OXYBUTYNIN XINAFOATE

Details

Stereochemistry	RACEMIC
Molecular Formula	C22H31NO3.C11H8O3
Molecular Weight	545.6671
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.c1ccc2c(c1)ccc(c2O)C(=O)O

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	C22H31NO3
Molecular Weight	357.4873
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Molecular Formula	C11H8O3
Molecular Weight	188.1798
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 49 Target ID: CHEMBL211 Sources: http://www.drugbank.ca/drugs/DB01062	Antagonist 1131	8.1 nM [Ki]
Muscarinic acetylcholine receptor M1 78 Target ID: CHEMBL216 Sources: http://www.drugbank.ca/drugs/DB01062	Antagonist 1131	1.0 nM [Ki]
Muscarinic acetylcholine receptor M3 73 Target ID: CHEMBL245 Sources: http://www.drugbank.ca/drugs/DB01062	Antagonist 1131	0.78 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Overactive bladder 16 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/017577s034,018211s017,020897s018lbl.pdf	Primary		Approved 4033	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 882 inhibitor 753	inhibitor 825 substrate 530	substrate 610 inhibitor 894	inhibitor 775

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCT1 254 OCT2 297 OCT3 82 CYP1A 38 CYP2A6 334 CYP2E1 424 BSEP 185 K+ channels 23 L-type Ca2+ channels 14	P-gp 724 OCT1 158 OCT2 157 OCT3 39 CYP2B6 338 CYP2C8 354 CYP2E1 332 CYP2C19 500 CYP3A5 203

Drug as perpetrator

Target	Modality	Activity
CYP1A 63	inhibitor 1612 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1600-0773.1998.tb01418.x Page: 164.0	no
CYP2A6 356	inhibitor 1612 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1600-0773.1998.tb01418.x Page: 164.0	no
CYP2C9 851	inhibitor 1612 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1600-0773.1998.tb01418.x Page: 164.0	no
CYP2E1 467	inhibitor 1612 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1600-0773.1998.tb01418.x Page: 164.0	no
OCT2 298	inhibitor 1612 Sources: https://link.springer.com/content/pdf/10.1007/s00210-010-0590-x.pdf Page: 205.0	yes [IC50 128 uM]
OCT3 82	inhibitor 1612 Sources: https://link.springer.com/content/pdf/10.1007/s00210-010-0590-x.pdf Page: 205.0	yes [IC50 130 uM]
OCT1 266	inhibitor 1612 Sources: https://link.springer.com/content/pdf/10.1007/s00210-010-0590-x.pdf Page: 205.0	yes [IC50 20 uM]
BSEP 186	inhibitor 1612 Sources: https://academic.oup.com/toxsci/article/118/2/485/1652105 Page: 496.0	yes [IC50 27.4 uM]
CYP3A4 920	inhibitor 1612 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1600-0773.1998.tb01418.x Page: abstract	yes [IC50 7.7 uM]
CYP2D6 908	inhibitor 1612 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1600-0773.1998.tb01418.x Page: abstract	yes [IC50 9.5 uM]
K+ channels 23	inhibitor 1612 Sources: https://journals.lww.com/cardiovascularpharm/Fulltext/2000/02000/Analysis_of_the_Electrophysiologic_Effects_of.24.aspx Page: abstract	yes
L-type Ca2+ channels 15	inhibitor 1612 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 882	substrate 1689 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 338	substrate 1689 Sources: https://europepmc.org/article/med/9825837 Page: 451.0	no
CYP2C19 500	substrate 1689 Sources: https://www.tandfonline.com/doi/abs/10.1080/00498250600976088 Page: abstract	no
CYP2C8 354	substrate 1689 Sources: https://europepmc.org/article/med/9825837 Page: 451.0	no
CYP2C9 530	substrate 1689 Sources: https://www.tandfonline.com/doi/abs/10.1080/00498250600976088 Page: abstract	no
CYP2D6 610	substrate 1689 Sources: https://europepmc.org/article/med/9825837 Page: abstract	no
CYP2E1 332	substrate 1689 Sources: https://europepmc.org/article/med/9825837 Page: 451.0	no
CYP3A5 203	substrate 1689 Sources: https://www.tandfonline.com/doi/abs/10.1080/00498250600976088 Page: abstract	no
P-gp 724	substrate 1689 Sources: https://bpspubs.onlinelibrary.wiley.com/doi/abs/10.1111/j.1365-2125.2011.03961.x Page: 235.0	no
OCT1 158	substrate 1689 Sources: https://link.springer.com/content/pdf/10.1007/s00210-010-0590-x.pdf Page: 206.0	yes
OCT2 157	substrate 1689 Sources: https://link.springer.com/content/pdf/10.1007/s00210-010-0590-x.pdf Page: 206.0	yes
OCT3 39	substrate 1689 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 796	inhibitor 786 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
Combined pharmacotherapy for nocturnal enuresis.	2001 Aug	11519898
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
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
Intravesical treatment of bladder dysfunction.	2001 Dec	11696743
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
Effect of TAK-637, a tachykinin NK1-receptor antagonist, on lower urinary tract function in cats.	2001 Jun	11459118
Influence of pump compliance (peristaltic vs. infusion) on urodynamic measurement during cystometry in conscious rats.	2001 May-Jun	11755385
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
Tolterodine: an overview.	2001 Nov	11760779
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
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
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
S-oxybutynin.	2002	12001823
Tolterodine: selectivity for the urinary bladder over the eye (as measured by visual accommodation) in healthy volunteers.	2002	12001821
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
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
Urinary antispasmodic use and the risks of ventricular arrhythmia and sudden death in older patients.	2002 Jan	12028256
A long-term follow-up of autoaugmentation in myelodysplastic children.	2002 Jun	12010242
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
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
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
Overactive bladder patients and role of the pharmacist.	2002 May-Jun	12030634
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

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 `Sat Jun 26 03:07:56 UTC 2021` Edited by `admin` on `Sat Jun 26 03:07:56 UTC 2021`
Record UNII	7425U24ZN4
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OXYBUTYNIN XINAFOATE

Common Name

English

2-NAPHTHALENECARBOXYLIC ACID, 1-HYDROXY-, COMPD. WITH 4-(DIETHYLAMINO)-2-BUTYN-1-YL .ALPHA.-CYCLOHEXYL-.ALPHA.-HYDROXYBENZENEACETATE (1:1)

Systematic Name

English

Code System Code Type Description

FDA UNII

7425U24ZN4

Created by admin on Sat Jun 26 03:07:56 UTC 2021 , Edited by admin on Sat Jun 26 03:07:56 UTC 2021

PRIMARY

CAS

1447998-30-2

Created by admin on Sat Jun 26 03:07:56 UTC 2021 , Edited by admin on Sat Jun 26 03:07:56 UTC 2021

PRIMARY

PUBCHEM

53477276

Created by admin on Sat Jun 26 03:07:56 UTC 2021 , Edited by admin on Sat Jun 26 03:07:56 UTC 2021

PRIMARY

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OXYBUTYNIN

PARENT -> SALT/SOLVATE

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OXYBUTYNIN

ACTIVE MOIETY

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