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

Details

Stereochemistry RACEMIC
Molecular Formula C22H31NO3.ClH
Molecular Weight 393.9481
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OXYBUTYNIN CHLORIDE

SMILES

CCN(CC)CC#CCOC(=O)C(c1ccccc1)(C2CCCCC2)O.Cl

InChI

InChIKey=SWIJYDAEGSIQPZ-UHFFFAOYSA-N
InChI=1S/C22H31NO3.ClH/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;1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C22H31NO3
Molecular Weight 357.4873
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
Enuresis.
2001
Preformulation studies on the S-isomer of oxybutynin hydrochloride, an Improved Chemical Entity (ICE).
2001 Apr
Clinical experiences with tolterodine.
2001 Apr 27
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
Prescribing for multiple sclerosis patients in general practice: a case-control study.
2001 Dec
Intravesical oxybutynin: mode of action assessed by passive diffusion and electromotive administration with pharmacokinetics of oxybutynin and N-desethyl oxybutynin.
2001 Dec
Intravesical oxybutynin for treating incontinence resulting from an overactive detrusor.
2001 Jun
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
Oxybutynin and the overactive bladder.
2001 Nov
Tolterodine: an overview.
2001 Nov
Which muscarinic receptor is important in the 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
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
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
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
Urinary antispasmodic use and the risks of ventricular arrhythmia and sudden death in older patients.
2002 Jan
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
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
Pharmacotherapy of the overactive bladder and advances in drug delivery.
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
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
Assessment and conservative management of the neuropathic bladder.
2002 May
Overactive bladder patients and role of the pharmacist.
2002 May-Jun
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.
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:04:29 UTC 2021
Edited
by admin
on Fri Jun 25 21:04:29 UTC 2021
Record UNII
L9F3D9RENQ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OXYBUTYNIN CHLORIDE
ORANGE BOOK   USAN   USP   USP-RS   VANDF  
USAN  
Official Name English
TROPAX
Brand Name English
OXYBUTYNIN CHLORIDE [USP-RS]
Common Name English
OXYBUTYNIN HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
OXYBUTYNIN HYDROCHLORIDE [MART.]
Common Name English
BENEZENEACTETIC ACID, .ALPHA.-CYCLOHEXYL-.ALPHA.-HYDROXY-,4-(DIETHYLAMINO-2-BUTUNYL ESTER HYDROCHLORIDE,(+/-)-
Common Name English
OXYBUTYNIN HYDROCHLORIDE [MI]
Common Name English
OXYBUTYNIN CHLORIDE [ORANGE BOOK]
Common Name English
NSC-759108
Code English
OXYBUTYNIN HYDROCHLORIDE
MART.   MI   USP   WHO-DD  
Common Name English
OXYBUTYNIN HYDROCHLORIDE [USP]
Common Name English
POLLAKISU
Brand Name English
4-(DIETHYLAMINO)-2-BUTYNYL (+/-)-,ALPHA.-PHENYLCYCLOHEXANEGLYCOLATE HYDROCHLORIDE
Common Name English
MJ-4309-1
Code English
OXYBUTYNIN HYDROCHLORIDE [JAN]
Common Name English
OXYBUTYNIN CHLORIDE [USAN]
Common Name English
MJ 4309-1
Code English
OXYBUTYNIN CHLORIDE [VANDF]
Common Name English
DITROPAN
Common Name English
OXYBUTYNIN HYDROCHLORIDE [WHO-DD]
Common Name English
BENZENEACETIC ACID, .ALPHA.-CYCLOHEXYL-.ALPHA.-HYDROXY-, 4-(DIETHYLAMINO)-2-BUTYNYL ESTER HYDROCHLORIDE, (+/-)-
Common Name English
OXYBUTYNIN CHLORIDE [USP MONOGRAPH]
Common Name English
OXYBUTYNIN CHLORIDE [USP]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29704
Created by admin on Fri Jun 25 21:04:29 UTC 2021 , Edited by admin on Fri Jun 25 21:04:29 UTC 2021
Code System Code Type Description
RXCUI
54251
Created by admin on Fri Jun 25 21:04:29 UTC 2021 , Edited by admin on Fri Jun 25 21:04:29 UTC 2021
PRIMARY RxNorm
CAS
1508-65-2
Created by admin on Fri Jun 25 21:04:29 UTC 2021 , Edited by admin on Fri Jun 25 21:04:29 UTC 2021
PRIMARY
NCI_THESAURUS
C73597
Created by admin on Fri Jun 25 21:04:29 UTC 2021 , Edited by admin on Fri Jun 25 21:04:29 UTC 2021
PRIMARY
EPA CompTox
1508-65-2
Created by admin on Fri Jun 25 21:04:29 UTC 2021 , Edited by admin on Fri Jun 25 21:04:29 UTC 2021
PRIMARY
USP_CATALOG
1485103
Created by admin on Fri Jun 25 21:04:29 UTC 2021 , Edited by admin on Fri Jun 25 21:04:29 UTC 2021
PRIMARY USP-RS
DRUG BANK
DBSALT000430
Created by admin on Fri Jun 25 21:04:29 UTC 2021 , Edited by admin on Fri Jun 25 21:04:29 UTC 2021
PRIMARY
ECHA (EC/EINECS)
216-139-7
Created by admin on Fri Jun 25 21:04:29 UTC 2021 , Edited by admin on Fri Jun 25 21:04:29 UTC 2021
PRIMARY
EVMPD
SUB03581MIG
Created by admin on Fri Jun 25 21:04:29 UTC 2021 , Edited by admin on Fri Jun 25 21:04:29 UTC 2021
PRIMARY
ChEMBL
CHEMBL1231
Created by admin on Fri Jun 25 21:04:29 UTC 2021 , Edited by admin on Fri Jun 25 21:04:29 UTC 2021
PRIMARY
PUBCHEM
91505
Created by admin on Fri Jun 25 21:04:29 UTC 2021 , Edited by admin on Fri Jun 25 21:04:29 UTC 2021
PRIMARY
FDA UNII
L9F3D9RENQ
Created by admin on Fri Jun 25 21:04:29 UTC 2021 , Edited by admin on Fri Jun 25 21:04:29 UTC 2021
PRIMARY
MERCK INDEX
M8324
Created by admin on Fri Jun 25 21:04:29 UTC 2021 , Edited by admin on Fri Jun 25 21:04:29 UTC 2021
PRIMARY Merck Index
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