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 120 Target ID: CHEMBL211 Sources: http://www.drugbank.ca/drugs/DB01062	Antagonist 2760	8.1 nM [Ki]
Muscarinic acetylcholine receptor M1 168 Target ID: CHEMBL216 Sources: http://www.drugbank.ca/drugs/DB01062	Antagonist 2760	1.0 nM [Ki]
Muscarinic acetylcholine receptor M3 158 Target ID: CHEMBL245 Sources: http://www.drugbank.ca/drugs/DB01062	Antagonist 2760	0.78 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Overactive bladder 38 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/017577s034,018211s017,020897s018lbl.pdf	Primary		Approved 8360	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 1.74614397E11

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 1709 inhibitor 1579	inhibitor 1752 substrate 1010	substrate 1193 inhibitor 1837	inhibitor 1599

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCT1 506 OCT2 638 OCT3 149 CYP1A 72 CYP2A6 704 CYP2E1 876 BSEP 401 K+ channels 56 L-type Ca2+ channels 26	P-gp 1527 OCT1 322 OCT2 348 OCT3 79 CYP2B6 660 CYP2C8 688 CYP2E1 648 CYP2C19 985 CYP3A5 391

Drug as perpetrator

Target	Modality	Activity
CYP1A 121	inhibitor 3240 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1600-0773.1998.tb01418.x Page: 164.0	no
CYP2A6 736	inhibitor 3240 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1600-0773.1998.tb01418.x Page: 164.0	no
CYP2C9 1803	inhibitor 3240 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1600-0773.1998.tb01418.x Page: 164.0	no
CYP2E1 964	inhibitor 3240 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1600-0773.1998.tb01418.x Page: 164.0	no
OCT2 639	inhibitor 3240 Sources: https://link.springer.com/content/pdf/10.1007/s00210-010-0590-x.pdf Page: 205.0	yes [IC50 128 uM]
OCT3 149	inhibitor 3240 Sources: https://link.springer.com/content/pdf/10.1007/s00210-010-0590-x.pdf Page: 205.0	yes [IC50 130 uM]
OCT1 523	inhibitor 3240 Sources: https://link.springer.com/content/pdf/10.1007/s00210-010-0590-x.pdf Page: 205.0	yes [IC50 20 uM]
BSEP 402	inhibitor 3240 Sources: https://academic.oup.com/toxsci/article/118/2/485/1652105 Page: 496.0	yes [IC50 27.4 uM]
CYP3A4 1909	inhibitor 3240 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1600-0773.1998.tb01418.x Page: abstract	yes [IC50 7.7 uM]
CYP2D6 1875	inhibitor 3240 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1600-0773.1998.tb01418.x Page: abstract	yes [IC50 9.5 uM]
K+ channels 56	inhibitor 3240 Sources: https://journals.lww.com/cardiovascularpharm/Fulltext/2000/02000/Analysis_of_the_Electrophysiologic_Effects_of.24.aspx Page: abstract	yes
L-type Ca2+ channels 28	inhibitor 3240 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 1709	substrate 3326 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 660	substrate 3326 Sources: https://europepmc.org/article/med/9825837 Page: 451.0	no
CYP2C19 985	substrate 3326 Sources: https://www.tandfonline.com/doi/abs/10.1080/00498250600976088 Page: abstract	no
CYP2C8 688	substrate 3326 Sources: https://europepmc.org/article/med/9825837 Page: 451.0	no
CYP2C9 1010	substrate 3326 Sources: https://www.tandfonline.com/doi/abs/10.1080/00498250600976088 Page: abstract	no
CYP2D6 1193	substrate 3326 Sources: https://europepmc.org/article/med/9825837 Page: abstract	no
CYP2E1 648	substrate 3326 Sources: https://europepmc.org/article/med/9825837 Page: 451.0	no
CYP3A5 391	substrate 3326 Sources: https://www.tandfonline.com/doi/abs/10.1080/00498250600976088 Page: abstract	no
P-gp 1527	substrate 3326 Sources: https://bpspubs.onlinelibrary.wiley.com/doi/abs/10.1111/j.1365-2125.2011.03961.x Page: 235.0	no
OCT1 322	substrate 3326 Sources: https://link.springer.com/content/pdf/10.1007/s00210-010-0590-x.pdf Page: 206.0	yes
OCT2 348	substrate 3326 Sources: https://link.springer.com/content/pdf/10.1007/s00210-010-0590-x.pdf Page: 206.0	yes
OCT3 79	substrate 3326 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 1632	inhibitor 1613 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
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
eMolecules	902251	https://www.emolecules.com/cgi-bin/more?vid=902251

PubMed

Title	Date	PubMed



Intravesical oxybutynin affects bladder permeability.	2001	11583352
Combined pharmacotherapy for nocturnal enuresis.	2001 Aug	11519898
Cost-Effectiveness of tolterodine for patients with urge incontinence who discontinue initial therapy with oxybutynin: a Canadian perspective.	2001 Dec	11813937
Urethral catheterization in hypospadias surgery: Should the device enter the bladder or be made a urethral stent?	2001 Dec	11733916
Prescribing for multiple sclerosis patients in general practice: a case-control study.	2001 Dec	11722681
Oxybutynin, desmopressin and enuresis.	2001 Dec	11696812
Intravesical treatment of bladder dysfunction.	2001 Dec	11696743
Oxybutynin and the overactive bladder.	2001 Nov	11760780
Tolterodine: an overview.	2001 Nov	11760779
Which muscarinic receptor is important in the bladder?	2001 Nov	11760777
Medical treatment of overactive bladder.	2001 Nov	11702910
Evidence based management of nocturnal enuresis.	2001 Nov 17	11711411
Evidence for the efficacy and safety of tolterodine in the treatment of overactive bladder.	2001 Oct	11825311
Transdermally-delivered oxybutynin (Oxytrol(R) for overactive bladder.	2001 Oct	11776281
Combination therapy for nocturnal enuresis.	2001 Oct	11771862
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
Treatment of childhood nocturnal enuresis: an examination of clinically relevant principles.	2001 Oct	11678752
POEMS (patient-oriented evidence that matters) spark discussion.	2001 Oct	11674898
[Continence problems after radical prostatectomy: medical treatment].	2001 Sep	11822060
Effects of antimuscarinic drugs on both urinary frequency and cognitive impairment in conscious, nonrestrained rats.	2001 Sep	11676195
S-oxybutynin.	2002	12001823
Tolterodine: selectivity for the urinary bladder over the eye (as measured by visual accommodation) in healthy volunteers.	2002	12001821
Actions of the new antimuscarinic compound Lu 25-109 on isolated human and pig detrusor.	2002	11835429
Oxybutynin chloride: alterations in drug delivery and improved therapeutic index.	2002 Apr	11934349
M(3) receptor antagonism by the novel antimuscarinic agent solifenacin in the urinary bladder and salivary gland.	2002 Aug	12122494
Pharmacokinetics, efficacy, and safety of intravesical formulation of oxybutynin in patients with detrusor overactivity.	2002 Feb	12002352
Highlights of the 22nd French pharmacovigilance meeting.	2002 Feb	11985373
Medication update.	2002 Feb	11846243
Enuresis.	2002 Feb	11846242
Binding study of desethyloxybutynin using high-performance frontal analysis method.	2002 Feb 25	11939552
Plasma protein binding study of oxybutynin by high-performance frontal analysis.	2002 Feb 25	11939551
Once-daily, extended-release formulations of antimuscarinic agents in the treatment of overactive bladder: a review.	2002 Jan	11999467
[Sling suspension of incontinent urinary reservoir].	2002 Jan	11842543
Current pharmacotherapeutic strategies for overactive bladder.	2002 Jul	12083983
Inappropriate medication prescribing in residential care/assisted living facilities.	2002 Jun	12110058
Effect of muscarinic antagonists on micturition pressure measured by cystometry in normal, conscious rats.	2002 Jun	12031395
Extractionless and sensitive method for high-throughput quantitation of cetirizine in human plasma samples by liquid chromatography-tandem mass spectrometry.	2002 Jun 25	12031836
Preliminary study of the safety and efficacy of extended-release oxybutynin in children.	2002 Mar	11880086
Efficacy of botulinum-a toxin in children with detrusor hyperreflexia due to myelomeningocele: preliminary results.	2002 Mar	11880062
Vesicoureteral reflux and bladder management in spinal cord injury patients.	2002 Mar	11859443
Tolterodine: as effective but better tolerated than oxybutynin in Asian patients with symptoms of overactive bladder.	2002 May	12060436
Advances in anticholinergic therapy delivery systems.	2002 May	12040601
The management of urinary incontinence in the exstrophy complex, posterior urethral valves, and infrasphincteric ureters.	2002 May	11973765
Assessment and conservative management of the neuropathic bladder.	2002 May	11973763
A dynamic mechanical method for determining the silicone elastomer solubility of drugs and pharmaceutical excipients in silicone intravaginal drug delivery rings.	2002 Sep	12109683
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 `Thu Jul 06 02:01:10 UTC 2023` Edited by `admin` on `Thu Jul 06 02:01:10 UTC 2023`
Record UNII	K9P6MC7092
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Oxybutynin

Official Name

English

OXYBUTYNIN [HSDB]

Common Name

English

oxybutynin [INN]

Common Name

English

Benzeneacetic acid, α-cyclohexyl-α-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

KENTERA

Brand Name

English

Classification Tree Code System Code

NDF-RT

N0000000125