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Identification
Name Lansoprazole
Accession Number DB00448 (APRD00077)
Type small molecule
Groups approved
Description

Lansoprazole is a proton pump inhibitor which prevents the stomach from producing acid. It is manufactured by TAP Pharmaceutical Products. Lansoprazole has been marketed for many years and is one of several PPI’s available.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
AG 1749
Salts Not Available
Brand names
Name Company
Agopton
Amarin
Aprazol
Bamalite
Biuret
Biuret Gr
Biuret Reagent Solution
Blason
Compraz
Dakar
Ilsatec
Ketian
Lancid
Lanproton
Lansopep
Lansoprazol [INN-Spanish]
Lansoprazole [Usan:Ban:Inn]
Lansoprazolum [INN-Latin]
Lanston
Lanz
Lanzol-30
Lanzopral
Lanzor
Lasoprol
Limpidex
Mesactol
Monolitum
Ogast
Ogastro
Opiren
Prevacid
Prevacid Iv
Prevacid Solutab
Prezal
Pro Ulco
Promp
Prosogan
Suprecid
Takepron
Ulpax
Zoprol
Zoton
First Prev Next Last
Brand mixtures Not Available
Categories
  • Anti-Infective Agents
  • Anti-Infectives
  • Anti-Ulcer Agents
  • Enzyme Inhibitors
  • Proton-pump Inhibitors
CAS number 103577-45-3
Weight Average: 369.361
Monoisotopic: 369.075882012
Chemical Formula C16H14F3N3O2S
InChI Key InChIKey=MJIHNNLFOKEZEW-UHFFFAOYSA-N
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)
Plain Text
IUPAC Name
2-({[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methane}sulfinyl)-1H-1,3-benzodiazole
SMILES
CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Benzimidazoles
  • Ethers
Substructures
  • Benzimidazoles
  • Pyridines and Derivatives
  • Ethers
  • Halogen Derivatives
  • Benzene and Derivatives
  • Imidazoles
  • Heterocyclic compounds
  • Aromatic compounds
  • Imines
  • Cyanamides
  • Sulfoxides
Pharmacology
Indication For the treatment of acid-reflux disorders (GERD), peptic ulcer disease, H. pylori eradication, and prevention of gastroinetestinal bleeds with NSAID use.
Pharmacodynamics Lansoprazole, an acid proton-pump inhibitor similar to omeprazole, is used as an untiulcer drug in the treatment and maintenance of healing of duodenal or gastric ulcers, erosive and reflux esophagitis, NSAID-induced ulcer, Zollinger-Ellison syndrome, and Barrett's esophagus. Lansoprozole is active against Helicobacter pylori. The plasma elimination half-life of lansoprazole does not reflect its duration of suppression of gastric acid secretion. Thus, the plasma elimination half-life is less than two hours, while the acid inhibitory effect lasts more than 24 hours.
Mechanism of action Lansoprazole belongs to a class of antisecretory compounds, the substituted benzimidazoles, that do not exhibit anticholinergic or histamine H2-receptor antagonist properties, but rather suppress gastric acid secretion by specific inhibition of the (H+,K+)-ATPase enzyme system at the secretory surface of the gastric parietal cell. Because this enzyme system is regarded as the acid (proton) pump within the parietal cell, Lansoprazole has been characterized as a gastric acid-pump inhibitor, in that it blocks the final step of acid production. This effect is dose-related and leads to inhibition of both basal and stimulated gastric acid secretion irrespective of the stimulus.
Absorption The absorption of lansoprazole is rapid, with mean Cmax occurring approximately 1.7 hours after oral dosing, and relatively complete with absolute bioavailability over 80%.
Volume of distribution Not Available
Protein binding 97%
Metabolism Hepatic. Two metabolites have been identified in measurable quantities in plasma (the hydroxylated sulfinyl and sulfone derivatives of lansoprazole). These metabolites have very little or no antisecretory activity. Lansoprazole is thought to be transformed into two active species which inhibit acid secretion by (H+,K+)-ATPase within the parietal cell canaliculus, but are not present in the systemic circulation.
Route of elimination Following single-dose oral administration of PREVACID, virtually no unchanged lansoprazole was excreted in the urine. In one study, after a single oral dose of 14C-lansoprazole, approximately one-third of the administered radiation was excreted in the urine and two-thirds was recovered in the feces. This implies a significant biliary excretion of the lansoprazole metabolites.
Half life 1.5 (± 1.0) hours
Clearance Not Available
Toxicity Symptoms of overdose include abdominal pain, nausea and diarrhea.
Affected organisms
  • Humans and other mammals
Pathways
Pathway Name SMPDB ID
Smp00227 Lansoprazole Pathway SMP00227
Pharmacoeconomics
Manufacturers
  • Matrix laboratories ltd
  • Teva pharmaceuticals usa
  • Takeda pharmaceuticals north america inc
  • Novartis consumer health inc
  • Sandoz inc
Packagers
Dosage forms
Form Route Strength
Capsule, delayed release Oral
Tablet, delayed release Oral
Prices
Unit description Cost Unit
Prevacid SoluTab 100 15 mg Dispersible Tablet Box 620.65 USD box
Prevacid NapraPAC 84 15-500 mg Kit Box 175.8 USD box
Prevpac Miscellaneous 32.02 USD ea
Prevpac patient pack 28.22 USD each
Lansoprazole 100% powder 27.54 USD g
Prevacid iv 30 mg vial 27.31 USD vial
Prevacid dr 15 mg capsule 6.25 USD capsule
Prevacid SoluTab 30 mg Dispersible Tablet 6.21 USD dispersible tablet
Prevacid 15 mg capsule dr 6.0 USD capsule
Prevacid 30 mg capsule dr 6.0 USD capsule
Prevacid dr 30 mg capsule 5.91 USD capsule
Lansoprazole 15 mg Delayed Release Capsule 5.9 USD capsule
Lansoprazole 30 mg Delayed Release Capsule 5.9 USD capsule
Prevacid 15 mg solutab 5.73 USD tablet
Prevacid 30 mg solutab 5.73 USD tablet
Lansoprazole dr 15 mg capsule 5.67 USD capsule
Lansoprazole dr 30 mg capsule 5.67 USD capsule
Prevacid 30 mg Delayed Release Capsule 4.45 USD capsule
Prevacid 15 mg Delayed Release Capsule 4.32 USD capsule
Apo-Lansoprazole 15 mg Delayed Release Capsule 1.17 USD capsule
Apo-Lansoprazole 30 mg Delayed Release Capsule 1.17 USD capsule
Novo-Lansoprazole 15 mg Delayed Release Capsule 1.17 USD capsule
Novo-Lansoprazole 30 mg Delayed Release Capsule 1.17 USD capsule
Prevacid 24hr dr 15 mg capsule 0.86 USD capsule
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DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Country Patent Number Approved Expires (estimated)
United States 7396841 2002-02-17 2022-02-17
United States 4628098 1992-11-10 2009-11-10
Canada 2419067 2008-12-23 2021-08-17
Canada 1327010 1994-02-15 2011-02-15
Properties
State solid
Experimental Properties
Property Value Source
melting point 178-182 °C Not Available
water solubility 0.97 mg/L Not Available
logP 1.9 Not Available
Predicted Properties
Property Value Source
water solubility 2.50e-01 g/l ALOGPS
logP 2.84 ALOGPS
logP 3.03 ChemAxon
logS -3.2 ALOGPS
pKa (strongest acidic) 9.35 ChemAxon
pKa (strongest basic) 4.16 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 4 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 67.87 ChemAxon
rotatable bond count 6 ChemAxon
refractivity 87.61 ChemAxon
polarizability 34.59 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00355 Link_out
PubChem Compound 3883 Link_out
PubChem Substance 46508975 Link_out
ChemSpider 3746 Link_out
ChEBI 6375 Link_out
ChEMBL 6375 Link_out
Therapeutic Targets Database DAP000725 Link_out
PharmGKB PA450180 Link_out
Drug Product Database 2165503 Link_out
RxList http://www.rxlist.com/cgi/generic/lansop.htm Link_out
Drugs.com http://www.drugs.com/lansoprazole.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Lansoprazole Link_out
ATC Codes
  • A02BC03
AHFS Codes
  • 56:28.36
PDB Entries Not Available
FDA label show (114 KB)
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Atazanavir This gastric pH modifier decreases the levels/effects of atazanavir
Cefditoren Proton pump inhibitors such as lansoprazole may decrease the serum concentration of cefditoren. If possible, avoid use of cefditoren with proton pump inhibitors (PPIs). Consider alternative methods to minimize/control acid reflux (eg, diet modification) or alternative antimicrobial therapy if use of PPIs can not be avoided.
Clopidogrel Lansoprazole may decrease serum concentrations of the active metabolite(s) of clopidogrel. Due to the possible risk for impaired clopidogrel effectiveness with this combination, clinicians should carefully consider the need for concurrent lansoprazole therapy in patients receiving clopidogrel. Monitor response to clopidogrel closely when using clopidogrel with lansoprazole. Whether there are differences among individual proton pump inhibitors is unclear. Other acid-lowering therapies (e.g., H2-receptor antagonists, antacids, etc.) do not appear to share this interaction with clopidogrel.
Enoxacin Lansoprazole may decrease the absorption of enoxacin.
Indinavir Omeprazole decreases the absorption of indinavir
Itraconazole The proton pump inhibitor, lansoprazole, may decrease the absorption of itraconazole.
Ketoconazole The proton pump inhibitor, lansoprazole, may decrease the absorption of ketoconazole.
Prasugrel Lansoprazole is a CYP2C19 substrate which decreases AUC and Cmax of prasugrel. Despite these decreases, there was no significant reduction of inhibition of platelet aggregation.
Sucralfate Sucralfate decreases the effect of lansoprazole
Food Interactions
  • Avoid alcohol.
  • Food reduces bioavailabilty, but this has very little clinical impact.
  • Take 30-60 minutes before meals.
Targets

1. Potassium-transporting ATPase alpha chain 1

Pharmacological action: yes
Actions: inhibitor

Catalyzes the hydrolysis of ATP coupled with the exchange of H(+) and K(+) ions across the plasma membrane. Responsible for acid production in the stomach

Organism class: human
UniProt ID: P20648 Link_out
Gene: ATP4A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Matheson AJ, Jarvis B: Lansoprazole: an update of its place in the management of acid-related disorders. Drugs. 2001;61(12):1801-33. Pubmed
  2. Langtry HD, Wilde MI: Lansoprazole. An update of its pharmacological properties and clinical efficacy in the management of acid-related disorders. Drugs. 1997 Sep;54(3):473-500. Pubmed
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
Enzymes

1. Cytochrome P450 3A4

Actions: substrate, inhibitor, inducer

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide

UniProt ID: P08684 Link_out
Gene: CYP3A4
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: 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. Epub 2009 Sep 1. Pubmed
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 2C19

Actions: substrate, inhibitor

Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine

UniProt ID: P33261 Link_out
Gene: CYP2C19 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  2. Zhou SF, Zhou ZW, Yang LP, Cai JP: 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. Epub 2009 Sep 1. Pubmed
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

3. Cytochrome P450 2C9

Actions: substrate, inhibitor, inducer

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S- warfarin, diclofenac, phenytoin, tolbutamide and losartan

UniProt ID: P11712 Link_out
Gene: CYP2C9
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: 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. Epub 2009 Sep 1. Pubmed
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

4. Cytochrome P450 1A1

Actions: inducer

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics

UniProt ID: P04798 Link_out
Gene: CYP1A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

5. Cytochrome P450 1A2

Actions: inducer

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen

UniProt ID: P05177 Link_out
Gene: CYP1A2
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

6. Cytochrome P450 1B1

Actions: inducer

Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development

UniProt ID: Q16678 Link_out
Gene: CYP1B1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

7. Cytochrome P450 2C18

Actions: substrate

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics

UniProt ID: P33260 Link_out
Gene: CYP2C18 Link_out
Protein Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

8. Cytochrome P450 2C8

Actions: substrate, inhibitor

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti- cancer drug paclitaxel (taxol)

UniProt ID: P10632 Link_out
Gene: CYP2C8
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

9. Cytochrome P450 2D6

Actions: inhibitor

Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants

UniProt ID: P10635 Link_out
Gene: CYP2D6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

10. Cytochrome P450 4A11

Actions: inducer

Catalyzes the omega- and (omega-1)-hydroxylation of various fatty acids such as laurate, myristate and palmitate. Has little activity towards prostaglandins A1 and E1

UniProt ID: Q02928 Link_out
Gene: CYP4A11 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
Transporters

1. Multidrug resistance protein 1

Actions: substrate, inhibitor

Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells

UniProt ID: P08183 Link_out
Gene: ABCB1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Pauli-Magnus C, Rekersbrink S, Klotz U, Fromm MF: Interaction of omeprazole, lansoprazole and pantoprazole with P-glycoprotein. Naunyn Schmiedebergs Arch Pharmacol. 2001 Dec;364(6):551-7. Pubmed
  2. Kodaira C, Sugimoto M, Nishino M, Yamade M, Shirai N, Uchida S, Ikuma M, Yamada S, Watanabe H, Hishida A, Furuta T: Effect of MDR1 C3435T polymorphism on lansoprazole in healthy Japanese subjects. Eur J Clin Pharmacol. 2009 Jun;65(6):593-600. Epub 2009 Feb 24. Pubmed

2. ATP-binding cassette sub-family G member 2

Actions: inhibitor

Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. May be involved in brain-to-blood efflux. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. When overexpressed, the transfected cells become resistant to mitoxantrone, daunorubicin and doxorubicin, display diminished intracellular accumulation of daunorubicin, and manifest an ATP- dependent increase in the efflux of rhodamine 123

UniProt ID: Q9UNQ0 Link_out
Gene: ABCG2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Suzuki K, Doki K, Homma M, Tamaki H, Hori S, Ohtani H, Sawada Y, Kohda Y: Co-administration of proton pump inhibitors delays elimination of plasma methotrexate in high-dose methotrexate therapy. Br J Clin Pharmacol. 2009 Jan;67(1):44-9. Epub 2008 Nov 17. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19