Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C22H31NO2 |
Molecular Weight | 341.487 |
Optical Activity | ( + ) |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)N(CC[C@H](C1=CC=CC=C1)C2=C(O)C=CC(CO)=C2)C(C)C
InChI
InChIKey=DUXZAXCGJSBGDW-HXUWFJFHSA-N
InChI=1S/C22H31NO2/c1-16(2)23(17(3)4)13-12-20(19-8-6-5-7-9-19)21-14-18(15-24)10-11-22(21)25/h5-11,14,16-17,20,24-25H,12-13,15H2,1-4H3/t20-/m1/s1
Molecular Formula | C22H31NO2 |
Molecular Weight | 341.487 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/19835561 | DOI: 10.1002/(SICI)1520-6777(1996)15:4<249::AID-NAU1>3.0.CO;2-F | https://www.ncbi.nlm.nih.gov/pubmed/9353847https://www.ncbi.nlm.nih.gov/pubmed/19835561Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/18279452
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19835561 | DOI: 10.1002/(SICI)1520-6777(1996)15:4<249::AID-NAU1>3.0.CO;2-F | https://www.ncbi.nlm.nih.gov/pubmed/9353847https://www.ncbi.nlm.nih.gov/pubmed/19835561
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/18279452
Fesoterodine (trade name Toviaz) is a prodrug of 5-hydroxymethyl tolterodine, which is also the active metabolite of tolterodine. Fesoterodine and its active metabolites are nonsubtype selective, competitive antagonists of human muscarinic receptors, but 5-hydroxymethyl tolterodine has greater potency than the parent compound. A prodrug approach was necessary for systemic bioavailability of 5-hydroxymethyl tolterodine after oral administration. Fesoterodine was originated by Schwarz Pharma (later a subsidiary of UCB) and is being developed by Pfizer for the treatment of overactive bladder and urinary urge incontinence. The agent is launched in several countries for the treatment of overactive bladder, including the US, Japan, Canada, Europe and Asia.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21392072https://www.ncbi.nlm.nih.gov/pubmed/22390261 | https://www.ncbi.nlm.nih.gov/pubmed/21392072
Curator's Comment: Fesoterodine is a substrate for permeability-glycoprotein (P-gp) and, therefore, is actively transported away from the brain.
Originator
Sources: DOI: 10.1002/(SICI)1520-6777(1996)15:4<249::AID-NAU1>3.0.CO;2-Fhttp://adisinsight.springer.com/drugs/800010689
Curator's Comment: Gillberg, P-G, Sparf, B, Nilvebrant, L. Pharmacological in vitro and in vivo profile of DD01, a major metabolite of tolterodine (abstract). Neurourol Urodyn. 1996;15:308–309.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL216 Sources: DOI: 10.1002/(SICI)1520-6777(1996)15:4<249::AID-NAU1>3.0.CO;2-F |
2.3 nM [Ki] | ||
Target ID: CHEMBL211 Sources: DOI: 10.1002/(SICI)1520-6777(1996)15:4<249::AID-NAU1>3.0.CO;2-F |
2.0 nM [Ki] | ||
Target ID: CHEMBL245 Sources: DOI: 10.1002/(SICI)1520-6777(1996)15:4<249::AID-NAU1>3.0.CO;2-F |
2.5 nM [Ki] | ||
Target ID: CHEMBL1821 Sources: DOI: 10.1002/(SICI)1520-6777(1996)15:4<249::AID-NAU1>3.0.CO;2-F |
2.8 nM [Ki] | ||
Target ID: CHEMBL2035 Sources: DOI: 10.1002/(SICI)1520-6777(1996)15:4<249::AID-NAU1>3.0.CO;2-F |
2.9 nM [Ki] | ||
Target ID: CHEMBL216 |
8.0 null [pKi] | ||
Target ID: CHEMBL211 |
7.7 null [pKi] | ||
Target ID: CHEMBL245 |
7.4 null [pKi] | ||
Target ID: CHEMBL1821 |
7.3 null [pKi] | ||
Target ID: CHEMBL2035 |
7.5 null [pKi] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Sources: DOI: 10.1002/(SICI)1520-6777(1996)15:4<249::AID-NAU1>3.0.CO;2-F https://www.ncbi.nlm.nih.gov/pubmed/9353847 |
Primary | Unknown Approved UseUnknown |
||
Primary | Unknown Approved UseUnknown |
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Palliative | TOVIAZ Approved UseToviaz is a muscarinic antagonist indicated for the treatment of overactive bladder with symptoms of urge urinary incontinence, urgency, and frequency. Launch Date2008 |
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Primary | TOVIAZ Approved UseToviaz® is a muscarinic antagonist indicated for the treatment of overactive bladder with symptoms of urge urinary incontinence, urgency, and frequency. Toviaz is a muscarinic antagonist indicated for the treatment of overactive bladder with symptoms of urge urinary incontinence, urgency, and frequency. Launch Date2008 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.89 ng/mL |
4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered: |
5-HYDROXYMETHYL TOLTERODINE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
2.464 ng/mL |
4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered: |
DESFESOTERODINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
5.519 ng/mL |
8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: |
DESFESOTERODINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
10.863 ng/mL |
16 mg single, oral dose: 16 mg route of administration: Oral experiment type: SINGLE co-administered: |
DESFESOTERODINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
1.96 ng/mL |
4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered: |
DESFESOTERODINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2.89 ng/mL |
8 mg 1 times / day single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: |
DESFESOTERODINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2.32 ng/mL |
4 mg 1 times / day multiple, oral dose: 4 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DESFESOTERODINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
3.59 ng/mL |
8 mg 1 times / day multiple, oral dose: 8 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DESFESOTERODINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
24.461 ng × h/mL |
4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered: |
DESFESOTERODINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
53.715 ng × h/mL |
8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: |
DESFESOTERODINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
111.091 ng × h/mL |
16 mg single, oral dose: 16 mg route of administration: Oral experiment type: SINGLE co-administered: |
DESFESOTERODINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
19.9 ng × h/mL |
4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered: |
DESFESOTERODINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
26.9 ng × h/mL |
8 mg 1 times / day single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: |
DESFESOTERODINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
23.4 ng × h/mL |
4 mg 1 times / day multiple, oral dose: 4 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DESFESOTERODINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
32.8 ng × h/mL |
8 mg 1 times / day multiple, oral dose: 8 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DESFESOTERODINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7.31 h |
4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered: |
5-HYDROXYMETHYL TOLTERODINE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
9.671 h |
4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered: |
DESFESOTERODINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
9.37 h |
8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: |
DESFESOTERODINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
7.58 h |
16 mg single, oral dose: 16 mg route of administration: Oral experiment type: SINGLE co-administered: |
DESFESOTERODINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
8.13 h |
4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered: |
DESFESOTERODINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
6.86 h |
8 mg 1 times / day single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: |
DESFESOTERODINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
5.13 h |
4 mg 1 times / day multiple, oral dose: 4 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DESFESOTERODINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
4.86 h |
8 mg 1 times / day multiple, oral dose: 8 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DESFESOTERODINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
50% |
4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered: |
5-HYDROXYMETHYL TOLTERODINE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
50% |
DESFESOTERODINE plasma | Homo sapiens |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 12.0 |
no | |||
Page: 12.0 |
no | |||
Page: 12.0 |
no | |||
Page: 12.0 |
no | |||
Page: 12.0 |
no | |||
Page: 12.0 |
no | |||
Page: 12.0 |
no | |||
Page: 12.0 |
no | |||
Page: 12.0 |
no | |||
Page: 12.0 |
no | |||
Page: 12.0 |
no | |||
Page: 12.0 |
no | |||
Page: 12.0 |
no | |||
weak | ||||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022030s000_PharmR_P1.pdf#page=58 Page: 58.0 |
yes [Inhibition 15 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022030s000_ClinPharmR.pdf#page=38 Page: 38.0 |
yes | yes (co-administration study) Comment: Following blockade of CYP3A4 by coadministration of the potent CYP3A4 inhibitor ketoconazoles, Cmax and AUC of the active metabolite of fesoterodine increased 2.0- and 2.3-fold, respectively, after oral administration of Toviaz to CYP2D6 extensive metabolizers. In CYP2D6 poor metabolizers, Cmax and AUC of the active metabolite of fesoterodine increased 2.1- and 2.5-fold, respectively, during coadministration of ketoconazole. Cmax and AUC were 4.5- and 5.7-fold higher, respectively, in subjects who were CYP2D6 poor metabolizers and taking ketoconazole; Following induction of CYP3A4 by coadministration of rifampicin (inducer), Cmax and AUC of the active metabolite of fesoterodine decreased by approximately 70% and 75%, respectively, after oral administration of Toviaz Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022030s000_ClinPharmR.pdf#page=38 Page: 38.0 |
||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022030s000_ClinPharmR.pdf#page=38 Page: 38.0 |
yes | yes (pharmacogenomic study) Comment: CYP2D6 PMs have values for AUC and Cmax that are about 2-fold higher that CYP2D6 EMs Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022030s000_ClinPharmR.pdf#page=38 Page: 38.0 |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022030s000_PharmR_P1.pdf#page=57 Page: 57.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Efficacy, safety and tolerability of fesoterodine for overactive bladder syndrome. | 2007 Dec |
|
Pharmacological characterization of a novel investigational antimuscarinic drug, fesoterodine, in vitro and in vivo. | 2008 Apr |
|
Toviaz approved for overactive bladder. | 2008 Dec 1 |
|
Fesoterodine dose response in subjects with overactive bladder syndrome. | 2008 May |
|
Effects of flexible-dose fesoterodine on overactive bladder symptoms and treatment satisfaction: an open-label study. | 2009 Apr |
|
Assessment of the effects of renal impairment on the pharmacokinetic profile of fesoterodine. | 2009 Apr |
|
Efficacy and tolerability of fesoterodine in women with overactive bladder. | 2009 Jul |
|
New drugs: milnacipran hydrochloride, fesoterodine fumarate, and silodosin. | 2009 Mar-Apr |
|
Tolterodine extended-release for overactive bladder. | 2009 Sep |
|
Modeling dose-response relationships of the effects of fesoterodine in patients with overactive bladder. | 2010 Aug 19 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9353847
2-203 nM/kg [0.001-0.1 mg/kg]
Route of Administration:
Intravenous
In terms of IC50 values (mean of 3-6 experiments), Desfesoterodine was >900 times more potent in blocking bladder muscarinic receptors (IC50 5.7 nM) than calcium channels (papillary muscle: IC50 5.4 uM; atrium: IC50 15 uM, bladder IC50 39 uM), alph-adrenoceptors (portal vein: IC50 100 uM) and histamine receptors (ileum: IC50 6.1 uM).
Substance Class |
Chemical
Created
by
admin
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Edited
Mon Mar 31 18:34:49 GMT 2025
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Record UNII |
YU871O78GR
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Record Status |
Validated (UNII)
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Record Version |
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G04BD13
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SUB179842
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C169886
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100000165970
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Desfesoterodine
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YU871O78GR
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207679-81-0
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DB15578
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Related Record | Type | Details | ||
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BINDER->LIGAND |
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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SALT/SOLVATE -> PARENT |
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METABOLIC ENZYME -> SUBSTRATE |
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SALT/SOLVATE -> PARENT |
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TARGET -> INHIBITOR |
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Related Record | Type | Details | ||
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METABOLITE INACTIVE -> PARENT |
FECAL
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PARENT -> METABOLITE ACTIVE | |||
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METABOLITE INACTIVE -> PARENT |
PLASMA
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METABOLITE INACTIVE -> PARENT |
PLASMA
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METABOLITE INACTIVE -> PARENT |
URINE
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METABOLITE INACTIVE -> PARENT |
FECAL
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METABOLITE INACTIVE -> PARENT |
FECAL
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METABOLITE INACTIVE -> PARENT |
URINE
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METABOLITE INACTIVE -> PARENT |
PLASMA
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METABOLITE INACTIVE -> PARENT |
URINE
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PRODRUG -> METABOLITE ACTIVE |
MAJOR
URINE
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PRODRUG -> METABOLITE ACTIVE |
Extensive hydrolysis by nonspecific esterases
MAJOR
PLASMA
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PRODRUG -> METABOLITE ACTIVE |
FECAL
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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INTRAVENOUS ADMINISTRATION |
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Tmax | PHARMACOKINETIC |
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ORAL ADMINISTRATION |
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