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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=C(OC(=O)C(C)C)C=CC(CO)=C2)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 C4H4O4
Molecular Weight 116.0722
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula C26H37NO3
Molecular Weight 411.5769
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Desfesoterodine is an active metabolite of antimuscarinic drugs for the treatment of overactive bladder fesoterodine and tolterodine. In contrast to the cytochrome P450 (CYP) 2D6-mediated metabolism of tolterodine, desfesoterodine formation from fesoterodine occurs via ubiquitous nonspecific esterases. Serum levels of the desfesoterodine in humans are generally comparable to those of tolterodine following oral administration of the parent compound. The pharmacological in vitro and in vivo profiles of desfesoterodine are almost identical to those of tolterodin. The potent antimuscarinic action of desfesoterodine on the urinary bladder was confirmed in the in vivo studies and, like tolterodine, desfesoterodine was significantly more potent in inhibiting bladder contractions than salivation in the anaesthetised cat. Desfesoterodine is more potent than tolterodine in vivo. The apparent difference in potency in vivo might be explained by the degree of serum protein binding of the two compounds. The fraction of unbound drug in serum is larger for desfesoterodine than for tolterodine. Desfesoterodine may contribute to the therapeutical action of tolterodine.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
2.3 nM [Ki]
2.0 nM [Ki]
2.5 nM [Ki]
2.8 nM [Ki]
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

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Palliative
TOVIAZ
Primary
TOVIAZ

Cmax

ValueDoseCo-administeredAnalytePopulation
1.89 ng/mL
4 mg single, oral
5-HYDROXYMETHYL TOLTERODINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
7.31 h
4 mg single, oral
5-HYDROXYMETHYL TOLTERODINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
50%
4 mg single, oral
5-HYDROXYMETHYL TOLTERODINE plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
The recommended starting dose of Toviaz (fesoterodine fumarate) is 4 mg once daily. Based upon individual response and tolerability, the dose may be increased to 8 mg once daily. The daily dose of Toviaz should not exceed 4 mg in the following populations: • Patients with severe renal insufficiency (CLCR <30 mL/min). • Patients taking potent CYP3A4 inhibitors, such as ketoconazole, itraconazole and clarithromycin.
Route of Administration: Oral
In Vitro Use Guide
In organ-bath studies (rat bladder) fesoterodine and 5-hydroxymethyl tolterodine, induced a concentration-dependent rightward shift of the concentration-response curve for carbachol (1 µM to 1 mM).
Substance Class Chemical
Record UNII
EOS72165S7
Record Status Validated (UNII)
Record Version