pilocarpine   Click here for help

GtoPdb Ligand ID: 305

Synonyms: pilocarpine hydrochloride | pilocarpine nitrate | pilokarpin | Salagen® | Vuity® (pilocarpine HCI ophthalmic solution)
Approved drug PDB Ligand
pilocarpine is an approved drug (FDA (1974))
Compound class: Synthetic organic
Comment: Pilocarpine is a parasympathomimetic alkaloid type cholinergic drug, exerting its clinical effects via activation of muscarinic acetylcholine M3 receptors.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 44.12
Molecular weight 208.12
XLogP 1.08
No. Lipinski's rules broken 0
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Canonical SMILES CCC1C(=O)OCC1Cc1cncn1C
Isomeric SMILES CC[C@@H]1C(=O)OC[C@@H]1Cc1cncn1C
InChI InChI=1S/C11H16N2O2/c1-3-10-8(6-15-11(10)14)4-9-5-12-7-13(9)2/h5,7-8,10H,3-4,6H2,1-2H3/t8-,10-/m0/s1
1. Berizzi AE, Gentry PR, Rueda P, Den Hoedt S, Sexton PM, Langmead CJ, Christopoulos A. (2016)
Molecular Mechanisms of Action of M5 Muscarinic Acetylcholine Receptor Allosteric Modulators.
Mol Pharmacol, 90 (4): 427-36. [PMID:27461343]
2. Dong GZ, Kameyama K, Rinken A, Haga T. (1995)
Ligand binding properties of muscarinic acetylcholine receptor subtypes (m1-m5) expressed in baculovirus-infected insect cells.
J Pharmacol Exp Ther, 274 (1): 378-84. [PMID:7616422]
3. Grant MK, El-Fakahany EE. (2005)
Persistent binding and functional antagonism by xanomeline at the muscarinic M5 receptor.
J Pharmacol Exp Ther, 315 (1): 313-9. [PMID:16002459]
4. Jakubík J, Bacáková L, El-Fakahany EE, Tucek S. (1997)
Positive cooperativity of acetylcholine and other agonists with allosteric ligands on muscarinic acetylcholine receptors.
Mol Pharmacol, 52 (1): 172-9. [PMID:9224827]
5. Mei L, Lai J, Roeske WR, Fraser CM, Venter JC, Yamamura HI. (1989)
Pharmacological characterization of the M1 muscarinic receptors expressed in murine fibroblast B82 cells.
J Pharmacol Exp Ther, 248 (2): 661-70. [PMID:2537406]
6. Richards MH, van Giersbergen PL. (1995)
Human muscarinic receptors expressed in A9L and CHO cells: activation by full and partial agonists.
Br J Pharmacol, 114 (6): 1241-9. [PMID:7620715]