CHEBI:144552 - (R)-oxybutynin

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ChEBI Name (R)-oxybutynin
ChEBI ID CHEBI:144552
ChEBI ASCII Name (R)-oxybutynin
Definition A 4-(diethylamino)but-2-yn-1-ol that has R configuration. It is responsible for virtually all of the antimuscarinic activity of (racemic) oxybutynin.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C22H31NO3
Net Charge 0
Average Mass 357.494
Monoisotopic Mass 357.23039
InChI InChI=1S/C22H31NO3/c1-3-23(4-2)17-11-12-18-26-21(24)22(25,19-13-7-5-8-14-19)20-15-9-6-10-16-20/h5,7-8,13-14,20,25H,3-4,6,9-10,15-18H2,1-2H3/t22-/m0/s1
InChIKey XIQVNETUBQGFHX-QFIPXVFZSA-N
SMILES C1(CCCCC1)[C@@](C2=CC=CC=C2)(C(OCC#CCN(CC)CC)=O)O
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): cholinergic antagonist
Any drug that binds to but does not activate cholinergic receptors, thereby blocking the actions of acetylcholine or cholinergic agonists.
calcium channel blocker
One of a class of drugs that acts by selective inhibition of calcium influx through cell membranes or on the release and binding of calcium in intracellular pools.
Application(s): cholinergic antagonist
Any drug that binds to but does not activate cholinergic receptors, thereby blocking the actions of acetylcholine or cholinergic agonists.
local anaesthetic
Any member of a group of drugs that reversibly inhibit the propagation of signals along nerves. Wide variations in potency, stability, toxicity, water-solubility and duration of action determine the route used for administration, e.g. topical, intravenous, epidural or spinal block.
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ChEBI Ontology
Outgoing (R)-oxybutynin (CHEBI:144552) has role calcium channel blocker (CHEBI:38215)
(R)-oxybutynin (CHEBI:144552) has role cholinergic antagonist (CHEBI:48873)
(R)-oxybutynin (CHEBI:144552) has role local anaesthetic (CHEBI:36333)
(R)-oxybutynin (CHEBI:144552) is a 4-(diethylamino)but-2-yn-1-ol (CHEBI:144551)
(R)-oxybutynin (CHEBI:144552) is enantiomer of esoxybutynin (CHEBI:51329)
Incoming oxybutynin (CHEBI:7856) has part (R)-oxybutynin (CHEBI:144552)
esoxybutynin (CHEBI:51329) is enantiomer of (R)-oxybutynin (CHEBI:144552)
IUPAC Name
4-(diethylamino)but-2-yn-1-yl (2R)-cyclohexyl(hydroxy)phenylacetate
Manual Xrefs Databases
EP1286591 Patent
US6123961 Patent
WO0193683 Patent
View more database links
Registry Number Type Source
119618-21-2 CAS Registry Number Wikipedia
Citations Waiting for Citations Types Sources
17473442 PubMed citation Europe PMC
24036364 PubMed citation Europe PMC
25215879 PubMed citation Europe PMC
Last Modified
26 September 2019