Details of the Drug

General Information of Drug (ID: DMXYLQ3)

Drug Name
Lansoprazole
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
Disease Entry ICD 11 Status REF
Gastric ulcer DA60 Approved [1]
Gastrinoma 2C10.1 Approved [1]
Peptic ulcer DA61 Approved [1]
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 369.4
Logarithm of the Partition Coefficient (xlogp) 2.8
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 8
ADMET Property
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 1.7 h [2]
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [3]
Bioavailability
The bioavailability of drug is 80-90% [2]
Clearance
The clearance of drug is 400-650 mL/min [4]
Elimination
14-23% of drug is eliminated in the urine with this percentage range including both conjugated and unconjugated hydroxylated metabolites [5]
Half-life
The concentration or amount of drug in body reduced by one-half in less than 2 hours [2]
Metabolism
The drug is metabolized via the liver [4]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 1.35366 micromolar/kg/day [6]
Unbound Fraction
The unbound fraction of drug in plasma is 0.021% [7]
Vd
The volume of distribution (Vd) of drug is 0.4 L/kg [4]
Water Solubility
The ability of drug to dissolve in water is measured as 0.00097 mg/mL [3]
Chemical Identifiers
Formula
C16H14F3N3O2S
IUPAC Name
2-[[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl]-1H-benzimidazole
Canonical SMILES
CC1=C(C=CN=C1CS(=O)C2=NC3=CC=CC=C3N2)OCC(F)(F)F
InChI
MJIHNNLFOKEZEW-UHFFFAOYSA-N
InChIKey
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)
Cross-matching ID
PubChem CID
3883
ChEBI ID
CHEBI:6375
CAS Number
103577-45-3
DrugBank ID
DB00448
INTEDE ID
DR0915
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [8]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [9]
Mephenytoin 4-hydroxylase (CYP2C19)
Main DME 		DEGTFWK CP2CJ_HUMAN Substrate [10]
Cytochrome P450 2C8 (CYP2C8) DES5XRU CP2C8_HUMAN Substrate [11]
Cytochrome P450 2C18 (CYP2C18) DEZMWRE CP2CI_HUMAN Substrate [12]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Apolipoprotein E (APOE) OTFOWL2H APOE_HUMAN Gene/Protein Processing [13]
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Drug Response [14]
Cytochrome P450 1A1 (CYP1A1) OTE4EFH8 CP1A1_HUMAN Gene/Protein Processing [15]
Cytochrome P450 1A2 (CYP1A2) OTLLBX48 CP1A2_HUMAN Gene/Protein Processing [16]
Cytochrome P450 1B1 (CYP1B1) OTYXFLSD CP1B1_HUMAN Gene/Protein Processing [16]
Cytochrome P450 2C18 (CYP2C18) OTY687L9 CP2CI_HUMAN Biotransformations [12]
Cytochrome P450 2C8 (CYP2C8) OTHCWT42 CP2C8_HUMAN Biotransformations [11]
Cytochrome P450 2C9 (CYP2C9) OTGLBN29 CP2C9_HUMAN Biotransformations [17]
Cytochrome P450 3A4 (CYP3A4) OTQGYY83 CP3A4_HUMAN Gene/Protein Processing [15]
Epidermal growth factor receptor (EGFR) OTAPLO1S EGFR_HUMAN Gene/Protein Processing [18]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Lansoprazole FDA Label
2 Pharmacology of proton pump inhibitors. Curr Gastroenterol Rep. 2008 Dec;10(6):528-34.
3 BDDCS applied to over 900 drugs
4 Thijssen HH, Mattie H: Active metabolites of isoxazolylpencillins in humans. Antimicrob Agents Chemother. 1976 Sep;10(3):441-6. doi: 10.1128/aac.10.3.441.
5 Barradell LB, Faulds D, McTavish D: Lansoprazole. A review of its pharmacodynamic and pharmacokinetic properties and its therapeutic efficacy in acid-related disorders. Drugs. 1992 Aug;44(2):225-50. doi: 10.2165/00003495-199244020-00007.
6 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
7 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
8 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.
9 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.
10 Effects of clarithromycin on lansoprazole pharmacokinetics between CYP2C19 genotypes. Br J Clin Pharmacol. 2005 Mar;59(3):302-9.
11 Identification of the human P450 enzymes involved in lansoprazole metabolism. J Pharmacol Exp Ther. 1996 May;277(2):805-16.
12 Oxidative metabolism of lansoprazole by human liver cytochromes P450. Mol Pharmacol. 1995 Feb;47(2):410-8.
13 Proton pump inhibitor lansoprazole is a nuclear liver X receptor agonist. Biochem Pharmacol. 2010 May 1;79(9):1310-6. doi: 10.1016/j.bcp.2009.12.018. Epub 2010 Jan 8.
14 Effect of MDR1 C3435T polymorphism on lansoprazole in healthy Japanese subjects. Eur J Clin Pharmacol. 2009 Jun;65(6):593-600. doi: 10.1007/s00228-009-0625-8. Epub 2009 Feb 24.
15 Measurement of cytochrome P450 gene induction in human hepatocytes using quantitative real-time reverse transcriptase-polymerase chain reaction. Drug Metab Dispos. 2000 Jul;28(7):781-8.
16 Time-dependent transcriptional induction of CYP1A1, CYP1A2 and CYP1B1 mRNAs by H+/K+ -ATPase inhibitors and other xenobiotics. Xenobiotica. 2003 Feb;33(2):107-18.
17 Stereoselective metabolism of lansoprazole by human liver cytochrome P450 enzymes. Drug Metab Dispos. 2003 Oct;31(10):1227-34.
18 Effect of chronic duodenal ulceration and its treatment with lanzoprazole or sucralfate on gastroduodenal mucosal protein turnover and TGF-alpha, bFGF, and EGF receptor expression in humans. Dig Dis Sci. 1998 Dec;43(12):2764-70. doi: 10.1023/a:1026680017329.