General Information of Drug (ID: DR0915)
Drug Name
Lansoprazole
Prodrug Info Lansoprazole is the prodrug of AG2000 Free Base
Synonyms
Lancid; Lanproton; Lansopep; Lansoprazol; Lansoprazol [INN-Spanish]; Lansoprazole [USAN:BAN:INN]; Lansoprazolum; Lansoprazolum [INN-Latin]; Lansox; Lanston; Lanzol-30; Lanzopral; Lanzor; Lasoprol; Limpidex; Mesactol; Monolitum; Ogastro; Opiren; Agopton; Aprazol; Bamalite; Blason; Compraz; Ilsatec; Ketian; Prevacid; Prevacid 24HR; Prevacid Iv; Prevacid NapraPAC; Prevacid SoluTab; Prezal; Pro Ulco; Prosogan; Suprecid; Takepron; Zoprol; lansoprazole; 103577-45-3; A-65006; AG 1749; AG-1749; CHEBI:6375; Dakar; HSDB 7204; Lanz; Lanzo; Ogast; Promp; Ulpax; Zoton
Indication Duodenal ulcer [ICD11: DA63] 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
3883
ChEBI ID
CHEBI:6375
CAS Number
103577-45-3
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)
InChIKey
MJIHNNLFOKEZEW-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
5-hydroxylansoprazole DM000207
9800271
Oxidation - Hydroxylation 1 [3] , [2]
AG2000 Free Base DM020054
163862
Other reaction - Acid environment 1 [8]
Lansoprazole metabolite M1 DM000210 N. A. Reduction - Reduction 1 [9]
Lansoprazole metabolite M2 DM000211 N. A. Reduction - Reduction 1 [9]
Lansoprazole sulfide DM000209
1094080
Unclear 1 [3]
Lansoprazole Sulfone DM000208
10385385
Oxidation - Sulfoxidation 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001413 Lansoprazole 5-hydroxylansoprazole Oxidation - Hydroxylation CYP3A4 ... [3], [2]
MR001414 Lansoprazole Lansoprazole sulfone Oxidation - Sulfoxidation CYP2C19 [3]
MR001415 Lansoprazole Lansoprazole sulfide Unclear Non-ME [3]
MR001416 Lansoprazole Lansoprazole metabolite M1 Reduction - Reduction Unclear [9]
MR001417 Lansoprazole Lansoprazole metabolite M2 Reduction - Reduction Unclear [9]
MR014191 Lansoprazole AG2000 Free Base Other reaction - Acid environment Unclear [8]
⏷ Show the Full List of 6 MR(s)
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
[3]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[5]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[6]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[7]
⏷ Show the Full List of 6  DME(s)
References
1 Lansoprazole was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Oxidative metabolism of lansoprazole by human liver cytochromes P450. Mol Pharmacol. 1995 Feb;47(2):410-8.
3 Identification of the human P450 enzymes involved in lansoprazole metabolism. J Pharmacol Exp Ther. 1996 May;277(2):805-16.
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 An evaluation of the cytochrome P450 induction potential of pantoprazole in primary human hepatocytes. Chem Biol Interact. 1998 Jul 3;114(1-2):1-13.
6 Identification of the human P450 enzymes involved in lansoprazole metabolism J Pharmacol Exp Ther. 1996 May;277(2):805-16.
7 Effects of clarithromycin on lansoprazole pharmacokinetics between CYP2C19 genotypes. Br J Clin Pharmacol. 2005 Mar;59(3):302-9.
8 The gastric H,K-ATPase blocker lansoprazole is an inhibitor of chloride channels
9 Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 1725

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