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]
Affected Organisms
Humans and other mammals
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
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
Cross-matching ID
PubChem CID
3883
ChEBI ID
CHEMBL480
CAS Number
103577-45-3
UNII
0K5C5T2QPG
DrugBank ID
DB00448
INTEDE ID
DR0915
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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
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Drug Response [13]
Interleukin-8 (CXCL8) OTS7T5VH IL8_HUMAN Gene/Protein Processing [14]
Nuclear receptor subfamily 1 group I member 2 (NR1I2) OTC5U0N5 NR1I2_HUMAN Gene/Protein Processing [15]
Phosphoethanolamine/phosphocholine phosphatase (PHOSPHO1) OT43A0JA PHOP1_HUMAN Gene/Protein Processing [16]
Phospholipid-transporting ATPase ABCA1 (ABCA1) OT94G6BQ ABCA1_HUMAN Gene/Protein Processing [17]
Pro-opiomelanocortin (POMC) OTV41F7T COLI_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 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.
14 Enhanced expression of interleukin-8 and activation of nuclear factor kappa-B in endoscopy-negative gastroesophageal reflux disease. Am J Gastroenterol. 2004 Apr;99(4):589-97. doi: 10.1111/j.1572-0241.2004.04110.x.
15 Screening of a chemical library reveals novel PXR-activating pharmacologic compounds. Toxicol Lett. 2015 Jan 5;232(1):193-202. doi: 10.1016/j.toxlet.2014.10.009. Epub 2014 Oct 16.
16 Functional involvement of PHOSPHO1 in matrix vesicle-mediated skeletal mineralization. J Bone Miner Res. 2007 Apr;22(4):617-27. doi: 10.1359/jbmr.070108.
17 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.
18 Comparison of the effects of proton pump inhibitors on human plasma adrenocorticotropic hormone and cortisol levels under the starved condition. Biomed Pharmacother. 2006 Apr;60(3):109-12. doi: 10.1016/j.biopha.2006.01.004. Epub 2006 Feb 21.