LACIDIPINE

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C26H33NO6
Molecular Weight	455.5433
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCOC(=O)C1=C(C)NC(C)=C(C1C2=CC=CC=C2\C=C\C(=O)OC(C)(C)C)C(=O)OCC

InChI

InChIKey=GKQPCPXONLDCMU-CCEZHUSRSA-N

InChI=1S/C26H33NO6/c1-8-31-24(29)21-16(3)27-17(4)22(25(30)32-9-2)23(21)19-13-11-10-12-18(19)14-15-20(28)33-26(5,6)7/h10-15,23,27H,8-9H2,1-7H3/b15-14+

HIDE SMILES / InChI

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/14524737

Lacidipine (tradenames Lacipil (GSK) or Motens (Boehringer Ingelheim) is a once-daily, orally-administered, lipophilic dihydropyridine calcium antagonist with an intrinsically slow onset of activity, resulting in a lack of reflex tachycardia. It has a long duration of action and a high degree of vascular selectivity. In addition to calcium channel-modulated vasodilation, lacidipine displays antioxidant activity greater than that of other dihydropyridine calcium antagonists. During long-term treatment for 4 or 5 years in patients with isolated systolic hypertension or essential hypertension, the incidence of cardiovascular events and mortality with lacidipine was similar to that with chlorthalidone or atenolol

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Voltage-gated calcium channel 37 Target ID: CHEMBL2363032 Sources: http://www.ncbi.nlm.nih.gov/pubmed/1725443	Antagonist 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 575 Sources: http://www.ncbi.nlm.nih.gov/pubmed/14524737	Primary		Phase III 665	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Investigation of effects of Lacidipine, Ramipril and Valsartan on DNA damage and oxidative stress occurred in acute and chronic periods following isoproterenol-induced myocardial infarct in rats.	2009-08	19296206
Lercanidipine in the treatment of hypertension.	2007-03	17341540
Mechanisms of plaque stabilization for the dihydropyridine calcium channel blocker amlodipine: review of the evidence.	2002-12	12417269
Tolerability of long-term treatment with lercanidipine versus amlodipine and lacidipine in elderly hypertensives.	2002-11	12441211
Carvedilol and lacidipine prevent cardiac hypertrophy and endothelin-1 gene overexpression after aortic banding.	1999-12	10601118
[Preclinical study of the action of a calcium channel blocker during salt load].	1997-02	9235228
Relative efficacy and tolerability of lacidipine and amlodipine in patients with mild-to-moderate hypertension: a randomized double-blind study.	1996-08	8856491
Lacidipine: a calcium antagonist with potent and long-lasting antihypertensive effects in animal studies.	1990-04	1691398
Haemodynamic parameters in hypertensive patients: changes induced by lacidipine and nifedipine.	1989-12	2698940

Patents

Sample Use Guides

In Vivo Use Guide

2 mg tablet once-daily every morning

Route of Administration: Oral

In Vitro Use Guide

Lacidipine (10(-8) -10(-6) M) dose-dependently decreased contractility of driven sheep Purkinje fibers. For concentrations less than or equal to 10(-7) M, this effect was associated with a selective decrease of the plateau height. Higher concentrations (3 X 10(-7) and 10(-6) M), however, affected action potential amplitude, overshoot, and maximum rate of depolarization. In the same range of concentrations, lacidipine did not affect normal automaticity of guinea-pig sinus node and sheep Purkinje fibers. Lacidipine (10(-6) M) consistently blocked barium-induced abnormal automaticity in Purkinje fibers and reduced the amplitude and Vmax of the slow action potentials induced by histamine (10(-5) M) in guinea pig papillary muscle depolarized by potassium (22 mM). The effect of lacidipine on the slow inward current (Isi) was studied in shortened Purkinje fibers under voltage-clamp conditions.

Name

Type

Language

LACIDIPINE

Official Name

English

MOTENS

Preferred Name

English

GR-43659X

Code

English

lacidipine [INN]

Common Name

English

LACIDIPINE [VANDF]

Common Name

English

LACIDIPINE [MI]

Common Name

English

GR 43659X

Code

English

LACIDIPINE [JAN]

Common Name

English

LACIDIPINE [USAN]

Common Name

English

LACIDIPINE [MART.]

Common Name

English

3,5-PYRIDINEDICARBOXYLIC ACID, 4-(2-(3-(1,1-DIMETHYLETHOXY)-3-OXO-1-PROPENYL)PHENYL)-1,4-DIHYDRO-2,6-DIMETHYL-, DIETHYL ESTER, (E)-

Common Name

English

4-[O-[(E)-2-Carboxyvinyl]phenyl]-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acid, 4-tert-butyl diethyl ester

Common Name

English

Lacidipine [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-ATC

C08CA09