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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

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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T Natsukawa et al.
General pharmacology, 30(1), 137-142 (1998-02-11)
1. NS-21 [(+/-)-4-diethylamino-1,1-dimethylbut-2-yn-1-yl 2-cyclohexyl-2-hydroxy-2-phenylacetate monohydrochloride monohydrate], its active metabolite, RCC-36, and terodiline, are mixed anticholinergic-Ca2+ antagonistic drugs. Among them, terodiline has been shown to cause torsade de pointes, a serious polymorphic ventricular tachycardia. It remains unknown, however, whether NS-21 or
Justyna Szczurek et al.
Molecular pharmaceutics, 14(4), 1071-1081 (2017-02-24)
In this paper, we investigated the molecular mobility and physical stability of amorphous bicalutamide, a poorly water-soluble drug widely used in prostate cancer treatment. Our broadband dielectric spectroscopy measurements and differential scanning calorimetry studies revealed that amorphous BIC is a
L M Shuba et al.
The Journal of pharmacology and experimental therapeutics, 290(3), 1417-1426 (1999-08-24)
Terodiline was widely prescribed for urinary incontinence before reports of adverse cardiac effects that included bradycardia, QT lengthening, and ventricular tachyarrhythmia. The present study on guinea pig papillary muscles and ventricular myocytes was undertaken to gain insight into the cardioactive
S E Jones et al.
European journal of pharmacology, 370(3), 319-327 (1999-05-20)
The antispasmodic agent terodiline has cardiotoxic effects that include QT lengthening. To determine whether inhibition of inwardly-rectifying K+ current (I(K1)) might be a factor in the cardiotoxicity, we measured I(K1) in guinea pig ventricular myocytes. Terodiline reduced outward I(K1) with
D A Stewart et al.
European journal of clinical pharmacology, 42(6), 577-580 (1992-01-01)
Recent reports have suggested an association between terodiline hydrochloride and cardiac arrhythmias. We report 4 patients presenting over a six month period who developed polymorphic ventricular tachycardia (polymorphic VT) while receiving treatment with this agent. In each case there was
View All Related Papers

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