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Identification
Name Glycopyrrolate
Accession Number DB00986 (APRD01000)
Type small molecule
Groups approved
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]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • glycopyrrolate
  • Glycopyrronium bromide
Brand names
  • Asecryl
  • Gastrodyn
  • Nodapton
  • Robanul
  • Robinal
  • Robinul
  • Tarodyl
  • Tarodyn
Brand name mixtures Not Available
Categories
  • Adjuvants, Anesthesia
  • Muscarinic Antagonists
  • Anti-cholinergic Agents
CAS number 596-51-0
Weight Average: 318.4305
Monoisotopic: 318.206918767
Chemical Formula C19H28NO3
InChI Key InChIKey=ANGKOCUUWGHLCE-UHFFFAOYSA-N
InChI
InChI=1S/C19H28NO3/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/q+1
Plain Text
IUPAC Name
3-[(2-cyclopentyl-2-hydroxy-2-phenylacetyl)oxy]-1,1-dimethylpyrrolidin-1-ium
SMILES
C[N+]1(C)CCC(C1)OC(=O)C(O)(C1CCCC1)C1=CC=CC=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenylacetates
Substructures
  • Carboxylic Acids and Derivatives
  • Hydroxy Compounds
  • Benzyl Alcohols and Derivatives
  • Acetates
  • Phenylacetates
  • Short-chain Hydroxy Acids
  • Pyrrolidines
  • Ethers
  • Benzene and Derivatives
  • Quaternary Ammonium Salts
  • Alcohols and Polyols
  • Heterocyclic compounds
  • Aromatic compounds
  • Cations
Pharmacology
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.
Pharmacodynamics 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
Mechanism of action 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.
Absorption Rapidly absorbed (1-2 minutes) after intravenous injection
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Route of elimination Not Available
Half life 0.6-1.2 hours
Clearance Not Available
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
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Abraxis pharmaceutical products
  • Hospira inc
  • Luitpold pharmaceuticals inc
  • Teva parenteral medicines inc
  • Watson laboratories inc
  • Baxter healthcare corp anesthesia and critical care
  • Ah robins co
  • Shionogi pharma inc
  • Corepharma llc
  • Dr reddys laboratories ltd
  • Par pharmaceutical inc
  • Ranbaxy inc
  • Vintage pharmaceuticals llc
  • West ward pharmaceutical corp
Packagers
Dosage forms
Form Route Strength
Liquid Intravenous
Prices
Unit description Cost Unit
Glycopyrrolate powder 278.46 USD g
Robinul-Forte 2 mg tablet 6.46 USD tablet
Robinul forte 2 mg tablet 6.21 USD tablet
Robinul 1 mg tablet 3.96 USD tablet
Glycopyrrolate 0.2 mg/ml 3.63 USD ml
Glycopyrrolate 1 mg/5 ml syr 2.91 USD ml
Glycopyrrolate 2 mg tablet 2.24 USD tablet
Glycopyrrolate 1 mg tablet 1.34 USD tablet
Robinul 0.2 mg/ml vial 1.26 USD ml
Glycopyrrolate 0.2 mg/ml vial 0.85 USD ml
Patents
Country Patent Number Approved Expires
United States 7091236 2004-04-24 2024-04-24
Properties
State solid
Melting point 192.5 oC
Experimental Properties
Property Value Source
logP -0.99 PhysProp
Predicted Properties
Property Value Source
water solubility 9.44e-04 g/l ALOGPS
logP -1.20 ALOGPS
logP -1.41 ChemAxon Molconvert
logS -5.57 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 2 ChemAxon Molconvert
hydrogen donor count 1 ChemAxon Molconvert
polar surface area 46.53 ChemAxon Molconvert
rotatable bond count 5 ChemAxon Molconvert
refractivity 101.08 ChemAxon Molconvert
polarizability 35.88 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  1. 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
Resource Link
KEGG Drug D00540 Link_out
PubChem Compound 3494 Link_out
PubChem Substance 46509133 Link_out
ChemSpider 3374 Link_out
Therapeutic Targets Database DAP001116 Link_out
PharmGKB PA449795 Link_out
Drug Product Database 2039508 Link_out
RxList http://www.rxlist.com/cgi/generic3/glycopyrrolate.htm Link_out
Drugs.com http://www.drugs.com/cdi/glycopyrrolate.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Glycopyrrolate Link_out
ATC Codes
  • A03AB02
AHFS Codes
  • 12:08.08
PDB Entries Not Available
FDA label show (193.2 KB)
MSDS show (73.7 KB)
Interactions
Drug Interactions Not Available
Food Interactions
  • Take without regard to meals.
Targets

1. Muscarinic acetylcholine receptor M1

Pharmacological action: yes
Actions: antagonist

The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover

Organism class: human
UniProt ID: P11229 Link_out
Gene: CHRM1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Ali-Melkkila T, Kanto J, Iisalo E: Pharmacokinetics and related pharmacodynamics of anticholinergic drugs. Acta Anaesthesiol Scand. 1993 Oct;37(7):633-42. Pubmed
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on November 10, 2010 13:44

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.