Details of the Drug

General Information of Drug (ID: DMQFDRC)

Drug Name
Idebenone
Synonyms
idebenone; 58186-27-9; Idebenona; Idebenonum; CV 2619; Idebenonum [Latin]; Idebenona [Spanish]; Idebenone [INN:JAN]; CV-2619; 2-(10-hydroxydecyl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione; UNII-HB6PN45W4J; BRN 2001459; 6-(10-Hydroxydecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone; HB6PN45W4J; 2-(10-Hydroxydecyl)-5,6-dimethoxy-3-methyl-1,4-benzoquinone; CHEBI:31687; JGPMMRGNQUBGND-UHFFFAOYSA-N; 2,5-Cyclohexadiene-1,4-dione, 2-(10-hydroxydecyl)-5,6-dimethoxy-3-methyl-; NCGC00160514-01; AK161748
Indication
Disease Entry ICD 11 Status REF
Cognitive impairment 6D71 Approved [1]
Friedreich's ataxia 8A03.10 Approved [1]
Leber hereditary optic neuropathy 8C73.Y Approved [2]
ATC Code
N06BX13: Idebenone
N06BX: Other psychostimulants and nootropics
N06B: PSYCHOSTIMULANTS, AGENTS USED FOR ADHD AND NOOTROPICS
N06: PSYCHOANALEPTICS
N: NERVOUS SYSTEM
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 338.4
Logarithm of the Partition Coefficient (xlogp) 4.3
Rotatable Bond Count (rotbonds) 12
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 5
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [3]
Bioavailability
The bioavailability of drug is 35% [4]
Elimination
After a single or repeated oral dose of 750 mg of idebenone, QS4+QS4-C were the most prominent idebenone-derived metabolites in urine, representing on average between 49.3% and 68.3% of the total administered dose [5]
Metabolism
The drug is metabolized via oxidative shortening of the side chain and by reduction of the quinone ring and conjugation to glucuronides and sulphates [5]
Chemical Identifiers
Formula
C19H30O5
IUPAC Name
2-(10-hydroxydecyl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione
Canonical SMILES
CC1=C(C(=O)C(=C(C1=O)OC)OC)CCCCCCCCCCO
InChI
InChI=1S/C19H30O5/c1-14-15(12-10-8-6-4-5-7-9-11-13-20)17(22)19(24-3)18(23-2)16(14)21/h20H,4-13H2,1-3H3
InChIKey
JGPMMRGNQUBGND-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
3686
ChEBI ID
CHEMBL252556
CAS Number
58186-27-9
UNII
HB6PN45W4J
DrugBank ID
DB09081
TTD ID
D0MM8N
INTEDE ID
DR0853
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Molecular Interaction Atlas of This Drug


Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 1A2 (CYP1A2)
Main DME 		DEJGDUW CP1A2_HUMAN Substrate [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 Leber Hereditary Optic Neuropathy. 2000 Oct 26 [updated 2021 Mar 11]. In: Adam MP, Feldman J, Mirzaa GM, Pagon RA, Wallace SE, Bean LJH, Gripp KW, Amemiya A, editors. GeneReviews(?) [Internet]. Seattle (WA): University of Washington, Seattle; 1993C2024.
3 BDDCS applied to over 900 drugs
4 Rook EJ, van Ree JM, van den Brink W, Hillebrand MJ, Huitema AD, Hendriks VM, Beijnen JH: Pharmacokinetics and pharmacodynamics of high doses of pharmaceutically prepared heroin, by intravenous or by inhalation route in opioid-dependent patients. Basic Clin Pharmacol Toxicol. 2006 Jan;98(1):86-96. doi: 10.1111/j.1742-7843.2006.pto_233.x.
5 EMA Product Label
6 Pharmacokinetic evaluation of idebenone. Expert Opin Drug Metab Toxicol. 2010 Nov;6(11):1437-44.