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Compound Detail

CHEMBL744

RILUZOLE
💊 Approved Drug
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💊 Approved Drug
Nc1nc2ccc(OC(F)(F)F)cc2s1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL744
Name RILUZOLE
Phase Approved
Structure Type MOL
InChI Key FTALBRSUTCGOEG-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

BHV-0223 Exservan NSC-753433 NSC-759823 Rilutek Riluzol Riluzole Riluzole zentiva RP 54274 RP-54274 Teglutik Tiglutik +1 more
9
Targets
24
Activities
3
Assay Types
18
PK Parameters
20
Publications
13
Known Names
20
Indications
1
Mechanisms

Molecular Properties

234.2
MW (Da)
2.78
ALogP
4
HBA
1
HBD
48.1
PSA (Ų)
0.82
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1995
Availability Prescription
Chirality Achiral

Routes of Administration

Oral
USAN Year 1995

Extended Properties

Molecular Formula C8H5F3N2OS
MW 234.20
Aromatic Rings 2
Heavy Atoms 15
NP-Likeness -2.02

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Sodium channel alpha subunit blocker BLOCKER Sodium channel alpha subunit ✓ ✓

Indications

Amyotrophic Lateral Sclerosis Huntington Disease Multiple System Atrophy Spinal Cord Diseases Spinocerebellar Ataxias Spinocerebellar Ataxias Supranuclear Palsy, Progressive Alzheimer Disease Atrial Fibrillation Bipolar Disorder Cerebellar Ataxia Child Development Disorders, Pervasive Depressive Disorder Depressive Disorder, Major Melanoma Multiple Sclerosis Multiple Sclerosis, Chronic Progressive Muscular Atrophy, Spinal Obsessive-Compulsive Disorder Peripheral Nervous System Diseases

ATC Classification

N07XX02
riluzole
Level 1: NERVOUS SYSTEM
Level 2: OTHER NERVOUS SYSTEM DRUGS

Activity Summary

IC50 20 meas. best 5.76
EC50 2 meas. best 5.0
Ki 2 meas. best 5.76

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent noradrenaline transporter
CHEMBL222
 IC50 5.76 5.76 1733.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
 Ki 5.76 5.76 1718.0 1
Sodium channel protein type 2 subunit alpha
CHEMBL4187
 IC50 5.66 5.66 2200.0 1
Unchecked
CHEMBL612545
 IC50 5.4 4.8967 4000.0 3
Pteridine reductase 1
CHEMBL6194
 Ki 5.4 5.4 4000.0 1
Sodium channel protein type 2 subunit alpha
CHEMBL3399
 IC50 5.33 5.33 4730.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.1 5.1 7943.3 1
Ryanodine receptor 2
CHEMBL4745
 EC50 5.0 5.0 9900.0 1
Sodium channel protein type 9 subunit alpha
CHEMBL4296
 IC50 4.39 4.32 41000.0 2
Pteridine reductase 1
CHEMBL6194
 IC50 4.3 4.165 50000.0 2
Sodium channel protein type 4 subunit alpha
CHEMBL2072
 IC50 4.29 4.245 51000.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 38.9 mL.min-1.g-1 Homo sapiens
Excretion 90.0 % Homo sapiens
Excretion 5.0 % Homo sapiens
F 79.0 % Homo sapiens
F 60.0 % Homo sapiens
F 60.0 % Homo sapiens
Fu 0.012 - Homo sapiens
Fu 0.017 - Macaca fascicularis
Fu 0.008 - Canis lupus familiaris
Fu 0.011 - Cavia porcellus
Fu 0.012 - Mus musculus
Fu 0.009 - Rattus norvegicus
Fu 0.011 - Rattus norvegicus
Fu 0.48 - Sepia officinalis
PPB 96.0 % Homo sapiens
T1/2 12.0 hr Homo sapiens
T1/2 12.0 hr Homo sapiens
Tmax 2.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent noradrenaline transporter IC50 = 1733.0 nM 5.76 DRUGMATRIX: Norepinephrine Transporter radioligand binding (ligand: [125I] RTI-5... -
Sodium-dependent noradrenaline transporter Ki = 1718.0 nM 5.76 DRUGMATRIX: Norepinephrine Transporter radioligand binding (ligand: [125I] RTI-5... -
Sodium channel protein type 2 subunit alpha IC50 = 2200.0 nM 5.66 Blockade of synaptosomal sodium channels, inhibition of [14C]guanidinium ion flu... -
Unchecked IC50 = 4000.0 nM 5.4 Inhibition of veratridine-induced guanidine flux in cardiac voltage-gated sodium... 11170622
Pteridine reductase 1 Ki = 4000.0 nM 5.4 Inhibition of Leishmania major PTR1 by Lineweaver-Burk analysis 21126022
Sodium channel protein type 2 subunit alpha IC50 = 4730.0 nM 5.33 Sodium channel block, determined by % block of [14C]guanidinium flux in CHO line... 9703475
Plasmodium falciparum IC50 = 7943.28 nM 5.1 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910
Ryanodine receptor 2 EC50 = 9900.0 nM 5.0 Inhibition of Full length wild type mouse RyR2 expressed in Flp-In-T-REx-293 cel... 37922828
Unchecked IC50 = 15100.0 nM 4.82 Inhibition of N-terminal His-tagged Trypanosoma brucei pteridine reductase 1 usi... 30908048
Unchecked IC50 = 34200.0 nM 4.47 Inhibition of voltage-dependent Ca(+) channel in Wistar rat brain piriform corte... 19950903
Sodium channel protein type 9 subunit alpha IC50 = 41000.0 nM 4.39 Inhibition of human Nav 1.7 expressed in HEK293T cells assessed as phasic block ... 37465302
Pteridine reductase 1 IC50 = 50000.0 nM 4.3 Inhibition of Leishmania major PTR1 21126022
Sodium channel protein type 4 subunit alpha IC50 = 51000.0 nM 4.29 Inhibition of human Nav 1.4 expressed in HEK293T cells assessed as phasic block ... 37465302
Sodium channel protein type 9 subunit alpha IC50 = 56000.0 nM 4.25 Inhibition of human Nav 1.7 expressed in HEK293T cells assessed as tonic block a... 37465302
Sodium channel protein type 4 subunit alpha IC50 = 63000.0 nM 4.2 Inhibition of human Nav 1.4 expressed in HEK293T cells assessed as tonic block a... 37465302
Pteridine reductase 1 IC50 = 94100.0 nM 4.03 Inhibition of Leishmania major pteridine reductase 1 using di-hydrobiopterine as... 30908048

Literature References

PubMed DOI Target Context # Activities
- 10.5281/zenodo.13943903 ADMET 89
31158845 10.1038/s41586-019-1291-3 ADMET 70
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
27923201 10.1016/j.ejmech.2016.11.053 SH-SY5Y 13
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
19950903 10.1021/jm901375r Cortex 6
19950903 10.1021/jm901375r Unchecked 6
37465302 10.1021/acsmedchemlett.3c00224 Mus musculus 6
22892214 10.1016/j.bmc.2012.07.004 Liver microsomes 5
21474681 10.1124/dmd.111.038778 Brain 5
29937981 10.1021/acsmedchemlett.8b00103 Unchecked 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
32738997 10.1016/j.bmcl.2020.127399 NACHT, LRR and PYD domains-containing protein 3 4
29937981 10.1021/acsmedchemlett.8b00103 Cortical neurone 4
21126022 10.1021/jm1010572 Dihydrofolate reductase 4
23484434 10.1021/jm3017317 Homo sapiens 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 3
20014752 10.1021/tx900326k Hepatotoxicity 3

Data from ChEMBL 36 via Core Engine