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
SMILES / InChI / InChIKey
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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
InChI Key OEXHQOGQTVQTAT-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1986))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name Click here for help
(8-methyl-8-propan-2-yl-8-azoniabicyclo[3.2.1]octan-3-yl) 3-hydroxy-2-phenylpropanoate
International Nonproprietary Names Click here for help
INN number INN
3263 ipratropium bromide
Synonyms Click here for help
Atrovent® | Ipraxa®
Database Links Click here for help
CAS Registry No. 60205-81-4
ChEBI CHEBI:5956
ChEMBL Ligand ChEMBL1615433
DrugBank Ligand DB00332
GtoPdb PubChem SID 135650410
PubChem CID 3746
Search Google for chemical match using the InChIKey OEXHQOGQTVQTAT-UHFFFAOYSA-N
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Search PubMed clinical trials ipratropium bromide
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Search UniChem for chemical match using the InChIKey OEXHQOGQTVQTAT-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone OEXHQOGQTVQTAT
Wikipedia Ipratropium