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Identification
Name Oxybutynin
Accession Number DB01062 (APRD00427)
Type small molecule
Groups approved
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Oxibutinina [INN-Spanish]
Oxibutyninum
Oxybutinin
Oxybutynin Base
Oxybutynin Chloride
Oxybutynin Hydrochloride
oxybutynin topical gel
Oxybutynine [INN-French]
Oxybutyninum [INN-Latin]
transdermal patch
Salts Not Available
Brand names
Name Company
Ditropan
Ditropan Xl
Oxytrol
Brand mixtures Not Available
Categories
  • Muscarinic Antagonists
  • Antispasmodics
  • Anticholinergic Agents
  • Parasympatholytics
  • Genitourinary Smooth Muscle Relaxants
CAS number 5633-20-5
Weight Average: 357.4864
Monoisotopic: 357.230393863
Chemical Formula C22H31NO3
InChI Key InChIKey=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
Plain Text
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenylacetates
Substructures
  • Carboxylic Acids and Derivatives
  • Hydroxy Compounds
  • Benzyl Alcohols and Derivatives
  • Acetates
  • Alkynes
  • Phenylacetates
  • Short-chain Hydroxy Acids
  • Ethers
  • Benzene and Derivatives
  • Aliphatic and Aryl Amines
  • Alcohols and Polyols
  • Aromatic compounds
Pharmacology
Indication For the treatment of overactive bladder.
Pharmacodynamics Oxybutynin 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 action Oxybutynin 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.
Absorption Rapidly absorbed from gastrointestinal tract.
Volume of distribution
  • 193 L
Protein binding 91%-93%
Metabolism
Hepatic, primarily by CYP3A4

Important The metabolism module of DrugBank is currently in beta. Questions or suggestions? Please contact us.

Substrate Enzymes Product
Oxybutynin
N-desethyloxybutynin Details
Route of elimination Oxybutynin 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 life 12.4-13.2 hours
Clearance Not Available
Toxicity LD50=1220 mg/kg (Orally in rats, Goldenthal)
Affected organisms
  • Humans and other mammals
Pathways Not Available
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
Form Route Strength
Patch Transdermal
Syrup Oral
Tablet Oral
Tablet, extended release Oral
Prices
Unit description Cost Unit
Oxybutynin chloride powder 54.47 USD g
Oxytrol 3.9 mg/24hr Patches 20.87 USD patch
Oxytrol 3.9 mg/24hr patch 20.06 USD patch
Gelnique 10% gel sachets 5.17 USD g
Ditropan XL 15 mg 24 Hour tablet 4.59 USD tablet
Ditropan XL 10 mg 24 Hour tablet 4.47 USD tablet
Ditropan XL 5 mg 24 Hour tablet 4.47 USD tablet
Ditropan xl 15 mg tablet 4.23 USD tablet
Ditropan xl 10 mg tablet 4.13 USD tablet
Ditropan xl 5 mg tablet 4.13 USD tablet
Ditropan xl 5 mg tablet sa 4.13 USD tablet
Oxybutynin Chloride 15 mg 24 Hour tablet 3.5 USD tablet
Oxybutynin Chloride 10 mg 24 Hour tablet 3.42 USD tablet
Oxybutynin Chloride 5 mg 24 Hour tablet 3.2 USD tablet
Ditropan 5 mg tablet 1.15 USD tablet
Oxybutynin Chloride 5 mg tablet 0.57 USD tablet
Ditropan 5 mg/5ml Syrup 0.26 USD ml
Apo-Oxybutynin 5 mg Tablet 0.26 USD tablet
Mylan-Oxybutynin 5 mg Tablet 0.26 USD tablet
Novo-Oxybutynin 5 mg Tablet 0.26 USD tablet
Nu-Oxybutyn 5 mg Tablet 0.26 USD tablet
Pms-Oxybutynin 5 mg Tablet 0.26 USD tablet
Oxybutynin Chloride 5 mg/5ml Syrup 0.21 USD ml
Oxybutynin 5 mg tablet 0.17 USD tablet
Pms-Oxybutynin 2.5 mg Tablet 0.14 USD tablet
Pms-Oxybutynin 1 mg/ml Syrup 0.08 USD ml
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Patents
Country Patent Number Approved Expires (estimated)
United States 6743441 2000-04-26 2020-04-26
United States 5164190 1993-12-11 2010-12-11
Canada 2218714 2005-08-23 2016-05-08
Properties
State solid
Experimental Properties
Property Value Source
melting point 129-130 °C Not Available
logP 4.3 Not Available
Predicted Properties
Property Value Source
water solubility 1.00e-02 g/l ALOGPS
logP 4.36 ALOGPS
logP 4.44 ChemAxon
logS -4.5 ALOGPS
pKa (strongest acidic) 11.53 ChemAxon
pKa (strongest basic) 8.77 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 3 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 49.77 ChemAxon
rotatable bond count 10 ChemAxon
refractivity 105.26 ChemAxon
polarizability 41.25 ChemAxon
References
Synthesis Reference Not Available
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
Resource Link
KEGG Drug D00465 Link_out
KEGG Compound C07360 Link_out
PubChem Compound 4634 Link_out
PubChem Substance 46508005 Link_out
ChemSpider 4473 Link_out
ChEBI 7856 Link_out
ChEMBL 7856 Link_out
Therapeutic Targets Database DAP001128 Link_out
PharmGKB PA164746030 Link_out
IUPHAR 359 Link_out
Guide to Pharmacology 359 Link_out
Drug Product Database 2260751 Link_out
RxList http://www.rxlist.com/cgi/generic/ditropan.htm Link_out
Drugs.com http://www.drugs.com/oxybutynin.html Link_out
PDRhealth http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/dit1143.shtml Link_out
Wikipedia http://en.wikipedia.org/wiki/Oxybutynin Link_out
ATC Codes
  • G04BD04
AHFS Codes
  • 86:12.00
PDB Entries Not Available
FDA label show (144 KB)
MSDS show (73 KB)
Interactions
Drug Interactions
Drug Interaction
Carbamazepine Oxybutynin may cause carbamazepine toxicity
Donepezil Possible antagonism of action
Galantamine Possible antagonism of action
Rivastigmine Possible antagonism of action
Tacrine The 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.
Trimethobenzamide Trimethobenzamide and Oxybutynin, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Triprolidine Triprolidine and Oxybutynin, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Trospium Trospium 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

Pharmacological action: yes
Actions: antagonist

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

Organism class: human
UniProt ID: P20309 Link_out
Gene: CHRM3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: yes
Actions: antagonist

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

Organism class: human
UniProt ID: P08172 Link_out
Gene: CHRM2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: yes
Actions: antagonist

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

Organism class: human
UniProt ID: P11229 Link_out
Gene: CHRM1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: substrate, inhibitor

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 xenobiotics. The enzyme also hydroxylates etoposide

UniProt ID: P08684 Link_out
Gene: CYP3A4
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: inhibitor

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 responsible for the metabolism the anti- cancer drug paclitaxel (taxol)

UniProt ID: P10632 Link_out
Gene: CYP2C8
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: inhibitor

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

UniProt ID: P10635 Link_out
Gene: CYP2D6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: substrate

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

UniProt ID: P20815 Link_out
Gene: CYP3A5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19