U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C20H27N.ClH
Molecular Weight 317.896
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TERODILINE HYDROCHLORIDE

SMILES

Cl.CC(CC(C1=CC=CC=C1)C2=CC=CC=C2)NC(C)(C)C

InChI

InChIKey=RNGHAJVBYQPLAZ-UHFFFAOYSA-N
InChI=1S/C20H27N.ClH/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;1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
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

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
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 Fri Dec 15 17:58:23 GMT 2023
Edited
by admin
on Fri Dec 15 17:58:23 GMT 2023
Record UNII
K2ZA89W43F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TERODILINE HYDROCHLORIDE
JAN   MART.   MI   USAN   WHO-DD  
USAN  
Official Name English
TERODILINE HYDROCHLORIDE [MART.]
Common Name English
(±)-N-TERT-BUTYL-1-METHYL-3,3-DIPHENYLPROPYLAMINE HYDROCHLORIDE
Systematic Name English
TERODILINE HYDROCHLORIDE [USAN]
Common Name English
N-TERT-BUTYL-1-METHYL-3,3-DIPHENYLPROPYLAMINE HYDROCHLORIDE
Systematic Name English
Terodiline hydrochloride [WHO-DD]
Common Name English
TERODILINE HYDROCHLORIDE [JAN]
Common Name English
TERODILINE HYDROCHLORIDE [MI]
Common Name English
BENZENEPROPANAMINE, N-(1,1-DIMETHYLETHYL)-.ALPHA.-METHYL-.GAMMA.-PHENYL-, HYDROCHLORIDE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C29696
Created by admin on Fri Dec 15 17:58:24 GMT 2023 , Edited by admin on Fri Dec 15 17:58:24 GMT 2023
NCI_THESAURUS C29698
Created by admin on Fri Dec 15 17:58:24 GMT 2023 , Edited by admin on Fri Dec 15 17:58:24 GMT 2023
Code System Code Type Description
MERCK INDEX
m954
Created by admin on Fri Dec 15 17:58:24 GMT 2023 , Edited by admin on Fri Dec 15 17:58:24 GMT 2023
PRIMARY Merck Index
FDA UNII
K2ZA89W43F
Created by admin on Fri Dec 15 17:58:24 GMT 2023 , Edited by admin on Fri Dec 15 17:58:24 GMT 2023
PRIMARY
CAS
7082-21-5
Created by admin on Fri Dec 15 17:58:24 GMT 2023 , Edited by admin on Fri Dec 15 17:58:24 GMT 2023
PRIMARY
ChEMBL
CHEMBL363295
Created by admin on Fri Dec 15 17:58:24 GMT 2023 , Edited by admin on Fri Dec 15 17:58:24 GMT 2023
PRIMARY
EPA CompTox
DTXSID1048968
Created by admin on Fri Dec 15 17:58:24 GMT 2023 , Edited by admin on Fri Dec 15 17:58:24 GMT 2023
PRIMARY
PUBCHEM
23479
Created by admin on Fri Dec 15 17:58:24 GMT 2023 , Edited by admin on Fri Dec 15 17:58:24 GMT 2023
PRIMARY
RXCUI
235839
Created by admin on Fri Dec 15 17:58:24 GMT 2023 , Edited by admin on Fri Dec 15 17:58:24 GMT 2023
PRIMARY RxNorm
NCI_THESAURUS
C152570
Created by admin on Fri Dec 15 17:58:24 GMT 2023 , Edited by admin on Fri Dec 15 17:58:24 GMT 2023
PRIMARY
EVMPD
SUB04728MIG
Created by admin on Fri Dec 15 17:58:24 GMT 2023 , Edited by admin on Fri Dec 15 17:58:24 GMT 2023
PRIMARY
SMS_ID
100000084814
Created by admin on Fri Dec 15 17:58:24 GMT 2023 , Edited by admin on Fri Dec 15 17:58:24 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY