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Details

Stereochemistry RACEMIC
Molecular Formula C22H31NO3.C11H8O3
Molecular Weight 545.6671
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OXYBUTYNIN XINAFOATE

SMILES

CCN(CC)CC#CCOC(=O)C(c1ccccc1)(C2CCCCC2)O.c1ccc2c(c1)ccc(c2O)C(=O)O

InChI

InChIKey=SRVJTUJNFIQJMD-UHFFFAOYSA-N
InChI=1S/C22H31NO3.C11H8O3/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;12-10-8-4-2-1-3-7(8)5-6-9(10)11(13)14/h5,7-8,13-14,20,25H,3-4,6,9-10,15-18H2,1-2H3;1-6,12H,(H,13,14)

HIDE SMILES / InChI

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 ( + / - )

Molecular Formula C11H8O3
Molecular Weight 188.1798
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Combined pharmacotherapy for nocturnal enuresis.
2001 Aug
Costs and resources associated with the treatment of overactive bladder using retrospective medical care claims data.
2001 Aug
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
Intravesical treatment of bladder dysfunction.
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
Effect of TAK-637, a tachykinin NK1-receptor antagonist, on lower urinary tract function in cats.
2001 Jun
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
Tolterodine: a clinical review.
2001 Oct
Effect of OROS controlled-release delivery on the pharmacokinetics and pharmacodynamics of oxybutynin chloride.
2001 Oct
Treatment of childhood nocturnal enuresis: an examination of clinically relevant principles.
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
S-oxybutynin.
2002
Tolterodine: selectivity for the urinary bladder over the eye (as measured by visual accommodation) in healthy volunteers.
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
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
A long-term follow-up of autoaugmentation in myelodysplastic children.
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
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
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 Sat Jun 26 03:07:56 UTC 2021
Edited
by admin
on Sat Jun 26 03:07:56 UTC 2021
Record UNII
7425U24ZN4
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OXYBUTYNIN XINAFOATE
Common Name English
2-NAPHTHALENECARBOXYLIC ACID, 1-HYDROXY-, COMPD. WITH 4-(DIETHYLAMINO)-2-BUTYN-1-YL .ALPHA.-CYCLOHEXYL-.ALPHA.-HYDROXYBENZENEACETATE (1:1)
Systematic Name English
Code System Code Type Description
FDA UNII
7425U24ZN4
Created by admin on Sat Jun 26 03:07:56 UTC 2021 , Edited by admin on Sat Jun 26 03:07:56 UTC 2021
PRIMARY
CAS
1447998-30-2
Created by admin on Sat Jun 26 03:07:56 UTC 2021 , Edited by admin on Sat Jun 26 03:07:56 UTC 2021
PRIMARY
PUBCHEM
53477276
Created by admin on Sat Jun 26 03:07:56 UTC 2021 , Edited by admin on Sat Jun 26 03:07:56 UTC 2021
PRIMARY
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