ipratropium   Click here for help

GtoPdb Ligand ID: 325

Synonyms: Atrovent® | Ipraxa®
Approved drug Immunopharmacology Ligand
ipratropium is an approved drug (FDA (1986))
Compound class: Synthetic organic
Comment: The approved drug and INN-assigned compound is ipratropium bromide, and is a racemic mixture of two enantiomers. We depict the non-bromide parent compound, and our structure does not specify stereochemistry and represents the mixture. The PubChem and ChEMBL entries linked to above also show the non-isomeric structure. The PubChem entries which represent the two enatiomers found in the racemate are CID 657309 and CID 43232. Bioactivity data on PubChem is split between the parent compound and the bromide form. Our references specify bioactivity data for the parent compound.
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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 6
Topological polar surface area 46.53
Molecular weight 332.22
XLogP 2.52
No. Lipinski's rules broken 0
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Canonical SMILES OCC(c1ccccc1)C(=O)OC1CC2CCC(C1)[N+]2(C)C(C)C
Isomeric SMILES OCC(c1ccccc1)C(=O)OC1CC2CCC(C1)[N+]2(C)C(C)C
InChI InChI=1S/C20H30NO3/c1-14(2)21(3)16-9-10-17(21)12-18(11-16)24-20(23)19(13-22)15-7-5-4-6-8-15/h4-8,14,16-19,22H,9-13H2,1-3H3/q+1
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
M1 receptor Hs Antagonist Antagonist 9.3 – 9.8 pKi - 2-3
pKi 9.3 – 9.8 [2-3]
M2 receptor Hs Antagonist Antagonist 9.3 – 9.8 pKi - 2-3
pKi 9.3 – 9.8 [2-3]
M3 receptor Primary target of this compound Hs Antagonist Antagonist 9.3 – 9.8 pKi - 1-3
pKi 9.3 – 9.8 [1-3]
M4 receptor Hs Antagonist Antagonist 9.2 pKi - 2
pKi 9.2 [2]
M5 receptor Hs Antagonist Antagonist 8.8 pKi - 2
pKi 8.8 [2]