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Details

Stereochemistry RACEMIC
Molecular Formula C22H31NO3
Molecular Weight 357.4864
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OXYBUTYNIN

SMILES

CCN(CC)CC#CCOC(=O)C(O)(C1CCCCC1)C2=CC=CC=C2

InChI

InChIKey=XIQVNETUBQGFHX-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Description

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. 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.

CNS Activity

Originator

Approval Year

1975
46
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2484
Urinary Bladder, Neurogenic
 1.0 nM [Ki]
Antagonist
2484
Urinary Bladder, Neurogenic
 8.1 nM [Ki]
Antagonist
2484
Urinary Bladder, Neurogenic
 0.78 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Muscarinic acetylcholine receptor M1
Muscarinic acetylcholine receptor M2
Muscarinic acetylcholine receptor M3
Approved
7888
DITROPAN
PubMed

PubMed

TitleDatePubMed
Intravesical oxybutynin affects bladder permeability.
2001
Enuresis.
2001
Tolterodine: a review of its use in the treatment of overactive bladder.
2001
Prospective randomized controlled trial of extended-release oxybutynin chloride and tolterodine tartrate in the treatment of overactive bladder: results of the OBJECT Study.
2001 Apr
Oxybutynin does not affect cyclosporin blood levels.
2001 Apr
Functional characterization of rat submaxillary gland muscarinic receptors using microphysiometry.
2001 Apr
Detrol LA and Diropan XL for overactive bladder.
2001 Apr 2
Clinical experiences with tolterodine.
2001 Apr 27
Comparison of the inhibitory effects of cromakalim and pinacidil (potassium channel openers) with those of oxybutynin on stimulated guinea pig and rabbit detrusor muscle strips.
2001 Aug
Combined pharmacotherapy for nocturnal enuresis.
2001 Aug
Costs and resources associated with the treatment of overactive bladder using retrospective medical care claims data.
2001 Aug
Nocturnal enuresis.
2001 Aug
Cost-Effectiveness of tolterodine for patients with urge incontinence who discontinue initial therapy with oxybutynin: a Canadian perspective.
2001 Dec
Is tolterodine (Detrol) or oxybutynin (Ditropan) the best for treatment of urge urinary incontinence?
2001 Dec
Urethral catheterization in hypospadias surgery: Should the device enter the bladder or be made a urethral stent?
2001 Dec
Prescribing for multiple sclerosis patients in general practice: a case-control study.
2001 Dec
Oxybutynin, desmopressin and enuresis.
2001 Dec
Intravesical treatment of bladder dysfunction.
2001 Dec
Intravesical oxybutynin: mode of action assessed by passive diffusion and electromotive administration with pharmacokinetics of oxybutynin and N-desethyl oxybutynin.
2001 Dec
Is extended-release oxybutynin (Ditropan XL) or tolterodine (Detrol) more effective in the treatment of an overactive bladder?
2001 Jul
Tolterodine versus oxybutynin in the treatment of urge urinary incontinence: a meta-analysis.
2001 Jul
A semiparametric deconvolution model to establish in vivo-in vitro correlation applied to OROS oxybutynin.
2001 Jun
Clarification--Drug risk in patients with glaucoma.
2001 Jun 11
Side-effects of oral or intravesical oxybutynin chloride in children with spina bifida.
2001 May
Tolterodine: superior tolerability than and comparable efficacy to oxybutynin in individuals 50 years old or older with overactive bladder: a randomized controlled trial.
2001 May
Influence of pump compliance (peristaltic vs. infusion) on urodynamic measurement during cystometry in conscious rats.
2001 May-Jun
Efficacy, tolerability and safety profile of propiverine in the treatment of the overactive bladder (non-neurogenic and neurogenic).
2001 Nov
Which muscarinic receptor is important in the bladder?
2001 Nov
Medical treatment of overactive bladder.
2001 Nov
Evidence based management of nocturnal enuresis.
2001 Nov 17
Transdermally-delivered oxybutynin (Oxytrol(R) for overactive bladder.
2001 Oct
Combination therapy for nocturnal enuresis.
2001 Oct
Identification of muscarinic receptor subtypes of cultured smooth muscle cells and tissue of human bladder body.
2001 Oct
Tolterodine: a clinical review.
2001 Oct
Effect of OROS controlled-release delivery on the pharmacokinetics and pharmacodynamics of oxybutynin chloride.
2001 Oct
Treatment of childhood nocturnal enuresis: an examination of clinically relevant principles.
2001 Oct
POEMS (patient-oriented evidence that matters) spark discussion.
2001 Oct
Is attempting suicide an adverse effect of oxybutynin in a child with enuresis nocturna?
2001 Oct
[Continence problems after radical prostatectomy: medical treatment].
2001 Sep
Effects of antimuscarinic drugs on both urinary frequency and cognitive impairment in conscious, nonrestrained rats.
2001 Sep
[Combined treatment of patients with detrusor instability].
2001 Sep-Oct
M(3) receptor antagonism by the novel antimuscarinic agent solifenacin in the urinary bladder and salivary gland.
2002 Aug
Highlights of the 22nd French pharmacovigilance meeting.
2002 Feb
Enuresis.
2002 Feb
Once-daily, extended-release formulations of antimuscarinic agents in the treatment of overactive bladder: a review.
2002 Jan
Current pharmacotherapeutic strategies for overactive bladder.
2002 Jul
The management of urinary incontinence in the exstrophy complex, posterior urethral valves, and infrasphincteric ureters.
2002 May
Assessment and conservative management of the neuropathic bladder.
2002 May
Overactive bladder patients and role of the pharmacist.
2002 May-Jun
Treatment can lead to a long dry spell.
2002 Spring
Patents

Patents

6524608
3
JP2002541233A
373
JP2005089467A
3
JP2006117688A
3
JP2009504271A
4
JP2009526755A
402
JP2009539548A
3
JP5296557B2
3

Sample Use Guides

In Vivo Use Guide
Tablets Adults: The usual dose is one 5-mg tablet two to three times a day. The maximum recommended dose is one 5-mg tablet four times a day. A lower starting dose of 2.5 mg two or three times a day is recommended for the frail elderly. Pediatric patients over 5 years of age: The usual dose is one 5-mg tablet two times a day. The maximum recommended dose is one 5-mg tablet three times a day.
Route of Administration: Oral
In Vitro Use Guide
Oxybutynin (1 uM) significantly depressed the frequency responses to carbachol (1 uM) in Isolated strips of porcine urothelium with lamina propria.
Name Type Language
OXYBUTYNIN
EMA EPAR   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
OXYBUTYNIN [HSDB]
Common Name English
BENZENEACETIC ACID, .ALPHA.-CYCLOHEXYL-.ALPHA.-HYDROXY-, 4-(DIETHYLAMINO)-2-BUTYNYL ESTER
Common Name English
4-(DIETHYLAMINO)-2-BUTYNYL .ALPHA.-PHENYLCYCLOHEXANEGLYCOLIC ACID ESTER
Common Name English
OXYBUTYNIN [INN]
Common Name English
OXYBUTYNIN [ORANGE BOOK]
Common Name English
OXYBUTYNIN [MI]
Common Name English
OXYBUTYNIN [MART.]
Common Name English
OXYBUTYNIN [EMA EPAR]
Common Name English
OXYTROL
Brand Name English
OXYBUTYNIN [USAN]
Common Name English
OXYBUTYNIN [VANDF]
Common Name English
KENTERA
Brand Name English
OXYBUTYNIN [WHO-DD]
Common Name English
Classification Tree Code System Code
NDF-RT N0000000125
Created by admin on Tue Oct 22 01:22:47 UTC 2019 , Edited by admin on Tue Oct 22 01:22:47 UTC 2019
WHO-ATC G04BD04
Created by admin on Tue Oct 22 01:22:47 UTC 2019 , Edited by admin on Tue Oct 22 01:22:47 UTC 2019
NDF-RT N0000000125
Created by admin on Tue Oct 22 01:22:47 UTC 2019 , Edited by admin on Tue Oct 22 01:22:47 UTC 2019
LIVERTOX 725
Created by admin on Tue Oct 22 01:22:47 UTC 2019 , Edited by admin on Tue Oct 22 01:22:47 UTC 2019
NDF-RT N0000000125
Created by admin on Tue Oct 22 01:22:47 UTC 2019 , Edited by admin on Tue Oct 22 01:22:47 UTC 2019
NDF-RT N0000175700
Created by admin on Tue Oct 22 01:22:47 UTC 2019 , Edited by admin on Tue Oct 22 01:22:47 UTC 2019
EMA ASSESSMENT REPORTS KENTERA (AUTHORIZED: URINARY INCONTINENCE, URGE)
Created by admin on Tue Oct 22 01:22:47 UTC 2019 , Edited by admin on Tue Oct 22 01:22:47 UTC 2019
WHO-VATC QG04BD04
Created by admin on Tue Oct 22 01:22:47 UTC 2019 , Edited by admin on Tue Oct 22 01:22:47 UTC 2019
NCI_THESAURUS C29704
Created by admin on Tue Oct 22 01:22:47 UTC 2019 , Edited by admin on Tue Oct 22 01:22:47 UTC 2019
Code System Code Type Description
MERCK INDEX
M8324
Created by admin on Tue Oct 22 01:22:47 UTC 2019 , Edited by admin on Tue Oct 22 01:22:47 UTC 2019
PRIMARY Merck Index
EVMPD
SUB09558MIG
Created by admin on Tue Oct 22 01:22:47 UTC 2019 , Edited by admin on Tue Oct 22 01:22:47 UTC 2019
PRIMARY
EPA CompTox
5633-20-5
Created by admin on Tue Oct 22 01:22:47 UTC 2019 , Edited by admin on Tue Oct 22 01:22:47 UTC 2019
PRIMARY
HSDB
5633-20-5
Created by admin on Tue Oct 22 01:22:47 UTC 2019 , Edited by admin on Tue Oct 22 01:22:47 UTC 2019
PRIMARY
PUBCHEM
4634
Created by admin on Tue Oct 22 01:22:47 UTC 2019 , Edited by admin on Tue Oct 22 01:22:47 UTC 2019
PRIMARY
CAS
5633-20-5
Created by admin on Tue Oct 22 01:22:47 UTC 2019 , Edited by admin on Tue Oct 22 01:22:47 UTC 2019
PRIMARY
DRUG BANK
DB01062
Created by admin on Tue Oct 22 01:22:47 UTC 2019 , Edited by admin on Tue Oct 22 01:22:47 UTC 2019
PRIMARY
IUPHAR
359
Created by admin on Tue Oct 22 01:22:47 UTC 2019 , Edited by admin on Tue Oct 22 01:22:47 UTC 2019
PRIMARY
LactMed
5633-20-5
Created by admin on Tue Oct 22 01:22:47 UTC 2019 , Edited by admin on Tue Oct 22 01:22:47 UTC 2019
PRIMARY
NCI_THESAURUS
C47647
Created by admin on Tue Oct 22 01:22:47 UTC 2019 , Edited by admin on Tue Oct 22 01:22:47 UTC 2019
PRIMARY
WIKIPEDIA
OXYBUTYNIN
Created by admin on Tue Oct 22 01:22:47 UTC 2019 , Edited by admin on Tue Oct 22 01:22:47 UTC 2019
PRIMARY
INN
1354
Created by admin on Tue Oct 22 01:22:47 UTC 2019 , Edited by admin on Tue Oct 22 01:22:47 UTC 2019
PRIMARY
MESH
C005419
Created by admin on Tue Oct 22 01:22:47 UTC 2019 , Edited by admin on Tue Oct 22 01:22:47 UTC 2019
PRIMARY
ChEMBL
CHEMBL1231
Created by admin on Tue Oct 22 01:22:47 UTC 2019 , Edited by admin on Tue Oct 22 01:22:47 UTC 2019
PRIMARY
RXCUI
32675
Created by admin on Tue Oct 22 01:22:47 UTC 2019 , Edited by admin on Tue Oct 22 01:22:47 UTC 2019
PRIMARY RxNorm
ACTIVE MOIETY
Structure of OXYBUTYNIN
METABOLITE ACTIVE (PARENT)
Structure of N-DESETHYLOXYBUTYNIN
METABOLITE INACTIVE (PARENT)
Structure of CYCLOHEXYLPHENYLGLYCOLIC ACID
SALT/SOLVATE (PARENT)
Structure of OXYBUTYNIN CHLORIDE
SALT/SOLVATE (PARENT)
Structure of OXYBUTYNIN XINAFOATE
NIH
NCATS
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