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
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
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 |
DescriptionCurator'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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23094215 http://www.ics.org/Abstracts/Publish/46/000185.pdf
Curator's Comment: Known to be CNS penetrant in rat. Human data not available
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL245 |
10.0 nM [Ki] | ||
125.0 nM [Ki] | |||
25.0 nM [Ki] | |||
7.73 null [pKi] | |||
7.46 null [pKi] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | VESICARE Approved UseVESIcare 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 Date1.10082235E12 |
Cmax
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 |
T1/2
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 |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2% |
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: 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 Sources: Page: p.1Anaphylactic reaction (rare) |
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: 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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-518_VESIcare_biopharmr.pdf#page=51 Page: 51.0 |
not significant | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-518_VESIcare_biopharmr.pdf#page=51 Page: 51.0 |
not significant | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-518_VESIcare_biopharmr.pdf#page=51 Page: 51.0 |
not significant | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-518_VESIcare_biopharmr.pdf#page=51 Page: 51.0 |
not significant | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-518_VESIcare_biopharmr.pdf#page=51 Page: 51.0 |
yes [Inhibition 1.04 uM] |
Drug as victim
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-518_VESIcare_pharmr.pdf#page=35 Page: 35.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Gateways to clinical trials. | 2003 Jul-Aug |
|
Gateways to clinical trials. | 2003 Jun |
|
Food does not affect the pharmacokinetics of solifenacin, a new muscarinic receptor antagonist: results of a randomized crossover trial. | 2004 Jul |
|
[Overactive bladder. New anticholinergic drug controls urinary urge]. | 2004 Jul 8 |
|
Gateways to clinical trials. | 2004 May |
|
Gateways to clinical trials. | 2004 Nov |
|
The emerging role of solifenacin in the treatment of overactive bladder. | 2004 Oct |
|
Overactive bladder in the elderly: a guide to pharmacological management. | 2005 |
|
[Neurological aspect of the hyperactive urinary bladder syndrome]. | 2005 |
|
Solifenacin and darifenacin for overactive bladder. | 2005 Aug |
|
[Medical therapy of urinary incontinence]. | 2005 Jan |
|
The Q-T interval and antimuscarinic drugs. | 2005 Nov |
|
Pharmacokinetic interaction of solifenacin with an oral contraceptive containing ethinyl estradiol and levonorgestrel in healthy women: a double-blind, placebo-controlled study. | 2005 Sep |
|
Gateways to clinical trials. | 2006 Apr |
|
The causes and consequences of overactive bladder. | 2006 Apr |
|
Patient-reported outcomes in overactive bladder: importance for determining clinical effectiveness of treatment. | 2006 Aug |
|
Open-label study of the safety and pharmacokinetics of solifenacin in subjects with hepatic impairment. | 2006 Dec |
|
New drugs 06, part I. | 2006 Feb |
|
Pharmacokinetic effect of ketoconazole on solifenacin in healthy volunteers. | 2006 Jul |
|
Gateways to clinical trials. | 2006 Jul-Aug |
|
Efficacy and tolerability of solifenacin in elderly subjects with overactive bladder syndrome: a pooled analysis. | 2006 Mar |
|
Gateways to clinical trials. | 2006 May |
|
Treatment of the overactive bladder syndrome with muscarinic receptor antagonists: a matter of metabolites? | 2006 Nov |
|
Reductions in overactive bladder-related incontinence from pooled analysis of phase III trials evaluating treatment with solifenacin. | 2006 Sep |
|
Effect of antimuscarinic drugs used for overactive bladder on learning in a rat passive avoidance response test. | 2007 Feb 28 |
|
Redefining response in overactive bladder syndrome. | 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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15178371
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
Edited
Wed Jul 05 23:52:46 UTC 2023
by
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on
Wed Jul 05 23:52:46 UTC 2023
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Record UNII |
A8910SQJ1U
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Record Status |
Validated (UNII)
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WHO-ATC |
G04CA53
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NDF-RT |
N0000000125
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WHO-ATC |
G04BD08
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NDF-RT |
N0000000125
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WHO-VATC |
QG04CA53
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LIVERTOX |
NBK548716
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NDF-RT |
N0000000125
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WHO-VATC |
QG04BD08
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NCI_THESAURUS |
C29704
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NDF-RT |
N0000175700
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C441209
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Solifenacin
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M10108
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SOLIFENACIN
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477364
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ALTERNATIVE |
Related Record | Type | Details | ||
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TARGET -> INHIBITOR |
Appears to be more bladder-selective for the M3 receptor relative to salivary glands.eptor
Ki
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SALT/SOLVATE -> PARENT |
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METABOLIC ENZYME -> SUBSTRATE |
MINOR
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TARGET->WEAK INHIBITOR |
Ki
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BINDER->LIGAND |
in vivo
BINDING
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EXCRETED UNCHANGED |
URINE
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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TARGET -> INHIBITOR |
Ki
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Related Record | Type | Details | ||
---|---|---|---|---|
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METABOLITE INACTIVE -> PARENT |
major in urine
MAJOR
PLASMA; URINE
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METABOLITE ACTIVE -> PARENT |
major in urine
MAJOR
PLASMA; URINE
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METABOLITE INACTIVE -> PARENT |
MINOR
PLASMA
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METABOLITE ACTIVE -> PARENT |
occurs at low concentrations and unlikely to contribute significantly to clinical activity
MINOR
PLASMA
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METABOLITE ACTIVE -> PARENT |
MAJOR
URINE
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METABOLITE ACTIVE -> PARENT |
FECAL
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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ORAL ADMINISTRATION |
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Biological Half-life | PHARMACOKINETIC |
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