pirenzepine   Click here for help

GtoPdb Ligand ID: 328

Approved drug
pirenzepine is an approved drug
Compound class: Synthetic organic
Comment: Pirenzepine muscarinic acetylcholine receptor antagonist, selective for the M1 receptor subtype.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 74.23
Molecular weight 351.17
XLogP 1.32
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CN1CCN(CC1)CC(=O)n1c2ccccc2c(=O)[nH]c2c1nccc2
Isomeric SMILES CN1CCN(CC1)CC(=O)n1c2ccccc2c(=O)[nH]c2c1nccc2
InChI InChI=1S/C19H21N5O2/c1-22-9-11-23(12-10-22)13-17(25)24-16-7-3-2-5-14(16)19(26)21-15-6-4-8-20-18(15)24/h2-8H,9-13H2,1H3,(H,21,26)
InChI Key RMHMFHUVIITRHF-UHFFFAOYSA-N
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
M1 receptor Primary target of this compound Hs Antagonist Antagonist 7.6 – 8.3 pKi - 1,4-7,12
pKi 7.6 – 8.3 [1,4-7,12]
M1 receptor Rn Antagonist Antagonist 7.8 – 7.9 pKi - 1,8
pKi 7.8 – 7.9 [1,8]
M4 receptor Hs Antagonist Antagonist 7.0 – 8.1 pKi - 2,4-7,12
pKi 8.1 (Ki 8x10-9 M) [2]
pKi 7.0 – 7.6 [4-7,12]
M4 receptor Rn Antagonist Antagonist 7.1 pKi - 8
pKi 7.1 [8]
M5 receptor Rn Antagonist Antagonist 7.1 pKi - 8
pKi 7.1 [8]
M5 receptor Hs Antagonist Antagonist 6.8 – 7.1 pKi - 5,7,12
pKi 6.8 – 7.1 [5,7,12]
M3 receptor Rn Antagonist Antagonist 6.7 pKi - 8
pKi 6.7 [8]
M3 receptor Hs Antagonist Antagonist 6.5 – 6.8 pKi - 1,4-7,12
pKi 6.5 – 6.8 [1,4-7,12]
M2 receptor Rn Antagonist Antagonist 5.3 – 7.4 pKi - 8-9,11
pKi 5.3 – 7.4 [8-9,11]
M2 receptor Hs Antagonist Antagonist 6.0 – 6.7 pKi - 1,4-7,9-10,12
pKi 6.0 – 6.7 [1,4-7,9-10,12]
TAS2R9 Hs Agonist Agonist 2.7 pEC50 - 3
pEC50 2.7 (EC50 1.8x10-3 M) [3]
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