U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C22H31NO3
Molecular Weight 357.4873
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(c1ccccc1)(C2CCCCC2)O

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
Curator's Comment:: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/017577s034,018211s017,020897s018lbl.pdf

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
8.1 nM [Ki]
1.0 nM [Ki]
0.78 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DITROPAN

Approved Use

DITROPAN® (oxybutynin chloride) is indicated for the relief of symptoms of bladder instability associated with voiding in patients with uninhibited neurogenic or reflex neurogenic bladder (i.e., urgency, frequency, urinary leakage, urge incontinence, dysuria).

Launch Date

1.74614397E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
6.73 ng/mL
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OXYBUTYNIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
9.24 ng × h/mL
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OXYBUTYNIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.44 h
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OXYBUTYNIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
yes [IC50 128 uM]
yes [IC50 130 uM]
yes [IC50 20 uM]
yes [IC50 27.4 uM]
yes [IC50 7.7 uM]
yes [IC50 9.5 uM]
yes
yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
major
yes (co-administration study)
Comment: itraconazole increased oxybutynin cmax, auc 2x
Page: 4.0
no
no
no
no
no
no
no
no
yes
yes
yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Enuresis.
2001
Tolterodine: a review of its use in the treatment of overactive bladder.
2001
Preformulation studies on the S-isomer of oxybutynin hydrochloride, an Improved Chemical Entity (ICE).
2001 Apr
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
Clinical experiences with tolterodine.
2001 Apr 27
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
Pharmacokinetics of the R- and S-enantiomers of oxybutynin and N-desethyloxybutynin following oral and transdermal administration of the racemate in healthy volunteers.
2001 Jul
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 crossover randomized trial of transcutaneous electrical nerve stimulation and oxybutynin in patients with detrusor instability.
2001 Jul
A short-term, multicenter, randomized double-blind dose titration study of the efficacy and anticholinergic side effects of transdermal compared to immediate release oral oxybutynin treatment of patients with urge urinary incontinence.
2001 Jul
Effect of TAK-637, a tachykinin NK1-receptor antagonist, on lower urinary tract function in cats.
2001 Jun
Intravesical oxybutynin for treating incontinence resulting from an overactive detrusor.
2001 Jun
Effects of tolterodine, trospium chloride, and oxybutynin on the central nervous system.
2001 Jun
The effects of intravesical lidocaine on bladder dynamics of children with myelomeningocele.
2001 Jun
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
A comparison of the effects on saliva output of oxybutynin chloride and tolterodine tartrate.
2001 May
Muscarinic receptor binding characteristics in rat tissues after oral administration of oxybutynin and propiverine.
2001 May
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
Tolterodine: an overview.
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
Identification of muscarinic receptor subtypes of cultured smooth muscle cells and tissue of human bladder body.
2001 Oct
Tolterodine: a clinical review.
2001 Oct
Is attempting suicide an adverse effect of oxybutynin in a child with enuresis nocturna?
2001 Oct
[Combined treatment of patients with detrusor instability].
2001 Sep-Oct
Oxybutynin intravesical--situs. I-oxy.
2002
Actions of the new antimuscarinic compound Lu 25-109 on isolated human and pig detrusor.
2002
Oxybutynin chloride: alterations in drug delivery and improved therapeutic index.
2002 Apr
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
Inappropriate medication prescribing in residential care/assisted living facilities.
2002 Jun
Preliminary study of the safety and efficacy of extended-release oxybutynin in children.
2002 Mar
Efficacy of botulinum-a toxin in children with detrusor hyperreflexia due to myelomeningocele: preliminary results.
2002 Mar
Urodynamic changes associated with behavioral and drug treatment of urge incontinence in older women.
2002 May
A dynamic mechanical method for determining the silicone elastomer solubility of drugs and pharmaceutical excipients in silicone intravaginal drug delivery rings.
2002 Sep
Treatment can lead to a long dry spell.
2002 Spring
New treatment options for overactive bladder and incontinence.
2002 Summer
Patents

Sample Use Guides

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
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 Sat Jun 26 00:10:46 UTC 2021 , Edited by admin on Sat Jun 26 00:10:46 UTC 2021
WHO-ATC G04BD04
Created by admin on Sat Jun 26 00:10:46 UTC 2021 , Edited by admin on Sat Jun 26 00:10:46 UTC 2021
NDF-RT N0000000125
Created by admin on Sat Jun 26 00:10:46 UTC 2021 , Edited by admin on Sat Jun 26 00:10:46 UTC 2021
LIVERTOX 725
Created by admin on Sat Jun 26 00:10:46 UTC 2021 , Edited by admin on Sat Jun 26 00:10:46 UTC 2021
NDF-RT N0000000125
Created by admin on Sat Jun 26 00:10:46 UTC 2021 , Edited by admin on Sat Jun 26 00:10:46 UTC 2021
NDF-RT N0000175700
Created by admin on Sat Jun 26 00:10:46 UTC 2021 , Edited by admin on Sat Jun 26 00:10:46 UTC 2021
EMA ASSESSMENT REPORTS KENTERA (AUTHORIZED: URINARY INCONTINENCE, URGE)
Created by admin on Sat Jun 26 00:10:46 UTC 2021 , Edited by admin on Sat Jun 26 00:10:46 UTC 2021
WHO-VATC QG04BD04
Created by admin on Sat Jun 26 00:10:46 UTC 2021 , Edited by admin on Sat Jun 26 00:10:46 UTC 2021
NCI_THESAURUS C29704
Created by admin on Sat Jun 26 00:10:46 UTC 2021 , Edited by admin on Sat Jun 26 00:10:46 UTC 2021
Code System Code Type Description
MERCK INDEX
M8324
Created by admin on Sat Jun 26 00:10:46 UTC 2021 , Edited by admin on Sat Jun 26 00:10:46 UTC 2021
PRIMARY Merck Index
EVMPD
SUB09558MIG
Created by admin on Sat Jun 26 00:10:46 UTC 2021 , Edited by admin on Sat Jun 26 00:10:46 UTC 2021
PRIMARY
EPA CompTox
5633-20-5
Created by admin on Sat Jun 26 00:10:46 UTC 2021 , Edited by admin on Sat Jun 26 00:10:46 UTC 2021
PRIMARY
HSDB
3270
Created by admin on Sat Jun 26 00:10:46 UTC 2021 , Edited by admin on Sat Jun 26 00:10:46 UTC 2021
PRIMARY
PUBCHEM
4634
Created by admin on Sat Jun 26 00:10:46 UTC 2021 , Edited by admin on Sat Jun 26 00:10:46 UTC 2021
PRIMARY
FDA UNII
K9P6MC7092
Created by admin on Sat Jun 26 00:10:46 UTC 2021 , Edited by admin on Sat Jun 26 00:10:46 UTC 2021
PRIMARY
CAS
5633-20-5
Created by admin on Sat Jun 26 00:10:46 UTC 2021 , Edited by admin on Sat Jun 26 00:10:46 UTC 2021
PRIMARY
LACTMED
Oxybutinyn
Created by admin on Sat Jun 26 00:10:46 UTC 2021 , Edited by admin on Sat Jun 26 00:10:46 UTC 2021
PRIMARY
DRUG BANK
DB01062
Created by admin on Sat Jun 26 00:10:46 UTC 2021 , Edited by admin on Sat Jun 26 00:10:46 UTC 2021
PRIMARY
IUPHAR
359
Created by admin on Sat Jun 26 00:10:46 UTC 2021 , Edited by admin on Sat Jun 26 00:10:46 UTC 2021
PRIMARY
NCI_THESAURUS
C47647
Created by admin on Sat Jun 26 00:10:46 UTC 2021 , Edited by admin on Sat Jun 26 00:10:46 UTC 2021
PRIMARY
WIKIPEDIA
OXYBUTYNIN
Created by admin on Sat Jun 26 00:10:46 UTC 2021 , Edited by admin on Sat Jun 26 00:10:46 UTC 2021
PRIMARY
INN
1354
Created by admin on Sat Jun 26 00:10:46 UTC 2021 , Edited by admin on Sat Jun 26 00:10:46 UTC 2021
PRIMARY
MESH
C005419
Created by admin on Sat Jun 26 00:10:46 UTC 2021 , Edited by admin on Sat Jun 26 00:10:46 UTC 2021
PRIMARY
ChEMBL
CHEMBL1231
Created by admin on Sat Jun 26 00:10:46 UTC 2021 , Edited by admin on Sat Jun 26 00:10:46 UTC 2021
PRIMARY
DRUG CENTRAL
2028
Created by admin on Sat Jun 26 00:10:46 UTC 2021 , Edited by admin on Sat Jun 26 00:10:46 UTC 2021
PRIMARY
RXCUI
32675
Created by admin on Sat Jun 26 00:10:46 UTC 2021 , Edited by admin on Sat Jun 26 00:10:46 UTC 2021
PRIMARY RxNorm