Identification

Name
Oxybutynin
Accession Number
DB01062  (APRD00427)
Type
Small Molecule
Groups
Approved, 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
Product Ingredients
IngredientUNIICASInChI Key
Oxybutynin ChlorideL9F3D9RENQ1508-65-2SWIJYDAEGSIQPZ-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Albert OxybutyninTablet5 mgOralAventis Pharma Ltd.1996-11-212002-07-29Canada
DitropanTablet5 mg/1OralAlza1975-07-162012-03-19Us
DitropanSyrup5 mg/5mLOralOrtho-McNeil Pharmaceutical, Inc.2006-08-292006-08-29Us
Ditropan Syrup 1mg/mlSyrup1 mgOralJanssen Pharmaceuticals1993-12-312007-02-21Canada
Ditropan Tablets 5mgTablet5 mgOralJanssen Pharmaceuticals1993-12-312006-08-04Canada
Ditropan XLTablet, extended release10 mg/1OralJanssen Pharmaceuticals, Inc.1999-06-26Not applicableUs
Ditropan XLTablet, extended release10 mg/1OralPhysicians Total Care, Inc.2003-06-23Not applicableUs
Ditropan XLTablet, extended release15 mgOralJanssen PharmaceuticalsNot applicableNot applicableCanada
Ditropan XLTablet, extended release10 mg/1OralAlza1999-06-262010-01-31Us
Ditropan XLTablet, extended release5 mg/1OralPhysicians Total Care, Inc.2002-05-292011-06-30Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-oxybutyninSyrup5 mgOralApotex Corporation1997-04-28Not applicableCanada
Apo-oxybutynin - Tab 5mgTablet5 mgOralApotex Corporation1995-12-31Not applicableCanada
Ava-oxybutyninTablet5 mgOralAvanstra Inc2011-08-222014-08-21Canada
Dom-oxybutynin 5 Mg TabletsTablet5 mgOralDominion Pharmacal1999-12-16Not applicableCanada
Mylan-oxybutyninTablet5 mgOralMylan Pharmaceuticals1997-04-242016-06-28Canada
Ntp-oxybutyninTablet5 mgOralTevaNot applicableNot applicableCanada
Nu-oxybutynSyrup1 mgOralNu Pharm IncNot applicableNot applicableCanada
Nu-oxybutyn - Tab 5mgTablet5 mgOralNu Pharm Inc1995-12-312012-09-04Canada
OxybutyninTablet, film coated, extended release5 mg/1OralNcs Health Care Of Ky, Inc Dba Vangard Labs2018-07-02Not applicableUs
OxybutyninTablet, film coated, extended release5 mg/1OralZydus Pharmaceuticals (USA) Inc.2017-08-10Not applicableUs
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Oxytrol For WomenPatch3.9 mg/1dTransdermalActavis Pharma Company2016-01-01Not applicableUs
Oxytrol For WomenPatch3.9 mg/1dTransdermalBayer Healthcare Llc.2013-08-192016-01-15Us
Oxytrol For WomenPatch3.9 mg/1dTransdermalBayer Healthcare Llc.2013-08-192016-01-15Us
Oxytrol for WomenPatch3.9 mg/1dTransdermalAllergan, Inc.2016-01-01Not applicableUs
International/Other Brands
Ditropan / Lenditro / Lyrinel XL
Categories
UNII
K9P6MC7092
CAS number
5633-20-5
Weight
Average: 357.4864
Monoisotopic: 357.230393863
Chemical Formula
C22H31NO3
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

Pharmacology

Indication

For the treatment of overactive bladder.

Associated Conditions
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.

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

Rapidly absorbed from gastrointestinal tract.

Volume of distribution
  • 193 L
Protein binding

91%-93%

Metabolism

Hepatic, primarily by CYP3A4

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

Estimated to be 26L/h.

Toxicity

LD50=1220 mg/kg (Orally in rats, Goldenthal)

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Oxybutynin.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Oxybutynin.
1,10-PhenanthrolineThe therapeutic efficacy of Oxybutynin can be decreased when used in combination with 1,10-Phenanthroline.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of Tachycardia can be increased when Oxybutynin is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of Tachycardia can be increased when Oxybutynin is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of Tachycardia can be increased when Oxybutynin is combined with 3,4-Methylenedioxyamphetamine.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Oxybutynin.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of Tachycardia can be increased when Oxybutynin is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Oxybutynin.
4-MethoxyamphetamineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Oxybutynin.
Food Interactions
  • Avoid alcohol.
  • Take with food.

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
Human Metabolome Database
HMDB0015195
KEGG Drug
D00465
KEGG Compound
C07360
PubChem Compound
4634
PubChem Substance
46508005
ChemSpider
4473
BindingDB
50165019
ChEBI
7856
ChEMBL
CHEMBL1231
Therapeutic Targets Database
DAP001128
PharmGKB
PA164746030
IUPHAR
359
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Oxybutynin
ATC Codes
G04BD04 — Oxybutynin
AHFS Codes
  • 86:12.04 — Antimuscarinics
FDA label
Download (144 KB)
MSDS
Download (73 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingOtherHeat Effect1
1CompletedNot AvailableHealthy Volunteers6
1CompletedBasic ScienceHealthy Volunteers1
1CompletedTreatmentUrinary Bladder, Overactive1
1, 2CompletedTreatmentObstructive Sleep Apnea (OSA)1
2CompletedTreatmentHealthy Volunteers1
2CompletedTreatmentMenopausal Hot Flushes / Menopause1
2CompletedTreatmentPost-nasal Drip / Rhinorrhea / Seasonal Allergic Rhinitis (SAR)1
2CompletedTreatmentUrinary Incontinence, Urge1
2Not Yet RecruitingTreatmentSpinal Cord Injuries (SCI) / Urinary Bladder, Neurogenic1
2RecruitingOtherMild Cognitive Impairment (MCI) / Urinary Bladder, Overactive1
3Active Not RecruitingSupportive CareBothered by Hot Flashes / Carcinoma, Breast / Ductal Breast Carcinoma In Situ / Lobular Breast Carcinoma In Situ / Menopausal Hot Flushes / No Evidence of Disease1
3CompletedPreventionNeurogenic Bladder Dysfunction1
3CompletedTreatmentDiabetic; Neuropathic, Polyneuropathy (Manifestation)1
3CompletedTreatmentHyperhidrosis1
3CompletedTreatmentNocturnal Enuresis1
3CompletedTreatmentUrge Urinary Incontinence / Urinary Frequency1
3CompletedTreatmentUrinary Bladder, Overactive2
3CompletedTreatmentUrinary Incontinence (UI)2
3CompletedTreatmentUrination Disorders1
3RecruitingTreatmentUrinary Bladder, Neurogenic1
3RecruitingTreatmentUrinary Bladder, Overactive1
3WithdrawnTreatmentHyperhidrosis1
4CompletedNot AvailableCognition1
4CompletedTreatmentCognition / Memory1
4CompletedTreatmentDetrusor Hyperreflexia2
4CompletedTreatmentHyperhidrosis1
4CompletedTreatmentNeurogenic Detrusor Overactivity / Spinal Cord Injuries (SCI)1
4CompletedTreatmentUrinary Bladder, Overactive2
4CompletedTreatmentUrinary Incontinence Mixed (Stress and Urge)1
4RecruitingTreatmentNeurogenic Bladder Dysfunction / Overactive Detrusor1
4TerminatedTreatmentUrinary Urge Incontinence1
4Unknown StatusTreatmentUrinary Bladder, Overactive1
Not AvailableActive Not RecruitingNot AvailableUrinary Bladder, Overactive1
Not AvailableCompletedNot AvailableHyperhidrosis1
Not AvailableCompletedNot AvailableUrinary Bladder Diseases / Urinary Bladder, Overactive / Urologic Diseases1
Not AvailableCompletedTreatmentAxillary Hyperhidrosis / Osmidrosis1
Not AvailableCompletedTreatmentHyperhidrosis2
Not AvailableCompletedTreatmentParkinson's Disease (PD) / Urinary Bladder, Overactive1
Not AvailableCompletedTreatmentSpinal Cord Injuries (SCI)1
Not AvailableCompletedTreatmentUrinary Incontinence (UI)1
Not AvailableCompletedTreatmentUrinary Incontinence, Urge1
Not AvailableNot Yet RecruitingDiagnosticUrinary Bladder, Overactive1
Not AvailableNot Yet RecruitingTreatmentDisorder of Urinary Stent1
Not AvailableRecruitingNot AvailableUrinary Bladder, Overactive1

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
TabletOral5 mg
SyrupOral1 mg
Tablet, extended releaseOral10 mg/1
Tablet, extended releaseOral5 mg/1
Tablet, extended releaseOral10 mg
Tablet, extended releaseOral5 mg
GelTopical10 %
GelTopical100 mg
GelTransdermal100 mg/1g
GelTransdermal28 mg/.92g
GelTransdermal90.7 mg/g
PatchTransdermal3.9 mg/24h
Tablet, film coated, extended releaseOral15 mg/1
SolutionOral5 mg/5mL
SyrupOral5 mg/5mL
TabletOral5 mg/1
Tablet, extended releaseOral15 mg/1
Tablet, film coated, extended releaseOral10 mg/1
Tablet, film coated, extended releaseOral5 mg/1
PatchTransdermal3.9 mg
PatchTransdermal3.9 mg/1d
SyrupOral5 mg
TabletOral2.5 mg
Tablet, extended releaseOral15 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)
US5164190No1992-11-172010-12-11Us
CA2218714No2005-08-232016-05-08Canada
US6743441No2004-06-012020-04-26Us
US7081249No2006-07-252020-04-26Us
US7081250No2006-07-252020-04-26Us
US7081251No2006-07-252020-04-26Us
US7081252No2006-07-252020-04-26Us
US7179483No2007-02-202020-04-26Us
US7198801No2007-04-032022-06-25Us
US7029694No2006-04-182020-04-26Us
US8241662No2012-08-142020-04-26Us
US8920392No2014-12-302031-03-26Us
US9259388No2016-02-162029-11-06Us
US6262115Yes2001-07-172015-11-22Us
US5912268Yes1999-06-152015-11-22Us
US5840754Yes1998-11-242015-11-22Us
US5674895Yes1997-10-072015-11-22Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)129-130 °CNot Available
logP4.3Not Available
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
Polarizability41.25 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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
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

Taxonomy

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
Monocyclic benzene moiety / Tertiary alcohol / Amino acid or derivatives / Carboxylic acid ester / Tertiary aliphatic amine / Tertiary amine / Carboxylic acid derivative / Monocarboxylic acid or derivatives / Alcohol / Aromatic alcohol
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
tertiary alcohol, tertiary amine, acetate ester, acetylenic compound (CHEBI:7856)

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...
Gene Name
CHRM3
Uniprot ID
P20309
Uniprot Name
Muscarinic acetylcholine receptor M3
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...
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. [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...
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. [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
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. [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]
  3. 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. [PubMed:9584328]
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 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. [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]
  3. Backman JT, Filppula AM, Niemi M, Neuvonen PJ: Role of Cytochrome P450 2C8 in Drug Metabolism and Interactions. Pharmacol Rev. 2016 Jan;68(1):168-241. doi: 10.1124/pr.115.011411. [PubMed:26721703]
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...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
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 un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
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]
  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. [PubMed:9584328]

Drug created on June 13, 2005 07:24 / Updated on December 18, 2018 05:46