U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C23H26N2O2
Molecular Weight 362.4647
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SOLIFENACIN

SMILES

O=C(O[C@H]1CN2CCC1CC2)N3CCC4=CC=CC=C4[C@@H]3C5=CC=CC=C5

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 362.4647
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including: http://www.rxlist.com/vesicare-drug.htm https://www.drugs.com/mtm/solifenacin.html 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

Curator's Comment: Known to be CNS penetrant in rat. Human data not available

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
10.0 nM [Ki]
125.0 nM [Ki]
25.0 nM [Ki]
7.73 null [pKi]
7.46 null [pKi]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

2004
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
14.1 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
820 ng × h/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
50.8 h
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
2%
SOLIFENACIN plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
100 mg single, oral
Highest studied dose
Dose: 100 mg
Route: oral
Route: single
Dose: 100 mg
Sources: Page: p.1028
healthy, 19-40
n = 6
Health Status: healthy
Age Group: 19-40
Sex: M
Population Size: 6
Sources: Page: p.1028
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: Page: p.1029
healthy, 20-35
n = 8
Health Status: healthy
Age Group: 20-35
Sex: M
Population Size: 8
Sources: Page: p.1029
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: Page: p.4
unhealthy
n = 1233
Health Status: unhealthy
Condition: Overactive bladder
Population Size: 1233
Sources: Page: p.4
Disc. AE: Dry mouth...
AEs leading to
discontinuation/dose reduction:
Dry mouth (1.5%)
Sources: Page: p.4
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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Overactive bladder
Sources: Page: p.1
Disc. AE: Angioedema, Anaphylactic reaction...
AEs leading to
discontinuation/dose reduction:
Angioedema
Anaphylactic reaction (rare)
Sources: Page: p.1
AEs

AEs

AESignificanceDosePopulation
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: Page: p.4
unhealthy
n = 1233
Health Status: unhealthy
Condition: Overactive bladder
Population Size: 1233
Sources: Page: p.4
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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Overactive bladder
Sources: Page: p.1
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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Overactive bladder
Sources: Page: p.1
Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Gateways to clinical trials.
2003 Jul-Aug
Gateways to clinical trials.
2003 Jun
Solifenacin: treatment of overactive bladder.
2004 Apr
Gateways to clinical trials.
2004 Dec
Randomized, double-blind placebo- and tolterodine-controlled trial of the once-daily antimuscarinic agent solifenacin in patients with symptomatic overactive bladder.
2004 Feb
Comparison of in vitro selectivity profiles of solifenacin succinate (YM905) and current antimuscarinic drugs in bladder and salivary glands: a Ca2+ mobilization study in monkey cells.
2004 Jan 2
Food does not affect the pharmacokinetics of solifenacin, a new muscarinic receptor antagonist: results of a randomized crossover trial.
2004 Jul
[In overactive bladder, above all urgency is stressful. The patients know the site of each toilet].
2004 May 27
Gateways to clinical trials.
2004 Nov
The emerging role of solifenacin in the treatment of overactive bladder.
2004 Oct
Solifenacin in overactive bladder syndrome: a viewpoint by Scott Serels.
2005
[Neurological aspect of the hyperactive urinary bladder syndrome].
2005
Solifenacin and darifenacin for overactive bladder.
2005 Aug
Improved quality of life in patients with overactive bladder symptoms treated with solifenacin.
2005 Jan
[Medical therapy of urinary incontinence].
2005 Jan
New drugs: acamprosate calcium and solifenacin succinate.
2005 Jan-Feb
Darifenacin in the treatment of overactive bladder.
2005 Jul
New treatment options for overactive bladder.
2005 Jun
Effect of age on the pharmacokinetics of solifenacin in men and women.
2005 May
[Drug discovery in the fields of urology: tamsulosin and solifenacin].
2005 Nov
Synthesis and antimuscarinic properties of quinuclidin-3-yl 1,2,3,4-tetrahydroisoquinoline-2-carboxylate derivatives as novel muscarinic receptor antagonists.
2005 Oct 20
Solifenacin is effective for the treatment of OAB dry patients: a pooled analysis.
2005 Sep
Solifenacin in overactive bladder syndrome.
2006
The causes and consequences of overactive bladder.
2006 Apr
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
[Pharmacological and clinical profile of solifenacin succinate (Vesicare) developed as a new therapeutic agent for overactive bladder].
2006 Dec
Pharmacoeconomic evaluation of antimuscarinic agents for the treatment of overactive bladder.
2006 Dec
Solifenacin provides effective antimuscarinic therapy for the complete management of overactive bladder.
2006 Dec
Newer agents for the management of overactive bladder.
2006 Dec 15
Muscarinic receptors in the bladder: from basic research to therapeutics.
2006 Feb
New drugs 06, part I.
2006 Feb
Efficacy of solifenacin in patients with severe symptoms of overactive bladder: a pooled analysis.
2006 Jan
Re: Chapple CR, Martinez-Garcia R, Selvaggi L, Toozs-Hobson P, Warnack W, Drogendijk T, Wright DM, Bolodeoku J. A comparison of the efficacy and tolerability of solifenacin succinate and extended release tolterodine at treating overactive bladder syndrome: results of the STAR trial. Eur Urol 2005;48:464-70.
2006 Jan
[Comment on the STAR study: Comparison of the efficacy and tolerance of solifenacin and tolterodine retard in the treatment of overactive bladder].
2006 Jul
Short- and long-term efficacy of solifenacin treatment in patients with symptoms of mixed urinary incontinence.
2006 Jun
Efficacy and tolerability of solifenacin in elderly subjects with overactive bladder syndrome: a pooled analysis.
2006 Mar
Gateways to clinical trials.
2006 May
Reductions in overactive bladder-related incontinence from pooled analysis of phase III trials evaluating treatment with solifenacin.
2006 Sep
Pharmacokinetics, safety, and tolerability of solifenacin in patients with renal insufficiency.
2007 Jan
Pharmacological characterization of a new antimuscarinic agent, solifenacin succinate, in comparison with other antimuscarinic agents.
2007 Jan
Solifenacin for overactive bladder with incontinence: symptom bother and health-related quality of life outcomes.
2007 Mar
An unusual cause of postoperative detrusor overactivity.
2007 Oct
Patents

Sample Use Guides

5 mg tablet taken once daily, and if well tolerated may be increased to 10 mg once daily.
Route of Administration: Oral
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 Dec 15 16:26:35 GMT 2023
Edited
by admin
on Fri Dec 15 16:26:35 GMT 2023
Record UNII
A8910SQJ1U
Record Status Validated (UNII)
Record Version
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Name Type Language
SOLIFENACIN
INN   MI   VANDF   WHO-DD  
INN  
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
Created by admin on Fri Dec 15 16:26:35 GMT 2023 , Edited by admin on Fri Dec 15 16:26:35 GMT 2023
NDF-RT N0000000125
Created by admin on Fri Dec 15 16:26:35 GMT 2023 , Edited by admin on Fri Dec 15 16:26:35 GMT 2023
WHO-ATC G04BD08
Created by admin on Fri Dec 15 16:26:35 GMT 2023 , Edited by admin on Fri Dec 15 16:26:35 GMT 2023
NDF-RT N0000000125
Created by admin on Fri Dec 15 16:26:35 GMT 2023 , Edited by admin on Fri Dec 15 16:26:35 GMT 2023
WHO-VATC QG04CA53
Created by admin on Fri Dec 15 16:26:35 GMT 2023 , Edited by admin on Fri Dec 15 16:26:35 GMT 2023
LIVERTOX NBK548716
Created by admin on Fri Dec 15 16:26:35 GMT 2023 , Edited by admin on Fri Dec 15 16:26:35 GMT 2023
NDF-RT N0000000125
Created by admin on Fri Dec 15 16:26:35 GMT 2023 , Edited by admin on Fri Dec 15 16:26:35 GMT 2023
WHO-VATC QG04BD08
Created by admin on Fri Dec 15 16:26:35 GMT 2023 , Edited by admin on Fri Dec 15 16:26:35 GMT 2023
NCI_THESAURUS C29704
Created by admin on Fri Dec 15 16:26:35 GMT 2023 , Edited by admin on Fri Dec 15 16:26:35 GMT 2023
NDF-RT N0000175700
Created by admin on Fri Dec 15 16:26:35 GMT 2023 , Edited by admin on Fri Dec 15 16:26:35 GMT 2023
Code System Code Type Description
RXCUI
322167
Created by admin on Fri Dec 15 16:26:35 GMT 2023 , Edited by admin on Fri Dec 15 16:26:35 GMT 2023
PRIMARY
MESH
C441209
Created by admin on Fri Dec 15 16:26:35 GMT 2023 , Edited by admin on Fri Dec 15 16:26:35 GMT 2023
PRIMARY
LACTMED
Solifenacin
Created by admin on Fri Dec 15 16:26:35 GMT 2023 , Edited by admin on Fri Dec 15 16:26:35 GMT 2023
PRIMARY
MERCK INDEX
m10108
Created by admin on Fri Dec 15 16:26:35 GMT 2023 , Edited by admin on Fri Dec 15 16:26:35 GMT 2023
PRIMARY Merck Index
INN
8155
Created by admin on Fri Dec 15 16:26:35 GMT 2023 , Edited by admin on Fri Dec 15 16:26:35 GMT 2023
PRIMARY
DRUG CENTRAL
2457
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PRIMARY
DRUG BANK
DB01591
Created by admin on Fri Dec 15 16:26:35 GMT 2023 , Edited by admin on Fri Dec 15 16:26:35 GMT 2023
PRIMARY
SMS_ID
100000084906
Created by admin on Fri Dec 15 16:26:35 GMT 2023 , Edited by admin on Fri Dec 15 16:26:35 GMT 2023
PRIMARY
EVMPD
SUB21589
Created by admin on Fri Dec 15 16:26:35 GMT 2023 , Edited by admin on Fri Dec 15 16:26:35 GMT 2023
PRIMARY
EPA CompTox
DTXSID3048289
Created by admin on Fri Dec 15 16:26:35 GMT 2023 , Edited by admin on Fri Dec 15 16:26:35 GMT 2023
PRIMARY
CAS
242478-37-1
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PRIMARY
IUPHAR
7483
Created by admin on Fri Dec 15 16:26:35 GMT 2023 , Edited by admin on Fri Dec 15 16:26:35 GMT 2023
PRIMARY
ChEMBL
CHEMBL1734
Created by admin on Fri Dec 15 16:26:35 GMT 2023 , Edited by admin on Fri Dec 15 16:26:35 GMT 2023
PRIMARY
NSC
759144
Created by admin on Fri Dec 15 16:26:35 GMT 2023 , Edited by admin on Fri Dec 15 16:26:35 GMT 2023
PRIMARY
DAILYMED
A8910SQJ1U
Created by admin on Fri Dec 15 16:26:35 GMT 2023 , Edited by admin on Fri Dec 15 16:26:35 GMT 2023
PRIMARY
NCI_THESAURUS
C75284
Created by admin on Fri Dec 15 16:26:35 GMT 2023 , Edited by admin on Fri Dec 15 16:26:35 GMT 2023
PRIMARY
FDA UNII
A8910SQJ1U
Created by admin on Fri Dec 15 16:26:35 GMT 2023 , Edited by admin on Fri Dec 15 16:26:35 GMT 2023
PRIMARY
PUBCHEM
154059
Created by admin on Fri Dec 15 16:26:35 GMT 2023 , Edited by admin on Fri Dec 15 16:26:35 GMT 2023
PRIMARY
WIKIPEDIA
SOLIFENACIN
Created by admin on Fri Dec 15 16:26:35 GMT 2023 , Edited by admin on Fri Dec 15 16:26:35 GMT 2023
PRIMARY
RXCUI
477364
Created by admin on Fri Dec 15 16:26:35 GMT 2023 , Edited by admin on Fri Dec 15 16:26:35 GMT 2023
ALTERNATIVE
Related Record Type Details
TARGET -> INHIBITOR
Appears to be more bladder-selective for the M3 receptor relative to salivary glands.eptor
Ki
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
MINOR
TARGET->WEAK INHIBITOR
Ki
BINDER->LIGAND
in vivo
BINDING
EXCRETED UNCHANGED
URINE
METABOLIC ENZYME -> SUBSTRATE
MAJOR
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
Ki
Related Record Type Details
METABOLITE INACTIVE -> PARENT
major in urine
MAJOR
PLASMA; URINE
METABOLITE ACTIVE -> PARENT
major in urine
MAJOR
PLASMA; URINE
METABOLITE INACTIVE -> PARENT
MINOR
PLASMA
METABOLITE ACTIVE -> PARENT
occurs at low concentrations and unlikely to contribute significantly to clinical activity
MINOR
PLASMA
METABOLITE ACTIVE -> PARENT
MAJOR
URINE
METABOLITE ACTIVE -> PARENT
FECAL
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Tmax PHARMACOKINETIC ORAL ADMINISTRATION

AT STEADY-STATE

Biological Half-life PHARMACOKINETIC