Details
Stereochemistry | RACEMIC |
Molecular Formula | C20H27N |
Molecular Weight | 281.4351 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(CC(C1=CC=CC=C1)C2=CC=CC=C2)NC(C)(C)C
InChI
InChIKey=UISARWKNNNHPGI-UHFFFAOYSA-N
InChI=1S/C20H27N/c1-16(21-20(2,3)4)15-19(17-11-7-5-8-12-17)18-13-9-6-10-14-18/h5-14,16,19,21H,15H2,1-4H3
Molecular Formula | C20H27N |
Molecular Weight | 281.4351 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Terodiline is a racemic compound, and its main indication was detrusor instability syndrome. With effects on detrusor muscles, terodiline was used for bladder incontinence. Terodiline has both anticholinergic and calcium antagonist properties and, as a result, effectively reduces abnormal bladder contractions caused by detrusor instability. When administered to adult patients with urge incontinence (generally as a 25mg twice-daily dose) terodiline reduces diurnal and nocturnal micturition frequency and incontinence episodes. The (R)-enantiomer of terodiline (R(+)-terodiline) can trigger cardiovascular toxicities, such as LQTS and TdP, which led to its withdrawal in 1991. Terodiline under the brand name Micturin was licensed and marketed in the United
Kingdom, in 1986, for the management of a specific
form of urinary incontinence, detrusor instability.
It was eventually marketed in 20 other countries,
mainly in Europe and Japan, but not the United
States of America.
CNS Activity
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
Is QT interval prolongation harmful? A regulatory perspective. | 1993 Aug 26 |
|
Safety profile of tolterodine as used in general practice in England: results of prescription-event monitoring. | 2001 |
|
Pharmacokinetic/pharmacodynamic assessment of the effects of E4031, cisapride, terfenadine and terodiline on monophasic action potential duration in dog. | 2001 Aug-Sep |
|
The relationship of clinical QT prolongation to outcome in the conscious dog using a beat-to-beat QT-RR interval assessment. | 2002 Aug |
|
Effect of muscarinic antagonists on micturition pressure measured by cystometry in normal, conscious rats. | 2002 Jun |
|
Drug therapy of urinary urge incontinence: a systematic review. | 2002 Nov |
|
Treatment of daytime urinary incontinence in children: a systematic review of randomized controlled trials. | 2003 Jul |
|
Estimating the contribution of genes and environment to variation in renal drug clearance. | 2003 Sep |
|
Contact guidance induced organization of extracellular matrix. | 2004 Aug |
|
Urodynamic effects of oxybutynin and tolterodine in conscious and anesthetized rats under different cystometrographic conditions. | 2005 Oct 11 |
|
hERG1 channels are overexpressed in glioblastoma multiforme and modulate VEGF secretion in glioblastoma cell lines. | 2005 Oct 3 |
|
In vitro preclinical cardiac assessment of tolterodine and terodiline: multiple factors predict the clinical experience. | 2006 Nov |
|
Analysis of pharmacological effects of drugs used for treatment of urinary disturbance based on anticholinergic and smooth muscle-relaxing effects. | 2007 Jul |
|
Towards automation of a valuable preclinical cardiac safety pharmacology assay: Evaluation of the effects of cardiac ion channel blockers on cardiac repolarisation in vitro. | 2007 Sep-Oct |
|
Assessing QT prolongation in conscious dogs: validation of a beat-to-beat method. | 2008 Aug |
|
A review of solifenacin in the treatment of urinary incontinence. | 2008 Feb |
|
Evaluation and outcome measures in the treatment of female urinary stress incontinence: International Urogynecological Association (IUGA) guidelines for research and clinical practice. | 2008 Jan |
|
Assessing QT prolongation in conscious dogs: validation of a beat-to-beat method. | 2008 May |
|
Oxybutynin extended release for the management of overactive bladder: a clinical review. | 2009 Sep 21 |
|
Stereoselective Inhibition of the hERG1 Potassium Channel. | 2010 |
|
Medical management of overactive bladder. | 2010 Apr |
|
Identification of human Ether-à-go-go related gene modulators by three screening platforms in an academic drug-discovery setting. | 2010 Dec |
|
New insights into molecular targets for urinary incontinence. | 2010 Oct |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2292235
When administered to adult patients with urge incontinence (generally as a 25mg twice-daily dose) terodiline reduces diurnal and nocturnal micturition frequency and incontinence episodes.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10334509
Terodiline reduced outward I(K1) with an IC50 of 7 uM in guinea pig ventricular myocytes; maximal reduction was 60% with 100-300 uM concentration. Inhibition was independent of current direction, and persisted after removal of the drug. Terodiline (3-5 uM) lengthened action potentials in guinea pig papillary muscles by ca.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 17:18:31 GMT 2023
by
admin
on
Sat Dec 16 17:18:31 GMT 2023
|
Record UNII |
70KG06964W
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
WHO-VATC |
QG04BD05
Created by
admin on Sat Dec 16 17:18:32 GMT 2023 , Edited by admin on Sat Dec 16 17:18:32 GMT 2023
|
||
|
NCI_THESAURUS |
C29696
Created by
admin on Sat Dec 16 17:18:32 GMT 2023 , Edited by admin on Sat Dec 16 17:18:32 GMT 2023
|
||
|
WHO-ATC |
G04BD05
Created by
admin on Sat Dec 16 17:18:32 GMT 2023 , Edited by admin on Sat Dec 16 17:18:32 GMT 2023
|
||
|
LIVERTOX |
942
Created by
admin on Sat Dec 16 17:18:32 GMT 2023 , Edited by admin on Sat Dec 16 17:18:32 GMT 2023
|
||
|
NCI_THESAURUS |
C29698
Created by
admin on Sat Dec 16 17:18:32 GMT 2023 , Edited by admin on Sat Dec 16 17:18:32 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
23480
Created by
admin on Sat Dec 16 17:18:32 GMT 2023 , Edited by admin on Sat Dec 16 17:18:32 GMT 2023
|
PRIMARY | |||
|
37815
Created by
admin on Sat Dec 16 17:18:32 GMT 2023 , Edited by admin on Sat Dec 16 17:18:32 GMT 2023
|
PRIMARY | RxNorm | ||
|
100000082692
Created by
admin on Sat Dec 16 17:18:32 GMT 2023 , Edited by admin on Sat Dec 16 17:18:32 GMT 2023
|
PRIMARY | |||
|
C010637
Created by
admin on Sat Dec 16 17:18:32 GMT 2023 , Edited by admin on Sat Dec 16 17:18:32 GMT 2023
|
PRIMARY | |||
|
SUB10929MIG
Created by
admin on Sat Dec 16 17:18:32 GMT 2023 , Edited by admin on Sat Dec 16 17:18:32 GMT 2023
|
PRIMARY | |||
|
70KG06964W
Created by
admin on Sat Dec 16 17:18:32 GMT 2023 , Edited by admin on Sat Dec 16 17:18:32 GMT 2023
|
PRIMARY | |||
|
C152569
Created by
admin on Sat Dec 16 17:18:32 GMT 2023 , Edited by admin on Sat Dec 16 17:18:32 GMT 2023
|
PRIMARY | |||
|
DB13725
Created by
admin on Sat Dec 16 17:18:32 GMT 2023 , Edited by admin on Sat Dec 16 17:18:32 GMT 2023
|
PRIMARY | |||
|
m954
Created by
admin on Sat Dec 16 17:18:32 GMT 2023 , Edited by admin on Sat Dec 16 17:18:32 GMT 2023
|
PRIMARY | Merck Index | ||
|
CHEMBL363295
Created by
admin on Sat Dec 16 17:18:32 GMT 2023 , Edited by admin on Sat Dec 16 17:18:32 GMT 2023
|
PRIMARY | |||
|
DTXSID60860001
Created by
admin on Sat Dec 16 17:18:32 GMT 2023 , Edited by admin on Sat Dec 16 17:18:32 GMT 2023
|
PRIMARY | |||
|
2077
Created by
admin on Sat Dec 16 17:18:32 GMT 2023 , Edited by admin on Sat Dec 16 17:18:32 GMT 2023
|
PRIMARY | |||
|
2603
Created by
admin on Sat Dec 16 17:18:32 GMT 2023 , Edited by admin on Sat Dec 16 17:18:32 GMT 2023
|
PRIMARY | |||
|
15793-40-5
Created by
admin on Sat Dec 16 17:18:32 GMT 2023 , Edited by admin on Sat Dec 16 17:18:32 GMT 2023
|
PRIMARY | |||
|
Terodiline
Created by
admin on Sat Dec 16 17:18:32 GMT 2023 , Edited by admin on Sat Dec 16 17:18:32 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |