istradefylline   Click here for help

GtoPdb Ligand ID: 5608

Synonyms: KW-6002 | KW6002 | Nourianz®
Approved drug
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
SMILES / InChI / InChIKey
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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+
InChI Key IQVRBWUUXZMOPW-PKNBQFBNSA-N
References
1. Chang LC, von Frijtag Drabbe Künzel JK, Mulder-Krieger T, Westerhout J, Spangenberg T, Brussee J, Ijzerman AP. (2007)
2,6,8-trisubstituted 1-deazapurines as adenosine receptor antagonists.
J Med Chem, 50 (4): 828-34. [PMID:17300165]
2. Dungo R, Deeks ED. (2013)
Istradefylline: first global approval.
Drugs, 73 (8): 875-82. [PMID:23700273]
3. Fredholm BB, IJzerman AP, Jacobson KA, Linden J, Müller CE. (2011)
International Union of Basic and Clinical Pharmacology. LXXXI. Nomenclature and classification of adenosine receptors--an update.
Pharmacol Rev, 63 (1): 1-34. [PMID:21303899]
4. Pretorius J, Malan SF, Castagnoli N, Bergh JJ, Petzer JP. (2008)
Dual inhibition of monoamine oxidase B and antagonism of the adenosine A(2A) receptor by (E,E)-8-(4-phenylbutadien-1-yl)caffeine analogues.
Bioorg Med Chem, 16 (18): 8676-84. [PMID:18723354]
5. Shimada J, Koike N Nonaka H, Shiozaki S, Yanagawa K, Kanda T, Kobayashi H, Ichimura M, Nakamura J, Kase H et al.. (1997)
Adenosine A2A antagonists with potent anti-cataleptic activity.
Bioorg Med Chem Lett, (7): 2349-2352.