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

General Information of Drug (ID: DR0906)
Drug Name
Ketoconazole
Synonyms
Ketoconazol; Ketoconazolum; Ketoderm; Nizoral; Ketoconazole; R 41400; Fungarest; Fungoral; KW-1414; 1-[4-[4-[[2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone; 65277-42-1; 79156-75-5; CHEBI:48339; NSC317629; cis-1-Acetyl-4-(4-((2-(2,4-dichlorophenyl)-2-(1H-1M-idazol-1-ylmethyl)-1,3-dioxolan-4-yl) methoxy) phenyl)-piperazine; piperazine, 1-acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-
Indication Dermatophytosis [ICD11: 1F28] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 531.4 Topological Polar Surface Area 69.1
Heavy Atom Count 36 Rotatable Bond Count 7
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
3823
PubChem SID
456469 ; 5316931 ; 8152421 ; 11407121 ; 29222942 ; 46506746 ; 46530753 ; 47261387 ; 51021382 ; 57322009 ; 85087144 ; 85174349 ; 85787593 ; 93620728 ; 103845251 ; 104014719 ; 104304628 ; 117361105 ; 117571495 ; 118836543 ; 125355519 ; 125357821 ; 125433866 ; 125544749 ; 126685446 ; 126728346 ; 127316656 ; 127316657 ; 127316658 ; 127316659 ; 127316660 ; 129708236 ; 135650454 ; 137100792 ; 142426911 ; 143837446 ; 152057681 ; 162022954 ; 162092001 ; 162914824 ; 163315720 ; 164811453 ; 164830408 ; 172824381 ; 179116748 ; 223677862 ; 223726587 ; 226399613 ; 252825836
ChEBI ID
ChEBI:47519
CAS Number
65277-42-1
TTD Drug ID
D0B4IF
Formula
C26H28Cl2N4O4
Canonical SMILES
CC(=O)N1CCN(CC1)C2=CC=C(C=C2)OCC3COC(O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl
InChI
1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3
InChIKey
XMAYWYJOQHXEEK-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
Ketoconazole epoxide intermediate DM002803 N. A. Unclear 1 [2]
M13 (Ketoconazole) DM002793
139600769
Oxidation - N-Oxidation 1 [2]
M14 (Ketoconazole) DM002794
10480684
Oxidation - Deacetylation 1 [2]
M7 (Ketoconazole) DM002795 N. A. Oxidation - Oxidation 1 [2]
M8 (Ketoconazole) DM002796 N. A. Oxidation - Hydroxylation 1 [2]
M9 (Ketoconazole) DM002798 N. A. Oxidation - Hydoxylation 1 [2]
Ketoconazole dihydroxyl intermediate DM002804 N. A. Other reaction - Hydration 2 [2]
Ketoconazole iminium ion DM002801 N. A. Other reaction - Dehydration 2 [2]
Ketoconazole ketone intermediate DM002808 N. A. Oxidation - Oxidation 2 [2]
M10 (Ketoconazole) DM002799 N. A. Oxidation - N-Dealkylation 2 [2]
M12 (Ketoconazole) DM002802 N. A. Oxidation - Oxidation 2 [2]
M6 (Ketoconazole) DM002797 N. A. Oxidation - Hydroxylation 2 [2]
Ketoconazole ketone hydroxyl intermediate DM002809 N. A. Other reaction - Hydration 3 [2]
M15 (Ketoconazole) DM002800
13019742
Oxidation - N-Dealkylation 3 [2]
M3 (Ketoconazole) DM002805 N. A. Oxidation - N-Dealkylation 3 [2]
M5' (Ketoconazole) DM002807 N. A. Oxidation - Oxidation 3 [2]
M2 (Ketoconazole) DM002811
133052789
Oxidation - N-Dealkylation 4 [2]
M4 (Ketoconazole) DM002806 N. A. Oxidation - N-Dealkylation 4 [2]
M5 (Ketoconazole) DM002810 N. A. Oxidation - Oxidation 4 [2]
⏷ Show the Full List of 19  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001352 Ketoconazole M13 (Ketoconazole) Oxidation - N-Oxidation CYP3A4 [2]
MR001353 Ketoconazole M14 (Ketoconazole) Oxidation - Deacetylation Unclear [2]
MR001354 Ketoconazole M7 (Ketoconazole) Oxidation - Oxidation CYP3A4 [2]
MR001355 Ketoconazole M8 (Ketoconazole) Oxidation - Hydroxylation CYP3A4 [2]
MR001356 Ketoconazole M9 (Ketoconazole) Oxidation - Hydoxylation Unclear [2]
MR001357 Ketoconazole Ketoconazole epoxide intermediate Unclear Unclear [2]
MR001344 Ketoconazole epoxide intermediate Ketoconazole dihydroxyl intermediate Other reaction - Hydration Unclear [2]
MR001345 Ketoconazole epoxide intermediate Ketoconazole ketone intermediate Oxidation - Oxidation Unclear [2]
MR001339 M8 (Ketoconazole) M6 (Ketoconazole) Oxidation - Hydroxylation CYP3A4 [2]
MR001340 M9 (Ketoconazole) M10 (Ketoconazole) Oxidation - N-Dealkylation Unclear [2]
MR001341 M9 (Ketoconazole) Ketoconazole iminium ion Other reaction - Dehydration Unclear [2]
MR001342 M9 (Ketoconazole) M12 (Ketoconazole) Oxidation - Oxidation Unclear [2]
MR001346 Ketoconazole dihydroxyl intermediate M3 (Ketoconazole) Oxidation - N-Dealkylation Unclear [2]
MR001347 Ketoconazole dihydroxyl intermediate M5' (Ketoconazole) Oxidation - Oxidation Unclear [2]
MR001349 Ketoconazole ketone intermediate Ketoconazole ketone hydroxyl intermediate Other reaction - Hydration Unclear [2]
MR001343 M10 (Ketoconazole) M15 (Ketoconazole) Oxidation - N-Dealkylation Unclear [2]
MR001350 Ketoconazole ketone hydroxyl intermediate M5 (Ketoconazole) Oxidation - Oxidation Unclear [2]
MR001351 Ketoconazole ketone hydroxyl intermediate M2 (Ketoconazole) Oxidation - N-Dealkylation CYP3A4 ... [2]
MR001348 M3 (Ketoconazole) M4 (Ketoconazole) Oxidation - N-Dealkylation Unclear [2]
⏷ Show the Full List of 19 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
References
1 Ketoconazole was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Revisiting the metabolism of ketoconazole using accurate mass Drug Metab Lett. 2009 Aug;3(3):191-8. doi: 10.2174/187231209789352085.
3 The metabolism of amiodarone by various CYP isoenzymes of human and rat, and the inhibitory influence of ketoconazole. J Pharm Pharm Sci. 2008;11(1):147-59.

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