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

Details

Stereochemistry RACEMIC
Molecular Formula C22H31NO3.C11H8O3
Molecular Weight 545.6659
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Oxybutynin xinafoate

SMILES

OC(=O)C1=C(O)C2=C(C=CC=C2)C=C1.CCN(CC)CC#CCOC(=O)C(O)(C3CCCCC3)C4=CC=CC=C4

InChI

InChIKey=SRVJTUJNFIQJMD-UHFFFAOYSA-N
InChI=1S/C22H31NO3.C11H8O3/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;12-10-8-4-2-1-3-7(8)5-6-9(10)11(13)14/h5,7-8,13-14,20,25H,3-4,6,9-10,15-18H2,1-2H3;1-6,12H,(H,13,14)

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 ( + / - )

Molecular Formula C11H8O3
Molecular Weight 188.1794
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Oxybutynin chloride inhibits proliferation and suppresses gene expression in bladder smooth muscle cells.
1999 Sep
Intravesical oxybutynin affects bladder permeability.
2001
Tolterodine: a review of its use in the treatment of overactive bladder.
2001
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
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
Oxybutynin, desmopressin and enuresis.
2001 Dec
Lack of effect of food on the pharmacokinetics of an extended-release oxybutynin formulation.
2001 Feb
Association between oxybutynin and neuropsychiatric adverse effects not confirmed in daily practice.
2001 Feb
Pharmacological characterization of muscarinic receptors in dog isolated ciliary and urinary bladder smooth muscle.
2001 Feb
Intravesical electromotive administration of oxybutynin in patients with detrusor hyperreflexia unresponsive to standard anticholinergic regimens.
2001 Feb
Psychological improvements associated with behavioral and drug treatment of urge incontinence in older women.
2001 Jan
[Results of a therapeutic strategy against monosymptomatic nocturnal enuresis].
2001 Jan
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
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
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
Cost effectiveness and quality of life considerations in the treatment of patients with overactive bladder.
2001 Mar
Overactive bladder: optimizing quality of care.
2001 Mar
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
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
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
S-oxybutynin.
2002
Oxybutynin intravesical--situs. I-oxy.
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
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
Medication update.
2002 Feb
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
A long-term follow-up of autoaugmentation in myelodysplastic children.
2002 Jun
Efficacy of botulinum-a toxin in children with detrusor hyperreflexia due to myelomeningocele: preliminary results.
2002 Mar
Advances in anticholinergic therapy delivery systems.
2002 May
Urodynamic changes associated with behavioral and drug treatment of urge incontinence in older women.
2002 May
The management of urinary incontinence in the exstrophy complex, posterior urethral valves, and infrasphincteric ureters.
2002 May
Overactive bladder patients and role of the pharmacist.
2002 May-Jun
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 Fri Dec 15 19:36:46 UTC 2023
Edited
by admin
on Fri Dec 15 19:36:46 UTC 2023
Record UNII
7425U24ZN4
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Oxybutynin xinafoate
Common Name English
2-Naphthalenecarboxylic acid, 1-hydroxy-, compd. with 4-(diethylamino)-2-butyn-1-yl α-cyclohexyl-α-hydroxybenzeneacetate (1:1)
Systematic Name English
Code System Code Type Description
FDA UNII
7425U24ZN4
Created by admin on Fri Dec 15 19:36:46 UTC 2023 , Edited by admin on Fri Dec 15 19:36:46 UTC 2023
PRIMARY
CAS
1447998-30-2
Created by admin on Fri Dec 15 19:36:46 UTC 2023 , Edited by admin on Fri Dec 15 19:36:46 UTC 2023
PRIMARY
PUBCHEM
53477276
Created by admin on Fri Dec 15 19:36:46 UTC 2023 , Edited by admin on Fri Dec 15 19:36:46 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY