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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H31NO3
Molecular Weight 357.4864
Optical Activity ( + )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Esoxybutynin

SMILES

CCN(CC)CC#CCOC(=O)[C@](O)(C1CCCCC1)C2=CC=CC=C2

InChI

InChIKey=XIQVNETUBQGFHX-JOCHJYFZSA-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/t22-/m1/s1

HIDE SMILES / InChI

Molecular Formula C22H31NO3
Molecular Weight 357.4864
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/12431028 | http://www.google.com/patents/WO1998000126A1 | https://www.ncbi.nlm.nih.gov/pubmed/7620236

Esoxybutynin is (S)-enantiomer of oxybutynin. Esoxybutynin exerts antimuscarinic properties. Racemic oxybutynin is used clinically to treat urinary incontinence. Sepracor was developing (S)-oxybutynin, a single-isomer version of Alza's Ditropan (racemic oxybutynin), a muscarinic acetylcholine receptor antagonist, as a potential treatment for urinary incontinence.

Approval Year

Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
24.3%
ESOXYBUTYNIN plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Augmentation ureterocystoplasty in bladder exstrophy: 5-year follow-up in two cases.
2002 Dec
Acupressure versus oxybutinin in the treatment of enuresis.
2003 Nov-Dec
[Prevalence of urinary incontinence and linked factors in men and women over 65].
2003 Oct 15
Oxybutynin extended-release: a review of its use in the management of overactive bladder.
2004
Drug approval highlights for 2003.
2004 Feb
Rapid and selective UV spectrophotometric and RP-HPLC methods for dissolution studies of oxybutynin immediate-release and controlled-release formulations.
2004 Nov 15
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Influence of micro-environmental pH on the gel layer behavior and release of a basic drug from various hydrophilic matrices.
2005 Mar 21
Canadian Urological Association guidelines on urinary incontinence.
2006 Jun
New transdermal bioadhesive film containing oxybutynin: In vitro permeation across rabbit ear skin.
2006 Nov 15
Naftopidil monotherapy vs naftopidil and an anticholinergic agent combined therapy for storage symptoms associated with benign prostatic hyperplasia: A prospective randomized controlled study.
2006 Oct
Analysis of pharmacological effects of drugs used for treatment of urinary disturbance based on anticholinergic and smooth muscle-relaxing effects.
2007 Jul
Formulation and optimization of porous osmotic pump-based controlled release system of oxybutynin.
2007 Jul 13
Intravesical treatments for painful bladder syndrome/ interstitial cystitis.
2007 Oct 17
Bladder dysfunction and vesicoureteral reflux.
2008
Treatment of urinary incontinence after stroke in adults.
2008 Jan 23
Polymeric matrix membrane sensors for stability-indicating potentiometric determination of oxybutynin hydrochloride and flavoxate hydrochloride urogenital system drugs.
2008 Nov-Dec
Application of oxybutynin selective sensors for monitoring the dissolution profile and assay of pharmaceutical dosage forms.
2010
Parasympathetic functions in children with sensory processing disorder.
2010
Posterior urethral valves: Morphological normalization of posterior urethra after fulguration is a significant factor in prognosis.
2010 Jul
[Isolated primary nocturnal enuresis: international evidence based management. Consensus recommendations by French expert group].
2010 May
Dose escalation improves therapeutic outcome: post hoc analysis of data from a 12-week, multicentre, double-blind, parallel-group trial of trospium chloride in patients with urinary urge incontinence.
2010 Sep 14
Patents

Sample Use Guides

from 100 mg to 1 000 mg/day. Phase IIB study, (S)-oxybutynin administered three times a day at 120 mg
Route of Administration: Oral
Membrane currents were recorded from whole-cell configured guinea-pig and rabbit ventricular myocytes, and action potentials were recorded from guinea-pig and rabbit papillary muscles. L-type Ca(2+) current (I:(Ca,L)), rapidly-activating K(+) current (I:(Kr)) and slowly-activating K(+) current (I:(Ks)) were unaffected by submicromolar S-oxybutynin and inhibited by higher concentrations; IC(50) values were 17.8 microM for I:(Ca,L), 12 microM for I:(Kr), and 41 microM for I:(Ks).
Substance Class Chemical
Created
by admin
on Sat Dec 16 00:09:16 GMT 2023
Edited
by admin
on Sat Dec 16 00:09:16 GMT 2023
Record UNII
39EY4NVB8T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Esoxybutynin
INN  
INN  
Official Name English
Benzeneacetic acid, α-cyclohexyl-α-hydroxy-, 4-(diethylamino)-2-butyn-1-yl ester, (αS)-
Systematic Name English
esoxybutynin [INN]
Common Name English
OXYBUTYNIN, (S)-
Common Name English
4-(diethylamino)but-2-yn-1-yl (S)-cyclohexyl(hydroxy)(phenyl)acetate
Systematic Name English
Code System Code Type Description
NCI_THESAURUS
C166661
Created by admin on Sat Dec 16 00:09:17 GMT 2023 , Edited by admin on Sat Dec 16 00:09:17 GMT 2023
PRIMARY
EPA CompTox
DTXSID901317439
Created by admin on Sat Dec 16 00:09:17 GMT 2023 , Edited by admin on Sat Dec 16 00:09:17 GMT 2023
PRIMARY
SMS_ID
300000036922
Created by admin on Sat Dec 16 00:09:17 GMT 2023 , Edited by admin on Sat Dec 16 00:09:17 GMT 2023
PRIMARY
PUBCHEM
206530
Created by admin on Sat Dec 16 00:09:17 GMT 2023 , Edited by admin on Sat Dec 16 00:09:17 GMT 2023
PRIMARY
INN
8379
Created by admin on Sat Dec 16 00:09:17 GMT 2023 , Edited by admin on Sat Dec 16 00:09:17 GMT 2023
PRIMARY
CHEBI
51329
Created by admin on Sat Dec 16 00:09:17 GMT 2023 , Edited by admin on Sat Dec 16 00:09:17 GMT 2023
PRIMARY
ChEMBL
CHEMBL1394756
Created by admin on Sat Dec 16 00:09:17 GMT 2023 , Edited by admin on Sat Dec 16 00:09:17 GMT 2023
PRIMARY
FDA UNII
39EY4NVB8T
Created by admin on Sat Dec 16 00:09:17 GMT 2023 , Edited by admin on Sat Dec 16 00:09:17 GMT 2023
PRIMARY
CAS
119618-22-3
Created by admin on Sat Dec 16 00:09:17 GMT 2023 , Edited by admin on Sat Dec 16 00:09:17 GMT 2023
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER
ENANTIOMER -> ENANTIOMER
SALT/SOLVATE -> PARENT