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Compound Detail

CHEMBL252556

IDEBENONE
💊 Approved Drug
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💊 Approved Drug
COC1=C(OC)C(=O)C(CCCCCCCCCCO)=C(C)C1=O

Basic Information

ChEMBL ID CHEMBL252556
Name IDEBENONE
Phase Approved
Structure Type MOL
InChI Key JGPMMRGNQUBGND-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Hydroxydecyl ubiquinone Idebenona Idebenone NSC-759228 Oristar hdu Raxone Sovrima
14
Targets
21
Activities
3
Assay Types
2
PK Parameters
20
Publications
7
Known Names
8
Indications
1
Mechanisms

Molecular Properties

338.4
MW (Da)
3.46
ALogP
5
HBA
1
HBD
72.8
PSA (Ų)
0.44
QED
0
Ro5 Violations
12
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2015
Availability Unknown
Chirality Achiral

Flags

Natural Product
USAN Year 2017

Extended Properties

Molecular Formula C19H30O5
MW 338.44
Aromatic Rings 0
Heavy Atoms 24
NP-Likeness 1.39

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Antioxidant and mitochondrial electron carrier - -

Indications

Attention Deficit Disorder with Hyperactivity Optic Atrophy, Hereditary, Leber Friedreich Ataxia Muscular Dystrophy, Duchenne MELAS Syndrome Huntington Disease Multiple Sclerosis, Chronic Progressive Non-alcoholic Fatty Liver Disease

ATC Classification

N06BX13
idebenone
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOANALEPTICS

Activity Summary

IC50 15 meas. best 6.1
EC50 5 meas. best 6.26
Ki 1 meas. best 5.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NON-PROTEIN TARGET
CHEMBL3879801
EC50 6.26 6.165 551.0 2
Fibroblast
CHEMBL613838
EC50 6.23 6.23 592.0 1
Unchecked
CHEMBL612545
EC50 6.14 6.085 730.0 2
Cytochrome P450 2C19
CHEMBL3622
IC50 6.1 6.1 800.0 1
Rattus norvegicus
CHEMBL376
IC50 5.89 5.89 1300.0 1
NAD-dependent protein deacetylase
CHEMBL4523517
IC50 5.72 5.72 1900.0 1
Cytochrome P450 2D6
CHEMBL289
IC50 5.52 5.52 3000.0 1
Unchecked
CHEMBL612545
Ki 5.4 5.4 4000.0 1
Cytochrome P450 2C9
CHEMBL3397
IC50 5.3 5.3 5000.0 1
Unchecked
CHEMBL612545
IC50 5.24 4.6825 5800.0 4
Cytochrome P450 3A4
CHEMBL340
IC50 5.16 5.16 7000.0 1
NAD-dependent protein deacetylase sirtuin-2
CHEMBL4462
IC50 4.81 4.81 15400.0 1
SH-SY5Y
CHEMBL614910
IC50 4.8 4.8 15900.0 1
Brain
CHEMBL613617
IC50 4.5 4.5 31500.0 1
HL-60
CHEMBL383
IC50 4.44 4.44 36000.0 1
HepG2
CHEMBL395
IC50 4.19 4.19 64500.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 -12.0 hr -
T1/2 -12.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NON-PROTEIN TARGET EC50 = 551.0 nM 6.26 Cytoprotective activity against BSO-induced cell death in human Friedreich's ata... 24900738
Fibroblast EC50 = 592.0 nM 6.23 Cytoprotective activity against BSO-induced human FRDA primary patient fibroblas... 22137789
Unchecked EC50 = 730.0 nM 6.14 Cytoprotection in diethyl maleate-treated human Friedreich's ataxia lymphocytes ... 22883028
Cytochrome P450 2C19 IC50 = 800.0 nM 6.1 DRUGMATRIX: CYP450, 2C19 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) -
NON-PROTEIN TARGET EC50 = 850.0 nM 6.07 Cytoprotectant activity against L-buthionine-(S,R)-sulfoximine-induced cell deat... 21600768
Unchecked EC50 = 940.0 nM 6.03 Suppression of rotenone-induced ATP depletion in human HepG2 cells incubated for... 33180495
Rattus norvegicus IC50 = 1300.0 nM 5.89 Inhibition of NADH-induced lipid peroxidation in rat brain microsome 18183943
NAD-dependent protein deacetylase IC50 = 1900.0 nM 5.72 Inhibition of recombinant Schistosoma mansoni sirtuin 2 (21 to 322 residues) exp... 31496251
Cytochrome P450 2D6 IC50 = 3000.0 nM 5.52 DRUGMATRIX: CYP450, 2D6 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) -
Unchecked Ki = 4000.0 nM 5.4 Inhibition of NADH-ubiquinone oxidoreductase in bovine heart mitochondria after ... 23313093
Cytochrome P450 2C9 IC50 = 5000.0 nM 5.3 DRUGMATRIX: CYP450, 2C9 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) -
Unchecked IC50 = 5800.0 nM 5.24 Inhibition of NADH-ubiquinone oxidoreductase activity in bovine heart submitocho... 23473946
Unchecked IC50 = 6000.0 nM 5.22 Inhibition of NADH-ubiquinone oxidoreductase in bovine heart mitochondria after ... 23313093
Cytochrome P450 3A4 IC50 = 7000.0 nM 5.16 DRUGMATRIX: CYP450, 3A4 enzyme inhibition (substrate: 7-Benzyloxy-4-(trifluorome... -
NAD-dependent protein deacetylase sirtuin-2 IC50 = 15400.0 nM 4.81 Inhibition of N-terminal His6 tagged human sirtuin 2 (25 to 389 residues) using ... 31496251
SH-SY5Y IC50 = 15900.0 nM 4.8 Cytotoxicity against human SH-SY5Y cells assessed as reduction in cell viability... 33180495
Brain IC50 = 31500.0 nM 4.5 Inhibition of Fe2+-induced lipid peroxidation in rat brain homogenate 18183943
HL-60 IC50 = 36000.0 nM 4.44 Antiproliferative activity against human HL60 cells after 48 hrs by MTT assay 23432053
HepG2 IC50 = 64500.0 nM 4.19 Cytotoxicity against human HepG2 cells assessed as reduction in cell viability i... 33180495
Unchecked IC50 = 70000.0 nM 4.16 Inhibition of tPMET complex in human mitochondrial gene-knockout HL60 cells afte... 23432053

Literature References

Data from ChEMBL 36 via Core Engine