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

General Information of Drug (ID: DR1705)
Drug Name
Vonoprazan
Synonyms
Vonoprazan; Vonoprazan [INN]; TAK-438 (free base); TAK-438 free base; SCHEMBL194487; 1-(5-(2-Fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl)-N-methylmethanamine; 1-[5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1h-pyrrol-3-yl]-n-methylmethanamine; 1-[5-(2-fluorophenyl)-1-pyridin-3-ylsulfonyl-pyrrol-3-yl]-~{N}-methyl-methanamine; 1-[5-(2-fluorophenyl)-1-pyridin-3-ylsulfonylpyrrol-3-yl]-N-methylmethanamine; 1R5L3J156G; 881681-00-1; BCP13240; CHEBI:136048; CHEMBL2079130; DTXSID20236869; KS-00000TU1; UNII-1R5L3J156G
Indication Gastro-oesophageal reflux disease [ICD11: DA22] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 345.4 Topological Polar Surface Area 72.4
Heavy Atom Count 24 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
15981397
ChEBI ID
CHEBI:136048
CAS Number
881681-00-1
Formula
C17H16FN3O2S
Canonical SMILES
CNCC1=CN(C(=C1)C2=CC=CC=C2F)S(=O)(=O)C3=CN=CC=C3
InChI
1S/C17H16FN3O2S/c1-19-10-13-9-17(15-6-2-3-7-16(15)18)21(12-13)24(22,23)14-5-4-8-20-11-14/h2-9,11-12,19H,10H2,1H3
InChIKey
BFDBKMOZYNOTPK-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
N-demethylated TAK-438 DM016701
141445145
Oxidation - N-demethylation 1 [3] , [2]
TAK-438 N-sulfate DM017940 N. A. Oxidation - Sulfonation 1 [6] , [2]
Vonoprazan M- DM017942 N. A. Unclear - Unclear 1 [6] , [2]
Vonoprazan M- DM016714
145740229
Unclear - Unclear 1 [6] , [2]
Vonoprazan M- DM016431
92135161
Unclear - Unclear 2 [6]
Vonoprazan M--G DM017939 N. A. Conjugation - Glucuronidation 2 [6]
Vonoprazan M--Sul DM017941 N. A. Oxidation - Hydroxylation 2 [6] , [2]
Vonoprazan M--G DM017938 N. A. Conjugation - Glucuronidation 3 [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013073 Vonoprazan Vonoprazan M- Unclear - Unclear CYP2B6 ... [6], [2]
MR013077 Vonoprazan TAK-438 N-sulfate Oxidation - Sulfonation SULT2A1 [6], [2]
MR013079 Vonoprazan N-demethylated TAK-438 Oxidation - N-demethylation CYP2B6 ... [3], [2]
MR013080 Vonoprazan Vonoprazan M- Unclear - Unclear CYP2B6 ... [6], [2]
MR013078 TAK-438 N-sulfate Vonoprazan M--Sul Oxidation - Hydroxylation CYP2C9 [6], [2]
MR013074 Vonoprazan M- Vonoprazan M- Unclear - Unclear Unclear [6]
MR013076 Vonoprazan M- Vonoprazan M--G Conjugation - Glucuronidation Unclear [6]
MR013075 Vonoprazan M- Vonoprazan M--G Conjugation - Glucuronidation Unclear [6]
⏷ Show the Full List of 8 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[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]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[5]
Sulfotransferase 2A1 (SULT2A1) DME0074 Homo sapiens
ST2A1_HUMAN
2.8.2.14
[2]
Sulfotransferase 2A1 (SULT2A1) DME0074 Homo sapiens
ST2A1_HUMAN
2.8.2.14
[3]
⏷ Show the Full List of 12  DME(s)
References
1 ClinicalTrials.gov (NCT03116841) Vonoprazan Study of Investigating the Effect on Sleep Disturbance Associated With Reflux Esophagitis- Exploratory Evaluation.
2 In vitro metabolism of TAK-438, vonoprazan fumarate, a novel potassium-competitive acid blocker. Xenobiotica. 2017 Dec;47(12):1027-1034.
3 Assessments of CYP?inhibition?based drug-drug interaction between vonoprazan and poziotinib in?vitro and in?vivo
4 Inhibitory Effect of Vonoprazan on the Metabolism of [(14)C]Prasugrel in Human Liver Microsomes
5 The First-in-Class Potassium-Competitive Acid Blocker, Vonoprazan Fumarate: Pharmacokinetic and Pharmacodynamic Considerations
6 Vonoprazan fumarate, a novel potassium-competitive acid blocker, in the management of gastroesophageal reflux disease: safety and clinical evidence to date

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