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Identification
NameOxybutynin
Accession NumberDB01062  (APRD00427)
TypeSmall Molecule
GroupsApproved, Investigational
Description

Oxybutynin is an anticholinergic medication used to relieve urinary and bladder difficulties, including frequent urination and inability to control urination, by decreasing muscle spasms of the bladder. It competitively antagonizes the M1, M2, and M3 subtypes of the muscarinic acetylcholine receptor.

Structure
Thumb
Synonyms
SynonymLanguageCode
4-(Diethylamino)-2-butynyl alpha-phenylcyclohexaneglycolic acid esterNot AvailableNot Available
4-Diethylamino-2-butinyl alpha-cyclohexylmandelatNot AvailableNot Available
4-Diethylamino-2-butynyl alpha-phenylcyclohexaneglycolateNot AvailableNot Available
Benzeneacetic acid, alpha-cyclohexyl-alpha-hydroxy-, 4-(diethylamino)-2-butynyl esterNot AvailableNot Available
Cyclohexaneglycolic acid, alpha-phenyl-, 4-(diethylamino)-2-butynyl esterNot AvailableNot Available
OxibutininaSpanishINN
OxybutyninNot AvailableNot Available
OxybutynineFrenchINN
OxybutyninumLatinINN
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Oxybutynin Chloridetablet, extended release15 mgoralMylan Pharmaceuticals Inc.2007-05-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet, extended release15 mgoralNcs Health Care Of Ky, Inc Dba Vangard Labs2007-05-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gelniquegel28 mg/.92gtransdermalWatson Pharma, Inc.2012-04-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gelniquegel100 mg/gtransdermalWatson Pharma, Inc.2009-05-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxytrolpatch3.9 mg/dtransdermalWatson Pharma, Inc.2003-02-26Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Gelniquegel100 mg/gtransdermalPhysicians Total Care, Inc.2010-09-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxytrolpatch36 mgtransdermalActavis Specialty Pharmaceuticals CoNot AvailableNot AvailableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Oxybutynin Chloridetablet, extended release5 mgoralTeva Pharmaceuticals USA Inc2007-05-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet, extended release10 mgoralTeva Pharmaceuticals USA Inc2007-05-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet, extended release15 mgoralTeva Pharmaceuticals USA Inc2006-11-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridesyrup5 mg/5mLoralPharmaceutical Associates, Inc.1998-12-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet, film coated, extended release5 mgoralMylan Pharmaceuticals Inc.2006-11-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet, film coated, extended release10 mgoralMylan Pharmaceuticals Inc.2006-11-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridesolution5 mg/5mLoralQualitest Pharmaceuticals2004-12-28Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet5 mgoralQualitest Pharmaceuticals1997-10-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet5 mgoralNcs Health Care Of Ky, Inc Dba Vangard Labs2012-10-30Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet, film coated, extended release5 mgoralNcs Health Care Of Ky, Inc Dba Vangard Labs2010-01-20Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet, film coated, extended release10 mgoralNcs Health Care Of Ky, Inc Dba Vangard Labs2010-01-20Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet5 mgoralUpsher Smith Laboratories, Inc.2011-11-07Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet5 mgoralMajor Pharmaceuticals2004-02-03Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet5 mgoralRebel Distributors Corp.1997-10-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet5 mgoralREMEDYREPACK INC.2013-04-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet5 mgoralAidarex Pharmaceuticals LLC1997-10-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet, extended release10 mgoralLake Erie Medical DBA Quality Care Products LLC2007-05-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet5 mgoralLake Erie Medical DBA Quality Care Products LLC1990-09-30Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet5 mgoralPd Rx Pharmaceuticals, Inc.1997-10-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet5 mgoralAphena Pharma Solutions Tennessee, Llc1997-10-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet, film coated, extended release10 mgoralAphena Pharma Solutions Tennessee, Inc.2009-03-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet5 mgoralREMEDYREPACK INC.2011-09-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet5 mgoralPliva Inc.1990-09-30Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet5 mgoralUnit Dose Services1990-09-30Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet, film coated, extended release5 mgoralMylan Institutional Inc.2006-11-27Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet, film coated, extended release10 mgoralMylan Institutional Inc.2006-11-27Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet, extended release10 mgoralREMEDYREPACK INC.2013-02-25Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet5 mgoralREMEDYREPACK INC.2013-07-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet5 mgoralREMEDYREPACK INC.2013-05-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet5 mgoralState of Florida DOH Central Pharmacy2009-07-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet5 mgoralState of Florida DOH Central Pharmacy2009-07-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet5 mgoralState of Florida DOH Central Pharmacy2013-01-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet5 mgoralA S Medication Solutions Llc1997-10-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridesyrup5 mg/5mLoralSilarx Pharmaceuticals, Inc2009-09-08Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet5 mgoralPhysicians Total Care, Inc.2006-12-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet, film coated, extended release10 mgoralPhysicians Total Care, Inc.2006-12-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet, film coated, extended release5 mgoralPhysicians Total Care, Inc.2007-01-08Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet, extended release15 mgoralPhysicians Total Care, Inc.2010-01-13Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet5 mgoralCardinal Health2004-02-03Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet5 mgoralCardinal Health1997-10-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet5 mgoralCardinal Health2011-05-20Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet5 mgoralCardinal Health2011-11-07Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet, film coated, extended release10 mgoralCardinal Health2010-07-28Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet, film coated, extended release5 mgoralCardinal Health2010-07-28Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet, film coated, extended release5 mgoralCardinal Health2006-11-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet, film coated, extended release10 mgoralCardinal Health2013-05-20Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet, film coated, extended release10 mgoralCardinal Health2006-11-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet5 mgoralCardinal Health2010-01-13Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridesyrup5 mg/5mLoralMorton Grove Pharmaceuticals, Inc.1997-02-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet5 mgoralSt Marys Medical Park Pharmacy2013-05-16Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet5 mgoralbryant ranch prepack1997-10-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet, extended release5 mgoralDispensing Solutions, Inc.2007-05-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet5 mgoralAmerican Health Packaging2010-01-13Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet, extended release5 mgoralCarilion Materials Management2007-05-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet5 mgoralMc Kesson Contract Packaging2011-12-23Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet, film coated, extended release5 mgoralMc Kesson Contract Packaging2011-10-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxybutynin Chloridetablet, film coated, extended release10 mgoralMc Kesson Contract Packaging2011-09-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Oxytrol For Womenpatch3.9 mg/dtransdermalMSD Consumer Care, Inc.2013-08-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxytrol For Womenpatch3.9 mg/dtransdermalMSD Consumer Care, Inc.2013-08-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
International Brands
NameCompany
DitropanNot Available
LenditroNot Available
Lyrinel XLNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Oxybutynin Chloride
Thumb
  • InChI Key: SWIJYDAEGSIQPZ-UHFFFAOYNA-N
  • Monoisotopic Mass: 393.207071602
  • Average Mass: 393.947
DBSALT000430
Categories
CAS number5633-20-5
WeightAverage: 357.4864
Monoisotopic: 357.230393863
Chemical FormulaC22H31NO3
InChI KeyXIQVNETUBQGFHX-UHFFFAOYSA-N
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
IUPAC Name
4-(diethylamino)but-2-yn-1-yl 2-cyclohexyl-2-hydroxy-2-phenylacetate
SMILES
CCN(CC)CC#CCOC(=O)C(O)(C1CCCCC1)C1=CC=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylacetic acid derivatives. These are compounds containing a phenylacetic acid moiety, which consists of a phenyl group substituted at the second position by an acetic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetic acid derivatives
Direct ParentPhenylacetic acid derivatives
Alternative Parents
Substituents
  • Phenylacetate
  • Tertiary alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of overactive bladder.
PharmacodynamicsOxybutynin is an antispasmodic, anticholinergic agent indicated for the treatment of overactive bladder with symptoms of urge urinary incontinence, urgency, and frequency. Oxybutynin relaxes bladder smooth muscle. Oxybutynin exhibits only one-fifth of the anticholinergic activity of atropine on the rabbit detrusor muscle, but four to ten times the antispasmodic activity. Antimuscarinic activity resides predominantly in the R-isomer.
Mechanism of actionOxybutynin exerts a direct antispasmodic effect on smooth muscle and inhibits the muscarinic action of acetylcholine on smooth muscle. No blocking effects occur at skeletal neuromuscular junctions or autonomic ganglia (antinicotinic effects). By inhibiting particularily the M1 and M2 receptors of the bladder, detrusor activity is markedly decreased.
AbsorptionRapidly absorbed from gastrointestinal tract.
Volume of distribution
  • 193 L
Protein binding91%-93%
Metabolism

Hepatic, primarily by CYP3A4

SubstrateEnzymesProduct
Oxybutynin
N-desethyloxybutyninDetails
Route of eliminationOxybutynin is metabolized primarily by the cytochrome P450 enzyme systems, particularly CYP3A4, found mostly in the liver and gut wall. Oxybutynin is extensively metabolized by the liver, with less than 0.1% of the administered dose excreted unchanged in the urine. Also, less than 0.1% of the administered dose is excreted as the metabolite N-desethyloxybutynin.
Half life12.4-13.2 hours
ClearanceNot Available
ToxicityLD50=1220 mg/kg (Orally in rats, Goldenthal)
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9225
Blood Brain Barrier+0.9418
Caco-2 permeable+0.5989
P-glycoprotein substrateSubstrate0.7244
P-glycoprotein inhibitor IInhibitor0.6809
P-glycoprotein inhibitor IIInhibitor0.7244
Renal organic cation transporterNon-inhibitor0.558
CYP450 2C9 substrateNon-substrate0.812
CYP450 2D6 substrateNon-substrate0.7985
CYP450 3A4 substrateNon-substrate0.5213
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 substrateInhibitor0.8949
CYP450 2D6 substrateInhibitor0.8932
CYP450 2C19 substrateInhibitor0.8994
CYP450 3A4 substrateInhibitor0.796
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7137
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.7038
BiodegradationNot ready biodegradable0.9878
Rat acute toxicity2.9059 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9548
hERG inhibition (predictor II)Inhibitor0.7337
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Geltransdermal100 mg/g
Geltransdermal28 mg/.92g
Patchtransdermal3.9 mg/d
Patchtransdermal36 mg
Solutionoral5 mg/5mL
Syruporal5 mg/5mL
Tabletoral5 mg
Tablet, extended releaseoral10 mg
Tablet, extended releaseoral15 mg
Tablet, extended releaseoral5 mg
Tablet, film coated, extended releaseoral10 mg
Tablet, film coated, extended releaseoral5 mg
Prices
Unit descriptionCostUnit
Oxybutynin chloride powder54.47USD g
Oxytrol 3.9 mg/24hr Patches20.87USD patch
Oxytrol 3.9 mg/24hr patch20.06USD patch
Gelnique 10% gel sachets5.17USD g
Ditropan XL 15 mg 24 Hour tablet4.59USD tablet
Ditropan XL 10 mg 24 Hour tablet4.47USD tablet
Ditropan XL 5 mg 24 Hour tablet4.47USD tablet
Ditropan xl 15 mg tablet4.23USD tablet
Ditropan xl 10 mg tablet4.13USD tablet
Ditropan xl 5 mg tablet4.13USD tablet
Ditropan xl 5 mg tablet sa4.13USD tablet
Oxybutynin Chloride 15 mg 24 Hour tablet3.5USD tablet
Oxybutynin Chloride 10 mg 24 Hour tablet3.42USD tablet
Oxybutynin Chloride 5 mg 24 Hour tablet3.2USD tablet
Ditropan 5 mg tablet1.15USD tablet
Oxybutynin Chloride 5 mg tablet0.57USD tablet
Ditropan 5 mg/5ml Syrup0.26USD ml
Apo-Oxybutynin 5 mg Tablet0.26USD tablet
Mylan-Oxybutynin 5 mg Tablet0.26USD tablet
Novo-Oxybutynin 5 mg Tablet0.26USD tablet
Nu-Oxybutyn 5 mg Tablet0.26USD tablet
Pms-Oxybutynin 5 mg Tablet0.26USD tablet
Oxybutynin Chloride 5 mg/5ml Syrup0.21USD ml
Oxybutynin 5 mg tablet0.17USD tablet
Pms-Oxybutynin 2.5 mg Tablet0.14USD tablet
Pms-Oxybutynin 1 mg/ml Syrup0.08USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
Canada22187142005-08-232016-05-08
United States51641901993-12-112010-12-11
United States67434412000-04-262020-04-26
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point129-130 °CNot Available
logP4.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.01 mg/mLALOGPS
logP4.36ALOGPS
logP4.44ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)11.53ChemAxon
pKa (Strongest Basic)8.77ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.77 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity105.26 m3·mol-1ChemAxon
Polarizability41.25 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Masakatsu Shibasaki, “Method of producing oxybutynin and its derivatives.” U.S. Patent US20040006243, issued January 08, 2004.

US20040006243
General Reference
  1. Tupker RA, Harmsze AM, Deneer VH: Oxybutynin therapy for generalized hyperhidrosis. Arch Dermatol. 2006 Aug;142(8):1065-6. Pubmed
  2. Mijnhout GS, Kloosterman H, Simsek S, Strack van Schijndel RJ, Netelenbos JC: Oxybutynin: dry days for patients with hyperhidrosis. Neth J Med. 2006 Oct;64(9):326-8. Pubmed
  3. Schollhammer M, Misery L: Treatment of hyperhidrosis with oxybutynin. Arch Dermatol. 2007 Apr;143(4):544-5. Pubmed
External Links
ATC CodesG04BD04
AHFS Codes
  • 86:12.00
PDB EntriesNot Available
FDA labelDownload (144 KB)
MSDSDownload (73 KB)
Interactions
Drug Interactions
Drug
CarbamazepineOxybutynin may cause carbamazepine toxicity
DonepezilPossible antagonism of action
GalantaminePossible antagonism of action
RivastigminePossible antagonism of action
TacrineThe therapeutic effects of the central acetylcholinesterase inhibitor, Tacrine, and/or the anticholinergic, Oxybutynin, may be reduced due to antagonism. The interaction may be beneficial when the anticholinergic action is a side effect. Monitor for decreased efficacy of both agents.
TrimethobenzamideTrimethobenzamide and Oxybutynin, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
TriprolidineTriprolidine and Oxybutynin, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
TrospiumTrospium and Oxybutynin, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Food Interactions
  • Avoid alcohol.
  • Take with food.

Targets

1. Muscarinic acetylcholine receptor M3

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M3 P20309 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Baldwin CM, Keating GM: Transdermal oxybutynin. Drugs. 2009;69(3):327-37. Pubmed
  4. Ito Y, Oyunzul L, Yoshida A, Fujino T, Noguchi Y, Yuyama H, Ohtake A, Suzuki M, Sasamata M, Matsui M, Yamada S: Comparison of muscarinic receptor selectivity of solifenacin and oxybutynin in the bladder and submandibular gland of muscarinic receptor knockout mice. Eur J Pharmacol. 2009 Aug 1;615(1-3):201-6. Epub 2009 May 13. Pubmed
  5. Sinha S, Gupta S, Malhotra S, Krishna NS, Meru AV, Babu V, Bansal V, Garg M, Kumar N, Chugh A, Ray A: AE9C90CB: a novel, bladder-selective muscarinic receptor antagonist for the treatment of overactive bladder. Br J Pharmacol. 2010 Jul;160(5):1119-27. Pubmed
  6. Oki T, Kageyama A, Takagi Y, Uchida S, Yamada S: Comparative evaluation of central muscarinic receptor binding activity by oxybutynin, tolterodine and darifenacin used to treat overactive bladder. J Urol. 2007 Feb;177(2):766-70. Pubmed
  7. Maruyama S, Oki T, Otsuka A, Shinbo H, Ozono S, Kageyama S, Mikami Y, Araki I, Takeda M, Masuyama K, Yamada S: Human muscarinic receptor binding characteristics of antimuscarinic agents to treat overactive bladder. J Urol. 2006 Jan;175(1):365-9. Pubmed
  8. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Muscarinic acetylcholine receptor M2

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M2 P08172 Details

References:

  1. Dmochowski R: Improving the tolerability of anticholinergic agents in the treatment of overactive bladder. Drug Saf. 2005;28(7):583-600. Pubmed
  2. Nelson CP, Nahorski SR, Challiss RA: Constitutive activity and inverse agonism at the M2 muscarinic acetylcholine receptor. J Pharmacol Exp Ther. 2006 Jan;316(1):279-88. Epub 2005 Sep 27. Pubmed
  3. Ito Y, Oyunzul L, Yoshida A, Fujino T, Noguchi Y, Yuyama H, Ohtake A, Suzuki M, Sasamata M, Matsui M, Yamada S: Comparison of muscarinic receptor selectivity of solifenacin and oxybutynin in the bladder and submandibular gland of muscarinic receptor knockout mice. Eur J Pharmacol. 2009 Aug 1;615(1-3):201-6. Epub 2009 May 13. Pubmed
  4. Sinha S, Gupta S, Malhotra S, Krishna NS, Meru AV, Babu V, Bansal V, Garg M, Kumar N, Chugh A, Ray A: AE9C90CB: a novel, bladder-selective muscarinic receptor antagonist for the treatment of overactive bladder. Br J Pharmacol. 2010 Jul;160(5):1119-27. Pubmed
  5. Oki T, Kageyama A, Takagi Y, Uchida S, Yamada S: Comparative evaluation of central muscarinic receptor binding activity by oxybutynin, tolterodine and darifenacin used to treat overactive bladder. J Urol. 2007 Feb;177(2):766-70. Pubmed

3. Muscarinic acetylcholine receptor M1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M1 P11229 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Sinha S, Gupta S, Malhotra S, Krishna NS, Meru AV, Babu V, Bansal V, Garg M, Kumar N, Chugh A, Ray A: AE9C90CB: a novel, bladder-selective muscarinic receptor antagonist for the treatment of overactive bladder. Br J Pharmacol. 2010 Jul;160(5):1119-27. Pubmed
  4. Oki T, Kageyama A, Takagi Y, Uchida S, Yamada S: Comparative evaluation of central muscarinic receptor binding activity by oxybutynin, tolterodine and darifenacin used to treat overactive bladder. J Urol. 2007 Feb;177(2):766-70. Pubmed
  5. Maruyama S, Oki T, Otsuka A, Shinbo H, Ozono S, Kageyama S, Mikami Y, Araki I, Takeda M, Masuyama K, Yamada S: Human muscarinic receptor binding characteristics of antimuscarinic agents to treat overactive bladder. J Urol. 2006 Jan;175(1):365-9. Pubmed

Enzymes

1. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Yaich M, Popon M, Medard Y, Aigrain EJ: In-vitro cytochrome P450 dependent metabolism of oxybutynin to N-deethyloxybutynin in humans. Pharmacogenetics. 1998 Oct;8(5):449-51. Pubmed
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 2C8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C8 P10632 Details

References:

  1. Walsky RL, Gaman EA, Obach RS: Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78. Pubmed
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

3. Cytochrome P450 2D6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

4. Cytochrome P450 3A5

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A5 P20815 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:13