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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H37NO3.C4H4O4
Molecular Weight 527.649
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of FESOTERODINE FUMARATE

SMILES

OC(=O)\C=C\C(O)=O.CC(C)N(CC[C@H](C1=CC=CC=C1)C2=CC(CO)=CC=C2OC(=O)C(C)C)C(C)C

InChI

InChIKey=MWHXMIASLKXGBU-RNCYCKTQSA-N
InChI=1S/C26H37NO3.C4H4O4/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;5-3(6)1-2-4(7)8/h7-13,16,18-20,23,28H,14-15,17H2,1-6H3;1-2H,(H,5,6)(H,7,8)/b;2-1+/t23-;/m1./s1

HIDE SMILES / InChI

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

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description
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

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

Targets

Primary TargetPharmacologyConditionPotency
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]
8.0 null [pKi]
7.7 null [pKi]
7.4 null [pKi]
7.3 null [pKi]
7.5 null [pKi]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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 Use

Unknown
Primary
Unknown

Approved Use

Unknown
Palliative
TOVIAZ

Approved Use

Toviaz is a muscarinic antagonist indicated for the treatment of overactive bladder with symptoms of urge urinary incontinence, urgency, and frequency.

Launch Date

2008
Primary
TOVIAZ

Approved Use

Toviaz® 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 Date

2008
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no
no
no
weak
yes [Inhibition 15 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
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
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
Page: 38.0
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Tolterodine--a new bladder selective muscarinic receptor antagonist: preclinical pharmacological and clinical data.
1997
Gateways to clinical trials.
2006 Dec
Gateways to clinical trials.
2006 Jul-Aug
Treatment of the overactive bladder syndrome with muscarinic receptor antagonists: a matter of metabolites?
2006 Nov
Toviaz approved for overactive bladder.
2008 Dec 1
Pharmacokinetic profile of fesoterodine.
2008 Nov
Comparison of fesoterodine and tolterodine in patients with overactive bladder.
2008 Nov
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
The safety and efficacy of tolterodine extended release in the treatment of overactive bladder in the elderly.
2009
Fesoterodine.
2009
Assessment of the effects of renal impairment on the pharmacokinetic profile of fesoterodine.
2009 Apr
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
Fesoterodine: a new agent for treating overactive bladder.
2009 Mar
[Anticholinergic treatment of overactive bladder syndrome. Is it all the same?].
2009 Mar
Comparison of receptor binding characteristics of commonly used muscarinic antagonists in human bladder detrusor and mucosa.
2009 Mar
The pharmacokinetic profile of fesoterodine: similarities and differences to tolterodine.
2009 Mar 7
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
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
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
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
Patents

Sample Use Guides

2-203 nM/kg [0.001-0.1 mg/kg]
Route of Administration: Intravenous
In Vitro Use Guide
Sources: DOI: 10.1002/(SICI)1520-6777(1996)15:4<249::AID-NAU1>3.0.CO;2-F
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
on Mon Mar 31 18:00:57 GMT 2025
Edited
by admin
on Mon Mar 31 18:00:57 GMT 2025
Record UNII
EOS72165S7
Record Status Validated (UNII)
Record Version
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Name Type Language
FESOTERODINE FUMARATE
DASH   EMA EPAR   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN  
Official Name English
TOVIAZ
Preferred Name English
FESOTERODINE FUMARATE [MI]
Common Name English
2-((1R)-3-(BIS(1-METHYLETHYL)AMINO)-1-PHENYLPROPYL)-4-(HYDROXYMETHYL)PHENYL 2-METHYLPROPANOATE HYDROGEN(2E)-BUTENEDIOATE (SALT)
Common Name English
SPM 907
Code English
FESOTERODINE FUMARATE [JAN]
Common Name English
FESOTERODINE FUMARATE [VANDF]
Common Name English
FESOTERODINE FUMARATE [MART.]
Common Name English
FESOTERODINE FUMARATE [ORANGE BOOK]
Common Name English
SPM-907
Code English
SPM-8272
Code English
FESOTERODINE FUMARATE [EMA EPAR]
Common Name English
SPM 8272
Code English
FESOTERODINE FUMARATE [USAN]
Common Name English
Fesoterodine Fumarate [WHO-DD]
Common Name English
PROPANOIC ACID,2-METHYL ,2-((1R)-3-(BIS(1-METHYLETHYL)AMINO)-1-PHENYLPROPYL)-4-(HYDROXYMETHYL)PHENYL ESTER,(2E)-2-BUTENEDIOATE (1:1)(SALT)
Common Name English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS TOVIAZ (AUTHORIZED: URINARY BLADDER, OVERACTIVE)
Created by admin on Mon Mar 31 18:00:57 GMT 2025 , Edited by admin on Mon Mar 31 18:00:57 GMT 2025
NCI_THESAURUS C29704
Created by admin on Mon Mar 31 18:00:57 GMT 2025 , Edited by admin on Mon Mar 31 18:00:57 GMT 2025
Code System Code Type Description
USAN
RR-41
Created by admin on Mon Mar 31 18:00:57 GMT 2025 , Edited by admin on Mon Mar 31 18:00:57 GMT 2025
PRIMARY
EPA CompTox
DTXSID00904655
Created by admin on Mon Mar 31 18:00:57 GMT 2025 , Edited by admin on Mon Mar 31 18:00:57 GMT 2025
PRIMARY
DAILYMED
EOS72165S7
Created by admin on Mon Mar 31 18:00:57 GMT 2025 , Edited by admin on Mon Mar 31 18:00:57 GMT 2025
PRIMARY
NCI_THESAURUS
C72779
Created by admin on Mon Mar 31 18:00:57 GMT 2025 , Edited by admin on Mon Mar 31 18:00:57 GMT 2025
PRIMARY
CAS
286930-03-8
Created by admin on Mon Mar 31 18:00:57 GMT 2025 , Edited by admin on Mon Mar 31 18:00:57 GMT 2025
PRIMARY
MERCK INDEX
m5365
Created by admin on Mon Mar 31 18:00:57 GMT 2025 , Edited by admin on Mon Mar 31 18:00:57 GMT 2025
PRIMARY Merck Index
DRUG BANK
DB06702
Created by admin on Mon Mar 31 18:00:57 GMT 2025 , Edited by admin on Mon Mar 31 18:00:57 GMT 2025
PRIMARY
RXCUI
797196
Created by admin on Mon Mar 31 18:00:57 GMT 2025 , Edited by admin on Mon Mar 31 18:00:57 GMT 2025
PRIMARY RxNorm
FDA UNII
EOS72165S7
Created by admin on Mon Mar 31 18:00:57 GMT 2025 , Edited by admin on Mon Mar 31 18:00:57 GMT 2025
PRIMARY
PUBCHEM
9849808
Created by admin on Mon Mar 31 18:00:57 GMT 2025 , Edited by admin on Mon Mar 31 18:00:57 GMT 2025
PRIMARY
SMS_ID
100000135413
Created by admin on Mon Mar 31 18:00:57 GMT 2025 , Edited by admin on Mon Mar 31 18:00:57 GMT 2025
PRIMARY
ChEMBL
CHEMBL1201764
Created by admin on Mon Mar 31 18:00:57 GMT 2025 , Edited by admin on Mon Mar 31 18:00:57 GMT 2025
PRIMARY
EVMPD
SUB70604
Created by admin on Mon Mar 31 18:00:57 GMT 2025 , Edited by admin on Mon Mar 31 18:00:57 GMT 2025
PRIMARY
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PARENT -> SALT/SOLVATE
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ACTIVE MOIETY