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

General Information of Drug (ID: DR1186)
Drug Name
Olanzapine
Synonyms
Olanzapine [INN]; Olanzapine [USAN]; Zyprexa Intramuscular; LY 170053; LY-170053; LY170053; Lanzac; Olansek; Zalasta; Zypadhera; Zyprexa; Zyprexa Velotab; Zyprexa Zydis; olanzapine; 132539-06-1; 2-Methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5]benzodiazepine; 2-Methyl-4-(4-methylpiperazin-1-yl)-10H-benzo[b]thieno[2,3-e][1,4]diazepine; 2-methyl-4-(4-methylpiperazin-1-yl)-10H-thieno[2,3-b][1,5]benzodiazepine; 2-methyl-4-(4-methylpiperazin-1-yl)-5H-thieno[3,2-c][1,5]benzodiazepine; C17H20N4S; UNII-N7U69T4SZR
Indication Schizophrenia [ICD11: 6A20] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 312.4 Topological Polar Surface Area 59.1
Heavy Atom Count 22 Rotatable Bond Count 1
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
135398745
PubChem SID
9530 ; 591970 ; 816938 ; 5025348 ; 7847520 ; 7980183 ; 11528747 ; 12014657 ; 14923451 ; 25819934 ; 26612730 ; 26719852 ; 26750094 ; 29215187 ; 29215188 ; 29223674 ; 42684855 ; 46386668 ; 46507666 ; 48416347 ; 49665994 ; 49666419 ; 49681733 ; 49830782 ; 53788662 ; 56310909 ; 56312010 ; 56312820 ; 56352944 ; 57288797 ; 57322337 ; 77029366 ; 81092909 ; 85174531 ; 85209215 ; 85213702 ; 85753333 ; 89736112 ; 92307994 ; 92308375 ; 92308920 ; 92712529 ; 93166490 ; 93167156 ; 93618268 ; 99637141 ; 103195217 ; 103950390 ; 104253651 ; 104306829
ChEBI ID
ChEBI:7735
CAS Number
132539-06-1
TTD Drug ID
D0V4QS
Formula
C17H20N4S
Canonical SMILES
CC1=CC2=C(NC3=CC=CC=C3N=C2S1)N4CCN(CC4)C
InChI
1S/C17H20N4S/c1-12-11-13-16(21-9-7-20(2)8-10-21)18-14-5-3-4-6-15(14)19-17(13)22-12/h3-6,11,18H,7-10H2,1-2H3
InChIKey
KVWDHTXUZHCGIO-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
2-hydroxymethylolanzapine DM002280
135515431
Unclear 1 [4] , [6] , [7]
4'-N-desmethylolanzapine DM002279
135446209
Oxidation - N-Demethylation 1 [4] , [6]
7-hydroxyolanzapine DM002278
136198623
Oxidation - 7-Hydroxylation 1 [4] , [6]
N-oxide olanzapine metabolite DM002282
18315390
Oxidation - N-Oxidation 1 [4] , [7]
Olanzapine 10-N-glucuronide metabolite DM002281
74603552
Conjugation - Glucuronidation 1 [4] , [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001802 Olanzapine 7-hydroxyolanzapine Oxidation - 7-Hydroxylation CYP1A2 [4], [6]
MR001803 Olanzapine 4'-N-desmethylolanzapine Oxidation - N-Demethylation CYP1A2 [4], [6]
MR001804 Olanzapine 2-hydroxymethylolanzapine Unclear CYP2D6 [4], [6], [7]
MR001805 Olanzapine Olanzapine 10-N-glucuronide metabolite Conjugation - Glucuronidation CYP1A2 [4], [6]
MR001806 Olanzapine N-oxide olanzapine metabolite Oxidation - N-Oxidation FMO3 [4], [7]
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 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
Dimethylaniline oxidase 3 (FMO3) DME0039 Homo sapiens
FMO3_HUMAN
1.14.13.8
[4]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1364 Bacteroides coprophilus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [5]
⏷ Show the Full List of 6  DME(s)
References
1 Olanzapine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Interactions between the cytochrome P450 system and the second-generation antipsychotics. J Psychiatry Neurosci. 2003 Mar;28(2):99-112.
3 [Olanzapine: pharmacology, pharmacokinetics and therapeutic drug monitoring]. Fortschr Neurol Psychiatr. 2001 Nov;69(11):510-7.
4 Olanzapine. Pharmacokinetic and pharmacodynamic profile. Clin Pharmacokinet. 1999 Sep;37(3):177-93.
5 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
6 The Unique Human N10-Glucuronidated Metabolite Formation from Olanzapine in Chimeric NOG-TKm30 Mice with Humanized Livers. Drug Metab Dispos. 2023 Apr;51(4):480-491. doi: 10.1124/dmd.122.001102.
7 Quantification of olanzapine and its three metabolites by liquid chromatography-tandem mass spectrometry in human body fluids obtained from four deceased, and confirmation of the reduction from olanzapine N-oxide to olanzapine in whole blood in vitro. Forensic Toxicol. 2023 Jul;41(2):318-328. doi: 10.1007/s11419-023-00662-0.

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