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DILAZEP DIHYDROCHLORIDE

Product Name
DILAZEP DIHYDROCHLORIDE
CAS No.
20153-98-4
Chemical Name
DILAZEP DIHYDROCHLORIDE
Synonyms
cormelian;astac;k-285;C12954;C-4898;labitan;comelian;astac4898;Delazeol Hydrochloride;DILAZEP DIHYDROCHLORIDE
CBNumber
CB2143031
Molecular Formula
C31H46Cl2N2O10
Formula Weight
677.61
MOL File
20153-98-4.mol
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DILAZEP DIHYDROCHLORIDE Property

Melting point:
194-198° (monohydrate)
storage temp. 
2-8°C
solubility 
H2O: 10 mg/mL
form 
powder
color 
white
Water Solubility 
Soluble to 100 mM in water
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
2
RTECS 
DI0250000
Toxicity
LD50 in male mice, male rats (mg/kg): 26.6, 19.1 i.v.; 161, 90.1 i.p.; 3740, >2150 orally (Abel)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
D5294
Product name
Dilazep dihydrochloride
Purity
powder
Packaging
50mg
Price
$312
Updated
2024/03/01
Sigma-Aldrich
Product number
D5294
Product name
Dilazep dihydrochloride
Purity
powder
Packaging
100mg
Price
$583
Updated
2024/03/01
Alfa Aesar
Product number
J62459
Product name
Dilazep dihydrochloride
Packaging
50mg
Price
$178
Updated
2021/12/16
Cayman Chemical
Product number
29761
Product name
Dilazep (hydrochloride)
Packaging
5mg
Price
$62
Updated
2024/03/01
Cayman Chemical
Product number
29761
Product name
Dilazep (hydrochloride)
Packaging
10mg
Price
$104
Updated
2024/03/01
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DILAZEP DIHYDROCHLORIDE Chemical Properties,Usage,Production

Originator

Cormelian,Asta-Werke,W. Germany,1972

Uses

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.

Uses

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.

Uses

Vasodilatator;Adenosine uptake inhibitor

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

General Description

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.

storage

Store at RT

DILAZEP DIHYDROCHLORIDE Preparation Products And Raw materials

Raw materials

Preparation Products

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DILAZEP DIHYDROCHLORIDE Suppliers

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20153-98-4, DILAZEP DIHYDROCHLORIDERelated Search:


  • DILAZEP DIHYDROCHLORIDE
  • 1,4-BIS[3-(3,4,5-TRIMETHOXYBENZOYLOXY)PROPYL]HOMOPIPERAZINE DIHYDROCHLORIDE
  • N,N'-BIS[3-(3,4,5-TRIMETHOXY-BENZOYLOXY)PROPYL]HOMOPIPER-AZINE DIHYDROCHLORIDE
  • 1,4-bis(3-(3,4,5-trimethoxybenzoyloxy)-propyl)perhydro-1,4-diazepinedihydroc
  • astac
  • astac4898
  • benzoicacid,3,4,5-trimethoxy-,diesterwithtetrahydro-1h-1,4-diazepine-1,4(5
  • comelian
  • C-4898
  • C12954
  • cormelian
  • h)dipropanol,dihydrochloride
  • k-285
  • labitan
  • n,n’-(bis-omega-hydroxypropyl)homopiperazine3,4,5-trimethoxybenzoatedihydro
  • (tetrahydro-1H-1,4-diazepine-1,4(5H)-diyl)di(propane-1,3-diyl) bis(3,4,5-trimethoxybenzoate) dihydrochloride
  • DILAZEP DIHYDROCHLORIDE (COMELIAN, CORME LIAN, ASTA C) \ ADENOSINE UPTAKE INHIB
  • ASTA C 4898, Cormelian, N,Nμ-bis(3-[3,4,5-Trimethoxybenzoyloxy]propyl)homopiperazine dihydrochloride
  • (1,4-diazepane-1,4-diyl)bis(propane-3,1-diyl) bis(3,4,5-trimethoxybenzoate) dihydrochloride
  • ischemic,Adenosine,Dilazep dihydrochloride,uptake,vasodilation,potentiate,Inhibitor,cerebral,damage,inhibit,Dilazep
  • Delazeol Hydrochloride
  • 20153-98-4
  • C31H46N2O102Cl
  • C31H44N2O102HCl