SOLIFENACIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H26N2O2
Molecular Weight	362.4656
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

c1ccc(cc1)[C@@]2([H])c3ccccc3CCN2C(=O)O[C@@]4([H])CN5CCC4CC5

InChI

InChIKey=FBOUYBDGKBSUES-VXKWHMMOSA-N

InChI=1S/C23H26N2O2/c26-23(27-21-16-24-13-10-18(21)11-14-24)25-15-12-17-6-4-5-9-20(17)22(25)19-7-2-1-3-8-19/h1-9,18,21-22H,10-16H2/t21-,22-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C23H26N2O2
Molecular Weight	362.4656
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021518s016lbl.pdf
Curator's Comment:: http://www.wikidoc.org/index.php/Solifenacin

Solifenacin is a competitive muscarinic acetylcholine receptor antagonist. The binding of acetylcholine to these receptors, particularly the M3 receptor subtype, plays a critical role in the contraction of smooth muscle. By preventing the binding of acetylcholine to these receptors, solifenacin reduces smooth muscle tone in the bladder, allowing the bladder to retain larger volumes of urine. It is FDA approved for the treatment of overactive bladder with symptoms of urge urinary incontinence, urgency, and urinary frequency. Common adverse reactions include constipation, Xerostomia. Inhibitors of CYP3A4 may increase the concentration of Solifenacin. Vice versa, CYP3A4 Inducers decrease concentration.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Muscarinic acetylcholine receptor M3 150 Target ID: CHEMBL245 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021518s016lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/15190387 \| https://www.ncbi.nlm.nih.gov/pubmed/16465186 \| https://www.ncbi.nlm.nih.gov/pubmed/19446545 \| https://www.ncbi.nlm.nih.gov/pubmed/19029429 \| http://www.drugbank.ca/drugs/DB01591	Antagonist 2577	Overactive bladder with symptoms of urge urinary incontinence, urgency, and urinary frequency	10 nM [Ki]
Muscarinic acetylcholine receptor M2 114 Target ID: CHEMBL211 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021518s016lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/16465186 \| https://www.ncbi.nlm.nih.gov/pubmed/19446545 \| https://www.ncbi.nlm.nih.gov/pubmed/19029429 \| http://www.drugbank.ca/drugs/DB01591	Antagonist 2577		125 nM [Ki]
Muscarinic acetylcholine receptor M1 160 Target ID: CHEMBL216 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021518s016lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/16465186 \| https://www.ncbi.nlm.nih.gov/pubmed/19029429 \| http://www.drugbank.ca/drugs/DB01591	Antagonist 2577		25 nM [Ki]
Muscarinic acetylcholine receptor M4 77 Target ID: CHEMBL1821 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021518s016lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/19029429 \| http://www.drugbank.ca/drugs/DB01591	Antagonist 2577		7.73000000000000043 null [pKi]
Muscarinic acetylcholine receptor M5 55 Target ID: CHEMBL2035 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021518s016lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/19029429 \| http://www.drugbank.ca/drugs/DB01591	Antagonist 2577		7.45999999999999996 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Overactive bladder with symptoms of urge urinary incontinence, urgency, and urinary frequency 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021518s016lbl.pdf	Primary	Muscarinic acetylcholine receptor M3	Approved 7997	VESICARE Approved Use VESIcare is a muscarinic antagonist indicated for the treatment of overactive bladder with symptoms of urge urinary incontinence, urgency, and urinary frequency. VESIcare is a muscarinic antagonist indicated for the treatment of overactive bladder with symptoms of urge urinary incontinence, urgency, and urinary frequency (1) Launch Date 1100822400000

C_max

Value	Dose	Co-administered	Analyte	Population
14.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15206986	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		SOLIFENACIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
820 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15206986	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		SOLIFENACIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
50.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15206986	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		SOLIFENACIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
2% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021518s012lbl.pdf			SOLIFENACIN plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
100 mg single, oral Highest studied dose Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://pubmed.ncbi.nlm.nih.gov/15317830	healthy, 19-40 Health Status: healthy Age Group: 19-40 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/15317830	Sources: https://pubmed.ncbi.nlm.nih.gov/15317830
30 mg 1 times / day multiple, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: multiple Dose: 30 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15317830	healthy, 20-35 Health Status: healthy Age Group: 20-35 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/15317830	Sources: https://pubmed.ncbi.nlm.nih.gov/15317830
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021518s012lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021518s012lbl.pdf	Disc. AE: Dry mouth... AEs leading to discontinuation/dose reduction: Dry mouth (1.5%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021518s012lbl.pdf
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021518s012lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021518s012lbl.pdf	Disc. AE: Angioedema, Anaphylactic reaction... AEs leading to discontinuation/dose reduction: Angioedema Anaphylactic reaction (rare) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021518s012lbl.pdf

AEs

AE	Significance	Dose	Population
Dry mouth	1.5% Disc. AE	10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021518s012lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021518s012lbl.pdf
Angioedema	Disc. AE	10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021518s012lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021518s012lbl.pdf
Anaphylactic reaction	rare Disc. AE	10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021518s012lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021518s012lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1470 inhibitor 1172	inhibitor 1318	substrate 1038 inhibitor 1421	inhibitor 1360

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A 66 CYP2C19 1215	CYP2C19 830 CYP3A5 346 CYP2C8 586 CYP1A1 302 P-gp 1223

Drug as perpetrator

Target	Modality	Activity
CYP1A 105	inhibitor 2614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-518_VESIcare_biopharmr.pdf#page=51 Page: 51	not significant
CYP2C9 1362	inhibitor 2614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-518_VESIcare_biopharmr.pdf#page=51 Page: 51	not significant
CYP2D6 1455	inhibitor 2614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-518_VESIcare_biopharmr.pdf#page=51 Page: 51	not significant
CYP3A4 1462	inhibitor 2614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-518_VESIcare_biopharmr.pdf#page=51 Page: 51	not significant
CYP2C19 1277	inhibitor 2614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-518_VESIcare_biopharmr.pdf#page=51 Page: 51	yes [Inhibition 1.04 uM]

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP3A4 1470	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-518_VESIcare_biopharmr.pdf#page=22 Page: 22,52	major	yes (co-administration study) Comment: Label: coadministration with ketoconazole increased the mean Cmax and AUC of solifenacin by 1.5 and 2.7 fold, respectively; Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-518_VESIcare_biopharmr.pdf#page=22 Page: 22,52
CYP1A1 302	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-518_VESIcare_biopharmr.pdf#page=27 Page: 27	minor
CYP2C19 830	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-518_VESIcare_biopharmr.pdf#page=22 Page: 22,27	minor
CYP2C8 586	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-518_VESIcare_biopharmr.pdf#page=27 Page: 27	minor
CYP2D6 1038	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-518_VESIcare_biopharmr.pdf#page=27 Page: 27	minor
CYP3A5 346	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-518_VESIcare_biopharmr.pdf#page=27 Page: 27	minor
P-gp 1223	substrate 2752 Sources: https://bpspubs.onlinelibrary.wiley.com/doi/full/10.1111/j.1365-2125.2011.03961.x	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1392	inhibitor 1374 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-518_VESIcare_pharmr.pdf#page=35 Page: 35

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P0022GR
1PlusChem LLC	1P0039KH
1PlusChem LLC	1P019G9F
A2B Chem	AB51569
AChemBlock	L14551
AK Scientific	4058AH
AK Scientific	E476
AK Scientific	X4689
APExBIO	B1614
APExBIO	B3415
AbovChem LLC	HY-A0002
AbovChem LLC	HY-I0230
Alfa Chemistry	ACM242478371
Alfa Chemistry	ACM242478382
Ambeed	A284622
Angene	AGN-PC-0QBT0V
Angene	AGN-PC-0R0471
AsisChem	F36099
AstaTech	43238
AstaTech	C15135
BLDpharm	BD630474
BOC Sciences	180272-14-4
BOC Sciences	180468-39-7
BOC Sciences	242478-37-1
BOC Sciences	242478-38-2
Bide Pharmatech	BD32830
BioSynth	Q-101001
Capot Chemical	18822
Capot Chemical	20236
Capot Chemical	23264
Cayman Chemical	17320
Chem Scene	CS-0371
Chem Scene	CS-2661
Chem Scene	CS-8096
ChemShuttle	151802
ChemShuttle	157653
Compound Cloud	154059
Compound Cloud	216457
Debye Scientific	DB-001095
Enamine	EN300-717929
Hairui	HR112258
Hairui	HR134394
Hangzhou APIChem Technology	AC-25547
Hangzhou APIChem Technology	AC-747
Hangzhou Yuhao Chemical Technology	LX2069
Hangzhou Yuhao Chemical Technology	RT1781
Hangzhou Yuhao Chemical Technology	YH48847
HongKong Chemhere	180272-14-4
HongKong Chemhere	242478-37-1
HongKong Chemhere	869883-94-3
Innovapharm	VT-00687740
KeyOrganics	AS-12203
KeyOrganics	KS-1286
KeyOrganics	KS-5151
Lab Network	LN01341781
Lab Network	LN01345685
Lab Seeker	SC-80641
Lan Pharmatech	LQT-B00166
Lan Pharmatech	LQT-B00167
MedChem Express	HY-A0002
MedChem Express	HY-A0034
MedChem Express	HY-I0230
MolPort	MolPort-003-850-267
MolPort	MolPort-003-850-268
MolPort	MolPort-009-682-972
MolPort	MolPort-019-879-477
MolPort	MolPort-019-994-559
MolPort	MolPort-046-702-220
Molnova	M13700
MuseChem	M033958
MuseChem	R006276
MuseChem	R032067
PI Chemicals	PI-37169
PI Chemicals	PI-44884
Ryan Scientific	N-Acetyl-5-hydroxytryptamine
Selleck Chemicals	S3048
Selleck Chemicals	S5238
Sigma Aldrich	1615300
Sigma Aldrich	SML2141
Sigma Aldrich	Y0001743
Sigma Aldrich	Y0001763
StruChem	SC-80641
TargetMol	T0111
Tetrahedron	TS39419
Toronto Research Chemicals	S676690
Toronto Research Chemicals	S676700
Toronto Research Chemicals	S676701
Wonderchem	WD05G48
ZINC	ZINC000003936683	http://zinc15.docking.org/substances/ZINC000003936683
eMolecules	108759532
eMolecules	109650126
eMolecules	194915769
eMolecules	275073346
eMolecules	295312236
eMolecules	300560146
eMolecules	300673555
eMolecules	302063966
eMolecules	31590100
eMolecules	36557597
eMolecules	36754570
eMolecules	42855408
eMolecules	44841303
eMolecules	44841361
eMolecules	46009091
eMolecules	48669860
eMolecules	54868984
eMolecules	56967898
eMolecules	95704289
eNovation Chemicals	D572921
mcule	MCULE-1195195653
mcule	MCULE-1251772081
mcule	MCULE-2516231954
mcule	MCULE-4130479181
mcule	MCULE-9865563965

PubMed

Title	Date	PubMed
Drug treatment of overactive bladder: efficacy, cost and quality-of-life considerations.	2004	15257626
Solifenacin appears effective and well tolerated in patients with symptomatic idiopathic detrusor overactivity in a placebo- and tolterodine-controlled phase 2 dose-finding study.	2004 Jan	14678372
In vitro and in vivo tissue selectivity profile of solifenacin succinate (YM905) for urinary bladder over salivary gland in rats.	2004 May 25	15178371
Pharmacokinetics and safety of solifenacin succinate in healthy young men.	2004 Sep	15317830
[Neurological aspect of the hyperactive urinary bladder syndrome].	2005	16117151
Improved quality of life in patients with overactive bladder symptoms treated with solifenacin.	2005 Jan	15638900
Role of muscarinic receptor antagonists in urgency and nocturia.	2005 Sep	16083453
Gateways to clinical trials.	2006 Apr	16810345
Multiple doses of the antimuscarinic agent solifenacin do not affect the pharmacodynamics or pharmacokinetics of warfarin or the steady-state pharmacokinetics of digoxin in healthy subjects.	2006 Aug	16842396
Muscarinic receptors in the bladder: from basic research to therapeutics.	2006 Feb	16465186
New drugs 06, part I.	2006 Feb	16462265
[Comment on the STAR study: Comparison of the efficacy and tolerance of solifenacin and tolterodine retard in the treatment of overactive bladder].	2006 Jul	16816976
Solifenacin: as effective in mixed urinary incontinence as in urge urinary incontinence.	2006 Jun	16283422
Efficacy and tolerability of solifenacin in elderly subjects with overactive bladder syndrome: a pooled analysis.	2006 Mar	16730617
Pharmacologic management of overactive bladder: practical options for the primary care physician.	2006 Mar	16483865
Efficacy and tolerability of solifenacin in elderly subjects with overactive bladder syndrome: A pooled analysis.	2006 Sep	17062331
Pharmacokinetics, safety, and tolerability of solifenacin in patients with renal insufficiency.	2007 Jan	17251687

Patents

Sample Use Guides

In Vivo Use Guide

5 mg tablet taken once daily, and if well tolerated may be increased to 10 mg once daily.

Route of Administration: Oral

In Vitro Use Guide

The inhibitory effect of solifenacin (dose range: 10^-10 - 10^-6 M) for bladder smooth muscle cells (pK(i)=8.12) was 3.6-fold more potent than that for salivary gland cells (pK(i)=7.57).

Substance Class	Chemical Created by `admin` on `Fri Jun 25 22:09:49 UTC 2021` Edited by `admin` on `Fri Jun 25 22:09:49 UTC 2021`
Record UNII	A8910SQJ1U
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SOLIFENACIN

Official Name

English

SOLIFENACIN [INN]

Common Name

English

NSC-759144

Code

English

SOLIFENACIN [MI]

Common Name

English

SOLIFENACIN [WHO-DD]

Common Name

English

SOLIFENACIN [VANDF]

Common Name

English

Classification Tree Code System Code

WHO-ATC

G04CA53