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

General Information of Drug (ID: DR0627)
Drug Name
Esomeprazole
Prodrug Info Esomeprazole is the prodrug of 5-hydroxyomeprazole
Synonyms
Esomeprazole (INN); Esomeprazole Sodium; Esomeprazole [INN:BAN]; Inexium paranova; Inexium paranova (TN); Nexiam; Nexium; esomeprazol; esomeprazolum; Alenia; Esofag; (-)-Omeprazole; (S)-(-)-Omeprazole; (S)-5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole; (S)-6-Methoxy-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)sulfinyl)-1H-benzo[d]imidazole; (S)-Esomeprazole; (S)-Omeprazole; 119141-88-7; CHEBI:50275; Escz; N3PA6559FT; UNII-N3PA6559FT
Indication Duodenal ulcer [ICD11: DA63] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 345.4 Topological Polar Surface Area 96.3
Heavy Atom Count 24 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
9568614
PubChem SID
591076 ; 14875947 ; 14900571 ; 44707139 ; 56394969 ; 80295315 ; 93166178 ; 96024613 ; 124759673 ; 124968856 ; 126525308 ; 126670961 ; 129288902 ; 129288903 ; 137001228 ; 137752931 ; 139533883 ; 152040240 ; 160825217 ; 163092495 ; 163384365 ; 163840367 ; 164044845 ; 175267781 ; 175269116 ; 175437905 ; 178102135 ; 189657728 ; 198993898 ; 204429634 ; 211535433 ; 223971225 ; 226409261 ; 246378786 ; 249855831 ; 250200763 ; 251886328 ; 251964001 ; 252074449 ; 252430137
ChEBI ID
ChEBI:50275
CAS Number
161796-78-7
TTD Drug ID
D0C6DT
Formula
C17H19N3O3S
Canonical SMILES
CC1=CN=C(C(=C1OC)C)CS(=O)C2=NC3=C(N2)C=C(C=C3)OC
InChI
1S/C17H19N3O3S/c1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)/t24-/m0/s1
InChIKey
SUBDBMMJDZJVOS-DEOSSOPVSA-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
5-hydroxyomeprazole DM002300
119560
Oxidation - 5-Hydroxylation 1 [3]
5-O-Desmethylomeprazole DM002023
29918914
Oxidation - O-Dealkylation 1 [4]
Active metabolite of Esomeprazole DM002021
5311467
Unclear 1 [5]
Omeprazole sulfone metabolite DM002022
145900
Oxidation - S-Oxidation 1 [6] , [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000953 Esomeprazole Active metabolite of Esomeprazole Unclear Unclear [5]
MR000954 Esomeprazole Omeprazole sulfone metabolite Oxidation - S-Oxidation CYP3A4 [6], [3]
MR000955 Esomeprazole 5-O-Desmethylomeprazole Oxidation - O-Dealkylation CYP2C19 [4]
MR000956 Esomeprazole 5-hydroxyomeprazole Oxidation - 5-Hydroxylation CYP2C19 [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
References
1 Esomeprazole was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Predictive performance of physiologically based pharmacokinetic (PBPK) modeling of drugs extensively metabolized by major cytochrome P450s in children. Clin Pharmacol Ther. 2018 Jul;104(1):188-200.
3 Pharmacokinetic studies with esomeprazole, the (S)-isomer of omeprazole Clin Pharmacokinet. 2001;40(6):411-26. doi: 10.2165/00003088-200140060-00003.
4 Expression, activity and regulation of CYP3A in human and rodent brain Drug Metab Rev. 2008;40(1):149-68. doi: 10.1080/03602530701836712.
5 DrugBank(Pharmacology-Metabolism)Esomeprazole
6 Cytochrome P450 inactivation by pharmaceuticals and phytochemicals: therapeutic relevance Drug Metab Rev. 2008;40(1):101-47. doi: 10.1080/03602530701836704.

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