Captopril
(S) -1 - [( S)-2 -methyl-3 - sulfanylpropanoyl ] pyrrolidine-2 -carboxylic acid
C09AA01
Inhibition of the angiotensin- converting enzyme
104-108 ° C
Moderately in water (100 g · l-1 at 20 ° C)
Attention
Template: Infobox chemical / molecular formula search available
Captopril is a drug of the group of ACE inhibitors, in particular for the treatment of hypertension (high blood pressure) and heart failure is used. Its mechanism of action is based on inhibition of the angiotensin- converting enzyme (ACE).
Chemistry
Captopril was the ACE - inhibiting active peptides of the venom of the jararaca - lance (Bothrops jararaca ), a Brazilian snake modeled, and is the lead compound for the group of ACE inhibitors. The substance is formally a condensation product of the amino acid (S)- proline ( synonym: L- proline), and ( S)-3 -mercapto- 2-methylpropionic acid and the only ACE inhibitor with a SH group.
The technical procedure for the preparation of captopril based on the acylation of the natural amino acid (S)- proline, with (S )-2- methyl-3- acetylsulfanylpropanoylchlorid and the subsequent cleavage of the acetyl group.
Pharmacology
Areas of application
Captopril is used as monotherapy and in combination with diuretics for the treatment of arterial hypertension and heart failure, which occurs through synergistic effects to a reduction of blood pressure. In severe chronic forms of heart failure, a combination with digitalis and beta-blockers is possible and also displayed. Other applications include the short-term treatment (4 weeks) after myocardial infarction and diabetic nephropathy in diabetes mellitus patients with macroproteinuria type I
When Nierenszintigrafie captopril is often used to check kidney function under " stress conditions " can.
Mechanism of Action
Captopril leads as an inhibitor of angiotensin converting enzyme in a reduced formation of angiotensin II from angiotensin I. This reduced formation of angiotensin II causes a decrease in the tonus of the blood vessels and thus a decrease in blood pressure. Also the decrease in angiotensin II levels leads to a reduction of aldosterone release from the adrenal cortex and thus to influence the water budget (see also the renin -angiotensin -aldosterone system ). At the cellular level, a decrease in angiotensin II -mediated mitogenic effects on cells of the heart, in particular following myocardial infarction leading to unfavorable changes (remodeling ) may be observed.
Side effects
Most side effects of captopril to be associated with a conditional by ACE inhibitors slow degradation and the accumulation of bradykinin. These include skin reactions such as rashes and hives, and also angioneurotic edema. Severe allergic skin reactions are, however, only very rarely observed.
Among the side effects on the respiratory system include dry cough, hoarseness and sore throat. Asthma attacks and shortness of breath may also, though rarely, occur.
As a result, the main effect of captopril may cause an excessively high blood pressure. As a result, can be observed occasionally dizziness, headache and dizziness. From serious cardiovascular events such as angina pectoris, myocardial infarction, and syncope have been reported only in individual cases.
By intervening in the water and electrolyte balance functional renal dysfunction can be observed occasionally. Proteinuria ( excretion of proteins in urine ), however, was only rarely observed.
Since captopril, inter alia in pregnancy Growth and bone formation disorders in children, associated with increased mortality, may cause may, captopril not be taken at this time and should be replaced with other suitable therapeutic measures.
Interactions
Captopril potentiates the blood glucose lowering effect of insulin and oral hypoglycemic agents, and the blood- changing effects of immunosuppressants.
By intervening in the water and electrolyte excretion of electrolytes can be slowed down, which in therapy should be considered especially with lithium and potassium-sparing diuretics.
In combination with other antihypertensive drugs increased blood pressure reduction should be considered.
Trade names
ACE inhibitors ( D), Adocor (D), Captoflux (D), Captogamma (D), Captosol (CH ), cor tensobon (D), Debax (A), Jucapt (D), Lopirin aH (CH), Lopirin Cor (D), Tensiomin (D), Tensobon (D), Tensostad (D ), numerous generics (D, A)
ACE inhibitors comp. (D) Adocomp (D), Captogamma HCT (D), Captosol comp. (CH), Capozide (A, CH), Cardiagen HCT (D), Jutacor comp. (D) Tensobon comp. (D) Veracapt (A ) and various generics with the appendage "comp ", " plus" or " HCT ".