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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
4-(Diethylamino)-2-butynyl alpha-phenylcyclohexaneglycolic acid ester
4-Diethylamino-2-butinyl alpha-cyclohexylmandelat
4-Diethylamino-2-butynyl alpha-phenylcyclohexaneglycolate
Benzeneacetic acid, alpha-cyclohexyl-alpha-hydroxy-, 4-(diethylamino)-2-butynyl ester
Cyclohexaneglycolic acid, alpha-phenyl-, 4-(diethylamino)-2-butynyl ester
Oxibutinina
Oxybutynin
Oxybutynine
Oxybutyninum
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Albert Oxybutynintablet5 mgoralAventis Pharma Inc1996-11-212002-07-29Canada
Ava-oxybutynintablet5 mgoralAvanstra Inc2011-08-222014-08-21Canada
Ditropan Syrup 1mg/mlsyrup1 mgoralJanssen Inc1993-12-312007-02-21Canada
Ditropan Tablets 5mgtablet5 mgoralJanssen Inc1993-12-312006-08-04Canada
Ditropan XLtablet, extended release15 mg/1oralJanssen Pharmaceuticals, Inc.1999-06-262016-04-05Us
Ditropan XLtablet, extended release10 mg/1oralJanssen Pharmaceuticals, Inc.1999-06-262016-04-05Us
Ditropan XLtablet, extended release5 mg/1oralJanssen Pharmaceuticals, Inc.1999-06-262016-04-05Us
Ditropan XLtablet (extended-release)15 mgoralJanssen IncNot applicableNot applicableCanada
Ditropan XLtablet, extended release15 mg/1oralPhysicians Total Care, Inc.2003-06-252016-04-05Us
Ditropan XLtablet, extended release10 mg/1oralPhysicians Total Care, Inc.2003-06-232016-04-05Us
Ditropan XL -(10mg)tablet (extended-release)10 mgoralJanssen Inc2001-06-22Not applicableCanada
Ditropan XL -(5mg)tablet (extended-release)5 mgoralJanssen Inc2001-06-22Not applicableCanada
Dom-oxybutynin 5 Mg Tabletstablet5 mgoralDominion Pharmacal1999-12-16Not applicableCanada
Gelniquegel28 mg/.92gtransdermalActavis Pharma, Inc.2012-04-022016-04-05Us
Gelniquemetered-dose pump100 mgtopicalWatson Laboratories IncNot applicableNot applicableCanada
Gelniquegel100 mg/gtransdermalPhysicians Total Care, Inc.2010-09-152016-04-05Us
Gelniquegel100 mgtopicalActavis Specialty Pharmaceuticals Co2011-10-27Not applicableCanada
Gelniquegel100 mg/gtransdermalActavis Pharma, Inc.2009-05-152016-04-05Us
Mylan-oxybutynintablet5 mgoralMylan Pharmaceuticals Ulc1997-04-24Not applicableCanada
Ntp-oxybutynintablet5 mgoralTeva Canada LimitedNot applicableNot applicableCanada
Nu-oxybutynsyrup1 mgoralNu Pharm IncNot applicableNot applicableCanada
Nu-oxybutyn - Tab 5mgtablet5 mgoralNu Pharm Inc1995-12-312012-09-04Canada
Oxybutyn - 5mgtablet5 mgoralValeant Canada Lp Valeant Canada S.E.C.1996-10-31Not applicableCanada
Oxybutynintablet5 mgoralSanis Health Inc2010-05-12Not applicableCanada
Oxybutynin Chloridetablet, extended release15 mg/1oralMylan Pharmaceuticals Inc.2007-05-102016-04-23Us
Oxybutynin Chloridetablet, extended release15 mg/1oralPatriot Pharmaceuticals, LLC1999-06-262016-04-05Us
Oxybutynin Chloridetablet, extended release10 mg/1oralPatriot Pharmaceuticals, LLC1999-06-262016-04-05Us
Oxybutynin Chloridetablet, extended release5 mg/1oralPatriot Pharmaceuticals, LLC1999-06-262016-04-05Us
Oxybutynin Chloridetablet, extended release15 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs2007-05-102016-04-23Us
Oxybutynine-5 - Tab 5mgtablet5 mgoralPro Doc Limitee1996-12-06Not applicableCanada
Oxytrolpatch36 mgtransdermalActavis Specialty Pharmaceuticals Co2004-08-12Not applicableCanada
Oxytrolpatch3.9 mg/dtransdermalActavis Pharma, Inc.2003-02-262016-04-05Us
Pat-oxybutynin Chloride ERtablet (extended-release)10 mgoralPatriot A Division Of Janssen IncNot applicableNot applicableCanada
Pat-oxybutynin Chloride ERtablet (extended-release)5 mgoralPatriot A Division Of Janssen IncNot applicableNot applicableCanada
Pat-oxybutynin Chloride ERtablet (extended-release)15 mgoralPatriot A Division Of Janssen IncNot applicableNot applicableCanada
Penta-oxybutynin Chloride Tabletstablet5 mgoralPentapharm Ltd.Not applicableNot applicableCanada
PHL-oxybutynintablet2.5 mgoralPharmel Inc2004-12-02Not applicableCanada
PHL-oxybutynintablet5 mgoralPharmel Inc2002-05-29Not applicableCanada
PHL-oxybutyninsyrup1 mgoralPharmel Inc2004-12-06Not applicableCanada
PMS-oxybutyninsyrup1 mgoralPharmascience Inc1996-09-04Not applicableCanada
PMS-oxybutynintablet5 mgoralPharmascience Inc1999-11-22Not applicableCanada
PMS-oxybutynintablet2.5 mgoralPharmascience Inc1999-11-22Not applicableCanada
Riva-oxybutynintablet5 mgoralLaboratoire Riva Inc2000-05-052013-07-31Canada
Riva-oxybutynintablet5 mgoralLaboratoire Riva Inc2008-06-09Not applicableCanada
Teva-oxybutynintablet5 mgoralTeva Canada Limited1997-02-28Not applicableCanada
Uromaxtablet (extended-release)10 mgoralPurdue Pharma2006-05-152013-08-01Canada
Uromaxtablet (extended-release)15 mgoralPurdue Pharma2006-05-152013-08-01Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-oxybutyninsyrup1 mgoralApotex Inc1997-04-28Not applicableCanada
Apo-oxybutynin - Tab 5mgtablet5 mgoralApotex Inc1995-12-31Not applicableCanada
Oxybutynin Chloridetablet, film coated, extended release10 mg/1oralMylan Institutional Inc.2006-11-272016-04-05Us
Oxybutynin Chloridetablet, film coated, extended release10 mg/1oralAphena Pharma Solutions Tennessee, Inc.2009-03-012016-04-05Us
Oxybutynin Chloridetablet5 mg/1oralRebel Distributors Corp.1997-10-312016-04-05Us
Oxybutynin Chloridetablet, film coated, extended release5 mg/1oralCardinal Health2006-11-102016-04-05Us
Oxybutynin Chloridetablet5 mg/1oralPhysicians Total Care, Inc.2006-12-112016-04-05Us
Oxybutynin Chloridetablet, extended release10 mg/1oralREMEDYREPACK INC.2013-02-252016-04-05Us
Oxybutynin Chloridetablet5 mg/1oralBlenheim Pharmacal, Inc.2013-11-132016-04-05Us
Oxybutynin Chloridesolution5 mg/5mLoralQualitest Pharmaceuticals2004-12-282016-04-23Us
Oxybutynin Chloridetablet, extended release5 mg/1oralTeva Pharmaceuticals USA Inc2007-05-112016-04-23Us
Oxybutynin Chloridetablet5 mg/1oralAmerican Health Packaging2010-01-132016-04-05Us
Oxybutynin Chloridetablet, film coated, extended release10 mg/1oralCardinal Health2013-05-202016-04-05Us
Oxybutynin Chloridetablet, film coated, extended release5 mg/1oralCardinal Health2010-07-282015-12-29Us
Oxybutynin Chloridetablet, film coated, extended release5 mg/1oralMylan Institutional Inc.2006-11-272016-04-05Us
Oxybutynin Chloridetablet5 mg/1oralAphena Pharma Solutions Tennessee, Llc1997-10-312016-04-05Us
Oxybutynin Chloridetablet5 mg/1oralCardinal Health2011-11-072016-04-05Us
Oxybutynin Chloridesyrup5 mg/5mLoralSilarx Pharmaceuticals, Inc2009-09-082016-04-05Us
Oxybutynin Chloridetablet5 mg/1oralBlenheim Pharmacal, Inc.2013-10-022016-04-05Us
Oxybutynin Chloridetablet, film coated, extended release15 mg/1oralMylan Pharmaceuticals Inc.2006-11-102016-04-23Us
Oxybutynin Chloridetablet, extended release5 mg/1oralDispensing Solutions, Inc.2007-05-112016-04-05Us
Oxybutynin Chloridetablet, film coated, extended release10 mg/1oralCardinal Health2010-07-282015-12-29Us
Oxybutynin Chloridetablet5 mg/1oralCardinal Health2011-05-202016-04-05Us
Oxybutynin Chloridetablet5 mg/1oralA S Medication Solutions Llc1997-10-312016-04-05Us
Oxybutynin Chloridetablet5 mg/1oralMajor Pharmaceuticals2004-02-032016-04-05Us
Oxybutynin Chloridetablet, film coated, extended release10 mg/1oralMylan Pharmaceuticals Inc.2006-11-102016-04-23Us
Oxybutynin Chloridetablet, extended release15 mg/1oralAmneal Pharmaceuticals of New York, LLC2015-11-022016-04-05Us
Oxybutynin Chloridetablet, film coated, extended release5 mg/1oralAvera Mc Kennan Hospital2015-03-102016-04-05Us
Oxybutynin Chloridetablet, film coated, extended release10 mg/1oralMc Kesson Contract Packaging2011-09-192016-04-05Us
Oxybutynin Chloridetablet5 mg/1oralUnit Dose Services1990-09-302016-04-05Us
Oxybutynin Chloridetablet5 mg/1oralPd Rx Pharmaceuticals, Inc.1997-10-312016-04-05Us
Oxybutynin Chloridetablet5 mg/1oralUpsher Smith Laboratories, Inc.2011-11-072016-04-05Us
Oxybutynin Chloridetablet, film coated, extended release5 mg/1oralMylan Pharmaceuticals Inc.2006-11-102016-04-23Us
Oxybutynin Chloridetablet, extended release10 mg/1oralAmneal Pharmaceuticals of New York, LLC2015-11-022016-04-05Us
Oxybutynin Chloridetablet5 mg/1oralSt Marys Medical Park Pharmacy2013-05-162016-04-05Us
Oxybutynin Chloridetablet, extended release15 mg/1oralREMEDYREPACK INC.2016-02-242016-04-05Us
Oxybutynin Chloridetablet, film coated, extended release5 mg/1oralMc Kesson Contract Packaging2011-10-122016-04-05Us
Oxybutynin Chloridetablet5 mg/1oralCardinal Health1997-10-312016-02-25Us
Oxybutynin Chloridetablet5 mg/1oralState of Florida DOH Central Pharmacy2013-01-012016-04-05Us
Oxybutynin Chloridetablet, extended release5 mg/1oralAmneal Pharmaceuticals of New York, LLC2015-11-022016-04-05Us
Oxybutynin Chloridesyrup5 mg/5mLoralMorton Grove Pharmaceuticals, Inc.1997-02-122016-04-05Us
Oxybutynin Chloridetablet5 mg/1oralMc Kesson Contract Packaging2011-12-232016-04-05Us
Oxybutynin Chloridetablet5 mg/1oralLake Erie Medical DBA Quality Care Products LLC1990-09-302016-04-05Us
Oxybutynin Chloridetablet5 mg/1oralCardinal Health2004-02-032016-04-05Us
Oxybutynin Chloridetablet5 mg/1oralState of Florida DOH Central Pharmacy2009-07-012016-04-05Us
Oxybutynin Chloridetablet, film coated, extended release10 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs2010-01-202016-04-23Us
Oxybutynin Chloridetablet, extended release10 mg/1oralKAISER FOUNDATION HOSPITALS2015-10-142016-04-23Us
Oxybutynin Chloridetablet5 mg/1oralCardinal Health1997-10-312016-04-05Us
Oxybutynin Chloridetablet, film coated, extended release10 mg/1oralAvera Mc Kennan Hospital2015-03-232016-04-05Us
Oxybutynin Chloridetablet, extended release10 mg/1oralLake Erie Medical DBA Quality Care Products LLC2007-05-112016-04-05Us
Oxybutynin Chloridetablet, extended release15 mg/1oralPhysicians Total Care, Inc.2010-01-132016-04-05Us
Oxybutynin Chloridetablet5 mg/1oralState of Florida DOH Central Pharmacy2009-07-012016-04-05Us
Oxybutynin Chloridetablet, film coated, extended release5 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs2010-01-202016-04-23Us
Oxybutynin Chloridesyrup5 mg/5mLoralPharmaceutical Associates, Inc.1998-12-182016-04-23Us
Oxybutynin Chloridetablet5 mg/1oralPliva Inc.1990-09-302016-04-05Us
Oxybutynin Chloridetablet5 mg/1oralAidarex Pharmaceuticals LLC1997-10-312016-04-05Us
Oxybutynin Chloridetablet, film coated, extended release5 mg/1oralPhysicians Total Care, Inc.2007-01-082016-04-05Us
Oxybutynin Chloridetablet5 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs2012-10-302016-04-23Us
Oxybutynin Chloridetablet, extended release15 mg/1oralTeva Pharmaceuticals USA Inc2006-11-102016-04-23Us
Oxybutynin Chloridetablet, extended release10 mg/1oralbryant ranch prepack2007-05-112016-04-05Us
Oxybutynin Chloridetablet5 mg/1oralCardinal Health2010-01-132016-04-05Us
Oxybutynin Chloridetablet, extended release10 mg/1oralAv Kare, Inc.2016-01-082016-03-18Us
Oxybutynin Chloridetablet, extended release5 mg/1oralCarilion Materials Management2007-05-112016-04-05Us
Oxybutynin Chloridetablet5 mg/1oralREMEDYREPACK INC.2011-09-292016-04-05Us
Oxybutynin Chloridetablet5 mg/1oralREMEDYREPACK INC.2013-04-052016-04-05Us
Oxybutynin Chloridetablet, film coated, extended release10 mg/1oralPhysicians Total Care, Inc.2006-12-122016-04-05Us
Oxybutynin Chloridetablet5 mg/1oralREMEDYREPACK INC.2013-05-292016-04-05Us
Oxybutynin Chloridetablet5 mg/1oralQualitest Pharmaceuticals1997-10-312016-04-23Us
Oxybutynin Chloridetablet, extended release10 mg/1oralTeva Pharmaceuticals USA Inc2007-05-112016-04-23Us
Oxybutynin Chloridetablet5 mg/1oralbryant ranch prepack1997-10-312016-04-05Us
Oxybutynin Chloridetablet, film coated, extended release10 mg/1oralCardinal Health2006-11-102016-04-05Us
Oxybutynin Chloridetablet, extended release5 mg/1oralAv Kare, Inc.2016-01-082016-03-18Us
Oxybutynin Chloride Extended Releasetablet, extended release15 mg/1oralAv Kare, Inc.2016-03-092016-04-05Us
Oxybutynin Chloride Extended Releasetablet, extended release15 mg/1oralKremers Urban Pharmaceuticals Inc.2009-03-012016-04-05Us
Oxybutynin Chloride Extended Releasetablet, extended release10 mg/1oralAv Kare, Inc.2016-03-092016-04-05Us
Oxybutynin Chloride Extended Releasetablet, extended release5 mg/1oralAmerican Health Packaging2012-01-102016-04-05Us
Oxybutynin Chloride Extended Releasetablet, extended release10 mg/1oralKremers Urban Pharmaceuticals Inc.2009-03-012016-04-05Us
Oxybutynin Chloride Extended Releasetablet, extended release5 mg/1oralAv Kare, Inc.2016-03-092016-04-05Us
Oxybutynin Chloride Extended Releasetablet, extended release5 mg/1oralKremers Urban Pharmaceuticals Inc.2009-03-012016-04-05Us
Oxybutynin Chloride Extended Releasetablet, extended release15 mg/1oralAv Pak2012-05-162016-04-05Us
Oxybutynin Chloride Extended Releasetablet, extended release5 mg/1oralLake Erie Medical DBA Quality Care Products LLC2009-03-012016-04-05Us
Oxybutynin Chloride Extended Releasetablet, extended release10 mg/1oralAv Pak2012-05-172016-04-05Us
Oxybutynin Chloride Extended Releasetablet, extended release5 mg/1oralMc Kesson Packaging Services A Business Unit Of Mc Kesson Corporation2012-05-182016-04-05Us
Oxybutynin Chloride Extended Releasetablet, extended release5 mg/1oralAv Pak2012-05-172016-04-05Us
Oxybutynin Chloride Extended Releasetablet, extended release10 mg/1oralAmerican Health Packaging2012-08-312016-04-05Us
Oxybutynin Chlorideextended Release Extended Releasetablet, extended release10 mg/1oralREMEDYREPACK INC.2013-09-192016-04-05Us
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Oxytrol for Womenpatch3.9 mg/dtransdermalMSD Consumer Care, Inc.2013-08-192016-04-05Us
Oxytrol for Womenpatch3.9 mg/dtransdermalActavis Pharma, Inc.2016-01-012016-04-05Us
Oxytrol for Womenpatch3.9 mg/dtransdermalMSD Consumer Care, Inc.2013-08-192016-04-05Us
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
UNIIK9P6MC7092
CAS number5633-20-5
WeightAverage: 357.4864
Monoisotopic: 357.230393863
Chemical FormulaC22H31NO3
InChI KeyInChIKey=XIQVNETUBQGFHX-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.
Related Articles
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
Clearance

Estimated to be 26L/h.

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 inhibitorInhibitor0.8949
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorInhibitor0.796
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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Tabletoral5 mg
Tablet (extended-release)oral10 mg
Tablet (extended-release)oral5 mg
Geltopical100 mg
Geltransdermal100 mg/g
Geltransdermal28 mg/.92g
Metered-dose pumptopical100 mg
Solutionoral5 mg/5mL
Syruporal5 mg/5mL
Tabletoral5 mg/1
Tablet, extended releaseoral10 mg/1
Tablet, extended releaseoral15 mg/1
Tablet, extended releaseoral5 mg/1
Tablet, film coated, extended releaseoral10 mg/1
Tablet, film coated, extended releaseoral15 mg/1
Tablet, film coated, extended releaseoral5 mg/1
Patchtransdermal36 mg
Patchtransdermal3.9 mg/d
Syruporal1 mg
Tabletoral2.5 mg
Tablet (extended-release)oral15 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
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2218714 No2005-08-232016-05-08Canada
US5164190 No1993-12-112010-12-11Us
US5674895 Yes1995-11-222015-11-22Us
US5840754 Yes1995-11-222015-11-22Us
US5912268 Yes1995-11-222015-11-22Us
US6262115 Yes1995-11-222015-11-22Us
US6743441 No2000-04-262020-04-26Us
US7029694 No2000-04-262020-04-26Us
US7081249 No2000-04-262020-04-26Us
US7081250 No2000-04-262020-04-26Us
US7081251 No2000-04-262020-04-26Us
US7081252 No2000-04-262020-04-26Us
US7179483 No2000-04-262020-04-26Us
US7198801 No2002-06-252022-06-25Us
US8241662 No2000-04-262020-04-26Us
US8920392 No2011-03-262031-03-26Us
US9259388 No2009-11-062029-11-06Us
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 References
  1. Tupker RA, Harmsze AM, Deneer VH: Oxybutynin therapy for generalized hyperhidrosis. Arch Dermatol. 2006 Aug;142(8):1065-6. [PubMed:16924061 ]
  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:17057269 ]
  3. Schollhammer M, Misery L: Treatment of hyperhidrosis with oxybutynin. Arch Dermatol. 2007 Apr;143(4):544-5. [PubMed:17438194 ]
External Links
ATC CodesG04BD04
AHFS Codes
  • 86:12.00
PDB EntriesNot Available
FDA labelDownload (144 KB)
MSDSDownload (73 KB)
Interactions
Drug Interactions
Drug
AclidiniumAclidinium may increase the anticholinergic activities of Oxybutynin.
AmodiaquineThe serum concentration of Amodiaquine can be increased when it is combined with Oxybutynin.
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Oxybutynin.
AtazanavirThe serum concentration of Oxybutynin can be increased when it is combined with Atazanavir.
BoceprevirThe serum concentration of Oxybutynin can be increased when it is combined with Boceprevir.
Botulinum Toxin Type AOxybutynin may increase the anticholinergic activities of Botulinum Toxin Type A.
Botulinum Toxin Type BOxybutynin may increase the anticholinergic activities of Botulinum Toxin Type B.
CeritinibThe serum concentration of Oxybutynin can be increased when it is combined with Ceritinib.
Cimetropium BromideOxybutynin may increase the anticholinergic activities of Cimetropium Bromide.
ClarithromycinThe serum concentration of Oxybutynin can be increased when it is combined with Clarithromycin.
CobicistatThe serum concentration of Oxybutynin can be increased when it is combined with Cobicistat.
DarunavirThe serum concentration of Oxybutynin can be increased when it is combined with Darunavir.
DronabinolOxybutynin may increase the tachycardic activities of Dronabinol.
EluxadolineOxybutynin may increase the activities of Eluxadoline.
EthanolEthanol may increase the central nervous system depressant (CNS depressant) activities of Oxybutynin.
Glucagon recombinantThe risk or severity of adverse effects can be increased when Oxybutynin is combined with Glucagon recombinant.
IdelalisibThe serum concentration of Oxybutynin can be increased when it is combined with Idelalisib.
IndinavirThe serum concentration of Oxybutynin can be increased when it is combined with Indinavir.
Ipratropium bromideIpratropium bromide may increase the anticholinergic activities of Oxybutynin.
ItoprideThe therapeutic efficacy of Itopride can be decreased when used in combination with Oxybutynin.
ItraconazoleThe serum concentration of Oxybutynin can be increased when it is combined with Itraconazole.
KetoconazoleThe serum concentration of Oxybutynin can be increased when it is combined with Ketoconazole.
MianserinMianserin may increase the anticholinergic activities of Oxybutynin.
MirabegronThe risk or severity of adverse effects can be increased when Oxybutynin is combined with Mirabegron.
MorphineThe risk or severity of adverse effects can be increased when Oxybutynin is combined with Morphine.
NefazodoneThe serum concentration of Oxybutynin can be increased when it is combined with Nefazodone.
NelfinavirThe serum concentration of Oxybutynin can be increased when it is combined with Nelfinavir.
PosaconazoleThe serum concentration of Oxybutynin can be increased when it is combined with Posaconazole.
Potassium ChlorideOxybutynin may increase the ulcerogenic activities of Potassium Chloride.
PramlintidePramlintide may increase the anticholinergic activities of Oxybutynin.
ProcyclidineThe risk or severity of adverse effects can be increased when Procyclidine is combined with Oxybutynin.
RamosetronOxybutynin may increase the activities of Ramosetron.
RitonavirThe serum concentration of Oxybutynin can be increased when it is combined with Ritonavir.
SaquinavirThe serum concentration of Oxybutynin can be increased when it is combined with Saquinavir.
SecretinThe therapeutic efficacy of Secretin can be decreased when used in combination with Oxybutynin.
SulpirideThe therapeutic efficacy of Sulpiride can be decreased when used in combination with Oxybutynin.
TacrineThe therapeutic efficacy of Oxybutynin can be decreased when used in combination with Tacrine.
TelaprevirThe serum concentration of Oxybutynin can be increased when it is combined with Telaprevir.
TelithromycinThe serum concentration of Oxybutynin can be increased when it is combined with Telithromycin.
TiotropiumOxybutynin may increase the anticholinergic activities of Tiotropium.
TopiramateThe risk or severity of adverse effects can be increased when Oxybutynin is combined with Topiramate.
TrichlormethiazideThe serum concentration of Trichlormethiazide can be increased when it is combined with Oxybutynin.
UmeclidiniumUmeclidinium may increase the anticholinergic activities of Oxybutynin.
VoriconazoleThe serum concentration of Oxybutynin can be increased when it is combined with Voriconazole.
Food Interactions
  • Avoid alcohol.
  • Take with food.

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Receptor activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM3
Uniprot ID:
P20309
Molecular Weight:
66127.445 Da
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:17139284 ]
  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:17016423 ]
  3. Baldwin CM, Keating GM: Transdermal oxybutynin. Drugs. 2009;69(3):327-37. doi: 10.2165/00003495-200969030-00008. [PubMed:19275276 ]
  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. doi: 10.1016/j.ejphar.2009.04.068. Epub 2009 May 13. [PubMed:19446545 ]
  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. doi: 10.1111/j.1476-5381.2010.00752.x. [PubMed:20590605 ]
  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:17222678 ]
  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:16406943 ]
  8. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
G-protein coupled acetylcholine receptor activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition. Signaling promotes phospholipase C activity, leading to the release of inositol trisphosphate (IP3); this then trigge...
Gene Name:
CHRM2
Uniprot ID:
P08172
Molecular Weight:
51714.605 Da
References
  1. Dmochowski R: Improving the tolerability of anticholinergic agents in the treatment of overactive bladder. Drug Saf. 2005;28(7):583-600. [PubMed:15963006 ]
  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:16188951 ]
  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. doi: 10.1016/j.ejphar.2009.04.068. Epub 2009 May 13. [PubMed:19446545 ]
  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. doi: 10.1111/j.1476-5381.2010.00752.x. [PubMed:20590605 ]
  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:17222678 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Phosphatidylinositol phospholipase c activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM1
Uniprot ID:
P11229
Molecular Weight:
51420.375 Da
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:17139284 ]
  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:17016423 ]
  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. doi: 10.1111/j.1476-5381.2010.00752.x. [PubMed:20590605 ]
  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:17222678 ]
  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:16406943 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
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:9825837 ]
  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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular Weight:
55824.275 Da
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:15601807 ]
  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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular Weight:
57108.065 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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Drug created on June 13, 2005 07:24 / Updated on April 30, 2016 03:00