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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H31NO3.ClH
Molecular Weight 393.9481
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESOXYBUTYNIN CHLORIDE

SMILES

CCN(CC)CC#CCOC(=O)[C@@](c1ccccc1)(C2CCCCC2)O.Cl

InChI

InChIKey=SWIJYDAEGSIQPZ-VZYDHVRKSA-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/t22-;/m1./s1

HIDE SMILES / InChI

Molecular Formula C22H31NO3
Molecular Weight 357.4873
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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

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
Tolterodine: a review of its use in the treatment of overactive bladder.
2001
Effect of OROS controlled-release delivery on the pharmacokinetics and pharmacodynamics of oxybutynin chloride.
2001 Oct
Augmentation ureterocystoplasty in bladder exstrophy: 5-year follow-up in two cases.
2002 Dec
Pharmacokinetics, metabolism, and saliva output during transdermal and extended-release oral oxybutynin administration in healthy subjects.
2003 Jun
Oxybutynin transdermal (Oxytrol) for overactive bladder.
2003 May 12
[Prevalence of urinary incontinence and linked factors in men and women over 65].
2003 Oct 15
A population pharmacokinetic model with time-dependent covariates measured with errors.
2004 Jun
Oxybutynin for treatment of urge urinary incontinence and overactive bladder: an updated review.
2004 Nov
Rapid and selective UV spectrophotometric and RP-HPLC methods for dissolution studies of oxybutynin immediate-release and controlled-release formulations.
2004 Nov 15
[Urinary incontinence: anticholinergic treatment].
2004 Oct-Dec
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Canadian Urological Association guidelines on urinary incontinence.
2006 Jun
Improved efficacy of extended release oxybutynin in children with persistent daytime urinary incontinence converted from regular oxybutynin.
2006 Oct
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
Pharmacologic management of overactive bladder.
2007
Intravesical treatments for painful bladder syndrome/ interstitial cystitis.
2007 Oct 17
Patient perspectives in the management of overactive bladder, focus on transdermal oxybutynin.
2008 Feb 2
The neurogenic bladder: medical treatment.
2008 May
Generation of an agonistic binding site for blockers of the M(3) muscarinic acetylcholine receptor.
2008 May 15
Polymeric matrix membrane sensors for stability-indicating potentiometric determination of oxybutynin hydrochloride and flavoxate hydrochloride urogenital system drugs.
2008 Nov-Dec
Locked-in Syndrome in a Nigerian male with Multiple Sclerosis: a case report and literature review.
2008 Oct 30
Behavioral intervention versus pharmacotherapy or their combinations in the management of overactive bladder dysfunction.
2009
No difference in between-country variability in use of newly approved orphan and non- orphan medicinal products--a pilot study.
2009 Dec 14
Trospium chloride and oxybutynin hydrochloride in a german study of adults with urinary urge incontinence: results of a 12-week, multicenter, randomized, double-blind, parallel-group, flexible-dose noninferiority trial.
2009 Nov
Reversible bilateral optic neuritis after Infliximab discontinuation in a patient with Crohn's disease.
2009 Sep
Oxybutynin extended release for the management of overactive bladder: a clinical review.
2009 Sep 21
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
Liquid Chromatographic Determination of Flavoxate HCl in Pharmaceutical Formulation.
2010 Jul
Anesthetic management of the emergency laparotomy for a patient with multiple sclerosis -A case report-.
2010 Nov
Current practices in treatment of female genital fistula: a cross sectional study.
2010 Nov 10
Urological manifestations of Chikungunya fever: A single centre experience.
2010 Sep
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 Jun 26 02:59:12 UTC 2021
Edited
by admin
on Sat Jun 26 02:59:12 UTC 2021
Record UNII
S547MDN7WX
Record Status Validated (UNII)
Record Version
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Name Type Language
ESOXYBUTYNIN CHLORIDE
USAN  
USAN  
Official Name English
OXYBUTYNIN CHLORIDE, (S)-
Common Name English
4-(DIETHYLAMINO)BUT-2-YNYL (2S)-CYCLOHEXYLHYDROXYPHENYLACETATE HYDROCHLORIDE
Systematic Name English
BENZENEACETIC ACID, .ALPHA.-CYCLOHEXYL-.ALPHA.-HYDROXY-, 4-(DIETHYLAMINO)-2-BUTYNYL ESTER, HYDROCHLORIDE, (.ALPHA.S)-
Common Name English
ESOXYBUTYNIN HYDROCHLORIDE
Common Name English
OXYBUTYNIN HYDROCHLORIDE, (+)-
Common Name English
ESOXYBUTYNIN CHLORIDE [USAN]
Common Name English
OXYBUTYNIN HYDROCHLORIDE, (S)-
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29704
Created by admin on Sat Jun 26 02:59:12 UTC 2021 , Edited by admin on Sat Jun 26 02:59:12 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C73630
Created by admin on Sat Jun 26 02:59:12 UTC 2021 , Edited by admin on Sat Jun 26 02:59:12 UTC 2021
PRIMARY
ChEMBL
CHEMBL1394756
Created by admin on Sat Jun 26 02:59:12 UTC 2021 , Edited by admin on Sat Jun 26 02:59:12 UTC 2021
PRIMARY
CAS
230949-16-3
Created by admin on Sat Jun 26 02:59:12 UTC 2021 , Edited by admin on Sat Jun 26 02:59:12 UTC 2021
PRIMARY
PUBCHEM
206529
Created by admin on Sat Jun 26 02:59:12 UTC 2021 , Edited by admin on Sat Jun 26 02:59:12 UTC 2021
PRIMARY
FDA UNII
S547MDN7WX
Created by admin on Sat Jun 26 02:59:12 UTC 2021 , Edited by admin on Sat Jun 26 02:59:12 UTC 2021
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY