Amlodipine

  • (RS)- 3-ethyl -5-methyl -2 -(2- aminoethoxymethyl ) - 4 - (2- chlorophenyl ) -1,4 -dihydro -6-methyl -3 ,5- pyridinedicarboxylate
  • Latin Amlodipinum
  • C20H25ClN2O5 (amlodipine )
  • C20H25ClN2O5 · C4H4O4 ( hydrogen maleate amlodipine · )
  • C20H25ClN2O5 · C6H5SO3H (amlodipine · Hydrogenbenzolsulfonat )
  • 88150-42-9 (amlodipine )
  • 88150-47-4 (amlodipine · hydrogen maleate )
  • 111470-99-6 (amlodipine · Hydrogenbenzolsulfonat )

C08CA01

Calcium channel blockers

178-179 ° C (amlodipine · hydrogen maleate )

Low solubility in water ( amlodipine · Hydrogenbenzolsulfonat )

Risk

Template: Infobox chemical / molecular formula search available

Amlodipine is a antihypertensive drug from the group of calcium channel blockers of the nifedipine - type ( 1,4- dihydropyridines ). It has a long-lasting efficacy due to its long half-life.

Amlodipine is used as a basic therapeutic agent in an essential high blood pressure ( hypertension ). In chronic stable angina pectoris and Prinzmetal ( vasospastic angina) is used except for the treatment and the prevention of seizures.

Operation

As a calcium channel antagonist of the dihydropyridine type amlodipine blocks the L- type calcium channel by binding to the α1 - subunit. The reduced calcium influx into the smooth muscle cell reduces the muscle tone and thus the contractility ( inotropic negative ) and the oxygen consumption of the heart muscle cells. In contrast to the calcium channel antagonist of the verapamil type, the dihydropyridines have a vascular selectivity, so that a heart action does not occur only at high doses required for vasodilatation ( widening of the vessel ). In the usual dosage amlodipine acts mainly on the coronary arteries and the peripheral resistance vessels dilating. Amlodipine also acts as FIASMA ( functional inhibitors of acid sphingomyelinase ).

Pharmacokinetics

An important difference from other dihydropyridines (eg, nifedipine ) is the long half-life of 40 hours, which prevents blood pressure fluctuations caused by cardiovascular complications.

Side effects

The side effects are similar to those of the group of drugs called calcium channel blockers. As a typical side effect of dihydropyridines may occur, especially edema of the legs and especially the beginning of treatment to headache and facial flushing with heat sensation. Another common are also dizziness, fatigue, palpitations of the heart, abdominal pain and nausea, occasionally vomiting may occur. In very rare cases it can lead to allergic reactions.

Contraindications

Treatment with amlodipine is not indicated in a hypersensitivity to the substance or to other dihydropyridine derivatives in cardiac and circulatory shock, severe aortic stenosis, unstable angina pectoris or even with severe liver dysfunction.

Stereoisomerism

Amlodipine is a racemic mixture [1:1 mixture of (R) - amlodipine ( ) - and (S) - - () ] marketed. A method for the semi- preparative chromatographic separation of the enantiomers ( S) - ( -)- amlodipine and ( R) - ( )- amlodipine, is known.

Used salts and trade names

Pharmaceutically amlodipine is used as a salt of benzenesulfonic acid ( amlodipine besylate), methanesulfonic acid ( amlodipine ) or maleic acid ( amlodipine maleate ). They are effective after oral administration.

  • Monopreparations: Norvasc (A, D ), various generics (D, A, CH)
  • Combination products: Combination with valsartan: Copalia (A), Dafiro (A, D), Exforge (A, D, CH), Imprida (A) Combination with atorvastatin: Caduet (A, CH) Combination with olmesartan: Amelior (A), Vascord (CH), Vocado (D), Sevikar (A, CH, D)
CAS registry number Anatomical Therapeutic Chemical Classification System Dangerous Substances Directive (67/548/EEC) Active ingredient Prinzmetal's angina Inotrope Digital Object Identifier
57417
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