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

• ChemBase ID: 860
• Molecular Formular: C19H28BrNO3
• Molecular Mass: 398.33452
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(2-cyclopentyl-2-hydroxy-2-phenylacetyl)oxy]-1,1-dimethylpyrrolidin-1-ium bromide
• IUPAC Traditional name: glycopyrrolate bromide
• Brand Name: Asecryl; Gastrodyn; Nodapton; Robanul; Robinal; Robinul; Tarodyl; Tarodyn
• Synonyms: 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

Database IDs

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

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.533273
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -1.4080803
• LogD (pH = 7.4): -1.4074817
• Log P: -1.408088
• Molar Refractivity: 101.0809 cm^3
• Polarizability: 35.6508 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.2
• LOG S: -5.57
• Solubility (Water): 9.44e-04 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; H2O: ≥24 mg/mL; Methanol
• Apperance: White Solid; white to tan powder
• Melting Point: 192-195°C
• Hydrophobicity(logP): -0.99

Safety Information

• Storage Condition: desiccated; Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Storage Temperature: 2-8°C

Product Information

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

DETAILS

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.

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
• Kaltiala, E., et al.: J. Pharm. Pharmacol., 26, 352 (1974)
• Kongsrud, F., et al.: Acta Anaesthesiol. Scand., 26, 620 (1974)