istradefylline   Click here for help

GtoPdb Ligand ID: 5608

Synonyms: KW-6002 | KW6002 | Nourianz®
Approved drug PDB Ligand
istradefylline is an approved drug (Japan (2013), FDA (2019))
Compound class: Synthetic organic
Comment: Istradefylline is a high affinity, selective adenosine A2A receptor antagonist. Chemically it is a caffeine analogue. Istradefylline was developed to treat adult Parkinson's disease patients experiencing "OFF" episodes, as an adjunct to levodopa/carbidopa therapy.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 6
Topological polar surface area 80.28
Molecular weight 384.18
XLogP 4.05
No. Lipinski's rules broken 0
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Canonical SMILES COc1cc(C=Cc2nc3c(n2C)c(=O)n(c(=O)n3CC)CC)ccc1OC
Isomeric SMILES COc1cc(/C=C/c2nc3c(n2C)c(=O)n(c(=O)n3CC)CC)ccc1OC
InChI InChI=1S/C20H24N4O4/c1-6-23-18-17(19(25)24(7-2)20(23)26)22(3)16(21-18)11-9-13-8-10-14(27-4)15(12-13)28-5/h8-12H,6-7H2,1-5H3/b11-9+
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Summary of Clinical Use Click here for help
Istradefylline was approved for use in Japan for several years prior to its 2019 FDA approval [2]. Istradefylline is indicated as an adjunct to levodopa/carbidopa therapy in adults who are experiencing Parkinson's disease "off" episodes.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Istradefylline is an adenosine A2A receptor antagonist [1,3]. It is reported that in animal models istradefylline is able to reverse the motor impairments induced by dopamine depletion or antagonism, however this does not appear to translate to human Parkinson's patients with any significant improvement over placebo or levodopa in Phase 3 trial.