Esoxybutynin

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1993995
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

Targets

Primary Target	Pharmacology	Condition	Potency
Muscarinic acetylcholine receptor M1 168 Target ID: CHEMBL216 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1993995 \| http://www.genome.jp/dbget-bin/www_bget?dr:D04057	Antagonist 2849
Muscarinic acetylcholine receptor M2 121 Target ID: CHEMBL211 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1993995 \| http://www.genome.jp/dbget-bin/www_bget?dr:D04057	Antagonist 2849
Muscarinic acetylcholine receptor M3 160 Target ID: CHEMBL245 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1993995 \| http://www.genome.jp/dbget-bin/www_bget?dr:D04057	Antagonist 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Urinary incontinence 14 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12431028 http://www.google.com/patents/WO1998000126A1	Primary		Phase II 1147	Unknown Approved Use Unknown

F_unbound

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

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P007FYJ	https://www.1pchem.com/search?query=1P007FYJ
1PlusChem LLC	1P00IAIZ	https://www.1pchem.com/search?query=1P00IAIZ
A2B Chem	AD46475	http://a2bchem.com/prod/AD46475
A2B Chem	AI52651	http://a2bchem.com/prod/AI52651
AA Blocks	AA00I9ZJ	http://aablocks.com/goods/Goods/detail?id=AA00I9ZJ
AK Scientific	1329AL	https://aksci.com/item_detail.php?cat=1329AL
AK Scientific	H815	https://aksci.com/item_detail.php?cat=H815
AK Scientific	J10411	https://aksci.com/item_detail.php?cat=J10411
AK Scientific	J10527	https://aksci.com/item_detail.php?cat=J10527
AK Scientific	O222	https://aksci.com/item_detail.php?cat=O222
Ambeed	A144038	http://www.ambeed.com/search/Search.html?keyword=A144038
Angene	AGN-PC-0Q5BAV	http://www.angenechemical.com/productshow/AGN-PC-0Q5BAV.html
Angene	AGN-PC-0QZKFG	http://www.angenechemical.com/productshow/AGN-PC-0QZKFG.html
AstaTech	44862	http://astatechinc.com/CPSResult.php?CRNO=44862
AstaTech	A51042	http://astatechinc.com/CPSResult.php?CRNO=A51042
AstaTech	AB7701	http://astatechinc.com/CPSResult.php?CRNO=AB7701
BLD Pharm	BD49260	http://www.bldpharm.com/search/Search.html?keyword=BD49260
BOC Sciences	119618-22-3	http://www.bocsci.com/description.asp?cas=119618-22-3
BOC Sciences	1508-65-2	http://www.bocsci.com/description.asp?cas=1508-65-2
BOC Sciences	230949-16-3	http://www.bocsci.com/description.asp?cas=230949-16-3
BOC Sciences	5633-20-5	http://www.bocsci.com/description.asp?cas=5633-20-5
Chem Scene	CS-2255	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-2255
Chem Scene	CS-2256	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-2256
ChemShuttle	109904	https://www.chemshuttle.com/catalogsearch/result/?q=109904
ChemShuttle	141452	https://www.chemshuttle.com/catalogsearch/result/?q=141452
Combi-Blocks	OR-9586	http://www.combi-blocks.com/cgi-bin/find.cgi?OR-9586
Combi-Blocks	QA-1900	http://www.combi-blocks.com/cgi-bin/find.cgi?QA-1900
eMolecules	299974541	https://orderbb.emolecules.com/search/#?query=299974541
eMolecules	31526609	https://orderbb.emolecules.com/search/#?query=31526609
eMolecules	593014	https://orderbb.emolecules.com/search/#?query=593014
eMolecules	902251	https://orderbb.emolecules.com/search/#?query=902251
Enamine	EN300-123037	https://www.enaminestore.com/catalog/EN300-123037
Enamine	EN300-6478839	https://www.enaminestore.com/catalog/EN300-6478839
eNovation Chemicals	D516788	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D516788&searchbtn.x=0&searchbtn.y=0
Fluorochem	210680	http://www.fluorochem.co.uk/Products/Product?code=210680
Fluorochem	390166	http://www.fluorochem.co.uk/Products/Product?code=390166
Fluorochem	41375	http://www.fluorochem.co.uk/Products/Product?code=041375
Hairui	HR136750	http://www.hairuichem.com/en/product/search.do?q=HR136750
Hairui	HR136867	http://www.hairuichem.com/en/product/search.do?q=HR136867
KeyOrganics	AS-35343	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-35343
KeyOrganics	KS-1377	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=KS-1377
KeyOrganics	KS-5221	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=KS-5221
Lab Network	LN00224518	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00224518
Lab Network	LN01302544	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01302544
Lab Network	LN01349257	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01349257
Lab Seeker	SC-18892	http://www.labseeker.com/search.php?keywords=SC-18892&category=0
Lab Seeker	SC-26752	http://www.labseeker.com/search.php?keywords=SC-26752&category=0
LabSeeker	SC-18892	http://www.labseeker.com/search.php?keywords=SC-18892&category=0
LabSeeker	SC-26752	http://www.labseeker.com/search.php?keywords=SC-26752&category=0
Matrix Scientific	146752	http://www.matrixscientific.com/146752.html
mcule	MCULE-3407007074	https://mcule.com/MCULE-3407007074/
mcule	MCULE-5193326065	https://mcule.com/MCULE-5193326065/
MedChem Express	HY-B0267	https://www.medchemexpress.com/search.html?q=HY-B0267A&ft=&fa=&fp=
MedChem Express	HY-B0267A	https://www.medchemexpress.com/search.html?q=HY-B0267A&ft=&fa=&fp=
Molnova	M12107	https://www.molnova.com/en/serch-list.html?keywords=M12107
Molnova	M15049	https://www.molnova.com/en/serch-list.html?keywords=M15049
MolPort	MolPort-002-500-294	https://www.molport.com/shop/molecule-link/MolPort-002-500-294
MolPort	MolPort-003-666-668	https://www.molport.com/shop/molecule-link/MolPort-003-666-668
MolPort	MolPort-003-849-741	https://www.molport.com/shop/molecule-link/MolPort-003-849-741
MuseChem	A000922	https://www.musechem.com/product/A000922.html
MuseChem	R002907	https://www.musechem.com/product/R002907.html
Ryan Scientific	Estradiol	https://ryansci.com/products?q=Estradiol&list_q=&search_type=exact
Selleck Chemicals	S1754	http://www.selleckchem.com/search.html?searchDTO.searchParam=S1754
Selleck Chemicals	S3117	http://www.selleckchem.com/search.html?searchDTO.searchParam=S3117
ShangHai Biochempartner	BCP12138	http://www.biochempartner.com/search_BCP12138
ShangHai Biochempartner	BCP12179	http://www.biochempartner.com/search_BCP12179
Sigma Aldrich	BP701	http://www.sigmaaldrich.com/catalog/search?term=BP701&interface=All&N=0&mode=match%20partialmax&lang=en®ion=US&focus=product
TargetMol	T1049	https://www.targetmol.com/search?keyword=T1049L
TargetMol	T1049L	https://www.targetmol.com/search?keyword=T1049L
Tetrahedron	TS80832	http://www.thsci.com/search.do?q=TS80832
TimTec	ST51015085	http://www.echemstore.com/catalogsearch/result/?q=ST51015085
Toronto Research Chemicals	O868515	https://www.trc-canada.com/product-detail/?CatNum=O868515
Toronto Research Chemicals	O868525	https://www.trc-canada.com/product-detail/?CatNum=O868525
Vesino Industrial Co Ltd	VA11467	http://www.vsnchem.com/search.do?a=s&psize=20&q=VA11467
W&J PharmaChem	50C200423	http://wjpharmachem.com/new/searcht.php?keyword=50C200423
Wonderchem	WD05O0E	http://www.wonder-chem.com/search.html?text=WD05O0E

PubMed

Title	Date	PubMed
Combined pharmacotherapy for nocturnal enuresis.	2001 Aug	11519898
Pharmacokinetics, metabolism, and saliva output during transdermal and extended-release oral oxybutynin administration in healthy subjects.	2003 Jun	12934778
Acupressure versus oxybutinin in the treatment of enuresis.	2003 Nov-Dec	14708420
A population pharmacokinetic model with time-dependent covariates measured with errors.	2004 Jun	15180671
Oxybutynin for treatment of urge urinary incontinence and overactive bladder: an updated review.	2004 Nov	15500382
Rapid and selective UV spectrophotometric and RP-HPLC methods for dissolution studies of oxybutynin immediate-release and controlled-release formulations.	2004 Nov 15	15522548
Effect of controlled-release delivery on the pharmacokinetics of oxybutynin at different dosages: severity-dependent treatment of the overactive bladder.	2004 Oct	15476516
[Urinary incontinence: anticholinergic treatment].	2004 Oct-Dec	15810718
Canadian Urological Association guidelines on urinary incontinence.	2006 Jun	16813704
Analysis of pharmacological effects of drugs used for treatment of urinary disturbance based on anticholinergic and smooth muscle-relaxing effects.	2007 Jul	17603170
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	17473442
Bladder augmentation: Review of the literature and recent advances.	2007 Oct	19718303
Treatment of urinary incontinence after stroke in adults.	2008 Jan 23	18254050
Polymeric matrix membrane sensors for stability-indicating potentiometric determination of oxybutynin hydrochloride and flavoxate hydrochloride urogenital system drugs.	2008 Nov-Dec	19202792
Locked-in Syndrome in a Nigerian male with Multiple Sclerosis: a case report and literature review.	2008 Oct 30	21532893
Reversible bilateral optic neuritis after Infliximab discontinuation in a patient with Crohn's disease.	2009 Sep	21172274
Anesthetic management of the emergency laparotomy for a patient with multiple sclerosis -A case report-.	2010 Nov	21179301
Urological manifestations of Chikungunya fever: A single centre experience.	2010 Sep	20981198

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 `Mon Mar 31 20:32:06 GMT 2025` Edited by `admin` on `Mon Mar 31 20:32:06 GMT 2025`
Record UNII	39EY4NVB8T
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Esoxybutynin

Official Name

English

OXYBUTYNIN, (S)-

Preferred Name

English

Benzeneacetic acid, ?-cyclohexyl-?-hydroxy-, 4-(diethylamino)-2-butyn-1-yl ester, (?S)-

Systematic Name

English

esoxybutynin [INN]

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