2-(2,2-dicyclohexylethyl)piperidine

• ChemBase编号: 945
• 分子式: C19H35N
• 平均质量: 277.4879
• 单一同位素质量: 277.27695013
• SMILES: N1C(CC(C2CCCCC2)C2CCCCC2)CCCC1
• Canonical SMILES: C1CCC(NC1)CC(C1CCCCC1)C1CCCCC1
• InChI: InChI=1S/C19H35N/c1-3-9-16(10-4-1)19(17-11-5-2-6-12-17)15-18-13-7-8-14-20-18/h16-20H,1-15H2
• InChIKey: CYXKNKQEMFBLER-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-(2,2-dicyclohexylethyl)piperidine
• IUPAC传统名: @perhexiline; perhexiline
• 别名: Perhexilina [INN-Spanish]; Perhexilinum [INN-Latin]; 2-(2,2-Dicyclohexylethyl)piperidine; (-)-2-(2,2-Dicyclohexylethyl)piperidine; (+)-2-(2,2-Dicyclohexylethyl)piperidine; Perhexilene; Perhexilline; Perhexiline

登记号

• CAS号: 6621-47-2
• PubChem SID: 160964408; 46504471
• PubChem CID: 4746
• CHEBI ID: 35553
• ATC码: C08EX02
• CHEMBL: 75880
• Chemspider ID: 4584
• DrugBank ID: DB01074
• KEGG ID: D08340
• 美国药典/FDA物质标识码: KU65374X44
• 维基百科标题: Perhexiline

理论计算性质

JChem

• 质子受体: 1
• 质子供体: 1
• LogD (pH = 5.5): 2.2955542
• LogD (pH = 7.4): 2.6224937
• Log P: 5.5313087
• 摩尔折射率: 87.2286 cm^3
• 极化性: 35.12344 Å^3
• 极化表面积: 12.03 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 5.87
• LOG S: -7.01
• 溶解度: 2.72e-05 g/l

分子性质

理化性质

• 溶解度: 0.0608 mg/L
• 疏水性(logP): 6.2

药理学性质

• 给药途径: Oral
• 生物利用度: Dose Dependent
• 半衰期: Dose Dependent
• 代谢: Saturable Hepatic

详细说明

DrugBank - DB01074

• Drug Groups: approved
• Description: 2-(2,2-Dicyclohexylethyl)piperidine. Coronary vasodilator used especially for angina of effort. It may cause neuropathy and hepatitis. [PubChem]
• Indication: For the management of severe angina pectoris.
• Pharmacology: Used in the treatment of unresponsive or refractory angina. Perhexiline increases glucose metabolism at the expense of free-fatty-acid metabolism, enhancing oxygen efficiency during myocardial ischaemia. Perhexiline also potentiates platelet responsiveness to nitric oxide both in patients with angina and patients with acute coronary syndrome. The predominant mechanism of this particular perhexiline effect is an increase in platelet cGMP responsiveness. Perhexiline also may reduce the potential for nitric oxide clearance by neutrophil-derived oxygen. Perhexiline relieves symptoms of angina, improves exercise tolerance, and increases the workload needed to induce ischaemia when used as monotherapy. The primary therapeutic roles for perhexiline are as short-term therapy (less than 3 months duration) in patients with severe ischaemia awaiting coronary revascularisation or long-term therapy in patients with ischaemic symptoms refractory to other therapeutic measures.
• Toxicity: Oral LD₅₀ rat: 2150 mg/kg; Oral LD₅₀ Mouse: 2641 mg/kg. Short term adverse effects include nausea, transient dizziness, hypoglycaemia in diabetic patients, and torsade de pointes (rare).
• Affected Organisms: Humans and other mammals
• Biotransformation: The principal metabolites of perhexiline in man are monohydroxyperhexiline (which is excreted, in part, conjugated with glucuronic acid) and dihydroxyperhexiline that accounts for a relatively small proportion of the total metabolites. Two unidentified metabolites have also been found in the faeces. The pharmacological activity of the metabolites is not known. Hydroxylation of perhexiline is controlled by cytochrome P450 2D6 (CY P450 2D6).
• Absorption: Well absorbed (>80%) from the gastrointestinal tract following oral administration.
• Half Life: Variable and non-linear. Some reports show a half-life of 2-6 days, others indicate it could be as high as 30 days.
• Protein Binding: Perhexiline and its metabolites are highly protein bound (>90%).
• External Links: Wikipedia