Oxybutynin

Identification

Summary

Oxybutynin is an antimuscarinic agent that reduces detrusor muscle activity, relaxing the bladder and preventing the urge to void.

Brand Names
Ditropan, Gelnique, Kentera, Oxytrol
Generic Name
Oxybutynin
DrugBank Accession Number
DB01062
Background

Overactive bladder (OAB) is a common condition negatively impacting the lives of millions of patients worldwide. Due to its urinary symptoms that include nocturia, urgency, and frequency, this condition causes social embarrassment and a poor quality of life.4,5

Oxybutynin, also marketed as Ditropan XL, is an anticholinergic medication used for the relief of overactive bladder symptoms that has been optimized for high levels of safety and efficacy since initial FDA approval in 1975.2,14 This drug relieves undesirable urinary symptoms, increasing the quality of life for patients affected by OAB. It is often used as first-line therapy for OAB.3

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 357.4864
Monoisotopic: 357.230393863
Chemical Formula
C22H31NO3
Synonyms
  • 4-(Diethylamino)-2-butynyl alpha-phenylcyclohexaneglycolic acid ester
  • 4-Diethylamino-2-butinyl alpha-cyclohexylmandelat
  • 4-Diethylamino-2-butynyl alpha-phenylcyclohexaneglycolate
  • Oxibutinina
  • Oxybutynin
  • Oxybutynine
  • Oxybutyninum

Pharmacology

Indication

Oxybutynin is indicated for the symptomatic treatment of overactive bladder, which causes urge urinary incontinence and frequency, and urgency. Oxybutynin may also be used for children aged 6 and above for the symptomatic management of detrusor muscle overactivity which has been found to be related to a neurological condition. Spina bifida is an example of a neurological condition in which oxybutynin may be used to control urinary symptoms.14 On occasion, oxybutynin may be used off-label to relieve bladder spasms associated with ureteral stents or urinary catheters.12

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofBladder spasm••• •••••
Symptomatic treatment ofOveractive bladder (oab)••••••••••••••••••• •••••••• •••••••
Treatment ofDetruser overactivity•••••••••••••••••••••••••••• •••••••• •••••••• ••••••• •••• ••••••• •••••••• •••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Oxybutynin exerts antispasmodic actions on the bladder, relieving the uncomfortable symptoms of overactive bladder, including urinary urgency and frequency. These actions occur through the inhibition of muscarinic receptors.

A note on angioedema and anticholinergic effects

Symptoms of angioedema may occur with oxybutynin therapy. If angioedema is suspected, discontinue oxybutynin immediately and provide appropriate medical treatment.14 In addition, anticholinergic effects may occur with the administration of this drug. Some symptoms may include hallucinations, confusion, agitation, and drowsiness. It is advisable to avoid operating heavy machinery before the response to oxybutynin has been monitored. Dose adjustments may be required.14

Mechanism of action

Oxybutynin acts to relax the bladder by inhibiting the muscarinic action of acetylcholine on smooth muscle, and not skeletal muscle.14 The active of oxybutynin is metabolite is N-desethyloxybutynin. It competitively inhibits the postganglionic type 1, 2 and 3 muscarinic receptors. The above actions lead to increased urine capacity in the bladder, decreasing urinary urgency and frequency. In addition, oxybutynin delays the initial desire to void.12,14

TargetActionsOrganism
AMuscarinic acetylcholine receptor M3
antagonist
Humans
AMuscarinic acetylcholine receptor M2
antagonist
Humans
AMuscarinic acetylcholine receptor M1
antagonist
Humans
Absorption

Oxybutynin should be swallowed whole with the help of liquids.14 A pharmacokinetic study revealed that oxybutynin was rapidly absorbed, and peak concentrations were reached within about 1 hour of administration, measured at 8.2 ngml-1 and AUC was 16 ngml-1.1 The biovailability of oxybutynin is about 6%, and the plasma concentration of the active metabolite, desethyloxybutynin is 5 to 12 times greater than that of oxybutynin.2 Bioavailability is increased in the elderly.3 Food has been shown to increase the exposure to controlled-release oxybutynin.7

Volume of distribution

Oxybutynin has a wide volume of distribution of 193 L.14 In rats, oxybutynin penetrates the central nervous system.11

Protein binding

Oxybutynin enantiomers are more than 97% bound to plasma proteins, primarily to alpha-1 acid glycoprotein.8,14

Metabolism

Oxybutynin is heavily metabolized by the CYP3A4 enzyme system3 in both the liver and the wall of the intestine. It undergoes first-pass metabolism, and its resulting primary active metabolite, N-desethyloxybutynin circulates. It is active at the muscarinic receptors in both the bladder and the salivary gland.2 Hepatic biotransformation also produces its major inactive metabolite, phenylcyclohexylglycolic acid.3

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Route of elimination

Oxybutynin is heavily cleared by the liver.1 Under 0.1% of an administered dose is found as unchanged drug in the urine. Less than 0.1% of a single dose of oxybutynin is excreted as desethyloxybutynin.1,14

Half-life

The plasma elimination half-life is about 2 hours. In the elderly, the elimination half-life is prolonged up to 5 hours.2,3

Clearance

Not Available

Adverse Effects
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Toxicity

The acute oral LD50 in rats is 460 mg/kg.13

Overdose information

An overdose with oxybutynin may manifest clinically as CNS overactivity, fever, palpitations, cardiac arrhythmias, urinary retention, respiratory failure, paralysis, in addition to coma.12,14 Provide supportive care immediately. Activated charcoal in addition to a cathartic agent should be administered. There have been 2 reports of an overdose with a 100 mg dose of oxybutynin. One case was a 13-year-old boy and another was a 34-year-old woman. Alcohol was also ingested simultaneously in both cases. The patients received supportive treatment and fully recovered.12

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Oxybutynin can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Oxybutynin can be increased when combined with Abatacept.
AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with Oxybutynin.
AcalabrutinibThe serum concentration of Acalabrutinib can be increased when it is combined with Oxybutynin.
AcebutololThe metabolism of Acebutolol can be decreased when combined with Oxybutynin.
Food Interactions
  • Avoid alcohol.
  • Take with or without food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Oxybutynin chlorideL9F3D9RENQ1508-65-2SWIJYDAEGSIQPZ-UHFFFAOYSA-N
Product Images
International/Other Brands
Lenditro / Lyrinel XL
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Albert OxybutyninTablet5 mgOralAventis Pharma Ltd.1996-11-212002-07-29Canada flag
DitropanTablet5 mg/1OralAlza1975-07-162012-03-19US flag
DitropanSyrup5 mg/5mLOralOrtho-McNeil Pharmaceutical, Inc.2006-08-292006-08-29US flag
Ditropan Syrup 1mg/mlSyrup1 mg / mLOralJanssen Pharmaceuticals1993-12-312007-02-21Canada flag
Ditropan Tablets 5mgTablet5 mgOralJanssen Pharmaceuticals1993-12-312006-08-04Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-oxybutyninTablet5 mgOralApotex Corporation1995-12-31Not applicableCanada flag
Apo-oxybutyninSyrup1 mg / mLOralApotex Corporation1997-04-28Not applicableCanada flag
Ava-oxybutyninTablet5 mgOralAvanstra Inc2011-08-222014-08-21Canada flag
Dom-oxybutynin 5 Mg TabletsTablet5 mgOralDominion Pharmacal1999-12-16Not applicableCanada flag
Mylan-oxybutyninTablet5 mgOralMylan Pharmaceuticals1997-04-242016-06-28Canada flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Oxytrol For WomenPatch3.9 mg/1dTransdermalActavis Pharma, Inc.2016-01-012020-01-31US flag
Oxytrol For WomenPatch3.9 mg/1dTransdermalBayer Healthcare Llc.2013-08-192016-01-15US flag
Oxytrol for WomenPatch3.9 mg/1dTransdermalAllergan, Inc.2016-01-01Not applicableUS flag
Oxytrol For WomenPatch3.9 mg/1dTransdermalBayer Healthcare Llc.2013-08-192016-01-15US flag

Categories

ATC Codes
G04BD04 — Oxybutynin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Not Available
Direct Parent
Benzene and substituted derivatives
Alternative Parents
Tertiary alcohols / Trialkylamines / Carboxylic acid esters / Amino acids and derivatives / Monocarboxylic acids and derivatives / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds / Aromatic alcohols
Substituents
Alcohol / Amine / Amino acid or derivatives / Aromatic alcohol / Aromatic homomonocyclic compound / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Hydrocarbon derivative / Monocarboxylic acid or derivatives
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
tertiary alcohol, tertiary amine, acetate ester, acetylenic compound (CHEBI:7856)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
K9P6MC7092
CAS number
5633-20-5
InChI Key
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

References

Synthesis Reference

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

US20040006243
General References
  1. Douchamps J, Derenne F, Stockis A, Gangji D, Juvent M, Herchuelz A: The pharmacokinetics of oxybutynin in man. Eur J Clin Pharmacol. 1988;35(5):515-20. doi: 10.1007/bf00558247. [Article]
  2. Kennelly MJ: A comparative review of oxybutynin chloride formulations: pharmacokinetics and therapeutic efficacy in overactive bladder. Rev Urol. 2010 Winter;12(1):12-9. [Article]
  3. Yarker YE, Goa KL, Fitton A: Oxybutynin. A review of its pharmacodynamic and pharmacokinetic properties, and its therapeutic use in detrusor instability. Drugs Aging. 1995 Mar;6(3):243-62. doi: 10.2165/00002512-199506030-00007. [Article]
  4. Willis-Gray MG, Dieter AA, Geller EJ: Evaluation and management of overactive bladder: strategies for optimizing care. Res Rep Urol. 2016 Jul 27;8:113-22. doi: 10.2147/RRU.S93636. eCollection 2016. [Article]
  5. Plata M, Bravo-Balado A, Robledo D, Trujillo CG, Caicedo JI, Catano JG, Arenas J, Rondon M, Londono D: Prevalence of lower urinary tract symptoms and overactive bladder in men and women over 18 years old: The Colombian overactive bladder and lower urinary tract symptoms (COBaLT) study. Neurourol Urodyn. 2019 Jan;38(1):200-207. doi: 10.1002/nau.23828. Epub 2018 Sep 24. [Article]
  6. Aprile S, Canavesi R, Matucci R, Bellucci C, Del Grosso E, Grosa G: New insights in the metabolism of oxybutynin: evidence of N-oxidation of propargylamine moiety and rearrangement to enaminoketone. Xenobiotica. 2018 May;48(5):478-487. doi: 10.1080/00498254.2017.1342288. Epub 2017 Jul 6. [Article]
  7. Guay DR: Clinical pharmacokinetics of drugs used to treat urge incontinence. Clin Pharmacokinet. 2003;42(14):1243-85. doi: 10.2165/00003088-200342140-00004. [Article]
  8. Shibukawa A, Ishizawa N, Kimura T, Sakamoto Y, Ogita K, Matsuo Y, Kuroda Y, Matayatsu C, Nakagawa T, Wainer IW: Plasma protein binding study of oxybutynin by high-performance frontal analysis. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Feb 25;768(1):177-88. [Article]
  9. Sathyan G, Chancellor MB, Gupta SK: Effect of OROS controlled-release delivery on the pharmacokinetics and pharmacodynamics of oxybutynin chloride. Br J Clin Pharmacol. 2001 Oct;52(4):409-17. doi: 10.1046/j.0306-5251.2001.01463.x. [Article]
  10. Lukkari E, Hakonen T, Neuvonen PJ: The pharmacokinetics of oxybutynin is unaffected by gender and contraceptive steroids. Eur J Clin Pharmacol. 1998 Jan;53(5):351-4. doi: 10.1007/s002280050392. [Article]
  11. Callegari E, Malhotra B, Bungay PJ, Webster R, Fenner KS, Kempshall S, LaPerle JL, Michel MC, Kay GG: A comprehensive non-clinical evaluation of the CNS penetration potential of antimuscarinic agents for the treatment of overactive bladder. Br J Clin Pharmacol. 2011 Aug;72(2):235-46. doi: 10.1111/j.1365-2125.2011.03961.x. [Article]
  12. Jennifer Dwyer; Chad A. LaGrange (2019). Oxybutinin. StatPearls Publishing.
  13. HMDB MSDS, Oxybutinin [Link]
  14. Ditropan XL FDA label [Link]
Human Metabolome Database
HMDB0015195
KEGG Drug
D00465
KEGG Compound
C07360
PubChem Compound
4634
PubChem Substance
46508005
ChemSpider
4473
BindingDB
50165019
RxNav
32675
ChEBI
7856
ChEMBL
CHEMBL1231
Therapeutic Targets Database
DAP001128
PharmGKB
PA164746030
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Oxybutynin
MSDS
Download (73 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableCognitive Functioning1
4CompletedSupportive CareCystitis1
4CompletedTreatmentBenign Prostatic Hyperplasia (BPH)1
4CompletedTreatmentCognitive Functioning / Memory1
4CompletedTreatmentDetrusor Hyperreflexia2

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Alza Corp.
  • Atlantic Biologicals Corporation
  • Cardinal Health
  • Dept Health Central Pharmacy
  • Dispensing Solutions
  • Global Pharmaceuticals
  • Goldline Laboratories Inc.
  • Impax Laboratories Inc.
  • Janssen-Ortho Inc.
  • Liberty Pharmaceuticals
  • Major Pharmaceuticals
  • McNeil Laboratories
  • Medisca Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Ortho Mcneil Janssen Pharmaceutical Inc.
  • Physicians Total Care Inc.
  • Pliva Inc.
  • Qualitest
  • Redpharm Drug
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Schwarz Pharma Inc.
  • Teva Pharmaceutical Industries Ltd.
  • UDL Laboratories
  • USL Pharma Inc.
  • Vangard Labs Inc.
  • Vintage Pharmaceuticals Inc.
  • Watson Pharmaceuticals
Dosage Forms
FormRouteStrength
SyrupOral100 mg
Tablet, coatedOral5 mg
SyrupOral1 mg / mL
Tablet, extended releaseOral10 mg/1
Tablet, extended releaseOral10 mg
Tablet, extended releaseOral5 mg/1
TabletOral5 mg
GelTopical10 %
GelTransdermal100 mg/1g
GelTransdermal28 mg/.92g
Spray, meteredTopical100 mg / g
TabletOral
GelTransdermal4 mg/24hr
GelTransdermal90.7 mg/g
Patch, extended releaseTransdermal3.9 mg/24hr
PatchTransdermal3.9 mg/24h
TabletOral10 MG
SyrupOral0.1 g
SyrupOral100.000 mg
TabletOral5.000 mg
SolutionOral5 mg/5mL
SyrupOral5 mg/5mL
TabletOral2.5 mg/1
TabletOral5 mg/1
Tablet, extended releaseOral15 mg/1
Tablet, film coated, extended releaseOral10 mg/1
Tablet, film coated, extended releaseOral15 mg/1
Tablet, film coated, extended releaseOral5 mg/1
PatchTransdermal3.9 mg / 24 hour
PatchTransdermal3.9 mg/1d
TabletOral5 mg / tab
SyrupOral5 mg / 5 mL
TabletOral2.5 mg
Tablet, film coatedOral5 mg
TabletOral5.510 mg
TabletOral10.000 mg
Tablet, extended releaseOral15 mg
SolutionIntravesical1 MG/ML
SyrupOral
Tablet, extended releaseOral5 mg
PatchTransdermal73.5 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)Region
US5164190No1992-11-172010-12-11US flag
CA2218714No2005-08-232016-05-08Canada flag
US6743441No2004-06-012020-04-26US flag
US7081249No2006-07-252020-04-26US flag
US7081250No2006-07-252020-04-26US flag
US7081251No2006-07-252020-04-26US flag
US7081252No2006-07-252020-04-26US flag
US7179483No2007-02-202020-04-26US flag
US7198801No2007-04-032022-06-25US flag
US7029694No2006-04-182020-04-26US flag
US8241662No2012-08-142020-04-26US flag
US8920392No2014-12-302031-03-26US flag
US9259388No2016-02-162029-11-06US flag
US6262115Yes2001-07-172015-11-22US flag
US5912268Yes1999-06-152015-11-22US flag
US5840754Yes1998-11-242015-11-22US flag
US5674895Yes1997-10-072015-11-22US flag
US10272061No2019-04-302020-04-26US flag
US10449173No2019-10-222029-11-06US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)122-124https://www.chemicalbook.com/ChemicalProductProperty_US_CB0178112.aspx
water solubility50 mg/mLhttps://www.chemicalbook.com/ChemicalProductProperty_US_CB0178112.aspx
logP4.3http://www.hmdb.ca/metabolites/HMDB0015195
logS-4.6http://www.hmdb.ca/metabolites/HMDB0015195
pKa8.04https://www.chemicalbook.com/ChemicalProductProperty_US_CB2767266.aspx
Predicted Properties
PropertyValueSource
Water Solubility0.01 mg/mLALOGPS
logP4.36ALOGPS
logP4.44Chemaxon
logS-4.6ALOGPS
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
Polarizability41.37 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-000i-1900000000-3d4eca43606cc5f825e7
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0a4i-0239000000-ae8df1c9b5ec536100dd
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-0009000000-ca7fded3c414981568e1
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-6809000000-96b23747cce7288ac89a
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0597-9700000000-d3a66f5713202ca9c1a4
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0abc-9500000000-71ea5dc94f4b2826c6ab
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0abc-9400000000-4fd7390913d44a84a47e
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0adi-9200000000-4ee96335c41ac4541fdd
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0009000000-1db2750867b2b3a978a6
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-1309000000-8015ca27a0f3148e2038
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0596-8900000000-c19752bfc85d658650c9
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0abc-9600000000-2ba4db19cf29c878577a
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0adl-9300000000-79de4e5ce2d791c91567
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-0239000000-ae8df1c9b5ec536100dd
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-1529000000-23d56124ac4d3f859ebe
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-8609000000-b2a50c9ada94fb87686a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0009000000-fb0bfc2d0133adf65206
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0459000000-56620ddb6ab6156bc9a2
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0as0-3593000000-27c019c420d3d5e5e559
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0019-0971000000-1fc40cc0daf69c4e4b21
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0920000000-e396d58ae0a76862abab
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-053r-9210000000-499a6324cea8ef87bd7b
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-199.5471772
predicted
DarkChem Lite v0.1.0
[M-H]-183.7358
predicted
DeepCCS 1.0 (2019)
[M+H]+200.2975772
predicted
DarkChem Lite v0.1.0
[M+H]+186.0938
predicted
DeepCCS 1.0 (2019)
[M+Na]+200.4172772
predicted
DarkChem Lite v0.1.0
[M+Na]+192.47394
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
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...
Gene Name
CHRM3
Uniprot ID
P20309
Uniprot Name
Muscarinic acetylcholine receptor M3
Molecular Weight
66127.445 Da
References
  1. Baldwin CM, Keating GM: Transdermal oxybutynin. Drugs. 2009;69(3):327-37. doi: 10.2165/00003495-200969030-00008. [Article]
  2. 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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  6. Yarker YE, Goa KL, Fitton A: Oxybutynin. A review of its pharmacodynamic and pharmacokinetic properties, and its therapeutic use in detrusor instability. Drugs Aging. 1995 Mar;6(3):243-62. doi: 10.2165/00002512-199506030-00007. [Article]
  7. Jennifer Dwyer; Chad A. LaGrange (2019). Oxybutinin. StatPearls Publishing.
Kind
Protein
Organism
Humans
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...
Gene Name
CHRM2
Uniprot ID
P08172
Uniprot Name
Muscarinic acetylcholine receptor M2
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  6. Yarker YE, Goa KL, Fitton A: Oxybutynin. A review of its pharmacodynamic and pharmacokinetic properties, and its therapeutic use in detrusor instability. Drugs Aging. 1995 Mar;6(3):243-62. doi: 10.2165/00002512-199506030-00007. [Article]
  7. Jennifer Dwyer; Chad A. LaGrange (2019). Oxybutinin. StatPearls Publishing.
Kind
Protein
Organism
Humans
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...
Gene Name
CHRM1
Uniprot ID
P11229
Uniprot Name
Muscarinic acetylcholine receptor M1
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  6. Yarker YE, Goa KL, Fitton A: Oxybutynin. A review of its pharmacodynamic and pharmacokinetic properties, and its therapeutic use in detrusor instability. Drugs Aging. 1995 Mar;6(3):243-62. doi: 10.2165/00002512-199506030-00007. [Article]
  7. Jennifer Dwyer; Chad A. LaGrange (2019). Oxybutinin. StatPearls Publishing.

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
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. [Article]
  2. Lukkari E, Taavitsainen P, Juhakoski A, Pelkonen O: Cytochrome P450 specificity of metabolism and interactions of oxybutynin in human liver microsomes. Pharmacol Toxicol. 1998 Apr;82(4):161-6. doi: 10.1111/j.1600-0773.1998.tb01418.x. [Article]
  3. Kennelly MJ: A comparative review of oxybutynin chloride formulations: pharmacokinetics and therapeutic efficacy in overactive bladder. Rev Urol. 2010 Winter;12(1):12-9. [Article]
  4. McCrery RJ, Appell RA: Oxybutynin: an overview of the available formulations. Ther Clin Risk Manag. 2006 Mar;2(1):19-24. [Article]
  5. Ditropan XL FDA label [Link]
Kind
Protein
Organism
Humans
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 un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
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. [Article]
Kind
Protein
Organism
Humans
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...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Lukkari E, Taavitsainen P, Juhakoski A, Pelkonen O: Cytochrome P450 specificity of metabolism and interactions of oxybutynin in human liver microsomes. Pharmacol Toxicol. 1998 Apr;82(4):161-6. doi: 10.1111/j.1600-0773.1998.tb01418.x. [Article]
Kind
Protein
Organism
Humans
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 un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Lukkari E, Taavitsainen P, Juhakoski A, Pelkonen O: Cytochrome P450 specificity of metabolism and interactions of oxybutynin in human liver microsomes. Pharmacol Toxicol. 1998 Apr;82(4):161-6. doi: 10.1111/j.1600-0773.1998.tb01418.x. [Article]
  2. Mizushima H, Takanaka K, Abe K, Fukazawa I, Ishizuka H: Stereoselective pharmacokinetics of oxybutynin and N-desethyloxybutynin in vitro and in vivo. Xenobiotica. 2007 Jan;37(1):59-73. doi: 10.1080/00498250600976088. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Not Available
Specific Function
Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...
Gene Name
ORM1
Uniprot ID
P02763
Uniprot Name
Alpha-1-acid glycoprotein 1
Molecular Weight
23511.38 Da
References
  1. Shibukawa A, Ishizawa N, Kimura T, Sakamoto Y, Ogita K, Matsuo Y, Kuroda Y, Matayatsu C, Nakagawa T, Wainer IW: Plasma protein binding study of oxybutynin by high-performance frontal analysis. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Feb 25;768(1):177-88. [Article]
  2. Shibukaw A, Yoshikawa Y, Kimura T, Kuroda Y, Nakagawa T, Wainer IW: Binding study of desethyloxybutynin using high-performance frontal analysis method. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Feb 25;768(1):189-97. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Shibukawa A, Ishizawa N, Kimura T, Sakamoto Y, Ogita K, Matsuo Y, Kuroda Y, Matayatsu C, Nakagawa T, Wainer IW: Plasma protein binding study of oxybutynin by high-performance frontal analysis. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Feb 25;768(1):177-88. [Article]
  2. Shibukaw A, Yoshikawa Y, Kimura T, Kuroda Y, Nakagawa T, Wainer IW: Binding study of desethyloxybutynin using high-performance frontal analysis method. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Feb 25;768(1):189-97. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48