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

General Information of Drug (ID: DR1200)
Drug Name
Ondansetron
Synonyms
Ondansetron [INN]; Ondansetron [USAN]; SN-307; Zofran; Zofran ODT; Zophren; Zuplenz; ondansetron; ondansetron (Zofran); 1,2,3,9-Tetrahydro-9-methyl-3-((2-methyl-1H-imidazol-1-yl)methyl)-4H-carbazol-4-one; 116002-70-1; 9-Methyl-3-((2-methyl-1H-imidazol-1-yl)methyl)-2,3-dihydro-1H-carbazol-4(9H)-one; 9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-2,3,4,9-tetrahydro-1H-carbazol-4-one; 9-methyl-3-[(2-methylimidazol-1-yl)methyl]-2,3-dihydro-1H-carbazol-4-one; 99614-02-5; BRN 3622981; C18H19N3O; CHEBI:7773; GR 38032; GR 38032X; GR-38032F; GR38032; NCGC00179341-02; Zudan
Indication Gastritis [ICD11: DA42] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 293.4 Topological Polar Surface Area 39.8
Heavy Atom Count 22 Rotatable Bond Count 2
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
4595
PubChem SID
9533 ; 3206266 ; 3966923 ; 4696243 ; 7847522 ; 7980201 ; 8152820 ; 11137931 ; 11427135 ; 11467086 ; 11468206 ; 11486674 ; 11501532 ; 14873468 ; 29223684 ; 46504819 ; 47389509 ; 47686452 ; 47686453 ; 47909550 ; 47909551 ; 47984334 ; 48416352 ; 49698991 ; 49835876 ; 49901808 ; 50064204 ; 50949003 ; 53787007 ; 57322341 ; 58007430 ; 85174434 ; 85209216 ; 85787808 ; 85788905 ; 92309152 ; 93624973 ; 103166621 ; 103915041 ; 104170204 ; 104225172 ; 104306859 ; 105146690 ; 121362488 ; 124579243 ; 124893606 ; 125324981 ; 125360632 ; 125814185 ; 126525328
ChEBI ID
CHEBI:7773
CAS Number
99614-02-5
TTD Drug ID
D0K7WK
Formula
C18H19N3O
Canonical SMILES
CC1=NC=CN1CC2CCC3=C(C2=O)C4=CC=CC=C4N3C
InChI
1S/C18H19N3O/c1-12-19-9-10-21(12)11-13-7-8-16-17(18(13)22)14-5-3-4-6-15(14)20(16)2/h3-6,9-10,13H,7-8,11H2,1-2H3
InChIKey
FELGMEQIXOGIFQ-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-OH-ondansetron DM002308
20152440
Oxidation - Hydroxylation 1 [8]
7-hydroxyl-N-desmethyl-ondansetron DM002304
20152444
Oxidation - N-Demethylation 1 [8]
7-OH-ondansetron DM002303
71749264
Oxidation - Hydroxylation 1 [9] , [8]
8-hydroxyl-N-desmethyl-ondansetron DM002309 N. A. Oxidation - N-Demethylation 1 [8]
8-OH-ondansetron DM002306
19734439
Oxidation - Hydroxylation 1 [9]
N-desmethyl-ondansetron-7-O-beta-D-glucuronide metabolite DM002305 N. A. Conjugation - Glucuronidation 1 [8]
7-hydroxyl-N-desmethyl-ondansetron DM002304
20152444
Oxidation - N-Demethylation 2 [8]
8-hydroxyl-N-desmethyl-ondansetron metabolite DM002307 N. A. Oxidation - N-Demethylation 2 [8]
N-desmethyl-ondansetron-7-O-beta-D-glucuronide metabolite DM002305 N. A. Conjugation - Glucuronidation 2 [8]
N-desmethyl-ondansetron-7-O-beta-D-glucuronide metabolite DM002305 N. A. Conjugation - Glucuronidation 3 [8]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001836 Ondansetron 7-OH-ondansetron Oxidation - Hydroxylation CYP3A4 ... [9], [8]
MR001837 Ondansetron 7-hydroxyl-N-desmethyl-ondansetron Oxidation - N-Demethylation Unclear [8]
MR001838 Ondansetron N-desmethyl-ondansetron-7-O-beta-D-glucuronide metabolite Conjugation - Glucuronidation Unclear [8]
MR001839 Ondansetron 8-OH-ondansetron Oxidation - Hydroxylation CYP3A4 ... [9]
MR001840 Ondansetron 6-OH-ondansetron Oxidation - Hydroxylation CYP3A4 ... [8]
MR001841 Ondansetron 8-hydroxyl-N-desmethyl-ondansetron Oxidation - N-Demethylation Unclear [8]
MR001833 7-OH-ondansetron 7-hydroxyl-N-desmethyl-ondansetron Oxidation - N-Demethylation Unclear [8]
MR001835 8-OH-ondansetron 8-hydroxyl-N-desmethyl-ondansetron metabolite Oxidation - N-Demethylation Unclear [8]
MR001834 7-hydroxyl-N-desmethyl-ondansetron N-desmethyl-ondansetron-7-O-beta-D-glucuronide metabolite Conjugation - Glucuronidation Unclear [8]
⏷ Show the Full List of 9 MR(s)
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 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[3]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[4]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[5]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[6]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[7]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[7]
⏷ Show the Full List of 7  DME(s)
References
1 Ondansetron was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Effects of serotonin-3 receptor antagonists on cytochrome P450 activities in human liver microsomes. Biol Pharm Bull. 2006 Sep;29(9):1931-5.
3 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
4 Cytochrome P450 2D6 metabolism and 5-hydroxytryptamine type 3 receptor antagonists for postoperative nausea and vomiting. Med Sci Monit. 2005 Oct;11(10):RA322-8.
5 Characterization of the cytochrome P450 enzymes involved in the in vitro metabolism of dolasetron. Comparison with other indole-containing 5-HT3 antagonists. Drug Metab Dispos. 1996 May;24(5):602-9.
6 The effect of rifampin on the pharmacokinetics of oral and intravenous ondansetron. Clin Pharmacol Ther. 1999 Apr;65(4):377-81.
7 Multiple forms of cytochrome P450 are involved in the metabolism of ondansetron in humans. Drug Metab Dispos. 1995 Nov;23(11):1225-30.
8 Identification of novel ondansetron metabolites using LC/MS(n) and NMR J Chromatogr B Analyt Technol Biomed Life Sci. 2018 Sep 15;1095:138-141. doi: 10.1016/j.jchromb.2018.07.013.
9 Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218.

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