Istradefylline , ≥99% , 155270-99-8

Synonym(s):
(E)-8-(3,4-Dimethoxystyryl)-1,3-diethyl-7-methylxanthine;8-[(1E)-2-(3,4-Dimethoxyphenyl)ethenyl]-1,3-diethyl-3,7-dihydro-7-methyl-1H-purine-2,6-dione;KW-6002

CAS NO.：155270-99-8

Empirical Formula: C20H24N4O4

Molecular Weight: 384.43

MDL number: MFCD00928421

PRODUCT Properties

• Melting point: 191 °C
• Boiling point: 601.0±65.0 °C(Predicted)
• Density: 1.24±0.1 g/cm3(Predicted)
• storage temp.: 2-8°C
• solubility: DMSO: soluble5mg/mL (clear solution)
• form: powder
• pka: 0.47±0.70(Predicted)
• color: white to beige
• InChIKey: IQVRBWUUXZMOPW-PKNBQFBNSA-N
• CAS DataBase Reference: 155270-99-8

Description and Uses

In March 2013, istradefylline (also known as KW-6002) was approved in Japan for adjunctive treatment of Parkinson’s disease (PD). Istradefylline acts by antagonism of the adenosine A_2A receptor, which is colocalized with dopamine D₂ receptors in the striatum, to enhance dopamine D₂-dependent signaling. Istradefylline is a light-sensitive compound and has been evaluated in vitro under low-light conditions to prevent isomerization of the (E)-styryl group and decomposition. Istradefylline has a Ki of 2.2 nM for the rat adenosine A_2A receptor and an ED₅₀ of 0.03 mg/kg, po, in reversal of haloperidol-induced catalepsy in mice. Further characterization showed istradefylline to have a Ki of 12 nM for the human adenosine A_2A receptor, to be highly selective, and to be a functional competitive antagonist. Istradefylline has activity alone and in combination with levo-dopa in preclinical animal models of PD. The synthesis of istradefylline was accomplished by 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide-mediated coupling of 5,6-diamino-1,3-diethyluracil with 3,4-dimethoxycinnamic acid, followed by cyclization upon treatment with aqueous NaOH, and selective methylation (MeI, K₂CO₃, and DMF).

Treatment of Parkinson’s disease (adenosine A 2A receptor antagonist).

Safety

• Symbol(GHS): GHS06
• Signal word: Danger
• Hazard statements: H301
• Precautionary statements: P301+P310
• Hazard Codes: T
• Risk Statements: 25
• Safety Statements: 45
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• HS Code: 2933.99.7500