Alacepril

Bezeichnung:Alacepril

CAS-Nr74258-86-9

Englisch Name:Alacepril

CBNumberCB9198959

SummenformelC20H26N2O5S

Molgewicht406.5

MOL-Datei74258-86-9.mol

Alacepril physikalisch-chemischer Eigenschaften

Schmelzpunkt	155-156°
alpha	D25 -81.3° (c = 1.02 in ethanol)
Siedepunkt	679.1±55.0 °C(Predicted)
Dichte	1.281±0.06 g/cm3(Predicted)
storage temp.	2-8°C
pka	3.56±0.10(Predicted)
CAS Datenbank	74258-86-9(CAS DataBase Reference)

Sicherheit

Toxizität

LD50 in rats, mice (mg/kg): >5000, >5000 orally; >3000, >3000 s.c.; ~2000, ~3000 i.p. (Iida, pp 7033-40)

Gefahreninformationscode (GHS)

Alacepril Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
Alacepril is an angiotensin-converting enzyme (ACE) inhibitor useful in the treatment of essential and renal hypertension. Compared with captopril, alacepril is a weaker ACE inhibitor in vino, yet clinically it has a longer duration of action and appears to be more active due to an added component of norepinephrine antagonism.
Originator
Dainippon (Japan)
Definition
ChEBI: Alacepril is a thioacetate ester and a dipeptide. It has a role as an EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor.
Manufacturing Process
N-Methylmorpholine (1.03 g) was added to a solution of 1-(D-3-acetylthio-2- methylpropanoyl)-L-proline (2.65 g) in dry tetrahydrofuran (50 ml). The resulting solution was stirred and cooled at -20° to -15°C. Phenyl chloroformate (1.61 g) was added, and after 5 min, a solution of Lphenylalanine t-butyl ester hydrochloride (2.4 g) and N-methylmorpholine (1.03 g) in dry tetrahydrofuran (30 ml) was added. The mixture was stirred at -20° to -15°C for 1 h and then at room temperature overnight.
After removal of insoluble materials by filtration, the filtrate was concentrated under reduced pressure and the residue was dissolved in chloroform.
The chloroform solution was washed successively with 1 N sodium hydroxide, water, 10% citric acid, and water, dried and concentrated under reduced pressure. The residue was chromatographed on silica gel with chloroformmethanol (99:1) to give 4.2 g the 1-(D-3-acetylthio-2-methylpropanoyl)-Lprolyl- L-phenylalanine tert-butyl ester.
1-(D-3-Acetylthio-2-methylpropanoyl)-L-prolyl-L-phenylalanine tert-butyl ester (2.5 g) was dissolved in a mixture of anisole (18 ml) and trifluoroacetic acid (37 ml). The solution was allowed to stand at room temperature for 1 h and then concentrated to dryness under reduced pressure. The residue was crystallized from diethyl ether. The 1-(D-3-acetylthio-2-methylpropanoyl)-Lprolyl- L-phenylalanine was obtained (1.8 g), melting point 155°-156°C (recrystallization from ethanol/n-hexane).
Trademarks
Cetapril
Therapeutic Function
Antihypertensive

Alacepril Upstream-Materialien And Downstream Produkte

Alacepril Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

74258-86-9, Alacepril Verwandte Suche:

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