Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C26H37NO3 |
Molecular Weight | 411.5769 |
Optical Activity | UNSPECIFIED |
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=CC(CO)=CC=C2OC(=O)C(C)C)C(C)C
InChI
InChIKey=DCCSDBARQIPTGU-HSZRJFAPSA-N
InChI=1S/C26H37NO3/c1-18(2)26(29)30-25-13-12-21(17-28)16-24(25)23(22-10-8-7-9-11-22)14-15-27(19(3)4)20(5)6/h7-13,16,18-20,23,28H,14-15,17H2,1-6H3/t23-/m1/s1
Molecular Formula | C26H37NO3 |
Molecular Weight | 411.5769 |
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 |
|||
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 |
|||
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 |
---|---|---|
Tolterodine--a new bladder selective muscarinic receptor antagonist: preclinical pharmacological and clinical data. | 1997 |
|
Antimuscarinic potency and bladder selectivity of PNU-200577, a major metabolite of tolterodine. | 1997 Oct |
|
Efficacy, safety and tolerability of fesoterodine for overactive bladder syndrome. | 2007 Dec |
|
Clinical efficacy, safety, and tolerability of once-daily fesoterodine in subjects with overactive bladder. | 2007 Oct |
|
Impact of fesoterodine on quality of life: pooled data from two randomized trials. | 2008 Jul |
|
The effects of antimuscarinic treatments in overactive bladder: an update of a systematic review and meta-analysis. | 2008 Sep |
|
The design and development of fesoterodine as a prodrug of 5-hydroxymethyl tolterodine (5-HMT), the active metabolite of tolterodine. | 2009 |
|
Fesoterodine for the treatment of urinary incontinence and overactive bladder. | 2009 |
|
Fesoterodine. | 2009 |
|
Fesoterodine for the treatment of overactive bladder. | 2009 Aug |
|
Practical aspects of lifestyle modifications and behavioural interventions in the treatment of overactive bladder and urgency urinary incontinence. | 2009 Aug |
|
Fesoterodine for the treatment of overactive bladder. | 2009 Dec |
|
Basic mechanisms of urgency: roles and benefits of pharmacotherapy. | 2009 Dec |
|
Muscarinic receptor antagonists for overactive bladder treatment: does one fit all? | 2009 Jan |
|
Efficacy and tolerability of fesoterodine in women with overactive bladder. | 2009 Jul |
|
A meta-analysis of the placebo response in antimuscarinic drug trials for overactive bladder. | 2009 Jul 22 |
|
New drug information: Toviaz. | 2009 Jun |
|
Influence of food on the pharmacokinetic profile of fesoterodine. | 2009 Jun |
|
Evaluation of drug-drug interactions with fesoterodine. | 2009 Jun |
|
Fesoterodine: a new agent for treating overactive bladder. | 2009 Mar |
|
[Anticholinergic treatment of overactive bladder syndrome. Is it all the same?]. | 2009 Mar |
|
New drugs: milnacipran hydrochloride, fesoterodine fumarate, and silodosin. | 2009 Mar-Apr |
|
Fesoterodine (toviaz) for overactive bladder. | 2009 May 4 |
|
Influence of age, gender, and race on pharmacokinetics, pharmacodynamics, and safety of fesoterodine. | 2009 Sep |
|
Tolterodine extended-release for overactive bladder. | 2009 Sep |
|
Bladder dysfunction in diabetes mellitus. | 2010 |
|
Determination of fesoterodine in pharmaceutical formulations by using liquid chromatography-tandem mass spectrometry. | 2010 |
|
Medical management of overactive bladder. | 2010 Apr |
|
Durability of treatments for overactive bladder. | 2010 Apr |
|
Long-term safety, tolerability and efficacy of fesoterodine treatment in subjects with overactive bladder symptoms. | 2010 Apr |
|
Efficacy of fesoterodine over 24 hours in subjects with overactive bladder. | 2010 Apr |
|
The cost-effectiveness of solifenacin vs fesoterodine, oxybutynin immediate-release, propiverine, tolterodine extended-release and tolterodine immediate-release in the treatment of patients with overactive bladder in the UK National Health Service. | 2010 Aug |
|
Spinal effects of the fesoterodine metabolite 5-hydroxymethyl tolterodine and/or doxazosin in rats with or without partial urethral obstruction. | 2010 Aug |
|
The cost-effectiveness of solifenacin vs fesoterodine, oxybutynin immediate-release, propiverine, tolterodine extended-release and tolterodine immediate-release in the treatment of patients with overactive bladder in the UK National Health Service. | 2010 Aug |
|
Modeling dose-response relationships of the effects of fesoterodine in patients with overactive bladder. | 2010 Aug 19 |
|
Efficacy and tolerability of fesoterodine in older and younger subjects with overactive bladder. | 2010 Dec |
|
The pharmacokinetic profile of fesoterodine 8 mg with daytime or nighttime dosing. | 2010 Feb |
|
Fesoterodine fumarate. | 2010 Feb |
|
New Drugs2010, PART 1. | 2010 Feb |
|
Recent advances in management of bladder overactivity. | 2010 Feb 11 |
|
Comparison of fesoterodine and tolterodine extended release for the treatment of overactive bladder: a head-to-head placebo-controlled trial. | 2010 Jan |
|
Randomized, double-blind, placebo-controlled trial of flexible-dose fesoterodine in subjects with overactive bladder. | 2010 Jan |
|
The overlap of interstitial cystitis/painful bladder syndrome and overactive bladder. | 2010 Jan-Mar |
|
Urodynamic evaluation of fesoterodine metabolite, doxazosin and their combination in a rat model of partial urethral obstruction. | 2010 Jul |
|
Thorough QT study of the effect of fesoterodine on cardiac repolarization. | 2010 May |
|
Efficacy and tolerability of fesoterodine in men with overactive bladder: a pooled analysis of 2 phase III studies. | 2010 May |
|
Response to fesoterodine in patients with an overactive bladder and urgency urinary incontinence is independent of the urodynamic finding of detrusor overactivity. | 2010 May |
|
Fesoterodine in patients with overactive bladder syndrome: can the severity of baseline urgency urinary incontinence predict dosing requirement? | 2010 Sep |
|
Dose escalation improves therapeutic outcome: post hoc analysis of data from a 12-week, multicentre, double-blind, parallel-group trial of trospium chloride in patients with urinary urge incontinence. | 2010 Sep 14 |
|
Effects of the moderate CYP3A4 inhibitor, fluconazole, on the pharmacokinetics of fesoterodine in healthy subjects. | 2011 Aug |
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
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621G617227
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C29704
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Fesoterodine
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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Related Record | Type | Details | ||
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METABOLITE INACTIVE -> PARENT |
PLASMA; URINE
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METABOLITE INACTIVE -> PARENT |
PLASMA; URINE
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METABOLITE ACTIVE -> PRODRUG |
Extensive hydrolysis by nonspecific esterases
MAJOR
FECAL; PLASMA; URINE
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METABOLITE INACTIVE -> PARENT |
PLASMA; URINE
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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