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
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
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 | ( + / - ) |
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 |
|
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 |
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Jun 25 21:04:29 UTC 2021
by
admin
on
Fri Jun 25 21:04:29 UTC 2021
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Record UNII |
L9F3D9RENQ
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C29704
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54251
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1508-65-2
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C73597
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1508-65-2
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1485103
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DBSALT000430
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216-139-7
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SUB03581MIG
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CHEMBL1231
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91505
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L9F3D9RENQ
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M8324
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PRIMARY | Merck Index |
Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE | |||
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ENANTIOMER -> RACEMATE | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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ENANTIOMER -> RACEMATE | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
|
Related Record | Type | Details | ||
---|---|---|---|---|
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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||
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IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
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IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |