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

Details

Stereochemistry RACEMIC
Molecular Formula C22H31NO3
Molecular Weight 357.4864
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

Molecular Formula C22H31NO3
Molecular Weight 357.4864
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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
Intravesical oxybutynin affects bladder permeability.
2001
Combined pharmacotherapy for nocturnal enuresis.
2001 Aug
Cost-Effectiveness of tolterodine for patients with urge incontinence who discontinue initial therapy with oxybutynin: a Canadian perspective.
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
Oxybutynin and the overactive bladder.
2001 Nov
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
Evidence for the efficacy and safety of tolterodine in the treatment of overactive bladder.
2001 Oct
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
Treatment of childhood nocturnal enuresis: an examination of clinically relevant principles.
2001 Oct
POEMS (patient-oriented evidence that matters) spark discussion.
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
S-oxybutynin.
2002
Tolterodine: selectivity for the urinary bladder over the eye (as measured by visual accommodation) in healthy volunteers.
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
Pharmacokinetics, efficacy, and safety of intravesical formulation of oxybutynin in patients with detrusor overactivity.
2002 Feb
Highlights of the 22nd French pharmacovigilance meeting.
2002 Feb
Medication update.
2002 Feb
Enuresis.
2002 Feb
Binding study of desethyloxybutynin using high-performance frontal analysis method.
2002 Feb 25
Plasma protein binding study of oxybutynin by high-performance frontal analysis.
2002 Feb 25
Once-daily, extended-release formulations of antimuscarinic agents in the treatment of overactive bladder: a review.
2002 Jan
[Sling suspension of incontinent urinary reservoir].
2002 Jan
Current pharmacotherapeutic strategies for overactive bladder.
2002 Jul
Inappropriate medication prescribing in residential care/assisted living facilities.
2002 Jun
Effect of muscarinic antagonists on micturition pressure measured by cystometry in normal, conscious rats.
2002 Jun
Extractionless and sensitive method for high-throughput quantitation of cetirizine in human plasma samples by liquid chromatography-tandem mass spectrometry.
2002 Jun 25
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
Vesicoureteral reflux and bladder management in spinal cord injury patients.
2002 Mar
Tolterodine: as effective but better tolerated than oxybutynin in Asian patients with symptoms of overactive bladder.
2002 May
Advances in anticholinergic therapy delivery systems.
2002 May
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
A dynamic mechanical method for determining the silicone elastomer solubility of drugs and pharmaceutical excipients in silicone intravaginal drug delivery rings.
2002 Sep
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.
Substance Class Chemical
Created
by admin
on Thu Jul 06 02:01:10 UTC 2023
Edited
by admin
on Thu Jul 06 02:01:10 UTC 2023
Record UNII
K9P6MC7092
Record Status Validated (UNII)
Record Version
  • Download
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
oxybutynin [INN]
Common Name English
Benzeneacetic acid, α-cyclohexyl-α-hydroxy-, 4-(diethylamino)-2-butyn-1-yl ester
Systematic Name English
Oxybutynin [WHO-DD]
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
4-(diethylamino)but-2-yn-1-yl cyclohexyl(hydroxy)(phenyl)acetate
Systematic Name English
OXYBUTYNIN [USAN]
Common Name English
OXYBUTYNIN [VANDF]
Common Name English
KENTERA
Brand Name English
Classification Tree Code System Code
NDF-RT N0000000125
Created by admin on Thu Jul 06 02:01:10 UTC 2023 , Edited by admin on Thu Jul 06 02:01:10 UTC 2023
WHO-ATC G04BD04
Created by admin on Thu Jul 06 02:01:10 UTC 2023 , Edited by admin on Thu Jul 06 02:01:10 UTC 2023
NDF-RT N0000000125
Created by admin on Thu Jul 06 02:01:10 UTC 2023 , Edited by admin on Thu Jul 06 02:01:10 UTC 2023
LIVERTOX NBK548652
Created by admin on Thu Jul 06 02:01:10 UTC 2023 , Edited by admin on Thu Jul 06 02:01:10 UTC 2023
NDF-RT N0000000125
Created by admin on Thu Jul 06 02:01:10 UTC 2023 , Edited by admin on Thu Jul 06 02:01:10 UTC 2023
NDF-RT N0000175700
Created by admin on Thu Jul 06 02:01:10 UTC 2023 , Edited by admin on Thu Jul 06 02:01:10 UTC 2023
EMA ASSESSMENT REPORTS KENTERA (AUTHORIZED: URINARY INCONTINENCE, URGE)
Created by admin on Thu Jul 06 02:01:10 UTC 2023 , Edited by admin on Thu Jul 06 02:01:10 UTC 2023
WHO-VATC QG04BD04
Created by admin on Thu Jul 06 02:01:10 UTC 2023 , Edited by admin on Thu Jul 06 02:01:10 UTC 2023
NCI_THESAURUS C29704
Created by admin on Thu Jul 06 02:01:10 UTC 2023 , Edited by admin on Thu Jul 06 02:01:10 UTC 2023
Code System Code Type Description
MERCK INDEX
M8324
Created by admin on Thu Jul 06 02:01:10 UTC 2023 , Edited by admin on Thu Jul 06 02:01:10 UTC 2023
PRIMARY Merck Index
EVMPD
SUB09558MIG
Created by admin on Thu Jul 06 02:01:10 UTC 2023 , Edited by admin on Thu Jul 06 02:01:10 UTC 2023
PRIMARY
EPA CompTox
DTXSID0023406
Created by admin on Thu Jul 06 02:01:10 UTC 2023 , Edited by admin on Thu Jul 06 02:01:10 UTC 2023
PRIMARY
DAILYMED
K9P6MC7092
Created by admin on Thu Jul 06 02:01:10 UTC 2023 , Edited by admin on Thu Jul 06 02:01:10 UTC 2023
PRIMARY
HSDB
3270
Created by admin on Thu Jul 06 02:01:10 UTC 2023 , Edited by admin on Thu Jul 06 02:01:10 UTC 2023
PRIMARY
PUBCHEM
4634
Created by admin on Thu Jul 06 02:01:10 UTC 2023 , Edited by admin on Thu Jul 06 02:01:10 UTC 2023
PRIMARY
CHEBI
7856
Created by admin on Thu Jul 06 02:01:10 UTC 2023 , Edited by admin on Thu Jul 06 02:01:10 UTC 2023
PRIMARY
FDA UNII
K9P6MC7092
Created by admin on Thu Jul 06 02:01:10 UTC 2023 , Edited by admin on Thu Jul 06 02:01:10 UTC 2023
PRIMARY
CAS
5633-20-5
Created by admin on Thu Jul 06 02:01:10 UTC 2023 , Edited by admin on Thu Jul 06 02:01:10 UTC 2023
PRIMARY
LACTMED
Oxybutinyn
Created by admin on Thu Jul 06 02:01:10 UTC 2023 , Edited by admin on Thu Jul 06 02:01:10 UTC 2023
PRIMARY
DRUG BANK
DB01062
Created by admin on Thu Jul 06 02:01:10 UTC 2023 , Edited by admin on Thu Jul 06 02:01:10 UTC 2023
PRIMARY
IUPHAR
359
Created by admin on Thu Jul 06 02:01:10 UTC 2023 , Edited by admin on Thu Jul 06 02:01:10 UTC 2023
PRIMARY
NCI_THESAURUS
C47647
Created by admin on Thu Jul 06 02:01:10 UTC 2023 , Edited by admin on Thu Jul 06 02:01:10 UTC 2023
PRIMARY
SMS_ID
100000085472
Created by admin on Thu Jul 06 02:01:10 UTC 2023 , Edited by admin on Thu Jul 06 02:01:10 UTC 2023
PRIMARY
WIKIPEDIA
OXYBUTYNIN
Created by admin on Thu Jul 06 02:01:10 UTC 2023 , Edited by admin on Thu Jul 06 02:01:10 UTC 2023
PRIMARY
USAN
NN-54
Created by admin on Thu Jul 06 02:01:10 UTC 2023 , Edited by admin on Thu Jul 06 02:01:10 UTC 2023
PRIMARY
INN
1354
Created by admin on Thu Jul 06 02:01:10 UTC 2023 , Edited by admin on Thu Jul 06 02:01:10 UTC 2023
PRIMARY
MESH
C005419
Created by admin on Thu Jul 06 02:01:10 UTC 2023 , Edited by admin on Thu Jul 06 02:01:10 UTC 2023
PRIMARY
ChEMBL
CHEMBL1231
Created by admin on Thu Jul 06 02:01:10 UTC 2023 , Edited by admin on Thu Jul 06 02:01:10 UTC 2023
PRIMARY
DRUG CENTRAL
2028
Created by admin on Thu Jul 06 02:01:10 UTC 2023 , Edited by admin on Thu Jul 06 02:01:10 UTC 2023
PRIMARY
RXCUI
32675
Created by admin on Thu Jul 06 02:01:10 UTC 2023 , Edited by admin on Thu Jul 06 02:01:10 UTC 2023
PRIMARY RxNorm
Related Record Type Details
BINDER->LIGAND
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
ACTIVE ENANTIOMER->RACEMATE
TARGET -> INHIBITOR
TARGET -> INHIBITOR
TARGET -> INHIBITOR
Related Record Type Details
METABOLITE ACTIVE -> PARENT
MAJOR
PLASMA; URINE
METABOLITE INACTIVE -> PARENT
MAJOR
METABOLITE ACTIVE -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC Elimination
PHARMACOKINETIC
Elimination
PHARMACOKINETIC
Elimination
PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC Elimination
PHARMACOKINETIC
Elimination
PHARMACOKINETIC