Oxybutynin xinafoate

Details

Stereochemistry	RACEMIC
Molecular Formula	C22H31NO3.C11H8O3
Molecular Weight	545.6659
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)C1=CC=C2C=CC=CC2=C1O.CCN(CC)CC#CCOC(=O)C(O)(C3CCCCC3)C4=CC=CC=C4

InChI

InChIKey=SRVJTUJNFIQJMD-UHFFFAOYSA-N

InChI=1S/C22H31NO3.C11H8O3/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;12-10-8-4-2-1-3-7(8)5-6-9(10)11(13)14/h5,7-8,13-14,20,25H,3-4,6,9-10,15-18H2,1-2H3;1-6,12H,(H,13,14)

HIDE SMILES / InChI

Molecular Formula	C11H8O3
Molecular Weight	188.1794
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	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://www.drugbank.ca/drugs/DB01062
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/017577s034,018211s017,020897s018lbl.pdf

Oxybutynin is an antispasmodic, anticholinergic agent indicated for the treatment of overactive bladder with symptoms of urge urinary incontinence, urgency, and frequency. Oxybutynin relaxes bladder smooth muscle. Oxybutynin exhibits only one-fifth of the anticholinergic activity of atropine on the rabbit detrusor muscle, but four to ten times the antispasmodic activity. Antimuscarinic activity resides predominantly in the R-isomer. Oxybutynin exerts a direct antispasmodic effect on smooth muscle and inhibits the muscarinic action of acetylcholine on smooth muscle. No blocking effects occur at skeletal neuromuscular junctions or autonomic ganglia (antinicotinic effects). By inhibiting particularily the M1 and M2 receptors of the bladder, detrusor activity is markedly decreased.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Muscarinic acetylcholine receptor M2 121 Target ID: CHEMBL211 Sources: http://www.drugbank.ca/drugs/DB01062	Antagonist 2849	8.1 nM [Ki]
Muscarinic acetylcholine receptor M1 168 Target ID: CHEMBL216 Sources: http://www.drugbank.ca/drugs/DB01062	Antagonist 2849	1.0 nM [Ki]
Muscarinic acetylcholine receptor M3 160 Target ID: CHEMBL245 Sources: http://www.drugbank.ca/drugs/DB01062	Antagonist 2849	0.78 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Overactive bladder 39 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/017577s034,018211s017,020897s018lbl.pdf	Primary		Approved 8583	DITROPAN Approved Use DITROPAN® (oxybutynin chloride) is indicated for the relief of symptoms of bladder instability associated with voiding in patients with uninhibited neurogenic or reflex neurogenic bladder (i.e., urgency, frequency, urinary leakage, urge incontinence, dysuria). Launch Date 1975

C_max

Value	Dose	Co-administered	Analyte	Population
6.73 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3234461/	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:		OXYBUTYNIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
9.24 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3234461/	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:		OXYBUTYNIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.44 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3234461/	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:		OXYBUTYNIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252	inhibitor 2438 substrate 1193	substrate 1388 inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCT1 620 OCT2 779 OCT3 159 CYP1A 70 CYP2A6 879 CYP2E1 1060 BSEP 550 K+ channels 73 L-type Ca2+ channels 28	P-gp 2052 OCT1 393 OCT2 434 OCT3 92 CYP2B6 776 CYP2C8 810 CYP2E1 729 CYP2C19 1119 CYP3A5 446

Drug as perpetrator

Target	Modality	Activity
CYP1A 122	inhibitor 4027 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1600-0773.1998.tb01418.x Page: 164.0	no
CYP2A6 911	inhibitor 4027 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1600-0773.1998.tb01418.x Page: 164.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1600-0773.1998.tb01418.x Page: 164.0	no
CYP2E1 1146	inhibitor 4027 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1600-0773.1998.tb01418.x Page: 164.0	no
OCT2 782	inhibitor 4027 Sources: https://link.springer.com/content/pdf/10.1007/s00210-010-0590-x.pdf Page: 205.0	yes [IC50 128 uM]
OCT3 161	inhibitor 4027 Sources: https://link.springer.com/content/pdf/10.1007/s00210-010-0590-x.pdf Page: 205.0	yes [IC50 130 uM]
OCT1 656	inhibitor 4027 Sources: https://link.springer.com/content/pdf/10.1007/s00210-010-0590-x.pdf Page: 205.0	yes [IC50 20 uM]
BSEP 554	inhibitor 4027 Sources: https://academic.oup.com/toxsci/article/118/2/485/1652105 Page: 496.0	yes [IC50 27.4 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1600-0773.1998.tb01418.x Page: abstract	yes [IC50 7.7 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1600-0773.1998.tb01418.x Page: abstract	yes [IC50 9.5 uM]
K+ channels 73	inhibitor 4027 Sources: https://journals.lww.com/cardiovascularpharm/Fulltext/2000/02000/Analysis_of_the_Electrophysiologic_Effects_of.24.aspx Page: abstract	yes
L-type Ca2+ channels 30	inhibitor 4027 Sources: https://journals.lww.com/cardiovascularpharm/Fulltext/2000/02000/Analysis_of_the_Electrophysiologic_Effects_of.24.aspx Page: abstract	yes

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/017577s038lbl.pdf Page: 4.0	major	yes (co-administration study) Comment: itraconazole increased oxybutynin cmax, auc 2x Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/017577s038lbl.pdf Page: 4.0
CYP2B6 776	substrate 4014 Sources: https://europepmc.org/article/med/9825837 Page: 451.0	no
CYP2C19 1119	substrate 4014 Sources: https://www.tandfonline.com/doi/abs/10.1080/00498250600976088 Page: abstract	no
CYP2C8 810	substrate 4014 Sources: https://europepmc.org/article/med/9825837 Page: 451.0	no
CYP2C9 1193	substrate 4014 Sources: https://www.tandfonline.com/doi/abs/10.1080/00498250600976088 Page: abstract	no
CYP2D6 1388	substrate 4014 Sources: https://europepmc.org/article/med/9825837 Page: abstract	no
CYP2E1 729	substrate 4014 Sources: https://europepmc.org/article/med/9825837 Page: 451.0	no
CYP3A5 446	substrate 4014 Sources: https://www.tandfonline.com/doi/abs/10.1080/00498250600976088 Page: abstract	no
P-gp 2052	substrate 4014 Sources: https://bpspubs.onlinelibrary.wiley.com/doi/abs/10.1111/j.1365-2125.2011.03961.x Page: 235.0	no
OCT1 393	substrate 4014 Sources: https://link.springer.com/content/pdf/10.1007/s00210-010-0590-x.pdf Page: 206.0	yes
OCT2 434	substrate 4014 Sources: https://link.springer.com/content/pdf/10.1007/s00210-010-0590-x.pdf Page: 206.0	yes
OCT3 92	substrate 4014 Sources: https://link.springer.com/content/pdf/10.1007/s00210-010-0590-x.pdf Page: 206.0	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.tandfonline.com/doi/abs/10.1080/14740338.2018.1453496 Page: 12.0

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:7856	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7856
ChemicalBook	CB2767266	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2767266
ChemicalBook	CB42675235	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB42675235
ChemicalBook	CB4587899	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4587899
eMolecules	902251	https://www.emolecules.com/cgi-bin/more?vid=902251
MolPort	MolPort-003-849-741	https://www.molport.com/shop/molecule-link/MolPort-003-849-741
Selleck Chemicals	Oxybutynin(Ditropan)	http://www.selleckchem.com/products/Oxybutynin(Ditropan).html

PubMed

Title	Date	PubMed
Enuresis.	2001	11480766
Detrol LA and Diropan XL for overactive bladder.	2001 Apr 2	11283473
Nocturnal enuresis.	2001 Aug	11483553
Effects of AH-9700, (+)-pentazocine, DTG and oxybutynin on micturition in anesthetized rats with acetone-induced cystitis.	2001 Aug 24	11589509
Association between oxybutynin and neuropsychiatric adverse effects not confirmed in daily practice.	2001 Feb	11207885
Intravesical oxybutynin for treating incontinence resulting from an overactive detrusor.	2001 Jun	11412211
A semiparametric deconvolution model to establish in vivo-in vitro correlation applied to OROS oxybutynin.	2001 Jun	11357173
Cost effectiveness and quality of life considerations in the treatment of patients with overactive bladder.	2001 Mar	11261409
Overactive bladder: optimizing quality of care.	2001 Mar	11261408
Side-effects of oral or intravesical oxybutynin chloride in children with spina bifida.	2001 May	11350411
Tolterodine: superior tolerability than and comparable efficacy to oxybutynin in individuals 50 years old or older with overactive bladder: a randomized controlled trial.	2001 May	11342895
Efficacy, tolerability and safety profile of propiverine in the treatment of the overactive bladder (non-neurogenic and neurogenic).	2001 Nov	11760781
Oxybutynin and the overactive bladder.	2001 Nov	11760780
Identification of muscarinic receptor subtypes of cultured smooth muscle cells and tissue of human bladder body.	2001 Oct	11737484
Tolterodine: a clinical review.	2001 Oct	11703885
Effect of OROS controlled-release delivery on the pharmacokinetics and pharmacodynamics of oxybutynin chloride.	2001 Oct	11678784
Treatment of childhood nocturnal enuresis: an examination of clinically relevant principles.	2001 Oct	11678752
Actions of the new antimuscarinic compound Lu 25-109 on isolated human and pig detrusor.	2002	11835429
M(3) receptor antagonism by the novel antimuscarinic agent solifenacin in the urinary bladder and salivary gland.	2002 Aug	12122494
Highlights of the 22nd French pharmacovigilance meeting.	2002 Feb	11985373
Medication update.	2002 Feb	11846243
Enuresis.	2002 Feb	11846242
Extractionless and sensitive method for high-throughput quantitation of cetirizine in human plasma samples by liquid chromatography-tandem mass spectrometry.	2002 Jun 25	12031836
Efficacy of botulinum-a toxin in children with detrusor hyperreflexia due to myelomeningocele: preliminary results.	2002 Mar	11880062
Pharmacotherapy of the overactive bladder and advances in drug delivery.	2002 Mar	11862073
Vesicoureteral reflux and bladder management in spinal cord injury patients.	2002 Mar	11859443
Advances in anticholinergic therapy delivery systems.	2002 May	12040601
Overactive bladder patients and role of the pharmacist.	2002 May-Jun	12030634
Treatment can lead to a long dry spell.	2002 Spring	11974567
New treatment options for overactive bladder and incontinence.	2002 Summer	12116753

Patents

Sample Use Guides

In Vivo Use Guide

Tablets Adults: The usual dose is one 5-mg tablet two to three times a day. The maximum recommended dose is one 5-mg tablet four times a day. A lower starting dose of 2.5 mg two or three times a day is recommended for the frail elderly. Pediatric patients over 5 years of age: The usual dose is one 5-mg tablet two times a day. The maximum recommended dose is one 5-mg tablet three times a day.

Route of Administration: Oral

In Vitro Use Guide

Oxybutynin (1 uM) significantly depressed the frequency responses to carbachol (1 uM) in Isolated strips of porcine urothelium with lamina propria.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:50:51 GMT 2025` Edited by `admin` on `Mon Mar 31 19:50:51 GMT 2025`
Record UNII	7425U24ZN4
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

2-Naphthalenecarboxylic acid, 1-hydroxy-, compd. with 4-(diethylamino)-2-butyn-1-yl ?-cyclohexyl-?-hydroxybenzeneacetate (1:1)

Preferred Name

English

Oxybutynin xinafoate

Common Name

English

Code System Code Type Description

FDA UNII

7425U24ZN4

Created by admin on Mon Mar 31 19:50:51 GMT 2025 , Edited by admin on Mon Mar 31 19:50:51 GMT 2025

PRIMARY

CAS

1447998-30-2

Created by admin on Mon Mar 31 19:50:51 GMT 2025 , Edited by admin on Mon Mar 31 19:50:51 GMT 2025

PRIMARY

PUBCHEM

53477276

Created by admin on Mon Mar 31 19:50:51 GMT 2025 , Edited by admin on Mon Mar 31 19:50:51 GMT 2025

PRIMARY

Related Record Type Details


					K9P6MC7092

Oxybutynin

PARENT -> SALT/SOLVATE

Amount:

Related Record Type Details


					K9P6MC7092

Oxybutynin

ACTIVE MOIETY

Amount:

Details

SMILES

InChI

DescriptionSources: http://www.drugbank.ca/drugs/DB01062Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/017577s034,018211s017,020897s018lbl.pdf

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Cmax

AUC

T1/2

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: http://www.drugbank.ca/drugs/DB01062
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/017577s034,018211s017,020897s018lbl.pdf

C_max

T_1/2

Drug as perpetrator