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

General Information of Drug (ID: DR1196)
Drug Name
Omeprazole
Prodrug Info Omeprazole is the prodrug of 5'-OH omeprazole sulfide metabolite
Synonyms
Omapren; Omepral; Omeprazon; Omeprol; Omezol; Omisec; Omizac; Ompanyt; Ozoken; Parizac; Pepticum; Peptilcer; Prazentol; Prazidec; Audazol; Belmazol; Ceprandal; Demeprazol; Dizprazol; Dudencer; Emeproton; Epirazole; Gastrimut; Gastroloc; Gibancer; Indurgan; Inhibitron; Inhipump; Logastric; Mepral; Miracid; Mopral; Prazolit; Prilosec; Prysma; Ramezol; Regulacid; Sanamidol; Secrepina; Ulceral; Ulcesep; Ulcometion; Ulcozol; Zefxon; Zegerid; Zoltum; omeprazole; 73590-58-6; Antra; Desec; Elgam; Lomac; Losec; Miol; OMEP; Ocid; Omed; Omid; Ulsen; Ultop; Zimor
Indication Gastro-oesophageal reflux disease [ICD11: DA22] 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
4594
PubChem SID
9532 ; 640212 ; 855576 ; 3281991 ; 4696242 ; 5212304 ; 7847521 ; 7980199 ; 8152819 ; 10321754 ; 11112840 ; 11398365 ; 11466521 ; 11467641 ; 11486042 ; 11528599 ; 12013167 ; 14753960 ; 14875946 ; 22391484 ; 24897870 ; 26751452 ; 26751453 ; 26759296 ; 29223683 ; 46386973 ; 46487906 ; 46509065 ; 47365309 ; 47589088 ; 47589089 ; 48035237 ; 48170542 ; 48414255 ; 48416351 ; 49681572 ; 49698521 ; 49834935 ; 50100529 ; 50103932 ; 53788700 ; 56313300 ; 56313696 ; 56313928 ; 56422106 ; 57322340 ; 80295314 ; 81093370 ; 85174452 ; 85788870
ChEBI ID
ChEBI:7772
CAS Number
73590-58-6
TTD Drug ID
D01XNB
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)
InChIKey
SUBDBMMJDZJVOS-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
3-hydroxyomeprazole DM002302
71587579
Oxidation - 3-Hydroxylation 1 [4]
5'-O-Desmethyl omeprazole DM002301
10404448
Oxidation - 5'-O-Demethylation 1 [4]
5-hydroxyomeprazole DM002300
119560
Oxidation - 5-Hydroxylation 1 [4]
Omeprazole sulfone metabolite DM002022
145900
Oxidation - Sulfoxidation 1 [4]
5'-OH omeprazole sulfide metabolite DM002299
91990099
Oxidation - Hydroxylation 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001829 Omeprazole Omeprazole sulfone metabolite Oxidation - Sulfoxidation CYP3A4 [4]
MR001830 Omeprazole 5-hydroxyomeprazole Oxidation - 5-Hydroxylation CYP3A4 ... [4]
MR001831 Omeprazole 5'-O-Desmethyl omeprazole Oxidation - 5'-O-Demethylation CYP2C19 [4]
MR001832 Omeprazole 3-hydroxyomeprazole Oxidation - 3-Hydroxylation CYP3A4 [4]
MR001828 Omeprazole sulfone metabolite 5'-OH omeprazole sulfide metabolite Oxidation - Hydroxylation CYP102A1 [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C18 (CYP2C18) DME0017 Homo sapiens
CP2CI_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[3]
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
[5]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[4]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1253 Bacteroides oleiciplenus Not Available Not Available [7]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1257 Bifidobacterium longum Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1265 Escherichia coli Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1267 Anaerobutyricum hallii Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1355 Akkermansia muciniphila Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1357 Alistipes indistinctus Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1358 Anaerococcus hydrogenalis Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1360 Anaerostipes hadrus Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1361 Anaerotruncus colihominis Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1363 Bacteroides cellulosilyticus Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1364 Bacteroides coprophilus Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1366 Bacteroides eggerthii Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1367 Bacteroides finegoldii Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1375 Bacteroides intestinalis Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1376 Bacteroides ovatus Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1377 Bacteroides pectinophilus Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1378 Bacteroides uniformis Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1379 Bacteroides stercoris Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1386 Bifidobacterium adolescentis Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1388 Bifidobacterium breve Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1391 Bifidobacterium ruminatum Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1394 Blautia luti Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1398 Clostridioides difficile Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1399 Enterocloster asparagiformis Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1400 Enterocloster bolteae Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1401 Clostridium scindens Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1403 Clostridium spiroforme Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1404 Clostridium sporogenes Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1405 Clostridium symbiosum Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1407 Collinsella intestinalis Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1408 Coprococcus comes Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1412 Dorea formicigenerans Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1413 Edwardsiella tarda Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1415 Eggerthella lenta Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1416 Enterobacter cancerogenus Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1418 Enterococcus faecalis Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1420 Erysipelatoclostridium ramosum Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1425 Eubacterium rectale Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1427 Eubacterium ventriosum Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1431 Holdemanella biformis Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1432 Hungatella hathewayi Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1435 Lactobacillus reuteri Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1439 Marvinbryantia formatexigens Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1446 Parabacteroides johnsonii Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1447 Parabacteroides merdae Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1449 Prevotella copri Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1451 Proteus penneri Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1452 Providencia alcalifaciens Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1453 Providencia rettgeri Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1454 Providencia stuartii Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1456 Roseburia intestinalis Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1458 Ruminococcus gnavus Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1459 Ruminococcus lactaris Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1460 Ruminococcus torques Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1462 Salmonella enterica Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1467 Subdoligranulum variabile Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1470 Victivallis vadensis Not Available Not Available [6]
⏷ Show the Full List of 72  DME(s)
References
1 Omeprazole was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Human CYP2C19 is a major omeprazole 5-hydroxylase, as demonstrated with recombinant cytochrome P450 enzymes. Drug Metab Dispos. 1996 Oct;24(10):1081-7.
3 Comparison of inhibitory effects of the proton pump-inhibiting drugs omeprazole, esomeprazole, lansoprazole, pantoprazole, and rabeprazole on human cytochrome P450 activities. Drug Metab Dispos. 2004 Aug;32(8):821-7.
4 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
5 Impact of intestinal CYP2C19 genotypes on the interaction between tacrolimus and omeprazole, but not lansoprazole, in adult living-donor liver transplant patients. Drug Metab Dispos. 2009 Apr;37(4):821-6.
6 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
7 Metabolism of omeprazole by gut flora in rats. J Pharm Sci. 1995 Apr;84(4):516-7. Letter

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