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

General Information of Drug (ID: DR0469)
Drug Name
Dexlansoprazole
Synonyms
Dexilant Solutab; Dexlansoprazole (INN/USAN); Dexlansoprazole [USAN:INN]; Kapidex; R-(+)-LANSOPRAZOLE; T 168390; T-168390; TAK 390; TAK-390; TAK-390MR; UYE4T5I70X; dexilant; dexlansoprazole; (R)-2-(((3-Methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methyl)sulfinyl)-1H-benzo[d]imidazole; (R)-Lansoprazole; 138530-94-6; 2-((R)-((3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl)methyl)sulfinyl)-1H-benzimidazole; 2-[(R)-[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methylsulfinyl]-1H-benzimidazole; AK170558; UNII-UYE4T5I70X
Indication Gastro-oesophageal reflux disease [ICD11: DA22] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 369.4 Topological Polar Surface Area 87.1
Heavy Atom Count 25 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
9578005
PubChem SID
14901842 ; 15375021 ; 23998121 ; 25819922 ; 44715913 ; 80665304 ; 89736101 ; 96025586 ; 104179070 ; 104234371 ; 126682042 ; 128604168 ; 135156589 ; 137931058 ; 140767605 ; 162189572 ; 164178109 ; 164761527 ; 170503333 ; 175265917 ; 175269426 ; 175611039 ; 178102134 ; 184527042 ; 185965235 ; 210274918 ; 210280553 ; 223658647 ; 223798807 ; 226429139 ; 241033947 ; 251879797 ; 252151427 ; 252431524 ; 252811271
ChEBI ID
ChEBI:6375
CAS Number
103577-45-3
TTD Drug ID
D06YYD
Formula
C16H14F3N3O2S
Canonical SMILES
CC1=C(C=CN=C1CS(=O)C2=NC3=CC=CC=C3N2)OCC(F)(F)F
InChI
1S/C16H14F3N3O2S/c1-10-13(20-7-6-14(10)24-9-16(17,18)19)8-25(23)15-21-11-4-2-3-5-12(11)22-15/h2-7H,8-9H2,1H3,(H,21,22)/t25-/m1/s1
InChIKey
MJIHNNLFOKEZEW-RUZDIDTESA-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
4-sulfonyloxy dexlansoprazole DM000807
91810689
Conjugation - Sulfation 1 [2]
5-hydroxy dexlansoprazole DM000805
27339165
Oxidation - 5-Hydroxylation 1 [2]
Lansoprazole Sulfone DM000208
10385385
Oxidation - Oxidation 1 [2]
5-glucuronyloxy dexlansoprazol DM000806
91810690
Conjugation - Glucuronidation 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000794 Dexlansoprazole Lansoprazole Sulfone Oxidation - Oxidation CYP3A4 [2]
MR000795 Dexlansoprazole 5-hydroxy dexlansoprazole Oxidation - 5-Hydroxylation CYP2C19 [2]
MR000796 Dexlansoprazole 4-sulfonyloxy dexlansoprazole Conjugation - Sulfation Unclear [2]
MR000793 5-hydroxy dexlansoprazole 5-glucuronyloxy dexlansoprazol Conjugation - Glucuronidation Unclear [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[3]
References
1 Dexlansoprazole was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Absorption, distribution, metabolism and excretion of [14C]dexlansoprazole in healthy male subjects. Clin Drug Investig. 2012 May 1;32(5):319-32.
3 Pharmacological and safety profile of dexlansoprazole: a new proton pump inhibitor - implications for treatment of gastroesophageal reflux disease in the Asia Pacific region. J Neurogastroenterol Motil. 2016 Jul 30;22(3):355-66.

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