(S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol

• ChemBase编号: 784
• 分子式: C20H24N2O2
• 平均质量: 324.41676
• 单一同位素质量: 324.18377802
• SMILES: O[C@H]([C@@H]1N2C[C@@H]([C@H](C1)CC2)C=C)c1c2c(ncc1)ccc(OC)c2
• Canonical SMILES: C=C[C@H]1CN2CC[C@H]1C[C@@H]2[C@H](c1ccnc2c1cc(OC)cc2)O
• InChI: InChI=1S/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,19+,20-/m0/s1
• InChIKey: LOUPRKONTZGTKE-LHHVKLHASA-N

名称和登记号

名称

• IUPAC标准名: (S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol
• IUPAC传统名: quinidine; quinidine sulphate
• 商标名: Apo-Quinidine; Biquin Durules; Cardioquin; Chinidin; Cin-Quin; Coccinine; Conchinin; Conchinine; Conquinine; Duraquin; Kinidin; Novoquinidin; Pitayin; Pitayine; Quin-Release; Quinact; Quinaglute; Quinaglute Dura-Tabs; Quinalan; Quinate; Quinatime; Quindine; Quinicardine; Quinidex; Quinidex Extentabs; Quinora
• 别名: 奎尼丁; (1S)-(6-Methoxyquinolin-4-yl)((2R,4S,5R)-5-vinylquinuclidin-2-yl)methanol; (2-ethenyl- 4-azabicyclo [2.2.2] oct- 5-yl)- (6-methoxyquinolin- 4-yl)- methanol,; Quinidine; Quinidine Sulfate; Quinidine Gluconate; Quinidine; QUINIDINE GLUCONATE

登记号

• CAS号: 56-54-2
• EC号: 200-279-0
• MDL号: MFCD00135581
• Beilstein号: 91866
• PubChem SID: 160964247; 24853537; 24899331; 46505356
• PubChem CID: 441074
• CHEBI ID: 28593
• ATC码: C01BA01
• CHEMBL: 97
• Chemspider ID: 389880
• DrugBank ID: DB00908
• IUPHAR配体索引: 2342
• 美国药典/FDA物质标识码: ITX08688JL
• 维基百科标题: Quinidine

理论计算性质

JChem

• Acid pKa: 13.892048
• 质子受体: 4
• 质子供体: 1
• LogD (pH = 5.5): -0.7213722
• LogD (pH = 7.4): 0.863951
• Log P: 2.513464
• 摩尔折射率: 94.6936 cm^3
• 极化性: 38.350784 Å^3
• 极化表面积: 45.59 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.82
• LOG S: -2.99
• 溶解度: 3.34e-01 g/l

分子性质

理化性质

• 溶解度: 140 mg/L
• 熔点: 168-172 °C(lit.)
• 比旋光度: [α]20/D +265±5°, c = 0.8% in ethanol (dry matter)
• 疏水性(logP): 2.6

安全信息

• 保存注意事项: IRRITANT
• RTECS编号: VA4725000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 联合国危险货物编号: 2811
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 22
• 安全公开号: 36
• TSCA收录: false
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H301
• GHS警示性声明: P301 + P310
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3

药理学性质

• 给药途径: Oral
• 生物利用度: 70-80%
• 排泄: Renal
• 半衰期: 6-8h
• 代谢: 50-90% Hepatic
• 相关基因信息: human ... ABCB1(5243), CYP2D6(1565), CYP3A4(1576), KCNH1(3756)mouse ... Abcb1a(18671), Abcb1b(18669)rat ... Cyp2d1(266684), Cyp2d2(25053), Cyp2d3(24303), Cyp2d4v1(171522)

产品相关信息

• 纯度: ≥98.0% (dried material, NT); 95+%; 97%
• 级别: anhydrous
• 杂质: ~10% hydroquinidine (HPLC); ≤2% water; ≤20% Dihydroquinidine (according to USP specifications., actual content given on label)
• 品质说明: crystallized
• Empirical Formula (Hill Notation): C20H24N2O2

详细说明

MP Biomedicals - 05206337

MP Biomedicals Rare Chemical collection

DrugBank - DB00908

• Drug Groups: approved
• Description: An optical isomer of quinine, extracted from the bark of the Cinchona tree and similar plant species. This alkaloid dampens the excitability of cardiac and skeletal muscles by blocking sodium and potassium currents across cellular membranes. It prolongs cellular action potential, and decreases automaticity. Quinidine also blocks muscarinic and alpha-adrenergic neurotransmission. [PubChem]
• Indication: For the treatment of ventricular pre-excitation and cardiac dysrhythmias
• Pharmacology: Quinidine, a hydantoin anticonvulsant, is used alone or with phenobarbital or other anticonvulsants to manage tonic-clonic seizures, psychomotor seizures, neuropathic pain syndromes including diabetic neuropathy, digitalis-induced cardiac arrhythmias, and cardiac arrhythmias associated with QT-interval prolongation.
• Affected Organisms: Humans and other mammals
• Half Life: 6-8 hours
• Protein Binding: 80-88%
• Elimination: When the urine pH is less than 7, about 20% of administered quinidine appears unchanged in the urine, but this fraction drops to as little as 5% when the urine is more alkaline.
• Distribution: * 2 to 3 L/kg; * 0.5 L/kg [congestive heart failure]; * 3 to 5 L/kg [cirrhosis of the liver]
• Clearance: * 3 – 5 mL/min/kg [adults]
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - Q3625

Biochem/physiol Actions
IA 类抗心律失常药；钾通道阻断剂。
包装
5, 25 g in glass bottle

Sigma Aldrich - 22600

Biochem/physiol Actions
IA 类抗心律失常药；钾通道阻断剂。
Other Notes
手性催化剂，用于，例如，高度不对称 [2+2] 环加成反应1,2,3
包装
10, 50 g in poly bottle