CHEBI:7856 - oxybutynin

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ChEBI Name oxybutynin
ChEBI ID CHEBI:7856
Definition A racemate comprising equimolar amounts of (R)-oxybutynin and esoxybutynin. An antispasmodic used for the treatment of overactive bladder.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB6196202, eMolecules:716786, ZINC000000020244
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Diphenhydramine, sold under the brand name Benadryl among others, is an antihistamine and sedative. It is a first-generation H1-antihistamine and it works by blocking certain effects of histamine, which produces its antihistamine and sedative effects. Diphenhydramine is also a potent anticholinergic. It is mainly used to treat allergies, insomnia, and symptoms of the common cold. It is also less commonly used for tremors in parkinsonism, and nausea. It is taken by mouth, injected into a vein, injected into a muscle, or applied to the skin. Maximal effect is typically around two hours after a dose, and effects can last for up to seven hours. Common side effects include sleepiness, poor coordination, and upset stomach. There is no clear risk of harm when used during pregnancy; however, use during breastfeeding is not recommended. It was developed by George Rieveschl and put into commercial use in 1946. It is available as a generic medication, In 2022, it was the 258th most commonly prescribed medication in the United States, with more than 1 million prescriptions. Its sedative and deliriant effects have led to some cases of recreational use.
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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
InChIKey XIQVNETUBQGFHX-UHFFFAOYSA-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): parasympatholytic
Any cholinergic antagonist that inhibits the actions of the parasympathetic nervous system. The major group of drugs used therapeutically for this purpose is the muscarinic antagonists.
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.
muscarinic antagonist
A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
Application(s): parasympatholytic
Any cholinergic antagonist that inhibits the actions of the parasympathetic nervous system. The major group of drugs used therapeutically for this purpose is the muscarinic antagonists.
antispasmodic drug
A drug that suppresses spasms. These are usually caused by smooth muscle contraction, especially in tubular organs. The effect is to prevent spasms of the stomach, intestine or urinary bladder.
muscle relaxant
A drug used to produce muscle relaxation (excepting neuromuscular blocking agents). Its primary clinical and therapeutic use is the treatment of muscle spasm and immobility associated with strains, sprains, and injuries of the back and, to a lesser degree, injuries to the neck. Also used for the treatment of a variety of clinical conditions that have in common only the presence of skeletal muscle hyperactivity, for example, the muscle spasms that can occur in multiple sclerosis.
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.
muscarinic antagonist
A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
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ChEBI Ontology
Outgoing oxybutynin (CHEBI:7856) has part (R)-oxybutynin (CHEBI:144552)
oxybutynin (CHEBI:7856) has part esoxybutynin (CHEBI:51329)
oxybutynin (CHEBI:7856) has role antispasmodic drug (CHEBI:53784)
oxybutynin (CHEBI:7856) has role calcium channel blocker (CHEBI:38215)
oxybutynin (CHEBI:7856) has role local anaesthetic (CHEBI:36333)
oxybutynin (CHEBI:7856) has role muscarinic antagonist (CHEBI:48876)
oxybutynin (CHEBI:7856) has role muscle relaxant (CHEBI:51371)
oxybutynin (CHEBI:7856) has role parasympatholytic (CHEBI:50370)
oxybutynin (CHEBI:7856) is a racemate (CHEBI:60911)
oxybutynin (CHEBI:7856) is a tertiary amino compound (CHEBI:50996)
Incoming oxybutynin chloride (CHEBI:7857) has part oxybutynin (CHEBI:7856)
IUPAC Name
rac-4-(diethylamino)but-2-yn-1-yl cyclohexyl(hydroxy)phenylacetate
INNs Sources
oxibutinina ChemIDplus
oxybutynin ChemIDplus
oxybutynine ChemIDplus
oxybutyninum ChemIDplus
Synonyms Sources
ditropan DrugCentral
kentera DrugCentral
Oxybutynin KEGG COMPOUND
Brand Name Source
Ditropan ChEBI
Manual Xrefs Databases
2028 DrugCentral
C07360 KEGG COMPOUND
D00465 KEGG DRUG
DB01062 DrugBank
GB940540 Patent
LSM-5111 LINCS
Oxybutynin Wikipedia
View more database links
Registry Numbers Types Sources
2707356 Beilstein Registry Number Beilstein
5633-20-5 CAS Registry Number KEGG COMPOUND
5633-20-5 CAS Registry Number ChemIDplus
Last Modified
26 September 2019