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

General Information of Drug (ID: DR0331)
Drug Name
Cisapride
Synonyms
Cipride; Cisaprida [INN-Spanish]; Cisaprida [Spanish]; Cisapridum [INN-Latin]; Cisapridum [Latin]; Cisapron; Cisawal; Colinorm; Acpulsif; Alimix; Alimix Forte; Alipride; DCSUBABJRXZOMT-UHFFFAOYSA-N; Dispep; Enteropride; Esorid; Guptro; Kinestase; Prepulsid; Presid; Pridesia; Propulsid; Propulsid Quicksolv; Propulsin; Pulsid; R 51619; R-51619; Rapulid; Risamal; Syspride; Unamol; Unipride; Vomiprid; Vomipride; cisapride; 104860-73-3; 81098-60-4; Acenalin
Indication Gastro-oesophageal reflux disease [ICD11: DA22] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 465.9 Topological Polar Surface Area 86
Heavy Atom Count 32 Rotatable Bond Count 9
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
2769
PubChem SID
9127 ; 4816531 ; 7847340 ; 8151787 ; 10321734 ; 11466458 ; 11467578 ; 11486095 ; 14882747 ; 29221924 ; 48403970 ; 48415785 ; 49875392 ; 50113158 ; 51031281 ; 53786866 ; 57321449 ; 80953524 ; 85209640 ; 92125386 ; 92711730 ; 99418016 ; 103914221 ; 103919261 ; 104301556 ; 123090165 ; 125358025 ; 125663585 ; 126630574 ; 126657130 ; 126669689 ; 127715812 ; 131993450 ; 134337537 ; 135014802 ; 135650104 ; 137101280 ; 142378524 ; 144204250 ; 160963949 ; 162357904 ; 162771742 ; 164807926 ; 165700416 ; 170465200 ; 175611161 ; 178125987 ; 179148462 ; 184551724 ; 196112081
ChEBI ID
CHEBI:95129
CAS Number
81098-60-4
TTD Drug ID
D0BD8D
Formula
C23H29ClFN3O4
Canonical SMILES
COC1CN(CCC1NC(=O)C2=CC(=C(C=C2OC)N)Cl)CCCOC3=CC=C(C=C3)F
InChI
1S/C23H29ClFN3O4/c1-30-21-13-19(26)18(24)12-17(21)23(29)27-20-8-10-28(14-22(20)31-2)9-3-11-32-16-6-4-15(25)5-7-16/h4-7,12-13,20,22H,3,8-11,14,26H2,1-2H3,(H,27,29)
InChIKey
DCSUBABJRXZOMT-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
Cisapride Metabolite M2 DM016704
142644081
Oxidation - O-dealkylation 1 [2]
Cisapride Metabolite M4 DM018086 N. A. Oxidation - N-oxidation 1 [2]
Cisapride Metabolite M5 DM018088 N. A. Oxidation - Aromatic hydroxylation NIH-shift 1 [2]
Cisapride Metabolite M6 DM015846
13677777
Oxidation - O-dealkylation 1 [2]
Cisapride Metabolite M7 DM018087 N. A. Oxidation - Aromatic hydroxylation NIH-shift 1 [2]
Norcisapride DM018085 N. A. Unclear - N-deataelon 1 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009936 Cisapride Norcisapride Unclear - N-deataelon CYP3A4 [2]
MR009937 Cisapride Cisapride Metabolite M4 Oxidation - N-oxidation Unclear [2]
MR009938 Cisapride Cisapride Metabolite M2 Oxidation - O-dealkylation Unclear [2]
MR009939 Cisapride Cisapride Metabolite M6 Oxidation - O-dealkylation Unclear [2]
MR009940 Cisapride Cisapride Metabolite M7 Oxidation - Aromatic hydroxylation NIH-shift Unclear [2]
MR009941 Cisapride Cisapride Metabolite M5 Oxidation - Aromatic hydroxylation NIH-shift Unclear [2]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2A6 (CYP2A6) DME0005 Homo sapiens
CP2A6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[3]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[3]
⏷ Show the Full List of 8  DME(s)
References
1 Cisapride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Identification of the cytochrome P450 enzymes involved in the metabolism of cisapride: in vitro studies of potential co-medication interactions. Br J Pharmacol. 2000 Apr;129(8):1655-67.
3 Interaction of cisapride with the human cytochrome P450 system: metabolism and inhibition studies. Drug Metab Dispos. 2000 Jul;28(7):789-800.
4 Cisapride: a potential model substrate to assess cytochrome P4503A4 activity in vivo. Clin Pharmacol Ther. 2003 Mar;73(3):209-22.

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