Oxybutynin

Details

Stereochemistry	RACEMIC
Molecular Formula	C22H31NO3
Molecular Weight	357.4864
Optical Activity	( + / - )
Defined Stereocenters	0 / 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-UHFFFAOYSA-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

HIDE SMILES / InChI

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
A dynamic mechanical method for determining the silicone elastomer solubility of drugs and pharmaceutical excipients in silicone intravaginal drug delivery rings.	2002-09	12109683
M(3) receptor antagonism by the novel antimuscarinic agent solifenacin in the urinary bladder and salivary gland.	2002-08	12122494
Current pharmacotherapeutic strategies for overactive bladder.	2002-07	12083983
Extractionless and sensitive method for high-throughput quantitation of cetirizine in human plasma samples by liquid chromatography-tandem mass spectrometry.	2002-06-25	12031836
Inappropriate medication prescribing in residential care/assisted living facilities.	2002-06	12110058
Effect of muscarinic antagonists on micturition pressure measured by cystometry in normal, conscious rats.	2002-06	12031395
A long-term follow-up of autoaugmentation in myelodysplastic children.	2002-06	12010242
Overactive bladder patients and role of the pharmacist.	2002-05-28	12030634
Tolterodine: as effective but better tolerated than oxybutynin in Asian patients with symptoms of overactive bladder.	2002-05	12060436
Advances in anticholinergic therapy delivery systems.	2002-05	12040601
Urodynamic changes associated with behavioral and drug treatment of urge incontinence in older women.	2002-05	12028165
The management of urinary incontinence in the exstrophy complex, posterior urethral valves, and infrasphincteric ureters.	2002-05	11973765
Assessment and conservative management of the neuropathic bladder.	2002-05	11973763
Oxybutynin chloride: alterations in drug delivery and improved therapeutic index.	2002-04	11934349
Preliminary study of the safety and efficacy of extended-release oxybutynin in children.	2002-03	11880086
Efficacy of botulinum-a toxin in children with detrusor hyperreflexia due to myelomeningocele: preliminary results.	2002-03	11880062
Pharmacotherapy of the overactive bladder and advances in drug delivery.	2002-03	11862073
Vesicoureteral reflux and bladder management in spinal cord injury patients.	2002-03	11859443
Binding study of desethyloxybutynin using high-performance frontal analysis method.	2002-02-25	11939552
Plasma protein binding study of oxybutynin by high-performance frontal analysis.	2002-02-25	11939551
Pharmacokinetics, efficacy, and safety of intravesical formulation of oxybutynin in patients with detrusor overactivity.	2002-02	12002352
Highlights of the 22nd French pharmacovigilance meeting.	2002-02	11985373
Medication update.	2002-02	11846243
Enuresis.	2002-02	11846242
Influence of pump compliance (peristaltic vs. infusion) on urodynamic measurement during cystometry in conscious rats.	2002-01-05	11755385
Urinary antispasmodic use and the risks of ventricular arrhythmia and sudden death in older patients.	2002-01	12028256
Once-daily, extended-release formulations of antimuscarinic agents in the treatment of overactive bladder: a review.	2002-01	11999467
[Sling suspension of incontinent urinary reservoir].	2002-01	11842543
New treatment options for overactive bladder and incontinence.	2002	12116753
S-oxybutynin.	2002	12001823
Oxybutynin intravesical--situs. I-oxy.	2002	12001822
Tolterodine: selectivity for the urinary bladder over the eye (as measured by visual accommodation) in healthy volunteers.	2002	12001821
Treatment can lead to a long dry spell.	2002	11974567
Actions of the new antimuscarinic compound Lu 25-109 on isolated human and pig detrusor.	2002	11835429
Cost-Effectiveness of tolterodine for patients with urge incontinence who discontinue initial therapy with oxybutynin: a Canadian perspective.	2001-12	11813937
Is tolterodine (Detrol) or oxybutynin (Ditropan) the best for treatment of urge urinary incontinence?	2001-12	11742595
Urethral catheterization in hypospadias surgery: Should the device enter the bladder or be made a urethral stent?	2001-12	11733916
Prescribing for multiple sclerosis patients in general practice: a case-control study.	2001-12	11722681
Evidence based management of nocturnal enuresis.	2001-11-17	11711411
Efficacy, tolerability and safety profile of propiverine in the treatment of the overactive bladder (non-neurogenic and neurogenic).	2001-11	11760781
Oxybutynin and the overactive bladder.	2001-11	11760780
Tolterodine: an overview.	2001-11	11760779
Which muscarinic receptor is important in the bladder?	2001-11	11760777
Medical treatment of overactive bladder.	2001-11	11702910
Evidence for the efficacy and safety of tolterodine in the treatment of overactive bladder.	2001-10	11825311
Transdermally-delivered oxybutynin (Oxytrol(R) for overactive bladder.	2001-10	11776281
Combination therapy for nocturnal enuresis.	2001-10	11771862
Identification of muscarinic receptor subtypes of cultured smooth muscle cells and tissue of human bladder body.	2001-10	11737484
Tolterodine: a clinical review.	2001-10	11703885
[Continence problems after radical prostatectomy: medical treatment].	2001-09	11822060

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 19:22:10 GMT 2025` Edited by `admin` on `Mon Mar 31 19:22:10 GMT 2025`
Record UNII	K9P6MC7092
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

Oxybutynin

Official Name

English

KENTERA

Preferred Name

English

OXYBUTYNIN [HSDB]

Common Name

English

oxybutynin [INN]

Common Name

English

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

Systematic Name

English

Oxybutynin [WHO-DD]

Common Name

English

OXYBUTYNIN [ORANGE BOOK]

Common Name

English

OXYBUTYNIN [MI]

Common Name

English

OXYBUTYNIN [MART.]

Common Name

English

OXYBUTYNIN [EMA EPAR]

Common Name

English

OXYTROL

Brand Name

English

4-(diethylamino)but-2-yn-1-yl cyclohexyl(hydroxy)(phenyl)acetate

Systematic Name

English

OXYBUTYNIN [USAN]

Common Name

English

OXYBUTYNIN [VANDF]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000000125