mepenzolic acid   Click here for help

GtoPdb Ligand ID: 10470

Synonyms: (±)-mepenzolate | Cantril® | glycophenylate | mepenzolate | racemic mepenzolate
Approved drug
mepenzolic acid is an approved drug (FDA (1956))
Compound class: Synthetic organic
Comment: In in vitro binding assays, (R)-mepenzolate has a higher affinity for the human M2 and M3 muscarinic acetylcholine receptors than (S)-mepenzolate [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 46.53
Molecular weight 340.19
XLogP 2.95
No. Lipinski's rules broken 0
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Canonical SMILES O=C(C(c1ccccc1)(c1ccccc1)O)OC1CCC[N+](C1)(C)C
Isomeric SMILES O=C(C(c1ccccc1)(c1ccccc1)O)OC1CCC[N+](C1)(C)C
InChI InChI=1S/C21H26NO3/c1-22(2)15-9-14-19(16-22)25-20(23)21(24,17-10-5-3-6-11-17)18-12-7-4-8-13-18/h3-8,10-13,19,24H,9,14-16H2,1-2H3/q+1
1. Carr BJ, Mihara K, Ramachandran R, Saifeddine M, Nathanson NM, Stell WK, Hollenberg MD. (2018)
Myopia-Inhibiting Concentrations of Muscarinic Receptor Antagonists Block Activation of Alpha2A-Adrenoceptors In Vitro.
Invest Ophthalmol Vis Sci, 59 (7): 2778-2791. [PMID:29860464]
2. Yamashita Y, Tanaka K, Asano T, Yamakawa N, Kobayashi D, Ishihara T, Hanaya K, Shoji M, Sugai T, Wada M et al.. (2014)
Synthesis and biological comparison of enantiomers of mepenzolate bromide, a muscarinic receptor antagonist with bronchodilatory and anti-inflammatory activities.
Bioorg Med Chem, 22 (13): 3488-97. [PMID:24844758]