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 |
|
Preformulation studies on the S-isomer of oxybutynin hydrochloride, an Improved Chemical Entity (ICE). | 2001 Apr |
|
Functional characterization of rat submaxillary gland muscarinic receptors using microphysiometry. | 2001 Apr |
|
Clinical experiences with tolterodine. | 2001 Apr 27 |
|
Comparison of the inhibitory effects of cromakalim and pinacidil (potassium channel openers) with those of oxybutynin on stimulated guinea pig and rabbit detrusor muscle strips. | 2001 Aug |
|
Prescribing for multiple sclerosis patients in general practice: a case-control study. | 2001 Dec |
|
Intravesical electromotive administration of oxybutynin in patients with detrusor hyperreflexia unresponsive to standard anticholinergic regimens. | 2001 Feb |
|
Pharmacological actions of AH-9700 on micturition reflex in anesthetized rats. | 2001 Jan 26 |
|
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 |
|
Clarification--Drug risk in patients with glaucoma. | 2001 Jun 11 |
|
Muscarinic receptor binding characteristics in rat tissues after oral administration of oxybutynin and propiverine. | 2001 May |
|
Influence of pump compliance (peristaltic vs. infusion) on urodynamic measurement during cystometry in conscious rats. | 2001 May-Jun |
|
Which muscarinic receptor is important in the bladder? | 2001 Nov |
|
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 |
|
Medication update. | 2002 Feb |
|
Binding study of desethyloxybutynin using high-performance frontal analysis method. | 2002 Feb 25 |
|
Effect of muscarinic antagonists on micturition pressure measured by cystometry in normal, conscious rats. | 2002 Jun |
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 Dec 15 18:50:26 UTC 2023
by
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on
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Record UNII |
K9P6MC7092
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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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NDF-RT |
N0000000125
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WHO-ATC |
G04BD04
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NDF-RT |
N0000000125
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LIVERTOX |
NBK548652
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NDF-RT |
N0000000125
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NDF-RT |
N0000175700
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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
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m8324
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SUB09558MIG
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K9P6MC7092
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3270
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4634
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K9P6MC7092
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5633-20-5
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Oxybutinyn
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DB01062
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359
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C47647
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100000085472
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OXYBUTYNIN
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NN-54
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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 |
Related Record | Type | Details | ||
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BINDER->LIGAND |
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SALT/SOLVATE -> PARENT |
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ENANTIOMER -> RACEMATE |
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SALT/SOLVATE -> PARENT |
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ACTIVE ENANTIOMER->RACEMATE |
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TARGET -> INHIBITOR |
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TARGET -> INHIBITOR | |||
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TARGET -> INHIBITOR |
Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PARENT |
MAJOR
PLASMA; URINE
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METABOLITE INACTIVE -> PARENT |
MAJOR
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METABOLITE ACTIVE -> PARENT |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Elimination PHARMACOKINETIC PHARMACOKINETIC PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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Elimination PHARMACOKINETIC PHARMACOKINETIC |
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