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T4577

Sigma-Aldrich

Terodiline hydrochloride

≥98% (HPLC), solid

Synonym(s):

Bicor, N-(1,1-Dimethylethyl)-alpha-methyl-gamma-phenylbenzenepropamine hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C20H27N·HCl
CAS Number:
7082-21-5
Molecular Weight:
317.90
MDL number:
MFCD00941402
UNSPSC Code:
12352200
PubChem Substance ID:
329826797
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

solid

color

white to off-white

solubility

DMSO: >20 mg/mL

storage temp.

−20°C

SMILES string

Cl.CC(CC(c1ccccc1)c2ccccc2)NC(C)(C)C

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

InChI key

RNGHAJVBYQPLAZ-UHFFFAOYSA-N

Gene Information

human ... CACNA1A(773) , CACNA1B(774) , CACNA1C(775) , CACNA1D(776) , CACNA1E(777) , CACNA1F(778) , CACNA1G(8913) , CACNA1H(8912) , CACNA1I(8911) , CACNA1S(779) , CACNA2D1(781) , CACNA2D2(9254) , CACNA2D3(55799) , CACNA2D4(93589) , CACNB1(782) , CACNB2(783) , CACNB3(784) , CACNB4(785) , CACNG1(786) , CACNG2(10369) , CACNG3(10368) , CACNG4(27092) , CACNG5(27091) , CACNG6(59285) , CACNG7(59284) , CACNG8(59283) , CHRM1(1128) , CHRM2(1129) , CHRM3(1131) , CHRM4(1132) , CHRM5(1133)

Biochem/physiol Actions

Terodiline hydrochloride is a non-selective calcium channel antagonist with anticholinergic and vasodilatory activity.
Terodiline is known to increase corrected QT interval (QTc) and decrease resting heart rate in elderly patients. Furthermore, terodiline hydrochloride has been linked to cardiac arrhythmias1.

Features and Benefits

This compound is featured on the Calcium Channels page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Preparation Note

Terodiline hydrochloride is soluble in DMSO at a concentration that is greater than 20 mg/ml.

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302,H319,H400

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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G A Ford et al.
British journal of clinical pharmacology, 50(1), 77-80 (2000-07-25)
Terodiline has concentration dependent QT prolonging effects and thus the potential for cardiotoxicity. Pharmacogenetic variation in terodiline metabolism could be responsible for cardiotoxicity. We sought to determine whether CYP2D6 (debrisoquine hydroxylase) or CYP2C19 (S-mephenytoin hydroxylase) status is a risk factor
Leah R Gerber et al.
PloS one, 5(8), e12230-e12230 (2010-09-03)
In polygynous mating systems, males often increase their fecundity via aggressive defense of mates and/or resources necessary for successful mating. Here we show that both male and female reproductive behavior during the breeding season (June-August) affect female fecundity, a vital
R Webster et al.
Xenobiotica; the fate of foreign compounds in biological systems, 31(8-9), 633-650 (2001-09-25)
1. Torsades de pointes (TDP) is a potentially fatal ventricular tachycardia associated with increases in QT interval and monophasic action potential duration (MAPD). TDP is a side-effect that has led to withdrawal of several drugs from the market (e.g. terfenadine
Ruth L Martin et al.
Journal of cardiovascular pharmacology, 48(5), 199-206 (2006-11-18)
Terodiline and tolterodine are drugs used to treat urinary incontinence. Terodiline was removed from the market in 1991 for proarrhythmia, whereas tolterodine has a generally benign clinical cardiac profile. To assess differences in the electrophysiologic actions of these drugs, we
K Hartigan-Go et al.
Clinical pharmacology and therapeutics, 60(1), 89-98 (1996-07-01)
To study the cardiovascular and electrocardiographic (ECG) effects of the R(+)- and S(-)- enantiomers of terodiline. The racemic drug was previously used to treat detrusor instability but was withdrawn after it caused serious ventricular arrhythmias associated with prolongation of the
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