Structure via PubChem · Public domain (PubChem)
(RS)-oxybutynin
Sign in to saveAlso known as cyclohexaneglycolic acid, alpha-phenyl-, 4-(diethylamino)-2-butynyl ester, benzeneacetic acid, alpha-cyclohexyl-alpha-hydroxy-, 4-(diethylamino)-2-butynyl ester, 4-diethylamino-2-butynyl alpha-phenylcyclohexaneglycolate, 4-diethylamino-2-butinyl alpha-cyclohexylmandelat, 4-(diethylamino)-2-butynyl alpha-phenylcyclohexaneglycolic acid ester
Oxybutynin, sold under the brand name Ditropan among others, is an anticholinergic medication primarily used to treat overactive bladder. It is widely considered a first-line therapy for overactive bladder due to its well-studied side effect profile, broad applicability, and continued efficacy over long periods of time. It works similar to tolterodine, darifenacin, and solifenacin, although it is usually preferred over these medications. It is commonly prescribed after some types of bladder surgery to reduce bladder spasms and catheter-associated discomfort. It is sometimes used off-label for
Key facts
- Drug.PubChem
- 4634
- Drug.verifiedrevid
- 462267372
- Drug.image
- Oxybutynin.svg
- Drug.image_class
- skin-invert-image
- Drug.image2
- Oxybutynin 3d balls.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Ditropan, Gelnique, others
- Drug.MedlinePlus
- a682141
- Drug.DailyMedID
- Oxybutynin
- Drug.pregnancy_AU
- B1
- Drug.routes_of_administration
- By mouth, transdermal
- Drug.class
- Antimuscarinic
- Drug.ATC_prefix
- G04
- Drug.ATC_suffix
- BD04
- Drug.legal_AU
- S4
- Drug.legal_CA
- Rx-only
- Drug.legal_UK
- POM
- Drug.legal_US
- Rx-only
via Wikipedia infobox
Chemical data
- Formula
- C22H31NO3
- Molecular weight
- 357.5 g/mol
- IUPAC name
- 4-(diethylamino)but-2-ynyl 2-cyclohexyl-2-hydroxy-2-phenylacetate
- SMILES
- CCN(CC)CC#CCOC(=O)C(C1CCCCC1)(C2=CC=CC=C2)O
- InChIKey
- XIQVNETUBQGFHX-UHFFFAOYSA-N
- XLogP
- 4.2
- Polar surface area
- 49.8 Ų
- H-bond donors
- 1
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1975
- Admin. routes
- oral, topical
- Indications
- Neurogenic bladder, Urinary incontinence, overactive bladder, seasonal allergic rhinitis
via ChEMBL · EBI
Research
1 papers- Comparison of the antimuscarinic and antispasmodic actions of racemic oxybutynin and desethyloxybutynin and their enantiomers with those of racemic terodiline.Arzneimittel-Forschung · 1998
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 357.23
- Has use
- medication
Show 5 more facts
- chemical formula
- C₂₂H₃₁NO₃
- canonical SMILES
- CCN(CC)CC#CCOC(=O)C(C1CCCCC1)(C2=CC=CC=C2)O
- World Health Organisation international non-proprietary name
- oxybutynin
- Commons category
- Oxybutynin
- defined daily dose
- 15
Sources (6)
via Wikidata · CC0
~8 min read
Encyclopedic overview
10 sectionsContents
- Medical use
- Hyperhidrosis
- Adverse effects
- Contraindications
- Pharmacology
- Chemistry
- Society and culture
- Brand names
- Research
- References
Oxybutynin, sold under the brand name Ditropan among others, is an anticholinergic medication primarily used to treat overactive bladder. It is widely considered a first-line therapy for overactive bladder due to its well-studied side effect profile, broad applicability, and continued efficacy over long periods of time. It works similar to tolterodine, darifenacin, and solifenacin, although it is usually preferred over these medications. It is commonly prescribed after some types of bladder surgery to reduce bladder spasms and catheter-associated discomfort. It is sometimes used off-label for treatment of hyperhidrosis, or excessive sweating. It has also been used off-label to treat bedwetting in children, but this use has declined, as it is most likely ineffective in this role. It is taken by mouth or applied to the skin.
Common side effects include dry mouth, constipation, dizziness, trouble sleeping, and urinary tract infections. Serious side effects may include urinary retention and an increased risk of heat stroke. Use in pregnancy appears safe but has not been well studied while use in breastfeeding is of unclear safety. It is an antimuscarinic and works by blocking the effects of acetylcholine on smooth muscle.
Excerpted from Wikipedia’s “(RS)-oxybutynin” article, available under the CC BY-SA 4.0 licence.