OXYBUTYNIN

Details

Stereochemistry	RACEMIC
Molecular Formula	C22H31NO3
Molecular Weight	357.4873
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN(CC)CC#CCOC(=O)C(c1ccccc1)(C2CCCCC2)O

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

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 115 Target ID: CHEMBL211 Sources: http://www.drugbank.ca/drugs/DB01062	Antagonist 2575	8.1 nM [Ki]
Muscarinic acetylcholine receptor M1 160 Target ID: CHEMBL216 Sources: http://www.drugbank.ca/drugs/DB01062	Antagonist 2575	1.0 nM [Ki]
Muscarinic acetylcholine receptor M3 151 Target ID: CHEMBL245 Sources: http://www.drugbank.ca/drugs/DB01062	Antagonist 2575	0.78 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Overactive bladder 35 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/017577s034,018211s017,020897s018lbl.pdf	Primary		Approved 8043	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 1601 inhibitor 1467	inhibitor 1604 substrate 936	substrate 1118 inhibitor 1702	inhibitor 1475

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCT1 480 OCT2 594 OCT3 140 CYP1A 69 CYP2A6 627 CYP2E1 790 BSEP 376 K+ channels 50 L-type Ca2+ channels 25	P-gp 1400 OCT1 302 OCT2 316 OCT3 75 CYP2B6 616 CYP2C8 634 CYP2E1 606 CYP2C19 910 CYP3A5 367

Drug as perpetrator

Target	Modality	Activity
CYP1A 110	inhibitor 3045 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1600-0773.1998.tb01418.x Page: 164.0	no
CYP2A6 659	inhibitor 3045 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1600-0773.1998.tb01418.x Page: 164.0	no
CYP2C9 1648	inhibitor 3045 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1600-0773.1998.tb01418.x Page: 164.0	no
CYP2E1 871	inhibitor 3045 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1600-0773.1998.tb01418.x Page: 164.0	no
OCT2 595	inhibitor 3045 Sources: https://link.springer.com/content/pdf/10.1007/s00210-010-0590-x.pdf Page: 205.0	yes [IC50 128 uM]
OCT3 140	inhibitor 3045 Sources: https://link.springer.com/content/pdf/10.1007/s00210-010-0590-x.pdf Page: 205.0	yes [IC50 130 uM]
OCT1 495	inhibitor 3045 Sources: https://link.springer.com/content/pdf/10.1007/s00210-010-0590-x.pdf Page: 205.0	yes [IC50 20 uM]
BSEP 377	inhibitor 3045 Sources: https://academic.oup.com/toxsci/article/118/2/485/1652105 Page: 496.0	yes [IC50 27.4 uM]
CYP3A4 1772	inhibitor 3045 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1600-0773.1998.tb01418.x Page: abstract	yes [IC50 7.7 uM]
CYP2D6 1738	inhibitor 3045 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1600-0773.1998.tb01418.x Page: abstract	yes [IC50 9.5 uM]
K+ channels 50	inhibitor 3045 Sources: https://journals.lww.com/cardiovascularpharm/Fulltext/2000/02000/Analysis_of_the_Electrophysiologic_Effects_of.24.aspx Page: abstract	yes
L-type Ca2+ channels 27	inhibitor 3045 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 1601	substrate 3113 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 616	substrate 3113 Sources: https://europepmc.org/article/med/9825837 Page: 451.0	no
CYP2C19 910	substrate 3113 Sources: https://www.tandfonline.com/doi/abs/10.1080/00498250600976088 Page: abstract	no
CYP2C8 634	substrate 3113 Sources: https://europepmc.org/article/med/9825837 Page: 451.0	no
CYP2C9 936	substrate 3113 Sources: https://www.tandfonline.com/doi/abs/10.1080/00498250600976088 Page: abstract	no
CYP2D6 1118	substrate 3113 Sources: https://europepmc.org/article/med/9825837 Page: abstract	no
CYP2E1 606	substrate 3113 Sources: https://europepmc.org/article/med/9825837 Page: 451.0	no
CYP3A5 367	substrate 3113 Sources: https://www.tandfonline.com/doi/abs/10.1080/00498250600976088 Page: abstract	no
P-gp 1400	substrate 3113 Sources: https://bpspubs.onlinelibrary.wiley.com/doi/abs/10.1111/j.1365-2125.2011.03961.x Page: 235.0	no
OCT1 302	substrate 3113 Sources: https://link.springer.com/content/pdf/10.1007/s00210-010-0590-x.pdf Page: 206.0	yes
OCT2 316	substrate 3113 Sources: https://link.springer.com/content/pdf/10.1007/s00210-010-0590-x.pdf Page: 206.0	yes
OCT3 75	substrate 3113 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 1507	inhibitor 1489 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
Enuresis.	2001	11480766
Tolterodine: a review of its use in the treatment of overactive bladder.	2001	11341475
Preformulation studies on the S-isomer of oxybutynin hydrochloride, an Improved Chemical Entity (ICE).	2001 Apr	11411899
Prospective randomized controlled trial of extended-release oxybutynin chloride and tolterodine tartrate in the treatment of overactive bladder: results of the OBJECT Study.	2001 Apr	11322350
Oxybutynin does not affect cyclosporin blood levels.	2001 Apr	11294516
Clinical experiences with tolterodine.	2001 Apr 27	11392625
Nocturnal enuresis.	2001 Aug	11483553
Cost-Effectiveness of tolterodine for patients with urge incontinence who discontinue initial therapy with oxybutynin: a Canadian perspective.	2001 Dec	11813937
Is tolterodine (Detrol) or oxybutynin (Ditropan) the best for treatment of urge urinary incontinence?	2001 Dec	11742595
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
Pharmacokinetics of the R- and S-enantiomers of oxybutynin and N-desethyloxybutynin following oral and transdermal administration of the racemate in healthy volunteers.	2001 Jul	11496941
Is extended-release oxybutynin (Ditropan XL) or tolterodine (Detrol) more effective in the treatment of an overactive bladder?	2001 Jul	11485700
Tolterodine versus oxybutynin in the treatment of urge urinary incontinence: a meta-analysis.	2001 Jul	11483904
A crossover randomized trial of transcutaneous electrical nerve stimulation and oxybutynin in patients with detrusor instability.	2001 Jul	11435843
A short-term, multicenter, randomized double-blind dose titration study of the efficacy and anticholinergic side effects of transdermal compared to immediate release oral oxybutynin treatment of patients with urge urinary incontinence.	2001 Jul	11435842
Effect of TAK-637, a tachykinin NK1-receptor antagonist, on lower urinary tract function in cats.	2001 Jun	11459118
Intravesical oxybutynin for treating incontinence resulting from an overactive detrusor.	2001 Jun	11412211
Effects of tolterodine, trospium chloride, and oxybutynin on the central nervous system.	2001 Jun	11402632
The effects of intravesical lidocaine on bladder dynamics of children with myelomeningocele.	2001 Jun	11371945
A semiparametric deconvolution model to establish in vivo-in vitro correlation applied to OROS oxybutynin.	2001 Jun	11357173
Clarification--Drug risk in patients with glaucoma.	2001 Jun 11	11417565
A comparison of the effects on saliva output of oxybutynin chloride and tolterodine tartrate.	2001 May	11394733
Muscarinic receptor binding characteristics in rat tissues after oral administration of oxybutynin and propiverine.	2001 May	11379767
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
Influence of pump compliance (peristaltic vs. infusion) on urodynamic measurement during cystometry in conscious rats.	2001 May-Jun	11755385
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
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
Is attempting suicide an adverse effect of oxybutynin in a child with enuresis nocturna?	2001 Oct	11673723
[Combined treatment of patients with detrusor instability].	2001 Sep-Oct	11641975
Oxybutynin intravesical--situs. I-oxy.	2002	12001822
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
Highlights of the 22nd French pharmacovigilance meeting.	2002 Feb	11985373
Enuresis.	2002 Feb	11846242
Once-daily, extended-release formulations of antimuscarinic agents in the treatment of overactive bladder: a review.	2002 Jan	11999467
Inappropriate medication prescribing in residential care/assisted living facilities.	2002 Jun	12110058
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
Urodynamic changes associated with behavioral and drug treatment of urge incontinence in older women.	2002 May	12028165
A dynamic mechanical method for determining the silicone elastomer solubility of drugs and pharmaceutical excipients in silicone intravaginal drug delivery rings.	2002 Sep	12109683
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.

Name

Type

Language

OXYBUTYNIN

Official Name

English

OXYBUTYNIN [HSDB]

Common Name

English

BENZENEACETIC ACID, .ALPHA.-CYCLOHEXYL-.ALPHA.-HYDROXY-, 4-(DIETHYLAMINO)-2-BUTYNYL ESTER

Common Name

English

4-(DIETHYLAMINO)-2-BUTYNYL .ALPHA.-PHENYLCYCLOHEXANEGLYCOLIC ACID ESTER

Common Name

English

OXYBUTYNIN [INN]

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

OXYBUTYNIN [USAN]

Common Name

English

OXYBUTYNIN [VANDF]

Common Name

English

KENTERA

Brand Name

English

OXYBUTYNIN [WHO-DD]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000000125