Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR5439)
Drug Name
Ipratropium
Synonyms
Aerodose; Atrovent; Atrovent Hfa; Ipatropium Bromide; Ipratropium bromide; X8M; Apo-Ipravent; Apovent (TN); Atrovent (TN); Kendral-Ipratropium; [(5R)-8-methyl-8-propan-2-yl-8-azoniabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate; [(1R,5R)-8-methyl-8-propan-2-yl-8-azoniabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate; [(1R,5S)-8-methyl-8-propan-2-yl-8-azoniabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate; [(1R,5S)-8-methyl-8-propan-2-yl-8-azoniabicyclo[3.2.1]octan-3-yl] (2R)-3-hydroxy-2-phenylpropanoate; (3-endo,8-syn)-3-(3-Hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-(1-methylethyl)-8-azoniabicyclo(3.2.1)octane; (3-endo,8-syn)-3-[(3-hydroxy-2-phenylpropanoyl)oxy]-8-isopropyl-8-methyl-8-azoniabicyclo[3.2.1]octane; (8-methyl-8-propan-2-yl-8-azoniabicyclo[3.2.1]octan-3-yl) 3-hydroxy-2-phenylpropanoate; 3-[(3-hydroxy-2-phenylpropanoyl)oxy]-8-methyl-8-(propan-2-yl)-8-azoniabicyclo[3.2.1]octane
Indication Chronic obstructive pulmonary disease [ICD11: CA22] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 332.5 Topological Polar Surface Area 46.5
Heavy Atom Count 24 Rotatable Bond Count 6
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
657309
ChEBI ID
CHEBI:5956
CAS Number
60205-81-4
TTD Drug ID
D0S0AS
Formula
C20H30NO3+
Canonical SMILES
CC(C)[N+]1([C@@H]2CC[C@H]1CC(C2)OC(=O)C(CO)C3=CC=CC=C3)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/t16-,17+,18?,19?,21?
InChIKey
OEXHQOGQTVQTAT-BZQJJPTISA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
N-isopropylnortropine-ester DM016958 N. A. Hydrolysis - Hydrolysis 1 [2]
N-isopropylnortropium bromide DM016959 N. A. Multi-steps Reaction - Demethylation; Hydrolysis 1 [2]
N-isopropylnortropium methobromide DM016957 N. A. Reduction - Reduction 1 [3] , [2]
Phenyl acetic acid DM001228
999
Hydrolysis - Hydrolysis 1 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007822 Ipratropium N-isopropylnortropium methobromide Reduction - Reduction Unclear [3], [2]
MR007823 Ipratropium N-isopropylnortropine-ester Hydrolysis - Hydrolysis Unclear [2]
MR007824 Ipratropium Phenylacetic acid Hydrolysis - Hydrolysis Unclear [2]
MR007825 Ipratropium N-isopropylnortropium bromide Multi-steps Reaction - Demethylation; Hydrolysis Unclear [2]
References
1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 325).
2 Ipratropium bromide: drug metabolism and pharmacokinetics
3 Ipratropium bromide HFA

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