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
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
| 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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| Preformulation studies on the S-isomer of oxybutynin hydrochloride, an Improved Chemical Entity (ICE). | 2001 Apr |
|
| Combined pharmacotherapy for nocturnal enuresis. | 2001 Aug |
|
| 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 |
|
| Oxybutynin transdermal (Oxytrol) for overactive bladder. | 2003 May 12 |
|
| Drug approval highlights for 2003. | 2004 Feb |
|
| Oxybutynin for treatment of urge urinary incontinence and overactive bladder: an updated review. | 2004 Nov |
|
| [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 |
|
| Influence of micro-environmental pH on the gel layer behavior and release of a basic drug from various hydrophilic matrices. | 2005 Mar 21 |
|
| 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 |
|
| 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 |
|
| Pharmacokinetics/pharmacodynamics analysis of the relationship between the in vivo micturition pressure and receptor occupancy of (R)-oxybutynin and its metabolite in rats. | 2007 May |
|
| Intravesical treatments for painful bladder syndrome/ interstitial cystitis. | 2007 Oct 17 |
|
| Effects of the M3 receptor selective muscarinic antagonist darifenacin on bladder afferent activity of the rat pelvic nerve. | 2007 Sep |
|
| Bladder dysfunction and vesicoureteral reflux. | 2008 |
|
| The neurogenic bladder: medical treatment. | 2008 May |
|
| Locked-in Syndrome in a Nigerian male with Multiple Sclerosis: a case report and literature review. | 2008 Oct 30 |
|
| 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 |
|
| Parasympathetic functions in children with sensory processing disorder. | 2010 |
|
| Medical management of overactive bladder. | 2010 Apr |
|
| 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 |
|
| 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 |
39EY4NVB8T
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| Record Status |
Validated (UNII)
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C166661
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DTXSID901317439
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CHEMBL1394756
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39EY4NVB8T
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119618-22-3
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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RACEMATE -> ENANTIOMER |
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ENANTIOMER -> ENANTIOMER |
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SALT/SOLVATE -> PARENT |
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