Stereochemistry | RACEMIC |
Molecular Formula | C19H28NO3.Br |
Molecular Weight | 398.335 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Br-].C[N+]1(C)CC[C@@H](C1)OC(=O)[C@@](O)(C2CCCC2)C3=CC=CC=C3
InChI
InChIKey=VPNYRYCIDCJBOM-QQTWVUFVSA-M
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/t17-,19-;/m0./s1
Glycopyrrolate is a synthetic anticholinergic agent with a quaternary ammonium structure. Glycopyrrolate is a muscarinic competitive antagonist used as an antispasmodic, in some disorders of the gastrointestinal tract, and to reduce salivation with some anesthetics. Glycopyrrolate binds competitively to the muscarinic acetylcholine receptor. Like other anticholinergic (antimuscarinic) agents, it inhibits the action of acetylcholine on structures innervated by postganglionic cholinergic nerves and on smooth muscles that respond to acetylcholine but lack cholinergic innervation. These peripheral cholinergic receptors are present in the autonomic effector cells of smooth muscle, cardiac muscle, the sinoatrial node, the atrioventricular node, exocrine glands and, to a limited degree, in the autonomic ganglia. Thus, it diminishes the volume and free acidity of gastric secretions and controls excessive pharyngeal, tracheal, and bronchial secretions. Glycopyrrolate antagonizes muscarinic symptoms (e.g., bronchorrhea, bronchospasm, bradycardia, and
intestinal hypermotility) induced by cholinergic drugs such as the anticholinesterases.
The highly polar quaternary ammonium group of glycopyrrolate limits its passage across lipid
membranes, such as the blood-brain barrier, in contrast to atropine sulfate and scopolamine
hydrobromide, which are highly non-polar tertiary amines which penetrate lipid barriers easily. Glycopyrrolate is marketed under the brand names Robinul, Robinul Forte, Cuvposa. In October 2015, glycopyrrolate was approved by the FDA for use as a standalone treatment for Chronic obstructive pulmonary disease (COPD), as Seebri Neohaler.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
9.9 null [pIC50] | |||
9.3 null [pIC50] | |||
9.6 null [pIC50] | |||
9.8 null [pIC50] | |||
9.7 null [pIC50] | |||
9.9 null [pIC50] | |||
9.3 null [pIC50] | |||
9.6 null [pIC50] | |||
9.8 null [pIC50] | |||
9.7 null [pIC50] |
Doses
AEs
Overview
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
Sourcing
PubMed
Sample Use Guides
Usual Adult Dose for Anesthesia
Preanesthetic (reduction of secretions): 0.004 mg (0.02 mL)/kg IM 30 to 60 minutes prior to the anticipated time of induction of anesthesia or at the time the preanesthetic narcotic and/or sedative are administered.
Intraoperative: 0.1 mg (0.5 mL) IV repeated as needed every 2 to 3 minutes.
Reversal of neuromuscular blockade: 0.2 mg (1.0 mL) IV for each 1.0 mg of neostigmine or 5 mg of pyridostigmine.
Reversal of bradycardia, vagal reflexes (intraoperative): 0.1 mg IV repeated as needed at 2 to 3 minute intervals.
Usual Adult Dose for Peptic Ulcer
Parenteral: 0.1 mg (0.5 mL) IV or IM every 4 hours, 3 to 4 times daily. If a more profound effect is required the dose may be increased to 0.2 mg (1 mL).
1 mg oral tablet:
Initial dose: 1 mg orally 3 times daily or 1 mg in the morning, 1 mg in the early afternoon, and 2 mg at bedtime.
Maintenance dose: 1 mg orally twice daily to a maximum of 8 mg per day.
2 mg oral tablet: 2 mg orally 2 to 3 times daily to a maximum of 8 mg per day.
1.5 mg oral tablet: Used to provide intermediate titration doses based on patient response.
Usual Pediatric Dose for Anesthesia
Preanesthetic: 0.004 mg (0.02 mL)/kg IM 30 to 60 minutes prior to the anticipated time of induction of anesthesia or at the time the preanesthetic narcotic and/or sedative are administered. Children under 2 years of age may require up to 0.009 mg (0.45 mL)/kg.
Intraoperative: 0.004 mg (0.02 mL)/kg IV not to exceed 0.1 mg (0.5 mL) in a single dose, repeated as needed every 2 to 3 minutes.
Reversal of neuromuscular blockade: 0.4 mg (2 mL)/kg IV for each 1 mg of neostigmine or 5 mg of pyridostigmine.
Reversal of bradycardia, vagal reflexes (intraoperative): 4 mcg/kg/dose IV (maximum dose: 100 mcg/dose) at 2 to 3 minute intervals.
Usual Pediatric Dose for Excessive Salivation
3 years to 16 years with neurologic conditions associated with problem drooling:
Initiate dosing at 0.02 mg/kg orally three times daily and titrate in increments of 0.02 mg/kg every 5 to 7 days, based on therapeutic response and adverse reactions. Maximum recommended dose is 0.1 mg/kg three times daily, not to exceed 1.5 to 3 mg per dose based upon weight. Administer at least one hour before or two hours after meals.
Route of Administration:
Other
Glycopyrrolate inhibited contraction induced by EFS
(40 V, 0.5 ms, 4 Hz for 15 s every 4 min) in guinea-pig trachea
in a concentration-dependent manner (IC50=0.15 nM, n=5 ±
12). Glycopyrrolate inhibited contraction induced by EFS
(40 V, 0.5 ms, 8 Hz for 15 s every 4 min) in human trachea in
a concentration-dependent manner (IC50=0.44 nM, n=3 ± 8).