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

General Information of Drug (ID: DR1475)
Drug Name
Sertindole
Synonyms
SerLect; Serdolect; Sertindol; Sertindol [INN-Spanish]; Sertindolum; Sertindolum [INN-Latin]; Lu 23-174; Lu-23-174; SERTINDOLE; 1-(2-(4-(5-Chloro-1-(4-fluorophenyl)-1H-indole-3-yl)-1-piperidinyl)ethyl)-2-imidazolidinone; 1-(2-(4-(5-Chloro-1-(p-fluorophenyl)indol-3-yl)piperidino)ethyl)-2-imidazolidinone; 1-(2-{4-[5-chloro-1-(4-fluorophenyl)-1H-indol-3-yl]piperidin-1-yl}ethyl)imidazolidin-2-one; 106516-24-9; CHEBI:9122; CHEMBL12713; GVV4Z879SP; GZKLJWGUPQBVJQ-UHFFFAOYSA-N; MFCD00867749; NCGC00181782-02; UNII-GVV4Z879SP
Indication Schizophrenia [ICD11: 6A20] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 440.9 Topological Polar Surface Area 40.5
Heavy Atom Count 31 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
60149
PubChem SID
9770 ; 7784967 ; 7847627 ; 7980592 ; 8186683 ; 12014521 ; 14905937 ; 43117580 ; 46504717 ; 48404531 ; 48404532 ; 49658631 ; 49980396 ; 50126331 ; 57313990 ; 77724750 ; 85210033 ; 96099950 ; 103173691 ; 103916159 ; 104319988 ; 117509987 ; 124893731 ; 125680554 ; 126683187 ; 128028443 ; 134338112 ; 135018676 ; 135651037 ; 135697546 ; 136949646 ; 137001500 ; 141946620 ; 144206958 ; 144206971 ; 152102035 ; 160967846 ; 163123216 ; 164764990 ; 170465613 ; 175268585 ; 175611946 ; 176246043 ; 179149542 ; 186006552 ; 196408596 ; 204360402 ; 210275096 ; 210280735 ; 223382206
ChEBI ID
ChEBI:9122
CAS Number
106516-24-9
TTD Drug ID
D0OS6O
Formula
C24H26ClFN4O
Canonical SMILES
C1CN(CCC1C2=CN(C3=C2C=C(C=C3)Cl)C4=CC=C(C=C4)F)CCN5CCNC5=O
InChI
1S/C24H26ClFN4O/c25-18-1-6-23-21(15-18)22(16-30(23)20-4-2-19(26)3-5-20)17-7-10-28(11-8-17)13-14-29-12-9-27-24(29)31/h1-6,15-17H,7-14H2,(H,27,31)
InChIKey
GZKLJWGUPQBVJQ-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
3'-fluoro-4'-hydroxy-sertindole DM004881
101691471
Unclear 1 [3]
4-hydroxy-serindole DM004876
21460411
Oxidation - Hydrolyzationn 1 [3]
5-hydroxy-serindole DM004872
21460413
Oxidation - Hydrolyzationn 1 [3]
Norsertindole DM004875
101371028
Oxidation - N-dealkylation 1 [3] , [4]
4-0x0-sertindole DM004877
21460401
Oxidation - Oxidationn 2 [3]
4.5 Dihydroxy-serfindo DM004880
21460387
Oxidation - Hydrolyzationn 2 [3]
5-0x0-sertindole DM004879
18334936
Oxidation - Oxidationn 2 [3]
Dehydrosertindole DM004873
9824456
Oxidation - Oxidationn 2 [3]
3'-fluoro-4'-hydroxy-dehydro-sertindole DM004874
101691183
Unclear 3 [3]
4-0x0-5-h ydroxy-serfindole DM004878
21460393
Oxidation - Hydrolyzationn 3 [3]
Norsertindole DM004875
101371028
Oxidation - N-dealkylation 3 [3]
⏷ Show the Full List of 11  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005249 Sertindole 5-hydroxy-serindole Oxidation - Hydrolyzationn Unclear [3]
MR005253 Sertindole 4-hydroxy-serindole Oxidation - Hydrolyzationn Unclear [3]
MR005259 Sertindole Norsertindole Oxidation - N-dealkylation CYP2D6 ... [3], [4]
MR005260 Sertindole 3'-fluoro-4'-hydroxy-sertindole Unclear Unclear [3]
MR005254 4-hydroxy-serindole Dehydrosertindole Oxidation - Oxidationn CYP2D6 ... [3]
MR005255 4-hydroxy-serindole 4-0x0-sertindole Oxidation - Oxidationn Unclear [3]
MR005258 4-hydroxy-serindole 4.5 Dihydroxy-serfindo Oxidation - Hydrolyzationn Unclear [3]
MR005250 5-hydroxy-serindole Dehydrosertindole Oxidation - Oxidationn CYP2D6 ... [3]
MR005257 5-hydroxy-serindole 5-0x0-sertindole Oxidation - Oxidationn Unclear [3]
MR005256 4-0x0-sertindole 4-0x0-5-h ydroxy-serfindole Oxidation - Hydrolyzationn Unclear [3]
MR005251 Dehydrosertindole 3'-fluoro-4'-hydroxy-dehydro-sertindole Unclear Unclear [3]
MR005252 Dehydrosertindole Norsertindole Oxidation - N-dealkylation CYP2D6 ... [3]
⏷ Show the Full List of 12 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
[2]
References
1 Sertindole: efficacy and safety in schizophrenia. Expert Opin Pharmacother. 2006 Sep;7(13):1825-34.
2 Metabolic drug interactions with newer antipsychotics: a comparative review. Basic Clin Pharmacol Toxicol. 2007 Jan;100(1):4-22.
3 Metabolism of sertindole: identification of the metabolites in the rat and dog, and species comparison of liver microsomal metabolism
4 Sertindole : a review of its use in schizophrenia

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