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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 of LACIDIPINE

SMILES

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

Curator's Comment: Only traces of radioactivity were detected in the CNS and in rat foetuses

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Lacidipine: a calcium antagonist with potent and long-lasting antihypertensive effects in animal studies.
1990 Apr
Carvedilol and lacidipine prevent cardiac hypertrophy and endothelin-1 gene overexpression after aortic banding.
1999 Dec
Mechanisms of plaque stabilization for the dihydropyridine calcium channel blocker amlodipine: review of the evidence.
2002 Dec
Tolerability of long-term treatment with lercanidipine versus amlodipine and lacidipine in elderly hypertensives.
2002 Nov
Lercanidipine in the treatment of hypertension.
2007 Mar
Patents

Sample Use Guides

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
INN   MART.   MI   USAN   VANDF   WHO-DD  
INN   USAN  
Official 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
MOTENS
Brand Name English
Classification Tree Code System Code
WHO-ATC C08CA09
Created by admin on Sat Dec 16 15:47:30 UTC 2023 , Edited by admin on Sat Dec 16 15:47:30 UTC 2023
WHO-VATC QC08CA09
Created by admin on Sat Dec 16 15:47:30 UTC 2023 , Edited by admin on Sat Dec 16 15:47:30 UTC 2023
NCI_THESAURUS C333
Created by admin on Sat Dec 16 15:47:30 UTC 2023 , Edited by admin on Sat Dec 16 15:47:30 UTC 2023
Code System Code Type Description
ChEMBL
CHEMBL460291
Created by admin on Sat Dec 16 15:47:30 UTC 2023 , Edited by admin on Sat Dec 16 15:47:30 UTC 2023
PRIMARY
RXCUI
28382
Created by admin on Sat Dec 16 15:47:30 UTC 2023 , Edited by admin on Sat Dec 16 15:47:30 UTC 2023
PRIMARY RxNorm
EVMPD
SUB08383MIG
Created by admin on Sat Dec 16 15:47:30 UTC 2023 , Edited by admin on Sat Dec 16 15:47:30 UTC 2023
PRIMARY
CAS
103890-78-4
Created by admin on Sat Dec 16 15:47:30 UTC 2023 , Edited by admin on Sat Dec 16 15:47:30 UTC 2023
PRIMARY
FDA UNII
260080034N
Created by admin on Sat Dec 16 15:47:30 UTC 2023 , Edited by admin on Sat Dec 16 15:47:30 UTC 2023
PRIMARY
EPA CompTox
DTXSID1046429
Created by admin on Sat Dec 16 15:47:30 UTC 2023 , Edited by admin on Sat Dec 16 15:47:30 UTC 2023
PRIMARY
DRUG BANK
DB09236
Created by admin on Sat Dec 16 15:47:30 UTC 2023 , Edited by admin on Sat Dec 16 15:47:30 UTC 2023
PRIMARY
MERCK INDEX
m6649
Created by admin on Sat Dec 16 15:47:30 UTC 2023 , Edited by admin on Sat Dec 16 15:47:30 UTC 2023
PRIMARY Merck Index
MESH
C060285
Created by admin on Sat Dec 16 15:47:30 UTC 2023 , Edited by admin on Sat Dec 16 15:47:30 UTC 2023
PRIMARY
WIKIPEDIA
LACIDIPINE
Created by admin on Sat Dec 16 15:47:30 UTC 2023 , Edited by admin on Sat Dec 16 15:47:30 UTC 2023
PRIMARY
USAN
AA-42
Created by admin on Sat Dec 16 15:47:30 UTC 2023 , Edited by admin on Sat Dec 16 15:47:30 UTC 2023
PRIMARY
DRUG CENTRAL
1532
Created by admin on Sat Dec 16 15:47:30 UTC 2023 , Edited by admin on Sat Dec 16 15:47:30 UTC 2023
PRIMARY
INN
6093
Created by admin on Sat Dec 16 15:47:30 UTC 2023 , Edited by admin on Sat Dec 16 15:47:30 UTC 2023
PRIMARY
NCI_THESAURUS
C80881
Created by admin on Sat Dec 16 15:47:30 UTC 2023 , Edited by admin on Sat Dec 16 15:47:30 UTC 2023
PRIMARY
SMS_ID
100000087153
Created by admin on Sat Dec 16 15:47:30 UTC 2023 , Edited by admin on Sat Dec 16 15:47:30 UTC 2023
PRIMARY
PUBCHEM
5311217
Created by admin on Sat Dec 16 15:47:30 UTC 2023 , Edited by admin on Sat Dec 16 15:47:30 UTC 2023
PRIMARY