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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
Structure of Desfesoterodine

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

HIDE SMILES / InChI

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

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
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
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 18:34:49 GMT 2025
Edited
by admin
on Mon Mar 31 18:34:49 GMT 2025
Record UNII
YU871O78GR
Record Status Validated (UNII)
Record Version
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Name Type Language
desfesoterodine [INN]
Preferred Name English
Desfesoterodine
INN   WHO-DD  
INN  
Official Name English
(+)-N,N-DIISOPROPYL-3-(2-HYDROXY-5-HYDROXYMETHYLPHENYL)-3-PHENYLPROPYLAMINE
Systematic Name English
SPM-7605
Code English
(R)-(+)-2-(3-DIISOPROPYLAMINO-1-PHENYLPROPYL)-4-HYDROXYMETHYLPHENOL
Systematic Name English
Desfesoterodine [WHO-DD]
Common Name English
5-HYDROXYMETHYLTOLTERODINE
Common Name English
PNU-200577
Code English
BENZENEMETHANOL, 3-((1R)-3-(BIS(1-METHYLETHYL)AMINO)-1-PHENYLPROPYL)-4-HYDROXY-
Systematic Name English
Classification Tree Code System Code
WHO-ATC G04BD13
Created by admin on Mon Mar 31 18:34:49 GMT 2025 , Edited by admin on Mon Mar 31 18:34:49 GMT 2025
Code System Code Type Description
EVMPD
SUB179842
Created by admin on Mon Mar 31 18:34:49 GMT 2025 , Edited by admin on Mon Mar 31 18:34:49 GMT 2025
PRIMARY
NCI_THESAURUS
C169886
Created by admin on Mon Mar 31 18:34:49 GMT 2025 , Edited by admin on Mon Mar 31 18:34:49 GMT 2025
PRIMARY
SMS_ID
100000165970
Created by admin on Mon Mar 31 18:34:49 GMT 2025 , Edited by admin on Mon Mar 31 18:34:49 GMT 2025
PRIMARY
WIKIPEDIA
Desfesoterodine
Created by admin on Mon Mar 31 18:34:49 GMT 2025 , Edited by admin on Mon Mar 31 18:34:49 GMT 2025
PRIMARY
FDA UNII
YU871O78GR
Created by admin on Mon Mar 31 18:34:49 GMT 2025 , Edited by admin on Mon Mar 31 18:34:49 GMT 2025
PRIMARY
CAS
207679-81-0
Created by admin on Mon Mar 31 18:34:49 GMT 2025 , Edited by admin on Mon Mar 31 18:34:49 GMT 2025
PRIMARY
DRUG BANK
DB15578
Created by admin on Mon Mar 31 18:34:49 GMT 2025 , Edited by admin on Mon Mar 31 18:34:49 GMT 2025
PRIMARY
EPA CompTox
DTXSID40431319
Created by admin on Mon Mar 31 18:34:49 GMT 2025 , Edited by admin on Mon Mar 31 18:34:49 GMT 2025
PRIMARY
PUBCHEM
9819382
Created by admin on Mon Mar 31 18:34:49 GMT 2025 , Edited by admin on Mon Mar 31 18:34:49 GMT 2025
PRIMARY
INN
10020
Created by admin on Mon Mar 31 18:34:49 GMT 2025 , Edited by admin on Mon Mar 31 18:34:49 GMT 2025
PRIMARY
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC INTRAVENOUS ADMINISTRATION

Tmax PHARMACOKINETIC ORAL ADMINISTRATION