4-[2-(dipropylamino)ethyl]-2,3-dihydro-1H-indol-2-one

• ChemBase编号: 153
• 分子式: C16H24N2O
• 平均质量: 260.37456
• 单一同位素质量: 260.1888634
• SMILES: O=C1Nc2c(c(CCN(CCC)CCC)ccc2)C1
• Canonical SMILES: CCCN(CCC)CCc1cccc2c1CC(=O)N2
• InChI: InChI=1S/C16H24N2O/c1-3-9-18(10-4-2)11-8-13-6-5-7-15-14(13)12-16(19)17-15/h5-7H,3-4,8-12H2,1-2H3,(H,17,19)
• InChIKey: UHSKFQJFRQCDBE-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 4-[2-(dipropylamino)ethyl]-2,3-dihydro-1H-indol-2-one
• IUPAC传统名: ropinirole
• 商标名: Requip; ReQuip CR; ReQuip XL
• 别名: Ropinirol [INN-Spanish]; Ropinirole HCl; Ropinirole hydrochloride; Ropinirolum [INN-Latin]; ropinirole; Ropinirole

登记号

• CAS号: 91374-21-9
• PubChem SID: 160963616; 46507918
• PubChem CID: 5095

理论计算性质

JChem

• Acid pKa: 13.235698
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): -0.4123002
• LogD (pH = 7.4): 0.361759
• Log P: 3.0607688
• 摩尔折射率: 81.4278 cm^3
• 极化性: 30.66853 Å^3
• 极化表面积: 32.34 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: 3.16
• LOG S: -2.87
• 溶解度: 3.53e-01 g/l

分子性质

理化性质

• 溶解度: 133 mg/mL
• 疏水性(logP): 2.3

详细说明

DrugBank - DB00268

• Drug Groups: approved; investigational
• Description: Ropinirole is a non-ergoline dopamine agonist, manufactured by GlaxoSmithKline. It is used in the treatment of Parkinson's disease, and is also one of two medications in the United States with an FDA-approved indication for the treatment of restless legs syndrome (the other being Pramipexole). [Wikipedia]
• Indication: For the treatment of the signs and symptoms of idiopathic Parkinson's disease. Also used for the treatment of restless legs syndrome.
• Pharmacology: Ropinirole is a nonergot dopamine agonist with high relative in vitro specificity and full intrinsic activity at the D₂ subfamily of dopamine receptors, binding with higher affinity to D₃ than to D₂ or D₄ receptor subtypes. The relevance of D₃ receptor binding in Parkinson's disease is unknown. The mechanism of ropinirole-induced postural hypotension is presumed to be due to a D₂ -mediated blunting of the noradrenergic response to standing and subsequent decrease in peripheral vascular resistance.
• Toxicity: Symptoms of overdose include agitation, chest pain, confusion, drowsiness, facial muscle movements, grogginess, increased jerkiness of movement, symptoms of low blood pressure (dizziness, light-headedness)upon standing, nausea, and vomiting.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. Ropinirole is extensively metabolized to inactive metabolites via N -despropylation and hydroxylation pathways, largely by the P450 isoenzyme CYP1A2. N-despropyl ropinirole is the predominant metabolite found in urine (40%), followed by the carboxylic acid metabolite (10%), and the glucuronide of the hydroxy metabolite (10%).
• Absorption: Absolute bioavailability is 55%, indicating a first pass effect. Food does not affect the extent of absorption.
• Half Life: 6 hours
• Protein Binding: 40% bound to plasma proteins with a blood-to-plasma ratio of 1:1.
• Elimination: Ropinirole is extensively metabolized by the liver to inactive metabolites, and less than 10% of the administered dose is excreted as unchanged drug in urine.
• Distribution: * 7.5 L/kg; * 525 L
• Clearance: * 47 L/hr [after oral administration to Parkinson's disease patients and patients with Restless Legs Syndrome]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com