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HomeProduct name listZARDAVERINE

ZARDAVERINE

Synonym(s):6-(4-Difluoromethoxy-3-methoxyphenyl)-3(2H)-pyridazinone

ZARDAVERINE Structural

What is ZARDAVERINE?

Originator

Zardaverine,ZYF Pharm Chemical

The Uses of ZARDAVERINE

Zardaverine can selectively inhibit?phosphodiesterase III (PDE III) from human platelets and?phosphodiesterase IV (PDE IV) from human polymorphonuclear leucocytes (PMN).

The Uses of ZARDAVERINE

Bronchodilator;Phosphodiesterase III inhibitor

What are the applications of Application

Zardaverine is a pyridazinone derivative and a selective inhibitor of phosphodiesterase type III and IV

Definition

ChEBI: A pyridazinone derivative in which pyridazin-3(2H)-one is substituted at C-6 with a 4-(difluoromethoxy)-3-methoxyphenyl group. It is a phosphodiesterase inhibitor, selective for PDE3 and 4.

Manufacturing Process

20.8 g of 4-hydroxy-3-methoxyacetophenone are dissolved in 350 ml of dioxane and 350 ml of water by the addition of 30.0 g of sodium hydroxide, and the resulting solution is heated to 60°C. While stirring continuously, chlorodifluoromethane is passed into the solution until uptake of the gas stops (about 4 h). The solution is cooled, and the resulting precipitate is filtered off with suction and washed three times with 40 ml of diethyl ether each time. The solution is diluted with water to twice its volume and likewise extracted three times with 100 ml of diethyl ether each time. The combined ether extracts are dried over magnesium sulfate and evaporated in vacuum; the residue is crystallized from petroleum ether (boiling point 50°-70°C), 19.0 g (70.4% of theory) of 4-difluoromethoxy-3-methoxyacetophenone are obtained, melting point 68°C.
15.0 g of 4-difluoromethoxy-3-methoxyacetophenone are heated with 5.9 g of glyoxylic acid monohydrate at 110°C for 2 h. The melt is then cooled to 60°C, 30 ml of water are added, and dissolution is brought about by addition of 10 ml of concentrated aqueous ammonium solution. 3.2 g of hydrazine hydrate are added, and the mixture is boiled under reflux for 2 h, during which the title compound gradually crystallizes out. After cooling, the precipitate is filtered off with suction, thoroughly washed with water, dried and recrystallized from isopropanol. 10.8 g (58.1% of theory) of the 6-(4- difluoromethoxy-3-methoxyphenyl)-3(2H)pyridazinone are obtained, melting point 204°C.

Therapeutic Function

Bronchodilator, Anti-asthmatic

Biological Activity

Phosphodiesterase inhibitor, selective for PDE3 and 4 (IC 50 values are 0.5 and 0.8 μ M respectively). Also available as part of the Phosphodiesterase Inhibitor Tocriset™ .

storage

Store at RT

Properties of ZARDAVERINE

Density  1.38±0.1 g/cm3(Predicted)
storage temp.  Store at RT
solubility  DMSO : 100 mg/mL (372.83 mM; Need ultrasonic)
pka 10.89±0.40(Predicted)
form  Off-white to yellow solid.
color  White to light yellow
CAS DataBase Reference 101975-10-4

Safety information for ZARDAVERINE

Computed Descriptors for ZARDAVERINE

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