ARANIDIPINE

Bezeichnung:ARANIDIPINE

CAS-Nr86780-90-7

Englisch Name:ARANIDIPINE

CBNumberCB4386708

SummenformelC19H20N2O7

Molgewicht388.37

MOL-Datei86780-90-7.mol

ARANIDIPINE physikalisch-chemischer Eigenschaften

Schmelzpunkt	155°
Siedepunkt	530.0±50.0 °C(Predicted)
Dichte	1.284±0.06 g/cm3(Predicted)
storage temp.	2-8°C
Löslichkeit	DMSO : 125 mg/mL (321.86 mM)
Aggregatzustand	Solid
pka	2.56±0.70(Predicted)
Farbe	Light yellow to yellow

Sicherheit

Toxizität

LD50 in male, female mice, rats (mg/kg): 143, 193, 1982, 1459 orally; LD50 in male, female mice (mg/kg): 7.3, 9.1 i.p. (Nakano)

Gefahreninformationscode (GHS)

ARANIDIPINE Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
Aranidipine was launched in Japan as an antihypertensive agent. Its pharmacological effects are similar to other dihydropyridine derivatives, e.g., nefidipine, however, it is more potent and longer lasting. This is partially due to the fact that its initial metabolite (ketone reduction) is just as effective as the parent compound. Aranidipine exerts its activity by blocking Ca⁺² entry during depolarization via L-type voltagegated Ca channels. This causes decreased levels of intracellular Ca which leads to enhanced relaxation of smooth and cardiac muscle. It is a selective α₂-adrenoreceptor antagonist which inhibits vasoconstrictive responses. As a dihydropyridine derivative, it can be synthesized via a modified Hantsch synthesis. While sold as a racemate, the (S)-enantiomer is 150 times more active than the (R)- antipode.
Originator
Maruko Seiyaku (Japan)
Definition
ChEBI: Aranidipine is an organic molecular entity.
Manufacturing Process
100.0 mg of 50% sodium hydride was added to a mixture of 20.0 g of 2,2- ethylenedioxypropanol and 100 ml of benzene, and 20.0 g of diketene was added dropwise to the mixture while refluxing the mixture. After refluxing the mixture for 2 h, the solvent was distilled off and the resulting residue was distilled under reduced pressure to obtain 21.5 g (70% yield) of 2,2- ethylenedioxypropyl acetoacetate as a colorless oil, boiling point of 90°C (6 mm Hg).
Ammonia gas was passed through a mixture of 19.0 g of 2,2- ethylenedioxypropyl acetoacetate and 100 ml of methanol for 2.5 h under icecooling while stirring. The solvent was then distilled off and the residue was distilled under reduced pressure to obtain 16.0 g (84% yield) of 2,2- ethylenedioxypropyl 3-aminocrotonate as a pale yellow oil, boiling point of 120°C (5 mm Hg).
A mixture of methyl 2'-nitrobenzylidene acetoacetate, 2,2-ethylenedioxypropyl 3-aminocrotonate and ethanol was refluxed for 10 h. The resulting reaction solution was allowed to stand overnight, and the precipitated crystals were collected by filtration and recrystallized from ethanol to obtain methyl 2,2- ethylenedioxypropyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5- dicarboxylate.
Methyl 2,2-ethylenedioxypropyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4- dihydropyridine-3,5-dicarboxylate was refluxed in an ethanol solution containing 10% hydrochloric acid for 6 h. The solvent was then distilled off and the residue was crystallized from diethyl ether to give methyl 2-oxopropyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate as yellow prisms, melting point 155°C (recrystallized from a mixture of ethyl acetate and hexane).
Trademarks
Bec/Sapresta
Therapeutic Function
Antihypertensive

ARANIDIPINE Upstream-Materialien And Downstream Produkte

ARANIDIPINE Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

86780-90-7, ARANIDIPINE Verwandte Suche:

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