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
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
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 | ( + / - ) |
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 |
---|---|---|
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 |
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
Thu Jul 06 02:01:10 UTC 2023
by
admin
on
Thu Jul 06 02:01:10 UTC 2023
|
Record UNII |
K9P6MC7092
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 PHARMACOKINETIC PHARMACOKINETIC |
|
||
Biological Half-life | PHARMACOKINETIC |
|
|
|||
Volume of Distribution | PHARMACOKINETIC |
|
|
|||
Biological Half-life | PHARMACOKINETIC |
|
Elimination PHARMACOKINETIC PHARMACOKINETIC |
|
||