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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
Structure of DESFESOTERODINE

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

HIDE SMILES / InChI

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

Curator's Comment:: low CNS penetration

Originator

Sources: DOI: 10.1002/(SICI)1520-6777(1996)15:4<249::AID-NAU1>3.0.CO;2-F
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]
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
PubMed

PubMed

TitleDatePubMed
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
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 Sat Jun 26 13:54:45 UTC 2021
Edited
by admin
on Sat Jun 26 13:54:45 UTC 2021
Record UNII
YU871O78GR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DESFESOTERODINE
INN   WHO-DD  
INN  
Official Name English
(+)-N,N-DIISOPROPYL-3-(2-HYDROXY-5-HYDROXYMETHYLPHENYL)-3-PHENYLPROPYLAMINE
Systematic Name English
SPM 7605
Common Name English
(R)-(+)-2-(3-DIISOPROPYLAMINO-1-PHENYLPROPYL)-4-HYDROXYMETHYLPHENOL
Systematic Name English
DESFESOTERODINE [INN]
Common 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 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
EVMPD
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
NCI_THESAURUS
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
FDA UNII
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
CAS
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
DRUG BANK
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
EPA CompTox
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
PUBCHEM
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
INN
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
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BINDER->LIGAND
METABOLIC ENZYME -> SUBSTRATE
MAJOR
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
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TARGET -> INHIBITOR
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URINE
METABOLITE INACTIVE -> PARENT
FECAL
METABOLITE INACTIVE -> PARENT
FECAL
METABOLITE INACTIVE -> PARENT
URINE
METABOLITE INACTIVE -> PARENT
PLASMA
PARENT -> METABOLITE ACTIVE
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METABOLITE INACTIVE -> PARENT
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PRODRUG -> METABOLITE ACTIVE
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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