Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C22H31NO3.ClH |
| Molecular Weight | 393.947 |
| Optical Activity | ( + ) |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CCN(CC)CC#CCOC(=O)[C@](O)(C1CCCCC1)C2=CC=CC=C2
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
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| 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 |
DescriptionCurator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/12431028 | http://www.google.com/patents/WO1998000126A1 | https://www.ncbi.nlm.nih.gov/pubmed/7620236
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.
Originator
Approval Year
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
24.3% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11939551 |
ESOXYBUTYNIN plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Tolterodine: a review of its use in the treatment of overactive bladder. | 2001 |
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| 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 |
|
| 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 |
|
| [Urinary incontinence: anticholinergic treatment]. | 2004 Oct-Dec |
|
| High performance liquid chromatographic determination of oxeladin citrate and oxybutynin hydrochloride and their degradation products. | 2005 Aug |
|
| Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
| New transdermal bioadhesive film containing oxybutynin: In vitro permeation across rabbit ear skin. | 2006 Nov 15 |
|
| Improved efficacy of extended release oxybutynin in children with persistent daytime urinary incontinence converted from regular oxybutynin. | 2006 Oct |
|
| Pharmacologic management of overactive bladder. | 2007 |
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| Analysis of pharmacological effects of drugs used for treatment of urinary disturbance based on anticholinergic and smooth muscle-relaxing effects. | 2007 Jul |
|
| Intravesical treatments for painful bladder syndrome/ interstitial cystitis. | 2007 Oct 17 |
|
| Primary monosymptomatic nocturnal enuresis in children and adolescents. | 2007 Sep |
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| Bladder dysfunction and vesicoureteral reflux. | 2008 |
|
| Patient perspectives in the management of overactive bladder, focus on transdermal oxybutynin. | 2008 Feb 2 |
|
| Treatment of urinary incontinence after stroke in adults. | 2008 Jan 23 |
|
| 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 |
|
| 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 |
|
| Application of oxybutynin selective sensors for monitoring the dissolution profile and assay of pharmaceutical dosage forms. | 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 |
|
| 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 |
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
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| Record UNII |
S547MDN7WX
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| Record Status |
Validated (UNII)
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NCI_THESAURUS |
C29704
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C73630
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CHEMBL1394756
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DTXSID30945773
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300000044448
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230949-16-3
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206529
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OO-52
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S547MDN7WX
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RACEMATE -> ENANTIOMER |
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |
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