Oxybutynin Chloride

Details

Stereochemistry	RACEMIC
Molecular Formula	C22H31NO3.ClH
Molecular Weight	393.947
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CCN(CC)CC#CCOC(=O)C(O)(C1CCCCC1)C2=CC=CC=C2

InChI

InChIKey=SWIJYDAEGSIQPZ-UHFFFAOYSA-N

InChI=1S/C22H31NO3.ClH/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;1H

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
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 2778	8.1 nM [Ki]
Muscarinic acetylcholine receptor M1 169 Target ID: CHEMBL216 Sources: http://www.drugbank.ca/drugs/DB01062	Antagonist 2778	1.0 nM [Ki]
Muscarinic acetylcholine receptor M3 159 Target ID: CHEMBL245 Sources: http://www.drugbank.ca/drugs/DB01062	Antagonist 2778	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 8429	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 1737 inhibitor 1587	inhibitor 1767 substrate 1037	substrate 1217 inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCT1 512 OCT2 647 OCT3 150 CYP1A 72 CYP2A6 707 CYP2E1 882 BSEP 402 K+ channels 70 L-type Ca2+ channels 28	P-gp 1537 OCT1 327 OCT2 355 OCT3 80 CYP2B6 664 CYP2C8 693 CYP2E1 667 CYP2C19 991 CYP3A5 395

Drug as perpetrator

Target	Modality	Activity
CYP1A 121	inhibitor 3277 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1600-0773.1998.tb01418.x Page: 164.0	no
CYP2A6 739	inhibitor 3277 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1600-0773.1998.tb01418.x Page: 164.0	no
CYP2C9 1819	inhibitor 3277 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1600-0773.1998.tb01418.x Page: 164.0	no
CYP2E1 970	inhibitor 3277 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1600-0773.1998.tb01418.x Page: 164.0	no
OCT2 648	inhibitor 3277 Sources: https://link.springer.com/content/pdf/10.1007/s00210-010-0590-x.pdf Page: 205.0	yes [IC50 128 uM]
OCT3 150	inhibitor 3277 Sources: https://link.springer.com/content/pdf/10.1007/s00210-010-0590-x.pdf Page: 205.0	yes [IC50 130 uM]
OCT1 543	inhibitor 3277 Sources: https://link.springer.com/content/pdf/10.1007/s00210-010-0590-x.pdf Page: 205.0	yes [IC50 20 uM]
BSEP 403	inhibitor 3277 Sources: https://academic.oup.com/toxsci/article/118/2/485/1652105 Page: 496.0	yes [IC50 27.4 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1600-0773.1998.tb01418.x Page: abstract	yes [IC50 7.7 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1600-0773.1998.tb01418.x Page: abstract	yes [IC50 9.5 uM]
K+ channels 70	inhibitor 3277 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 3277 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 1737	substrate 3367 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 664	substrate 3367 Sources: https://europepmc.org/article/med/9825837 Page: 451.0	no
CYP2C19 991	substrate 3367 Sources: https://www.tandfonline.com/doi/abs/10.1080/00498250600976088 Page: abstract	no
CYP2C8 693	substrate 3367 Sources: https://europepmc.org/article/med/9825837 Page: 451.0	no
CYP2C9 1037	substrate 3367 Sources: https://www.tandfonline.com/doi/abs/10.1080/00498250600976088 Page: abstract	no
CYP2D6 1217	substrate 3367 Sources: https://europepmc.org/article/med/9825837 Page: abstract	no
CYP2E1 667	substrate 3367 Sources: https://europepmc.org/article/med/9825837 Page: 451.0	no
CYP3A5 395	substrate 3367 Sources: https://www.tandfonline.com/doi/abs/10.1080/00498250600976088 Page: abstract	no
P-gp 1537	substrate 3367 Sources: https://bpspubs.onlinelibrary.wiley.com/doi/abs/10.1111/j.1365-2125.2011.03961.x Page: 235.0	no
OCT1 327	substrate 3367 Sources: https://link.springer.com/content/pdf/10.1007/s00210-010-0590-x.pdf Page: 206.0	yes
OCT2 355	substrate 3367 Sources: https://link.springer.com/content/pdf/10.1007/s00210-010-0590-x.pdf Page: 206.0	yes
OCT3 80	substrate 3367 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 1647	inhibitor 1626 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
Propiverine-induced Parkinsonism: a case report and a pharmacokinetic/pharmacodynamic study in mice.	2000 May	10888308
Costs and resources associated with the treatment of overactive bladder using retrospective medical care claims data.	2001 Aug	11517841
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
Urethral catheterization in hypospadias surgery: Should the device enter the bladder or be made a urethral stent?	2001 Dec	11733916
Oxybutynin, desmopressin and enuresis.	2001 Dec	11696812
Psychological improvements associated with behavioral and drug treatment of urge incontinence in older women.	2001 Jan	11192337
[Results of a therapeutic strategy against monosymptomatic nocturnal enuresis].	2001 Jan	11181193
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 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
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
Clarification--Drug risk in patients with glaucoma.	2001 Jun 11	11417565
Use of tolterodine in children with dysfunctional voiding: an initial report.	2001 Mar	11176516
A comparison of the effects on saliva output of oxybutynin chloride and tolterodine tartrate.	2001 May	11394733
Which muscarinic receptor is important in the bladder?	2001 Nov	11760777
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
[Combined treatment of patients with detrusor instability].	2001 Sep-Oct	11641975
Enuresis.	2002 Feb	11846242
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
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
Preliminary study of the safety and efficacy of extended-release oxybutynin in children.	2002 Mar	11880086
The management of urinary incontinence in the exstrophy complex, posterior urethral valves, and infrasphincteric ureters.	2002 May	11973765
Treatment can lead to a long dry spell.	2002 Spring	11974567

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 `Fri Dec 15 16:42:46 GMT 2023` Edited by `admin` on `Fri Dec 15 16:42:46 GMT 2023`
Record UNII	L9F3D9RENQ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Oxybutynin Chloride

Official Name

English

TROPAX

Brand Name

English

OXYBUTYNIN CHLORIDE [USP-RS]

Common Name

English

OXYBUTYNIN HYDROCHLORIDE [EP MONOGRAPH]

Common Name

English

OXYBUTYNIN HYDROCHLORIDE [MART.]

Common Name

English

Oxybutynin hydrochloride [WHO-DD]

Common Name

English

OXYBUTYNIN HYDROCHLORIDE [MI]

Common Name

English

OXYBUTYNIN CHLORIDE [USP IMPURITY]

Common Name

English

OXYBUTYNIN CHLORIDE [ORANGE BOOK]

Common Name

English

OXYBUTYNIN HYDROCHLORIDE [USP IMPURITY]

Common Name

English

NSC-759108

Code

English

OXYBUTYNIN HYDROCHLORIDE

Common Name

English

POLLAKISU

Brand Name

English

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

Systematic Name

English

MJ-4309-1

Code

English

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

Systematic Name

English

OXYBUTYNIN HYDROCHLORIDE [JAN]

Common Name

English

OXYBUTYNIN CHLORIDE [USAN]

Common Name

English

MJ 4309-1

Code

English

OXYBUTYNIN CHLORIDE [VANDF]

Common Name

English

DITROPAN

Common Name

English

OXYBUTYNIN CHLORIDE [USP MONOGRAPH]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29704