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
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
DescriptionSources: http://www.drugbank.ca/drugs/DB01062Curator's Comment:: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/017577s034,018211s017,020897s018lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB01062
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.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL211 Sources: http://www.drugbank.ca/drugs/DB01062 |
8.1 nM [Ki] | ||
Target ID: CHEMBL216 Sources: http://www.drugbank.ca/drugs/DB01062 |
1.0 nM [Ki] | ||
Target ID: CHEMBL245 Sources: http://www.drugbank.ca/drugs/DB01062 |
0.78 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | DITROPAN Approved UseDITROPAN® (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 Date1.74614397E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6.73 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3234461/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
9.24 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3234461/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.44 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3234461/ |
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 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 164.0 |
no | |||
Page: 164.0 |
no | |||
Page: 164.0 |
no | |||
Page: 164.0 |
no | |||
Page: 205.0 |
yes [IC50 128 uM] | |||
Page: 205.0 |
yes [IC50 130 uM] | |||
Page: 205.0 |
yes [IC50 20 uM] | |||
Page: 496.0 |
yes [IC50 27.4 uM] | |||
Page: abstract |
yes [IC50 7.7 uM] | |||
Page: abstract |
yes [IC50 9.5 uM] | |||
yes | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 4.0 |
major | yes (co-administration study) Comment: itraconazole increased oxybutynin cmax, auc 2x Page: 4.0 |
||
Sources: https://europepmc.org/article/med/9825837 Page: 451.0 |
no | |||
Page: abstract |
no | |||
Sources: https://europepmc.org/article/med/9825837 Page: 451.0 |
no | |||
Page: abstract |
no | |||
Sources: https://europepmc.org/article/med/9825837 Page: abstract |
no | |||
Sources: https://europepmc.org/article/med/9825837 Page: 451.0 |
no | |||
Page: abstract |
no | |||
Page: 235.0 |
no | |||
Page: 206.0 |
yes | |||
Page: 206.0 |
yes | |||
Page: 206.0 |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 12.0 |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22001099
Oxybutynin (1 uM) significantly depressed the frequency responses to carbachol (1 uM) in Isolated strips of porcine urothelium with lamina propria.
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000000125
Created by
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WHO-ATC |
G04BD04
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NDF-RT |
N0000000125
Created by
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LIVERTOX |
725
Created by
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NDF-RT |
N0000000125
Created by
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NDF-RT |
N0000175700
Created by
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EMA ASSESSMENT REPORTS |
KENTERA (AUTHORIZED: URINARY INCONTINENCE, URGE)
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WHO-VATC |
QG04BD04
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NCI_THESAURUS |
C29704
Created by
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Code System | Code | Type | Description | ||
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M8324
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PRIMARY | Merck Index | ||
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SUB09558MIG
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PRIMARY | |||
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5633-20-5
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PRIMARY | |||
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3270
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PRIMARY | |||
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4634
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PRIMARY | |||
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K9P6MC7092
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PRIMARY | |||
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5633-20-5
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Oxybutinyn
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PRIMARY | |||
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DB01062
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PRIMARY | |||
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359
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C47647
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OXYBUTYNIN
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1354
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C005419
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CHEMBL1231
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2028
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32675
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PRIMARY | RxNorm |
ACTIVE MOIETY
METABOLITE ACTIVE (PARENT)
METABOLITE INACTIVE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)