Amlodipine Chemical Properties

Melting point:

178-179°C

Boiling point:

527.2±50.0 °C(Predicted)

Density 

1.227±0.06 g/cm3(Predicted)

RTECS 

US7968329

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

solubility 

Soluble in DMSO (up to 25 mg/ml), in DMF (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml).

pka

pKa 8.6 (Uncertain)

form 

Almost white crystal powder

color 

White

Water Solubility 

75.3 mg/L

BCS Class

1

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO, DMF, or ethanol may be stored at -20°C for up to 3 months.

CAS DataBase Reference

88150-42-9(CAS DataBase Reference)

EPA Substance Registry System

3,5-Pyridinedicarboxylic acid, 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-, 3-ethyl 5-methyl ester (88150-42-9)

Safety Information

HazardClass 

IRRITANT

HazardClass 

6.1

Hazardous Substances Data

88150-42-9(Hazardous Substances Data)

Toxicity

TDLo orl-chd: 400 mg/kg:BPR AJEMEN 18,581,2000

Amlodipine Usage And Synthesis

Description

Amlodipine is a dihydropyridine L-type calcium channel blocker that selectively inhibits calcium influx in cardiac and vascular smooth muscle. Acting as a vasodilator, amlodipine reduces blood pressure by relaxing the smooth muscle in the arterial wall, decreasing total peripheral resistance. It inhibits calcium-induced contractions in depolarized rat aorta with an IC₅₀ value of 1.9 nM, displaying a slow rate of association and dissociation in isolated vascular and cardiac tissues. Amlodipine also demonstrates actions independent of L-type calcium channel blockade by regulating membrane fluidity and cholesterol deposition, stimulating nitric oxide production, acting as an antioxidant, and regulating matrix deposition in vitro and in vivo. Formulations containing amlodipine have been used in the treatment of hypertension.

Chemical Properties

Yellow Solid

Uses

anti-hypertensive;calcium channel blocker

Uses

A deuterated dihydropyridine calcium channel blocker.;Application of Labeled APIs: Labeled Amlodipine, intended for use as an internal standard for the quantification of Amlodipine by GC- or LC-mass spectrometry.

Uses

A dihydropyridine calcium channel blocker; activity resides mainly in the (-)-isomer.

Definition

ChEBI: A fully substituted dialkyl 1,4-dihydropyridine-3,5-dicarboxylate derivative, which is used for the treatment of hypertension, chronic stable angina and confirmed or suspected vasospastic angina.

brand name

Norvasc (Pfizer).

General Description

Amlodipine, 2-[, for the treatment of hypertension. Amlodipineis also marketed as a combination therapy with atorvastatinunder the tradename Norvasc for the management of highcholesterol and high blood pressure.

Hazard

Human systemic effects.

Clinical Use

Calcium-channel blocker:
Hypertension
Angina prophylaxis

Safety Profile

Human systemic effects. Whenheated to decomposition it emits toxic vapors of NOx andCl^-.

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, concentration possibly reduced by St John’s wort.
Antiepileptics: effects probably reduced by phenobarbital and primidone.
Antifungals: negative inotropic effect possibly increased with itraconazole.
Antihypertensives: enhanced hypotensive effect; increased risk of first dose hypotensive effect of postsynaptic alpha-blockers.
Antivirals: concentration increased by telaprevir and possibly by ritonavir - reduce dose of amlodipine.
Ciclosporin: ciclosporin concentration may be increased by up to 40%.
Lipid lowering agents: possibly increased risk of myopathy - do not exceed 20 mg of simvastatin.1 Tacrolimus: possibly increased tacrolimus levels.

Metabolism

Amlodipine is extensively metabolised by the liver to inactive metabolites with 10% of the parent compound and 60% of metabolites excreted in the urine.

References

1) Mason et al. (2003), Novel vascular biology of third-generation L-type calcium channel antagonists: ancillary actions of amlodipine; Arterioscler. Thromb. Vasc. Biol., 23 2155 2) Asano et al. (2003), A calcium channel blocker activates both ecto-5(‘)-nucleotidase and NO synthase in HUVEC; Biochem. Biophys. Res. Commun., 311 625 3) Yu et al. (2003), Amlodipine modulates THP-1 cell adhesion to vascular endothelium via inhibition of protein kinase C signal transduction; Hypertension, 42 329 4) Zhou et al. (2004), Inhibition of oxidative stress and improvement of endothelial function by amlodipine in angiotensin II-infused rats; Am. J. Hypertension, 17 167 5) Ueda et al. (1993), A comparative assessment of the duration of action of amlodipine and nifedipine GITS in normotensive subjects; Br. J. Clin. Pharmacol., 36 561

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