0.9913155
• LogD (pH = 7.4): 2.7574787
• Log P: 3.7732625
• 摩尔折射率: 110.9416 cm^3
• 极化性: 44.744522 Å^3
• 极化表面积: 53.17 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.84
• LOG S: -5.51
• 溶解度: 1.18e-03 g/l

分子性质

理化性质

• 溶解度: Chloroform; Methanol; Readily soluble as hydrobromide formulation
• 外观: Yellow Solid
• 疏水性(logP): 3.9

安全信息

• 保存条件: Hygroscopic, Refrigerator, Under Inert Atmosphere

详细说明

DrugBank - DB00216

• Drug Groups: approved; investigational
• Description: Eletriptan is a second generation triptan drug developed by Pfizer Inc for the treatment of migraine headaches. [Wikipedia]
• Indication: For the acute treatment of migraine with or without aura in adults.
• Pharmacology: Eletriptan is a selective 5-hydroxytryptamine 1B/1D receptor agonist. In the anesthetized dog, eletriptan has been shown to reduce carotid arterial blood flow, with only a small increase in arterial blood pressure at high doses. While the effect on blood flow was selective for the carotid arterial bed, decreases in coronary artery diameter were observed. Eletriptan has also been shown to inhibit trigeminal nerve activity in the rat.
• Toxicity: Based on the pharmacology of the 5-HT1B/1D agonists, hypertension or other more serious cardiovascular symptoms could occur on overdose.
• Affected Organisms: Humans and other mammals
• Biotransformation: In vitro studies indicate that eletriptan is primarily metabolized by cytochrome P-450 enzyme CYP3A4. The N-demethylated metabolite of eletriptan is the only known active metabolite.
• Absorption: Well absorbed after oral administration with a mean absolute bioavailability of approximately 50%.
• Half Life: The terminal elimination half-life of eletriptan is approximately 4 hours.
• Protein Binding: Plasma protein binding is moderate and approximately 85%.
• Distribution: * 138 L
• Clearance: * Renal cl=3.9 L/h
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Toronto Research Chemicals - E505000

A serotonin 5-HTIB/ID receptor agonist. Antimigrene.

参考文献

• Willems, E., et al.: Arch. Pharmacol., 358, 212 (1998)
• Napier, C., et al.: Eur. J. Pharmacol., 368, 259 (1998)
• Goadsby, P.J., et al.: Neurology, 54, 156 (2000)