ChemicalBook > Product Catalog > Biochemical Engineering > Inhibitors > Metabolism > PDE inhibitors > Anagrelide hydrochloride
Anagrelide hydrochloride Chemical Properties
- Melting point:>280°C
- storage temp. Desiccate at +4°C
- solubility DMSO: soluble1mg/mL, clear (warmed)
- form powder
- color white to beige
- CAS DataBase Reference58579-51-4(CAS DataBase Reference)
Anagrelide hydrochloride Usage And Synthesis
- DescriptionAnagrelide hydrochloride was launched in the US for thrombocytosis (essential or associated with chronic myelogenous leukemia). The imidazoquinazoline derivative can be prepared from 2,5,6-trichloro-3,4-dihydropyrimidine via alkylation with ethyl bromoacetate followed by heating with ethanolic ammonia or treatment of N-(a-amino- 5,6-dichlorobenzyl)glycine ethyl ester with cyanogen bromide. As a result of its anti-cAMP phosphodiesterase (PDE Ⅲ) activity, Anagrelide hydrochloride was initially tested as a platelet aggregation inhibitor. However it was found that at much lower concentrations it became thrombocytopenic. While the mechanism is not fully understood, it did not shorten platelet survival nor inhibit the formation of colony-forming unitsmegakaryocytes (CFU-M) but primarily interfered with the maturation of megakaryocytes (reduction in size with altered ploidy). It did decrease peripheral vascular resistance and had a positive inotropic effect.
- Chemical PropertiesOff-White Powder
- OriginatorRoberts (US)
- UsesA phosphodiesterase inhibitor with antiplatelet activity. Used as an antithrombocythemic.
- UsesSignal Transduction Agents, Potent PDE3 inhibitor
- DefinitionChEBI: The hydrochloride salt of anagrelide.
- Manufacturing Process6,7-Dicloro-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one was produced
from 6-chloro-7-bromo-1,2,3,5-tetrahydroimidazo[2,1-b]quinozolin-2-one by
substitution the bromine an equimolar quantity chlorine.
6-Chloro-7-bromo-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one was produced next way: to a solution of 1.30 g (8 mmole) of anhydrous ferric chloride in 30 ml of nitromethane was added 1.30 g (5 mmole) of solid 6- chloro-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one and 0.80 g (5 mmole) of bromine. The system was stoppered, warmed to 50°C in an oil bath overnight, cooled to room temperature and the solvent removed in vacuo. The resulting solid was suspended in water (50 ml), the mixture was made basic (pH=10) with sodium bicarbonate and stirred at home temperature for 20 min. The solid was filtered under suction, washed with water, then isopropyl alcohol and dried yielding 1.19 g of 6-chloro-7-bromo- 1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one (78% yield). Purification was effected by formation of the hydrochloride salt (mp 275°C) from acetonitrile.
6-Chloro-1,2,3,5,-tetrahydroimidazo[2,1-b]quinazolin-2-one was produced from 6-chloro-2-nitrobenzylchloride, ethylglycine hydrochloride and cyanogen bromide in 3 steps.
- brand nameAgrylin (Shire).
- Therapeutic FunctionPlatelet aggregation inhibitor
- Biological ActivityPotent type III phosphodiesterase (PDE3) inhibitor (IC 50 = 36 nM). Inhibits platelet aggregation and produces potent thrombocytopenic effects via inhibition of megakaryocyte maturation.
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Anagrelide hydrochloride SupplierMore
- Company Name:Lancrix Chemicals Gold
- Company Name:J & K SCIENTIFIC LTD.
- Tel:400-666-7788 010-82848833-
- Company Name:3B Pharmachem (Wuhan) International Co.,Ltd.
- Tel:18930552037 821-50328103-801
- Company Name:Chembest Research Laboratories Limited
- Company Name:LGM Pharma