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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
OxibutininaSpanishINN
OxybutynineFrenchINN
OxybutyninumLatinINN
Salts
Name/CAS Structure Properties
Oxybutynin Chloride
Thumb
  • InChI Key: SWIJYDAEGSIQPZ-UHFFFAOYNA-N
  • Monoisotopic Mass: 393.207071602
  • Average Mass: 393.947
DBSALT000430
Brand names
NameCompany
DitropanNot Available
GelniqueNot Available
LenditroNot Available
Lyrinel XLNot Available
OxytrolNot Available
Brand mixturesNot Available
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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassPhenylacetic Acid Derivatives
Direct parentPhenylacetic Acid Derivatives
Alternative parentsTertiary Alcohols; Tertiary Amines; Carboxylic Acid Esters; Ethers; Enolates; Polyamines; Aldehydes
Substituentstertiary alcohol; tertiary amine; carboxylic acid ester; enolate; carboxylic acid derivative; ether; polyamine; organonitrogen compound; amine; alcohol; aldehyde
Classification descriptionThis compound belongs to the 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.
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
Property Value Probability
Human Intestinal Absorption + 0.9225
Blood Brain Barrier + 0.9418
Caco-2 permeable + 0.5989
P-glycoprotein substrate Substrate 0.7244
P-glycoprotein inhibitor I Inhibitor 0.6809
P-glycoprotein inhibitor II Inhibitor 0.7244
Renal organic cation transporter Non-inhibitor 0.558
CYP450 2C9 substrate Non-substrate 0.812
CYP450 2D6 substrate Non-substrate 0.7985
CYP450 3A4 substrate Non-substrate 0.5213
CYP450 1A2 substrate Inhibitor 0.9106
CYP450 2C9 substrate Inhibitor 0.8949
CYP450 2D6 substrate Inhibitor 0.8932
CYP450 2C19 substrate Inhibitor 0.8994
CYP450 3A4 substrate Inhibitor 0.796
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7137
Ames test Non AMES toxic 0.9132
Carcinogenicity Non-carcinogens 0.7038
Biodegradation Not ready biodegradable 0.9878
Rat acute toxicity 2.9059 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9548
hERG inhibition (predictor II) Inhibitor 0.7337
Pharmacoeconomics
Manufacturers
  • Watson laboratories inc
  • Ortho mcneil janssen pharmaceuticals inc
  • Mikart inc
  • Novex pharma
  • Pharmaceutical assoc inc div beach products
  • Silarx pharmaceuticals inc
  • Vintage pharmaceuticals inc
  • Wockhardt eu operations (swiss) ag
  • Impax pharmaceuticals
  • Mylan pharmaceuticals inc
  • Osmotica pharmaceutical corp
  • Pliva inc
  • Quantum pharmics ltd
  • Usl pharma inc
  • Janssen Pharmaceuticals, Inc
Packagers
Dosage forms
FormRouteStrength
PatchTransdermal
SyrupOral
TabletOral
Tablet, extended releaseOral
Prices
Unit descriptionCostUnit
Oxybutynin chloride powder54.47USDg
Oxytrol 3.9 mg/24hr Patches20.87USDpatch
Oxytrol 3.9 mg/24hr patch20.06USDpatch
Gelnique 10% gel sachets5.17USDg
Ditropan XL 15 mg 24 Hour tablet4.59USDtablet
Ditropan XL 10 mg 24 Hour tablet4.47USDtablet
Ditropan XL 5 mg 24 Hour tablet4.47USDtablet
Ditropan xl 15 mg tablet4.23USDtablet
Ditropan xl 10 mg tablet4.13USDtablet
Ditropan xl 5 mg tablet4.13USDtablet
Ditropan xl 5 mg tablet sa4.13USDtablet
Oxybutynin Chloride 15 mg 24 Hour tablet3.5USDtablet
Oxybutynin Chloride 10 mg 24 Hour tablet3.42USDtablet
Oxybutynin Chloride 5 mg 24 Hour tablet3.2USDtablet
Ditropan 5 mg tablet1.15USDtablet
Oxybutynin Chloride 5 mg tablet0.57USDtablet
Ditropan 5 mg/5ml Syrup0.26USDml
Apo-Oxybutynin 5 mg Tablet0.26USDtablet
Mylan-Oxybutynin 5 mg Tablet0.26USDtablet
Novo-Oxybutynin 5 mg Tablet0.26USDtablet
Nu-Oxybutyn 5 mg Tablet0.26USDtablet
Pms-Oxybutynin 5 mg Tablet0.26USDtablet
Oxybutynin Chloride 5 mg/5ml Syrup0.21USDml
Oxybutynin 5 mg tablet0.17USDtablet
Pms-Oxybutynin 2.5 mg Tablet0.14USDtablet
Pms-Oxybutynin 1 mg/ml Syrup0.08USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States67434412000-04-262020-04-26
United States51641901993-12-112010-12-11
Canada22187142005-08-232016-05-08
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point129-130 °CNot Available
logP4.3Not Available
Predicted Properties
PropertyValueSource
water solubility1.00e-02 g/lALOGPS
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 area49.77ChemAxon
rotatable bond count10ChemAxon
refractivity105.26ChemAxon
polarizability41.25ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
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
ResourceLink
KEGG DrugD00465
KEGG CompoundC07360
PubChem Compound4634
PubChem Substance46508005
ChemSpider4473
ChEBI7856
ChEMBLCHEMBL1231
Therapeutic Targets DatabaseDAP001128
PharmGKBPA164746030
IUPHAR359
Guide to Pharmacology359
Drug Product Database2260751
RxListhttp://www.rxlist.com/cgi/generic/ditropan.htm
Drugs.comhttp://www.drugs.com/oxybutynin.html
PDRhealthhttp://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/dit1143.shtml
WikipediaOxybutynin
ATC CodesG04BD04
AHFS Codes
  • 86:12.00
PDB EntriesNot Available
FDA labelshow(144 KB)
MSDSshow(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