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

General Information of Drug (ID: DR1732)
Drug Name
Ziprasidone
Synonyms
Zeldox; Ziprasidone; Ziprasidone [INN:BAN]; Ziprasidone hydrochloride; Ziprasidone mesylate trihydrate; ziprasidona; ziprasidonum; ziprazidone; Geodon; 146939-27-7; 2H-Indol-2-one, 5-[2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-; 5-[2-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]ethyl]-6-chloro-1,3-dihydroindol-2-one; 6UKA5VEJ6X; C21H21ClN4OS; CHEBI:10119; CHEMBL708; CP 88059; CP-88,059-1; DSSTox_CID_3753; DSSTox_GSID_23753; DSSTox_RID_77186; UNII-6UKA5VEJ6X
Indication Schizophrenia [ICD11: 6A20] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 412.9 Topological Polar Surface Area 76.7
Heavy Atom Count 28 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
60854
PubChem SID
9771 ; 7481431 ; 7980909 ; 8187099 ; 14782044 ; 26719835 ; 43118192 ; 46386625 ; 46507627 ; 48416712 ; 49830895 ; 49984774 ; 56352942 ; 57314152 ; 80112580 ; 81065539 ; 85175463 ; 85209383 ; 93166200 ; 96025370 ; 103194712 ; 103979184 ; 104321820 ; 119525882 ; 125341301 ; 126496584 ; 126618135 ; 126648879 ; 126671672 ; 127275844 ; 127275845 ; 127275846 ; 127275847 ; 127275848 ; 127275849 ; 127275850 ; 127275851 ; 127275852 ; 128655450 ; 131299396 ; 134337407 ; 134338706 ; 135026475 ; 135651359 ; 137001426 ; 142394815 ; 144205747 ; 144207074 ; 144224623 ; 152039802
ChEBI ID
ChEBI:10119
CAS Number
146939-27-7
TTD Drug ID
D0R1JV
Formula
C21H21ClN4OS
Canonical SMILES
C1CN(CCN1CCC2=C(C=C3C(=C2)CC(=O)N3)Cl)C4=NSC5=CC=CC=C54
InChI
1S/C21H21ClN4OS/c22-17-13-18-15(12-20(27)23-18)11-14(17)5-6-25-7-9-26(10-8-25)21-16-3-1-2-4-19(16)28-24-21/h1-4,11,13H,5-10,12H2,(H,23,27)
InChIKey
MVWVFYHBGMAFLY-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
(6-chloro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetic acid DM005361
22181639
Oxidation - Oxidationn N-dealkylation 1 [4]
6-chloro-5-(2-piperazin-1-yl-ethyl)-1,3-dihydro-indol-2-one DM005365
22181640
Other reaction - Deacylation 1 [4]
Dihydro-ziprasidone-sulfone DM005366 N. A. Multi-steps Reaction - Hydration; oxidation 1 [4]
ID-11614 DM003496
2772144
Oxidation - Oxidationn N-dealkylation 1 [4]
S-Methyl-dihydro-ziprasidone DM005363
9932353
Multi-steps Reaction - Methylationn; reductive cleavage 1 [4]
Ziprasidone Sulfoxide DM005359
15959407
Oxidation - Oxidationn 1 [4] , [5]
(6-chloro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetic acid glucuronide metabolite DM005362 N. A. Conjugation - Glucuronidation 2 [4]
3-(piperazine-1-yl)-1,2-benzisothiazole sulfoxide DM005356
15698633
Oxidation - Oxidationn 2 [4]
S-Methyl-dihydro-ziprasidone-sulfoxide DM005364
10026520
Oxidation - S-oxidation 2 [4]
Ziprasidone Sulfone DM005360
9889695
Oxidation - Oxidationn 2 [4] , [5]
3-(piperazine-1-yl)-1,2-benzisothiazole sulfone DM005357
695718
Oxidation - Oxidationn 3 [4]
3-(piperazine-1-yl)-1,2-benzisothiazole sulfone lactam DM005358
15169816
Oxidation - Oxidationn 4 [4]
⏷ Show the Full List of 12  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005684 Ziprasidone 3-(piperazine-1-yl)-1,2-benzisothiazole Oxidation - Oxidationn N-dealkylation Unclear [4]
MR005688 Ziprasidone Ziprasidone Sulfoxide Oxidation - Oxidationn CYP3A4 [4], [5]
MR005690 Ziprasidone (6-chloro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetic acid Oxidation - Oxidationn N-dealkylation Unclear [4]
MR005692 Ziprasidone S-Methyl-dihydro-ziprasidone Multi-steps Reaction - Methylationn; reductive cleavage Unclear [4]
MR005694 Ziprasidone 6-chloro-5-(2-piperazin-1-yl-ethyl)-1,3-dihydro-indol-2-one Other reaction - Deacylation Unclear [4]
MR005695 Ziprasidone Dihydro-ziprasidone-sulfone Multi-steps Reaction - Hydration; oxidation Unclear [4]
MR005691 (6-chloro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetic acid (6-chloro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetic acid glucuronide metabolite Conjugation - Glucuronidation Unclear [4]
MR005685 3-(piperazine-1-yl)-1,2-benzisothiazole 3-(piperazine-1-yl)-1,2-benzisothiazole sulfoxide Oxidation - Oxidationn Unclear [4]
MR005693 S-Methyl-dihydro-ziprasidone S-Methyl-dihydro-ziprasidone-sulfoxide Oxidation - S-oxidation Unclear [4]
MR005689 Ziprasidone Sulfoxide Ziprasidone Sulfone Oxidation - Oxidationn Unclear [4], [5]
MR005686 3-(piperazine-1-yl)-1,2-benzisothiazole sulfoxide 3-(piperazine-1-yl)-1,2-benzisothiazole sulfone Oxidation - Oxidationn Unclear [4]
MR005687 3-(piperazine-1-yl)-1,2-benzisothiazole sulfone 3-(piperazine-1-yl)-1,2-benzisothiazole sulfone lactam Oxidation - Oxidationn Unclear [4]
⏷ 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 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Unclear metabolic mechanism (DME-unclear) DME1265 Escherichia coli Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1357 Alistipes indistinctus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [3]
References
1 Ziprasidone was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Metabolism of atypical antipsychotics: involvement of cytochrome p450 enzymes and relevance for drug-drug interactions. Curr Drug Metab. 2008 Jun;9(5):410-8.
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
4 Metabolism and excretion of a new antipsychotic drug, ziprasidone, in humans
5 [Limits of jaw orthopedic treatment]

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