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

General Information of Drug (ID: DR1230)
Drug Name
Paliperidone
Synonyms
Paliperidone; R 76477; R-76477; RO-76477; 144598-75-4; 3-(2-(4-(6-fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)ethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one; Invega; PALLIPERIDONE; 3-[2-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one; 9-Hydroxyrisperidone; 9-OH-risperidone; CHEBI:83804; CHEMBL1621; MFCD00871802
Indication Bipolar disorder [ICD11: 6A60] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 426.5 Topological Polar Surface Area 82.2
Heavy Atom Count 31 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
115237
PubChem SID
10236700 ; 14905143 ; 22395187 ; 29296762 ; 46506296 ; 47207025 ; 50035150 ; 51002222 ; 57339070 ; 85229944 ; 85246150 ; 90341688 ; 92719038 ; 92729808 ; 103604037 ; 103910909 ; 104105311 ; 104397925 ; 118046559 ; 121361150 ; 125307525 ; 125341102 ; 126584511 ; 126621140 ; 126649064 ; 126650388 ; 126667060 ; 128939139 ; 131465791 ; 131549340 ; 134338126 ; 135072932 ; 136367845 ; 137166111 ; 142528484 ; 144116334 ; 152258953 ; 152344196 ; 160647798 ; 160810375 ; 160964597 ; 162185890 ; 163088563 ; 163371020 ; 163564516 ; 163981461 ; 164175255 ; 164785605 ; 170501956 ; 171063034
ChEBI ID
CHEBI:83804
CAS Number
199739-10-1
TTD Drug ID
D0B3UJ
Formula
C23H27FN4O3
Canonical SMILES
CC1=C(C(=O)N2CCCC(C2=N1)O)CCN3CCC(CC3)C4=NOC5=C4C=CC(=C5)F
InChI
1S/C23H27FN4O3/c1-14-17(23(30)28-9-2-3-19(29)22(28)25-14)8-12-27-10-6-15(7-11-27)21-18-5-4-16(24)13-20(18)31-26-21/h4-5,13,15,19,29H,2-3,6-12H2,1H3
InChIKey
PMXMIIMHBWHSKN-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
9-hydroxyrisperidone DM001160
115237
Unclear 1 [4]
Risperidone DM003081
5073
Oxidation - Dehydrogenation 1 [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001924 Paliperidone 9-hydroxyrisperidone Unclear CYP3A4 ... [4]
MR001925 Paliperidone Risperidone Oxidation - Dehydrogenation CYP3A4 ... [6]
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]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[4]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1267 Anaerobutyricum hallii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1357 Alistipes indistinctus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1358 Anaerococcus hydrogenalis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1361 Anaerotruncus colihominis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1362 Bacteroides caccae Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1388 Bifidobacterium breve Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1394 Blautia luti Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1399 Enterocloster asparagiformis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1401 Clostridium scindens Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1404 Clostridium sporogenes Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1405 Clostridium symbiosum Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1407 Collinsella intestinalis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1408 Coprococcus comes Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1416 Enterobacter cancerogenus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1425 Eubacterium rectale Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1456 Roseburia intestinalis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1459 Ruminococcus lactaris Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1467 Subdoligranulum variabile Not Available Not Available [5]
⏷ Show the Full List of 22  DME(s)
References
1 Paliperidone was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Interpreting serum risperidone concentrations. Pharmacotherapy. 2005 Feb;25(2):299-302.
3 ABCB1 polymorphisms influence steady-state plasma levels of 9-hydroxyrisperidone and risperidone active moiety. Ther Drug Monit. 2008 Oct;30(5):628-33.
4 Different enantioselective 9-hydroxylation of risperidone by the two human CYP2D6 and CYP3A4 enzymes. Drug Metab Dispos. 2001 Oct;29(10):1263-8.
5 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
6 S73 | METXBIODB | metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

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