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(RS)-oxybutynin

Structure via PubChem · Public domain (PubChem)

EntityQ1060922· pop 25· linked from 598 articles

(RS)-oxybutynin

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Also 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

Wikidata facts

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 sections
Contents
  • 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.

Gallery (4)