DILAZEP DIHYDROCHLORIDE Struktur

(Tetrahydro-1H-1,4-diazepin-1,4(5H)-diyl)di(propan-1,3-diyl)bis(3,4,5-trimethoxybenzoat)dihydrochlorid

Bezeichnung:(Tetrahydro-1H-1,4-diazepin-1,4(5H)-diyl)di(propan-1,3-diyl)bis(3,4,5-trimethoxybenzoat)dihydrochlorid

CAS-Nr20153-98-4

Englisch Name:DILAZEP DIHYDROCHLORIDE

CBNumberCB2143031

SummenformelC31H46Cl2N2O10

Molgewicht677.61

MOL-Datei20153-98-4.mol

Synonyma

(Tetrahydro-1H-1,4-diazepin-1,4(5H)-diyl)di(propan-1,3-diyl)bis(3,4,5-trimethoxybenzoat)dihydrochlorid

(Tetrahydro-1H-1,4-diazepin-1,4(5H)-diyl)di(propan-1,3-diyl)bis(3,4,5-trimethoxybenzoat)dihydrochlorid physikalisch-chemischer Eigenschaften

Schmelzpunkt	194-198° (monohydrate)
storage temp.	2-8°C
Löslichkeit	H₂O: 10 mg/mL
Aggregatzustand	powder
Farbe	white
Wasserlöslichkeit	Soluble to 100 mM in water

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36
WGK Germany	2
RTECS-Nr.	DI0250000
Toxizität	LD50 in male mice, male rats (mg/kg): 26.6, 19.1 i.v.; 161, 90.1 i.p.; 3740, >2150 orally (Abel)

Gefahreninformationscode (GHS)

DILAZEP DIHYDROCHLORIDE Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Originator
Cormelian,Asta-Werke,W. Germany,1972
Verwenden
Vasodilatator;Adenosine uptake inhibitor
Verwenden
Dilazep Dihydrochloride is a research product for neuroscience. This compound may exhibit neuroprotective properties. Angiotensin converting, adenosine reuptake inhibitor. Antiplatelet agent. Dilazep acts as a cerebral vasodialator.
Verwenden
Dilazep dihydrochloride has been used in estrogen receptor (ERα) antagonistic assay. It has also been used as an equilibrative nucleoside transporter inhibitor (ENT 1 and 2) in cancer cell lines.
Definition
ChEBI: Dilazep dihydrochloride is the dihydrochloride salt of dilazep. It inhibits adenosine uptake, ischemic damage, platelet aggregation, and membrane transport of nucleosides. It has a role as a cardioprotective agent, a platelet aggregation inhibitor and a vasodilator agent. It contains a dilazep(2+).
Manufacturing Process
528.8 grams of bis-(3-hydroxypropyl)-ethylene diamine [K. Schlgl and R. Schlgl, Monatschefte der Chemie 95 (1964) page 935] are dissolved in a mixture of 1,500 cc of anhydrous ethyl alcohol and 1,250 grams of triethylamine. 520 grams of 1,3-chlorobromopropane are added thereto dropwise over a period of about 3 hours while stirring and heating the reaction mixture in an oil bath of 50°C. After completion of the addition, the oil bath is heated to 60°C for 20 minutes while stirring of the reaction mixture is continued. With increasing reaction time, triethylamine hydrochloride is precipitated. After completion of the reaction, the mixture is allowed to cool to room temperature.
Triethylamine hydrochloride is separated by filtration and the filter cake is washed with 100 cc of anhydrous ethyl alcohol. The alcohol and the excess of triethylamine is distilled off in a vacuum of a water pump. The residue represents a light-yellowish brown viscous oil which is extracted 3 times with 500 cc of anhydrous benzene each time with stirring at 40° to 60°C. The benzene is distilled off on a water bath at 60°C. Thus, an oil is obtained which solidifies to a hard mass after some hours. This mass is crushed and dried over P2O5 in an exsiccator. The compound represents N,N'-bis-(3- hydroxypropyl)homopiperazine. Yield: 128.5 grams. FP: 46°-47°C; BP0.02mm: 141°-142°C.
21.6 grams of N,N'-bis-(3-hydroxypropyl)homopiperazine obtained as described and 63.8 grams of 3,4,5-trimethoxy benzoic acid chloride are dissolved in 600 parts by volume of anhydrous chloroform. The solution is heated to boiling for 5 hours. Thereafter, chloroform is distilled off in a vacuum. The residue is dissolved in water and the aqueous solution is washed with ether. Thereafter, the aqueous phase is rendered alkaline by the addition of soda lye and the separated oil base is extracted with ether. The ethereal solution is dried over Na2SO4. Ether is separated in a vacuum and the highly viscous residue is dissolved in 150 parts by volume of ethyl alcohol. The calculated equivalent amount of ethereal HCl is added thereto.
The soon crystallizing dihydrochloride is separated by filtration, dried and recrystallized from 120 parts by volume of ethanol. Thus, after drying for 3 days over P2O5, 40-50 grams (66-70% of the theoretical) of N,N'-bis-[(3,4,5- trimethoxy benzoloxy)propyl] homopiperazine dihydrochloride containing 1 mol of water of crystallization is obtained. This product has a melting point at 194°-198°C.
Therapeutic Function
Coronary vasodilator
Allgemeine Beschreibung
Dilazep comprises central cyclic?diamine and phenyl rings connected via alkyl linkers.
Biochem/physiol Actions
Dilazep is a equilibrative nucleoside transporter 1 (ENTs) inhibitor. It is an antianginal drug and an effective coronary vasodilator. Dilazep elicits anti-albuminuric effects and is an anti-platelet agent. It is a potent adenosine uptake inhibitor and suppresses effects of ischemia.
Lager
Store at RT

DILAZEP DIHYDROCHLORIDE Upstream-Materialien And Downstream Produkte

(Tetrahydro-1H-1,4-diazepin-1,4(5H)-diyl)di(propan-1,3-diyl)bis(3,4,5-trimethoxybenzoat)dihydrochlorid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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