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Compound Detail

CHEMBL431770

ISTRADEFYLLINE
💊 Approved Drug
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💊 Approved Drug
CCn1c(=O)c2c(nc(/C=C/c3ccc(OC)c(OC)c3)n2C)n(CC)c1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL431770
Name ISTRADEFYLLINE
Phase Approved
Structure Type MOL
InChI Key IQVRBWUUXZMOPW-PKNBQFBNSA-N
Therapeutic ✓ Yes

Known Names

Istradefilina Istradefylline KW-6002 Nourianz Nouriast
8
Targets
65
Activities
3
Assay Types
4
PK Parameters
20
Publications
5
Known Names
4
Indications
1
Mechanisms

Molecular Properties

384.4
MW (Da)
2.12
ALogP
8
HBA
0
HBD
80.3
PSA (Ų)
0.65
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2013
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product First in Class
USAN Stem -fylline
USAN Year 2003

Extended Properties

Molecular Formula C20H24N4O4
MW 384.44
Aromatic Rings 3
Heavy Atoms 28
NP-Likeness -0.68

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Adenosine A2a receptor antagonist ANTAGONIST Adenosine receptor A2a ✓ ✓

Indications

Parkinson Disease Amyotrophic Lateral Sclerosis Liver Diseases Substance-Related Disorders

ATC Classification

N04CX01
istradefylline
Level 1: NERVOUS SYSTEM
Level 2: ANTI-PARKINSON DRUGS

Activity Summary

Ki 60 meas. best 8.7
IC50 4 meas. best 6.64
Kd 1 meas. best 5.9

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Adenosine receptor A2a
CHEMBL302
 Ki 8.7 8.41 2.0 11
Adenosine receptor A2a
CHEMBL251
 Ki 8.66 7.56 2.2 20
Amine oxidase [flavin-containing] B
CHEMBL2039
 Ki 7.57 7.57 27.0 1
Adenosine receptor A1
CHEMBL318
 Ki 6.82 6.6156 150.0 9
Adenosine receptor A2a
CHEMBL302
 IC50 6.64 6.64 228.0 1
Adenosine receptor A1
CHEMBL226
 Ki 6.08 5.7742 841.0 12
Adenosine receptor A2a
CHEMBL251
 Kd 5.9 5.9 1258.9 1
Adenosine receptor A2b
CHEMBL255
 Ki 5.75 5.75 1800.0 2
Adenosine receptor A3
CHEMBL256
 Ki 5.35 5.35 4470.0 5
Adenosine receptor A2a
CHEMBL251
 IC50 5.28 5.28 5248.1 2
Cytochrome P450 2C9
CHEMBL3397
 IC50 4.89 4.89 13000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 11.0 ml/min Rattus norvegicus
CL 0.1 L/min Homo sapiens
T1/2 2.0 hr Rattus norvegicus
T1/2 64.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Adenosine receptor A2a Ki = 2.0 nM 8.7 Displacement of [3H]ZM241385 from rat recombinant adenosine A2A receptor express... 18189346
Adenosine receptor A2a Ki = 2.2 nM 8.66 Displacement of [3H]-CGS- 21680 from Adenosine A2a receptor of rat forebrain mem... -
Adenosine receptor A2a Ki = 2.2 nM 8.66 Binding affinity towards human Adenosine A2a receptor expressed in HEK293 cells ... 16250647
Adenosine receptor A2a Ki = 2.2 nM 8.66 Displacement of [3H]MSX2 from adenosine A2A receptor in rat brain striatal membr... 23631427
Adenosine receptor A2a Ki = 2.2 nM 8.66 Displacement of [3H]-ZM241385 from Adenosine A2A receptor in Lister hooded rat b... 26392370
Adenosine receptor A2a Ki = 4.4 nM 8.36 Displacement of [3H]CCPA from rat adenosine A2a receptor 30808606
Adenosine receptor A2a Ki = 4.46 nM 8.35 Displacement of [3H]NECA from Sprague-Dawley rat adenosine A2A receptor by scint... 18723354
Adenosine receptor A2a Ki = 4.46 nM 8.35 Displacement of [3H]CGS21680 from adenosine A2A receptor in rat brain after 60 m... 24139167
Adenosine receptor A2a Ki = 5.015 nM 8.3 Displacement of [3H]MSX2 from adenosine A2A receptor in rat brain striatal membr... 17827019
Adenosine receptor A2a Ki = 5.15 nM 8.29 Displacement of [3H]MSX-2 from adenosine A2A receptor in rat brain striatal memb... 21664729
Adenosine receptor A2a Ki = 5.15 nM 8.29 Displacement of [3H]MSX2 from adenosine A2A receptor in rat striatal membrane 17499511
Adenosine receptor A2a Ki = 6.0 nM 8.22 Displacement of [3H]ZM-241385 from human recombinant adenosine A2A receptor expr... 18189346
Adenosine receptor A2a Ki = 12.0 nM 7.92 Displacement of [3H]CGS21680 from human adenosine A2A receptor expressed in CHO ... 24139167
Adenosine receptor A2a Ki = 12.0 nM 7.92 Antagonist activity at adenosine A2A receptor (unknown origin) 29268131
Adenosine receptor A2a Ki = 12.0 nM 7.92 Displacement of [3H]ZM241385 from human adenosine A2A receptor expressed in HEK2... 35933788
Adenosine receptor A2a Ki = 12.0 nM 7.92 Antagonist activity at adenosine A2A receptor (unknown origin) 34695776
Adenosine receptor A2a Ki = 12.0 nM 7.92 Binding affinity to human adenosine A2A receptor by radioligand displacement ass... 30108984
Adenosine receptor A2a Ki = 12.0 nM 7.92 Antagonist activity at human adenosine A2A receptor assessed as cAMP level by ce... 23602401
Adenosine receptor A2a Ki = 12.0 nM 7.92 Inhibition of human recombinant adenosine receptor A2a 24164628
Adenosine receptor A2a Ki = 13.0 nM 7.89 In vitro binding affinity against Adenosine A2a receptor in rat forebrain membra... -

Literature References

PubMed DOI Target Context # Activities
21661720 10.1021/jm2003798 Adenosine receptor A2a 9
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
20973483 10.1021/jm100971t Mus musculus 4
24126093 10.1016/j.bmc.2013.09.043 No relevant target 4
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 3
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 3
23602401 10.1016/j.bmcl.2013.03.070 Adenosine receptor A2a 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 3
24815000 10.1016/j.bmc.2014.04.041 Mus musculus 3
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 3
23631427 10.1021/jm400336x Adenosine receptor A2a 3
23631427 10.1021/jm400336x Adenosine receptor A1 3
19362836 10.1016/j.bmcl.2009.03.142 Unchecked 3
37468498 10.1038/s41467-023-40064-9 Histamine H1 receptor 3
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
- 10.1016/S0960-894X(97)00440-X Adenosine receptor A2a 2
23631427 10.1021/jm400336x Adenosine receptor A3 2
18189346 10.1021/jm070623o Adenosine receptor A2a 2
17499511 10.1016/j.bmc.2007.04.018 Adenosine receptor A1 2
24139167 10.1016/j.bmc.2013.09.044 Adenosine receptor A2a 2

Data from ChEMBL 36 via Core Engine