103890-78-4

Basic information

• Product Name: Lacidipine
• Synonyms: 3,5-pyridinedicarboxylicacid,1,4-dihydro-2,6-dimethyl-4-(2-(3-(1,1-dimethylet;diethylester,(e)-hoxy)-3-oxo-1-propenyl)phenyl);MOTENS;GX-1048;GR-43659X;CALDINE;(E)-4-[2-[3-(1,1-DIMETHYLETHOXY)-3-OXO-1-PROPENYL]PHENYL]-1,4-DIHYDRO-2,6-DIMETHYL-3,5-PYRIDINEDICARBOXYLIC ACID DIETHYL ESTER;LACIPIL
• CAS NO: 103890-78-4
• Molecular Formula: C₂₆H₃₃NO₆
• Molecular Weight: 455.54
• EINECS: 1312995-182-4
• Product Categories: Active Pharmaceutical Ingredients;Dihydropyridine Class Chemicals;Intermediates & Fine Chemicals;Pharmaceuticals;Calcium channel;Dihydropyridine;API;Lacipil, Motens
• Mol File: 103890-78-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 174-175°C
• Boiling Point: 558.4 °C at 760 mmHg
• Flash Point: 291.5 °C
• Appearance: white to beige/
• Density: 1.127 g/cm³
• Vapor Pressure: 1.67E-12mmHg at 25°C
• Refractive Index: 1.54
• Storage Temp.: -20?C Freezer
• Solubility: DMSO: soluble20mg/mL, clear
• PKA: 3.00±0.70(Predicted)
• Merck: 14,5331
• CAS DataBase Reference: Lacidipine(CAS DataBase Reference)
• NIST Chemistry Reference: Lacidipine(103890-78-4)
• EPA Substance Registry System: Lacidipine(103890-78-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• RTECS: US7970200
• Hazardous Substances Data: 103890-78-4(Hazardous Substances Data)

Usage

Description

Lacidipine is a second-generation dihydropyridine calcium channel blocker, introduced as a once-a-day treatment for mild to moderate hypertension. It exhibits high selectivity for vascular smooth muscle and has a long duration of action. Lacidipine is also being investigated for its potential as an antiatherosclerotic agent.

Uses

Used in Pharmaceutical Industry:
Lacidipine is used as an antihypertensive agent for treating mild to moderate hypertension. It functions as a dihydropyridine calcium channel blocker, which helps in reducing blood pressure by relaxing the vascular smooth muscle.
Used in Cardiovascular Research:
Lacidipine is used as a research compound for studying its effects on isolated rat aorta, rabbit ear artery, rat colon and bladder, and guinea pig trachea. It induces relaxation in these tissues by inhibiting calcium-induced contractions.
Used in Hypertension Treatment:
Lacidipine is used as an antihypertensive medication in the treatment of high blood pressure in spontaneously hypertensive rats and renal hypertensive dogs. It reduces mean blood pressure with a transient increase in heart rate.
Used in Atherosclerosis Research:
Lacidipine is used as an agent for investigating its potential in reducing the extension of aortic atheromatous lesions and decreasing renal injury in ApoE-/mice in a model of Western diet-induced atherosclerosis.
Used in Antioxidant Studies:
Lacidipine is used in research to study its ability to inhibit copper-induced oxidation of isolated human LDL at concentrations of 1 and 5 μM.
Chemical Properties:
Lacidipine is a white-to-off-white crystalline solid.
Brand Names:
Lacidipine is marketed under the brand names Lacipil, Lacirex, and Viapres.

Originator

Glaxo (United Kingdom)

Biochem/physiol Actions

Lacidipine is a long-acting calcium antagonist that is used in the management of hypertension. Lacidipine is a L-type Ca(2+) channel blocker belonging to 1,4-dihydropyridine class. Also, Lacidipine inhibits ryanodine receptors on the ER membrane that enhances folding, trafficking and lysosomal activity of ERAD (ER-associated degradation) misfolded lysosomal glucocerebrosidase (GS).

Clinical Use

#N/A

Drug interactions

Potentially hazardous interactions with other drugs Aminophylline and theophylline: possibly increased aminophylline and theophylline concentration. Anaesthetics: enhanced hypotensive effect. Antibacterials: metabolism possibly inhibited by clarithromycin, erythromycin and telithromycin. Antidepressants: enhanced hypotensive effect with MAOIs. Antiepileptics: effect possibly reduced by carbamazepine, barbiturates, phenytoin and primidone. Antifungals: metabolism possibly inhibited by itraconazole and ketoconazole; negative inotropic effect possibly increased with itraconazole. Antihypertensives: enhanced hypotensive effect, increased risk of first dose hypotensive effect of postsynaptic alpha-blockers. Antivirals: concentration possibly increased by ritonavir. Ciclosporin: 10 kidney transplant patients on ciclosporin, prednisone and azathioprine were given 4 mg lacidipine daily. A very small increase in the trough serum levels (+6%) and AUC (+14%) of the ciclosporin occurred. Grapefruit juice: concentration increased - avoid concomitant use

Metabolism

Lacidipine undergoes extensive first-pass metabolism in the liver. The drug is eliminated primarily by hepatic metabolism (involving cytochrome P450 CYP3A4). The principal metabolites possess little, if any, pharmacodynamic activity. Approximately 70% of the administered dose is eliminated as metabolites in the faeces and the remainder as metabolites in the urine.

InChI:InChI=1/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+

Upstream product

• 103890-69-3 (E)-3-(2-formylphenyl)-2-propenoic acid 1,1-dimethylethylester 
• 144-55-8 sodium hydrogencarbonate 
• 626-34-6 ethyl 3-aminobut-2-enoate 
• 59159-39-6 (tert-butoxycarbonylmethyl)triphenylphosphonium bromide 
• 643-79-8 o-phthalic dicarboxaldehyde 
• 626-34-6 ethyl aminocrotonate 

Downstream Products

• 103890-71-7 (E)-3-(2-(3,5-bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridin-4-yl)phenyl)acrylic acid 
• 130996-24-6 diethyl (E)-4-<2-<3-(1,1-dimethylethoxy)-3-oxoprop-1-enyl>phenyl>-2,6-dimethylpyridine-3,5-dicarboxylate 

Related news

Formulation and optimization of Lacidipine (cas 103890-78-4) loaded niosomal gel for transdermal delivery: In-vitro characterization and in-vivo activity07/25/2019

The aim of the present research work is to formulate lacidipine (LAC) loaded niosomes formulation for the management of hypertension by thin film hydration technique. The developed formulations were statistically optimized by four factors, three levels Box–Behnken design and were evaluated for ...detailed

Virtual population pharmacokinetic using physiologically based pharmacokinetic model for evaluating bioequivalence of oral Lacidipine (cas 103890-78-4) formulations in dogs07/24/2019

The aim of the present study was to investigate virtual population pharmacokinetic using physiologically based pharmacokinetic (PBPK) model for evaluating bioequivalence of oral lacidipine formulations in dogs. The dissolution behaviors of three lacidipine formulations including one commercial p...detailed

Rapidly dissolving Lacidipine (cas 103890-78-4) nanoparticle strips for transbuccal administration07/22/2019

The purpose of this study was to prepare fast-dissolving film strips containing lacidipine (LCDP) nanoparticles for transbuccal administration. Nanoparticles were prepared using the solvent-antisolvent sonoprecipitation technique. The influence of different antisolvent phase stabilizers on parti...detailed

Lacidipine (cas 103890-78-4) attenuates TNF-α-induced cardiomyocyte apoptosis07/20/2019

This study was designed to investigate whether lacidipine elicited a protective role on cardiomyocyte against apoptosis induced by TNF-α. Neonatal rat cardiomyocytes were randomly assigned into different groups. TUNEL staining was utilized to detect apoptosis, and caspase-3 and caspse-12 were d...detailed

Synergetic effect of nucleation and crystal growth inhibitor on in vitro-in vivo performance of supersaturable Lacidipine (cas 103890-78-4) solid dispersion07/21/2019

Limited supersaturation maintaining duration is the main challenge for amorphous solid dispersion design. Nucleation or crystal growth inhibitors may function in different ways but the combination use of nucleation and crystal growth inhibitors in supersaturated system is rarely explored. Thus, ...detailed

Relevant articles and documents

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PROCESS FOR PREPARING LACIDIPINE

A process for preparing lacidipine, comprising reacting a t-butoxy carbonyl methyl aryl phosphonium halide with o-phthalaldehyde, and further reacting a product comprising (E)-3-(2-formylphenyl)-2-propenoic acid, 1,1-dimethyl ethyl ester, without isolation, with ethyl-3-amino crotonate.