TERODILINE HYDROCHLORIDE

Possibly Marketed Outside US

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 Search

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	C20H27N
Molecular Weight	281.4351
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2292235 | http://www.medscape.com/viewarticle/757499_10 | http://onlinelibrary.wiley.com/doi/10.1002/pds.2630010310/abstract

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
HERG 99 Target ID: CHEMBL240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17110801 \| https://www.ncbi.nlm.nih.gov/pubmed/9863639	Inhibitor 8504		375.0 nM [IC50]
Muscarinic receptor M1 and M2 2 Target ID: CHEMBL2111433 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3247311 \| https://www.ncbi.nlm.nih.gov/pubmed/10347840 \| https://www.ncbi.nlm.nih.gov/pubmed/8849312 \| https://www.ncbi.nlm.nih.gov/pubmed/1724648	Antagonist 2849		588.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Urinary incontinence 14 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2292235 http://www.medscape.com/viewarticle/757499_10 https://www.ncbi.nlm.nih.gov/pubmed/1609246	Primary		Approved 8583	Micturin Approved Use Main indication was detrusor instability syndrome Launch Date 1985

C_max

Value	Dose	Analyte	Population
41 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7617541/	12.5 mg single, oral dose: 12.5 mg route of administration: Oral experiment type: SINGLE co-administered:	TERODILINE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
76 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7617541/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	TERODILINE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
306 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7617541/	12.5 mg 2 times / day steady-state, oral dose: 12.5 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TERODILINE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
476 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7617541/	25 mg 2 times / day steady-state, oral dose: 25 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TERODILINE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
79 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3395665/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	TERODILINE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
5901 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3395665/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:		TERODILINE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
61 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7617541/	12.5 mg single, oral dose: 12.5 mg route of administration: Oral experiment type: SINGLE co-administered:	TERODILINE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
63 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7617541/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	TERODILINE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
66 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7617541/	12.5 mg 2 times / day steady-state, oral dose: 12.5 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TERODILINE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
62 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7617541/	25 mg 2 times / day steady-state, oral dose: 25 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TERODILINE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
60 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3395665/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	TERODILINE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Analyte	Population
8.9% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7617541/	12.5 mg 2 times / day steady-state, oral dose: 12.5 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TERODILINE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
6.6% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7617541/	25 mg 2 times / day steady-state, oral dose: 25 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TERODILINE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
13.5% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3395665/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	TERODILINE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Doses

Dose	Population	Adverse events
150 mg 3 times / day multiple, oral Highest studied dose Dose: 150 mg, 3 times / day Route: oral Route: multiple Dose: 150 mg, 3 times / day Sources: https://link.springer.com/article/10.1007/BF00567114	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://link.springer.com/article/10.1007/BF00567114	Disc. AE: Tremor, Paralytic ileus... Other AEs: Balance impaired NOS, Dysuria... AEs leading to discontinuation/dose reduction: Tremor (71%) Paralytic ileus (14%) Other AEs: Balance impaired NOS (grade 1-2, 57%) Dysuria (grade 1, 14%) Vertigo (grade 1, 57%) Visual disturbance (grade 1-2, 29%) Sources: https://link.springer.com/article/10.1007/BF00567114
20 mg single, intravenous Highest studied dose Dose: 20 mg Route: intravenous Route: single Dose: 20 mg Sources: https://pubmed.ncbi.nlm.nih.gov/7173296/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7173296/	Sources: https://pubmed.ncbi.nlm.nih.gov/7173296/
200 mg single, oral Highest studied dose Dose: 200 mg Route: oral Route: single Dose: 200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/8689817/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/8689817/	Other AEs: QT prolonged... Other AEs: QT prolonged Sources: https://pubmed.ncbi.nlm.nih.gov/8689817/

AEs

AE	Significance	Dose	Population
Paralytic ileus	14% Disc. AE	150 mg 3 times / day multiple, oral Highest studied dose Dose: 150 mg, 3 times / day Route: oral Route: multiple Dose: 150 mg, 3 times / day Sources: https://link.springer.com/article/10.1007/BF00567114	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://link.springer.com/article/10.1007/BF00567114
Tremor	71% Disc. AE	150 mg 3 times / day multiple, oral Highest studied dose Dose: 150 mg, 3 times / day Route: oral Route: multiple Dose: 150 mg, 3 times / day Sources: https://link.springer.com/article/10.1007/BF00567114	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://link.springer.com/article/10.1007/BF00567114
Dysuria	grade 1, 14%	150 mg 3 times / day multiple, oral Highest studied dose Dose: 150 mg, 3 times / day Route: oral Route: multiple Dose: 150 mg, 3 times / day Sources: https://link.springer.com/article/10.1007/BF00567114	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://link.springer.com/article/10.1007/BF00567114
Vertigo	grade 1, 57%	150 mg 3 times / day multiple, oral Highest studied dose Dose: 150 mg, 3 times / day Route: oral Route: multiple Dose: 150 mg, 3 times / day Sources: https://link.springer.com/article/10.1007/BF00567114	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://link.springer.com/article/10.1007/BF00567114
Visual disturbance	grade 1-2, 29%	150 mg 3 times / day multiple, oral Highest studied dose Dose: 150 mg, 3 times / day Route: oral Route: multiple Dose: 150 mg, 3 times / day Sources: https://link.springer.com/article/10.1007/BF00567114	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://link.springer.com/article/10.1007/BF00567114
Balance impaired NOS	grade 1-2, 57%	150 mg 3 times / day multiple, oral Highest studied dose Dose: 150 mg, 3 times / day Route: oral Route: multiple Dose: 150 mg, 3 times / day Sources: https://link.springer.com/article/10.1007/BF00567114	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://link.springer.com/article/10.1007/BF00567114
QT prolonged		200 mg single, oral Highest studied dose Dose: 200 mg Route: oral Route: single Dose: 200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/8689817/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/8689817/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMzYzMjk1In19

PubMed

Title	Date	PubMed
Identification of human Ether-à-go-go related gene modulators by three screening platforms in an academic drug-discovery setting.	2010-12	21158687
New insights into molecular targets for urinary incontinence.	2010-10	21206614
Medical management of overactive bladder.	2010-04	20877608
Stereoselective Inhibition of the hERG1 Potassium Channel.	2010	21833176
Oxybutynin extended release for the management of overactive bladder: a clinical review.	2009-09-21	19920931
Assessing QT prolongation in conscious dogs: validation of a beat-to-beat method.	2008-08	18938261
Assessing QT prolongation in conscious dogs: validation of a beat-to-beat method.	2008-05	18420278
A review of solifenacin in the treatment of urinary incontinence.	2008-02	18728701
Evaluation and outcome measures in the treatment of female urinary stress incontinence: International Urogynecological Association (IUGA) guidelines for research and clinical practice.	2008-01	18026681
Analysis of pharmacological effects of drugs used for treatment of urinary disturbance based on anticholinergic and smooth muscle-relaxing effects.	2007-07	17603170
Towards automation of a valuable preclinical cardiac safety pharmacology assay: Evaluation of the effects of cardiac ion channel blockers on cardiac repolarisation in vitro.	2007-02-23	17583537
In vitro preclinical cardiac assessment of tolterodine and terodiline: multiple factors predict the clinical experience.	2006-11	17110801
Urodynamic effects of oxybutynin and tolterodine in conscious and anesthetized rats under different cystometrographic conditions.	2005-10-11	16216132
hERG1 channels are overexpressed in glioblastoma multiforme and modulate VEGF secretion in glioblastoma cell lines.	2005-10-03	16175187
Contact guidance induced organization of extracellular matrix.	2004-08	15020137
Estimating the contribution of genes and environment to variation in renal drug clearance.	2003-09	12972957
Treatment of daytime urinary incontinence in children: a systematic review of randomized controlled trials.	2003-07	12796688
Drug therapy of urinary urge incontinence: a systematic review.	2002-11	12423868
The relationship of clinical QT prolongation to outcome in the conscious dog using a beat-to-beat QT-RR interval assessment.	2002-08	12130750
Effect of muscarinic antagonists on micturition pressure measured by cystometry in normal, conscious rats.	2002-06	12031395
Pharmacokinetic/pharmacodynamic assessment of the effects of E4031, cisapride, terfenadine and terodiline on monophasic action potential duration in dog.	2001-09-25	11569530
Safety profile of tolterodine as used in general practice in England: results of prescription-event monitoring.	2001	11522122
Is QT interval prolongation harmful? A regulatory perspective.	1993-08-26	8256756

Patents

Sample Use Guides

In Vivo Use Guide

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

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 `Mon Mar 31 18:58:14 GMT 2025` Edited by `admin` on `Mon Mar 31 18:58:14 GMT 2025`
Record UNII	K2ZA89W43F
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TERODILINE HYDROCHLORIDE [JAN]

Preferred Name

English

TERODILINE HYDROCHLORIDE

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 [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