Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0853)
Drug Name
Idebenone
Synonyms
Idebenona; Idebenona [Spanish]; Idebenone [INN:JAN]; Idebenonum; Idebenonum [Latin]; JGPMMRGNQUBGND-UHFFFAOYSA-N; idebenone; 2,5-Cyclohexadiene-1,4-dione, 2-(10-hydroxydecyl)-5,6-dimethoxy-3-methyl-; 2-(10-Hydroxydecyl)-5,6-dimethoxy-3-methyl-1,4-benzoquinone; 2-(10-hydroxydecyl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione; 58186-27-9; 6-(10-Hydroxydecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone; AK161748; BRN 2001459; CHEBI:31687; CV 2619; CV-2619; NCGC00160514-01; HB6PN45W4J; UNII-HB6PN45W4J
Indication Mitochondrial myopathy [ICD11: 8C73] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 338.4 Topological Polar Surface Area 72.8
Heavy Atom Count 24 Rotatable Bond Count 12
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
3686
PubChem SID
1916788 ; 4725770 ; 7848813 ; 8152329 ; 12012810 ; 14802277 ; 26719872 ; 29216196 ; 29222809 ; 46386682 ; 49681642 ; 49957336 ; 56313750 ; 57321939 ; 78556875 ; 81041137 ; 81093345 ; 85279384 ; 88800993 ; 92308516 ; 92308744 ; 92710538 ; 103060386 ; 103556242 ; 104304229 ; 124658851 ; 125353623 ; 126631778 ; 126658121 ; 126665893 ; 128272043 ; 131319704 ; 131905204 ; 135003257 ; 135692548 ; 135698082 ; 136990616 ; 137027889 ; 142735616 ; 143492810 ; 144075938 ; 144205417 ; 152242914 ; 160871272 ; 162022270 ; 162038194 ; 162173185 ; 163079053 ; 164802349 ; 169618917
ChEBI ID
CHEBI:31687
CAS Number
58186-27-9
TTD Drug ID
D0MM8N
Formula
C19H30O5
Canonical SMILES
CC1=C(C(=O)C(=C(C1=O)OC)OC)CCCCCCCCCCO
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
QS10 DM002550
3686
Oxidation - Oxidation 1 [4]
QS10C C* DM002557 N. A. Conjugation - Conjugation 2 [4]
QS8 DM002551 N. A. Oxidation - Oxidation 2 [4]
QS6 DM002552
12881463
Oxidation - Oxidation 3 [4]
QS8C C* DM002556 N. A. Conjugation - Conjugation 3 [4]
QS4 DM002553
12824128
Oxidation - Oxidation 4 [4]
QS6C C* DM002555 N. A. Conjugation - Conjugation 4 [4]
QS4C C* DM002554 N. A. Conjugation - Conjugation 5 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001166 Idebenone QS10 Oxidation - Oxidation CYP [4]
MR001159 QS10 QS8 Oxidation - Oxidation CYP [4]
MR001160 QS10 QS10C C* Conjugation - Conjugation Unclear [4]
MR001161 QS8 QS6 Oxidation - Oxidation CYP [4]
MR001162 QS8 QS8C C* Conjugation - Conjugation Unclear [4]
MR001163 QS6 QS4 Oxidation - Oxidation CYP [4]
MR001164 QS6 QS6C C* Conjugation - Conjugation Unclear [4]
MR001165 QS4 QS4C C* Conjugation - Conjugation Unclear [4]
⏷ Show the Full List of 8 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A43 (CYP3A43) DME0022 Homo sapiens
CP343_HUMAN
1.14.14.1
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1357 Alistipes indistinctus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1376 Bacteroides ovatus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1377 Bacteroides pectinophilus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1394 Blautia luti Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1400 Enterocloster bolteae Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1445 Parabacteroides distasonis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1456 Roseburia intestinalis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1459 Ruminococcus lactaris Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1467 Subdoligranulum variabile Not Available Not Available [3]
⏷ Show the Full List of 21  DME(s)
References
1 ClinicalTrials.gov (NCT02774005) Study to Assess the Efficacy and Safety of Raxone in LHON Patients.
2 Pharmacokinetic evaluation of idebenone. Expert Opin Drug Metab Toxicol. 2010 Nov;6(11):1437-44.
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
4 Pharmacokinetic properties and metabolism of idebenone J Neurol. 2009 Mar;256 Suppl 1:31-5. doi: 10.1007/s00415-009-1006-z.

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