glycopyrrolate   

GtoPdb Ligand ID: 7459

Synonyms: AHR-504 | Qbrexza® (glycopyrronium cloth) | Robinul® | Seebri Neohaler® | Tovanor Breezhaler®
glycopyrrolate is an approved drug (FDA (1961), EMA (2012))
Compound class: Synthetic organic
Comment: Glycopyrrolate is the active moiety of the approved drug glycopyrronium bromide. It is an anticholinergic drug.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 46.53
Molecular weight 318.21
XLogP 2.59
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES O=C(C(c1ccccc1)(C1CCCC1)O)OC1CC[N+](C1)(C)C
Isomeric SMILES O=C(C(c1ccccc1)(C1CCCC1)O)OC1CC[N+](C1)(C)C
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
InChI Key ANGKOCUUWGHLCE-UHFFFAOYSA-N
Bioactivity Comments
Glycopyrrolate has high, equipotent affinity for all muscarinic acetylcholine receptor subtypes (M1-5) [2].
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
M1 receptor Hs Antagonist Antagonist 9.9 pIC50 - 2
pIC50 9.9 (IC50 1.26x10-10 M) [2]
Description: Assay uses glycopyrronium bromide
M4 receptor Hs Antagonist Antagonist 9.8 pIC50 - 2
pIC50 9.8 (IC50 1.58x10-10 M) [2]
Description: Assay uses glycopyrronium bromide
M5 receptor Hs Antagonist Antagonist 9.7 pIC50 - 2
pIC50 9.7 (IC50 2x10-10 M) [2]
M3 receptor Hs Antagonist Antagonist 9.6 pIC50 - 2
pIC50 9.6 (IC50 2.51x10-10 M) [2]
Description: Assay uses glycopyrronium bromide
M2 receptor Hs Antagonist Antagonist 9.3 pIC50 - 2
pIC50 9.3 (IC50 5.01x10-10 M) [2]
Description: Assay uses glycopyrronium bromide