2-[(3S)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrrolidin-3-yl]-2,2-diphenylacetamide

• ChemBase编号: 379
• 分子式: C28H30N2O2
• 平均质量: 426.55
• 单一同位素质量: 426.23072821
• SMILES: O=C(N)C([C@@H]1CCN(C1)CCc1cc2c(OCC2)cc1)(c1ccccc1)c1ccccc1
• Canonical SMILES: NC(=O)C(c1ccccc1)(c1ccccc1)[C@@H]1CCN(C1)CCc1ccc2c(c1)CCO2
• InChI: InChI=1S/C28H30N2O2/c29-27(31)28(23-7-3-1-4-8-23,24-9-5-2-6-10-24)25-14-17-30(20-25)16-13-21-11-12-26-22(19-21)15-18-32-26/h1-12,19,25H,13-18,20H2,(H2,29,31)/t25-/m1/s1
• InChIKey: HXGBXQDTNZMWGS-RUZDIDTESA-N

名称和登记号

名称

• IUPAC标准名: 2-[(3S)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrrolidin-3-yl]-2,2-diphenylacetamide
• IUPAC传统名: enablex
• 商标名: Enablex; Emselex
• 别名: darifenacin; Darifenacin

登记号

• CAS号: 133099-04-4
• PubChem SID: 46508104; 160963842
• PubChem CID: 444031

理论计算性质

JChem

• Acid pKa: 16.212147
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 1.0715904
• LogD (pH = 7.4): 1.896206
• Log P: 4.540284
• 摩尔折射率: 128.3747 cm^3
• 极化性: 49.758102 Å^3
• 极化表面积: 55.56 Å^2
• 可自由旋转的化学键: 7
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 4.35
• LOG S: -6.16
• 溶解度: 2.98e-04 g/l

分子性质

理化性质

• 疏水性(logP): 4.5

详细说明

DrugBank - DB00496

• Drug Groups: approved; investigational
• Description: Darifenacin (Enablex?, Novartis) is a medication used to treat urinary incontinence.; ; Darifenacin works by blocking the M3 muscarinic acetylcholine receptor, which is primarily responsible for bladder muscle contractions. It thereby decreases the urgency to urinate. It should not be used in people with urinary retention.; ; It is not known whether this selectivity for the M3 receptor translates into any clinical advantage when treating symptoms of overactive bladder syndrome.
• Indication: For the treatment of overactive bladder with symptoms of urge urinary incontinence, urgency and frequency.
• Pharmacology: Darifenacin is a competitive muscarinic receptor antagonist. In vitro studies using human recombinant muscarinic receptor subtypes show that darifenacin has greater affinity for the M3 receptor than for the other known muscarinic receptors (9 and 12-fold greater affinity for M3 compared to M1 and M5, respectively, and 59-fold greater affinity for M3 compared to both M2 and M4). Muscarinic receptors play an important role in several major cholinergically mediated functions, including contractions of the urinary bladder smooth muscle and stimulation of salivary secretion. Adverse drug effects such as dry mouth, constipation and abnormal vision may be mediated through effects on M3 receptors in these organs.
• Toxicity: Overdosage can potentially result in severe central anticholinergic effects.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. Primarily mediated by the cytochrome P450 enzymes CYP2D6 and CYP3A4.
• Absorption: The mean oral bioavailability at steady state is estimated to be 15% and 19% for 7.5 mg and 15 mg tablets, respectively.
• Half Life: The elimination half-life of darifenacin following chronic dosing is approximately 13-19 hours.
• Protein Binding: Darifenacin is approximately 98% bound to plasma proteins (primarily to alpha-1-acid-glycoprotein).
• Distribution: * 163 L
• Clearance: * 40 L/h [extensive metabolizers]; * 32 L/h [poor metabolizers]
• External Links: Wikipedia; RxList; Drugs.com