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]
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
CHEBI:31687
CAS Number
58186-27-9
DrugBank ID
DB09081
TTD ID
D0MM8N
INTEDE ID
DR0853
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

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.