Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C22H31NO2 |
Molecular Weight | 341.4879 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)N(CC[C@]([H])(c1ccccc1)c2cc(ccc2O)CO)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 | 341.4879 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21392072
Curator's Comment:: low CNS penetration
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] |
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 |
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 |
|
The design and development of fesoterodine as a prodrug of 5-hydroxymethyl tolterodine (5-HMT), the active metabolite of tolterodine. | 2009 |
|
The pharmacokinetic profile of fesoterodine 8 mg with daytime or nighttime dosing. | 2010 Feb |
|
Urodynamic evaluation of fesoterodine metabolite, doxazosin and their combination in a rat model of partial urethral obstruction. | 2010 Jul |
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
on
Edited
Sat Jun 26 13:54:45 UTC 2021
by
admin
on
Sat Jun 26 13:54:45 UTC 2021
|
Record UNII |
YU871O78GR
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Systematic Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
WHO-ATC |
G04BD13
Created by
admin on Sat Jun 26 13:54:47 UTC 2021 , Edited by admin on Sat Jun 26 13:54:47 UTC 2021
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
SUB179842
Created by
admin on Sat Jun 26 13:54:47 UTC 2021 , Edited by admin on Sat Jun 26 13:54:47 UTC 2021
|
PRIMARY | |||
|
C169886
Created by
admin on Sat Jun 26 13:54:47 UTC 2021 , Edited by admin on Sat Jun 26 13:54:47 UTC 2021
|
PRIMARY | |||
|
YU871O78GR
Created by
admin on Sat Jun 26 13:54:47 UTC 2021 , Edited by admin on Sat Jun 26 13:54:47 UTC 2021
|
PRIMARY | |||
|
207679-81-0
Created by
admin on Sat Jun 26 13:54:47 UTC 2021 , Edited by admin on Sat Jun 26 13:54:47 UTC 2021
|
PRIMARY | |||
|
DB15578
Created by
admin on Sat Jun 26 13:54:47 UTC 2021 , Edited by admin on Sat Jun 26 13:54:47 UTC 2021
|
PRIMARY | |||
|
207679-81-0
Created by
admin on Sat Jun 26 13:54:47 UTC 2021 , Edited by admin on Sat Jun 26 13:54:47 UTC 2021
|
PRIMARY | |||
|
9819382
Created by
admin on Sat Jun 26 13:54:47 UTC 2021 , Edited by admin on Sat Jun 26 13:54:47 UTC 2021
|
PRIMARY | |||
|
10020
Created by
admin on Sat Jun 26 13:54:47 UTC 2021 , Edited by admin on Sat Jun 26 13:54:47 UTC 2021
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
BINDER->LIGAND |
|
||
|
METABOLIC ENZYME -> SUBSTRATE |
MAJOR
|
||
|
SALT/SOLVATE -> PARENT | |||
|
METABOLIC ENZYME -> SUBSTRATE |
MAJOR
|
||
|
TARGET -> INHIBITOR |
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE INACTIVE -> PARENT |
FECAL
|
||
|
METABOLITE INACTIVE -> PARENT |
PLASMA
|
||
|
METABOLITE INACTIVE -> PARENT |
PLASMA
|
||
|
METABOLITE INACTIVE -> PARENT |
URINE
|
||
|
METABOLITE INACTIVE -> PARENT |
FECAL
|
||
|
METABOLITE INACTIVE -> PARENT |
FECAL
|
||
|
METABOLITE INACTIVE -> PARENT |
URINE
|
||
|
METABOLITE INACTIVE -> PARENT |
PLASMA
|
||
|
PARENT -> METABOLITE ACTIVE |
MAJOR
|
||
|
METABOLITE INACTIVE -> PARENT |
URINE
|
||
|
PRODRUG -> METABOLITE ACTIVE |
MAJOR
URINE
|
||
|
PRODRUG -> METABOLITE ACTIVE |
FECAL
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
---|---|---|---|---|---|---|
Biological Half-life | PHARMACOKINETIC |
|
INTRAVENOUS ADMINISTRATION |
|
||
Tmax | PHARMACOKINETIC |
|
ORAL ADMINISTRATION |
|
||