3-[(2-cyclopentyl-2-hydroxy-2-phenylacetyl)oxy]-1,1-dimethylpyrrolidin-1-ium bromide

• ChemBase编号: 860
• 分子式: C19H28BrNO3
• 平均质量: 398.33452
• 单一同位素质量: 397.12525576
• SMILES: O(C1C[N+](CC1)(C)C)C(=O)C(O)(C1CCCC1)c1ccccc1.[Br-]
• Canonical SMILES: O=C(C(c1ccccc1)(C1CCCC1)O)OC1CC[N+](C1)(C)C.[Br-]
• InChI: InChI=1S/C19H28NO3.BrH/c1-20(2)13-12-17(14-20)23-18(21)19(22,16-10-6-7-11-16)15-8-4-3-5-9-15;/h3-5,8-9,16-17,22H,6-7,10-14H2,1-2H3;1H/q+1;/p-1
• InChIKey: VPNYRYCIDCJBOM-UHFFFAOYSA-M

名称和登记号

名称

• IUPAC标准名: 3-[(2-cyclopentyl-2-hydroxy-2-phenylacetyl)oxy]-1,1-dimethylpyrrolidin-1-ium bromide
• IUPAC传统名: glycopyrrolate bromide
• 商标名: Asecryl; Gastrodyn; Nodapton; Robanul; Robinal; Robinul; Tarodyl; Tarodyn
• 别名: 3-[(2-Cyclopentyl-2-hydroxy-2-phenylacetyl)oxy]-1,1-dimethylpyrrolidinium Bromide; Asecryl; NVA 237; Nodapton; Robanul; Robinul; Tarodyl; Tarodyn; Glycopyrrolate Bromide; Glycopyrronium bromide; glycopyrrolate; Glycopyrrolate; α-cyclopentylmandelic acid ester with 3-hydroxy-1,1-dimethylpyrrolidinium bromide; 1-methyl-3-pyrrolidyl α-cyclopentylmandelate methobromide; 1-methyl-3-pyrrolidyl α-phenyl-α-cyclopentylglycolate methobromide; 3-(2-phenyl-2-cyclopentylglycoloyloxy)-1,1-dimethylpyrrolidinium bromide; 3-hydroxy-1,1-dimethylpyrrolidinium bromide α-cyclopentylmandelate; AHR-504; Copyrrolate; Gastrodyn; NSC 250836; NSC 251251; NSC 251252; NVA-237; Glycopyrrolate

登记号

• CAS号: 596-51-0
• MDL号: MFCD00072137
• PubChem SID: 160964323; 46509133
• PubChem CID: 11693; 3494

理论计算性质

JChem

• Acid pKa: 11.533273
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): -1.4080803
• LogD (pH = 7.4): -1.4074817
• Log P: -1.408088
• 摩尔折射率: 101.0809 cm^3
• 极化性: 35.6508 Å^3
• 极化表面积: 46.53 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -1.2
• LOG S: -5.57
• 溶解度: 9.44e-04 g/l

分子性质

理化性质

• 溶解度: DMSO; H2O: ≥24 mg/mL; Methanol
• 外观: White Solid; white to tan powder
• 熔点: 192-195°C
• 疏水性(logP): -0.99

安全信息

• 保存条件: desiccated; Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H28NO3 · Br

详细说明

DrugBank - DB00986

• Drug Groups: approved; investigational
• Description: Glycopyrrolate is a synthetic anticholinergic agent with a quaternary ammonium structure. A muscarinic competitive antagonist used as an antispasmodic, in some disorders of the gastrointestinal tract, and to reduce salivation with some anesthetics. [PubChem]
• Indication: For use as a preoperative antimuscarinic to reduce salivary, tracheobronchial, and pharyngeal secretions, to reduce the volume and free acidity of gastric secretions and to block cardiac vagal inhibitory reflexes during induction of anesthesia and intubation.
• Pharmacology: Glycopyrrolate decreases acid secretion in the stomach. Hence it can be used for treating ulcers in the stomach and small intestine, in combination with other medications. In anesthesia, glycopyrrolate injection serves as a preoperative antimuscarinic operation that reduces salivary, tracheobronchial, and pharyngeal secretions, as well as decreases the acidity of gastric secretions blocks cardiac vagal inhibitory reflexes during intubation
• Toxicity: Side effects include dry mouth, difficult urinating, heachaches, diarrhea and constipation. The medication also induces drowsiness or blurred vision. LD₅₀=709 mg/kg (rat, oral).
• Affected Organisms: Humans and other mammals
• Absorption: Rapidly absorbed (1-2 minutes) after intravenous injection
• Half Life: 0.6-1.2 hours
• References: Ali-Melkkila T, Kanto J, Iisalo E: Pharmacokinetics and related pharmacodynamics of anticholinergic drugs. Acta Anaesthesiol Scand. 1993 Oct;37(7):633-42. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - SML0029

Biochem/physiol Actions
Glycopyrrolate is long-acting muscarinic antagonist (LAMA). It is kinetically selective muscarinic M3 receptor antagonist.

Toronto Research Chemicals - G656980

A synthetic, quaternary ammonium anticholinergic. Antispasmodic; preanesthetic medicant.

参考文献

• Ali-Melkkila T, Kanto J, Iisalo E: Pharmacokinetics and related pharmacodynamics of anticholinergic drugs. Acta Anaesthesiol Scand. 1993 Oct;37(7):633-42. Pubmed
• Kaltiala, E., et al.: J. Pharm. Pharmacol., 26, 352 (1974)
• Kongsrud, F., et al.: Acta Anaesthesiol. Scand., 26, 620 (1974)