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Identification
NameLansoprazole
Accession NumberDB00448  (APRD00077)
Typesmall molecule
Groupsapproved, investigational
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
Synonyms
SynonymLanguageCode
LansoprazolGerman/SpanishINN
LansoprazoleNot AvailableINN, BAN, USAN
LansoprazolumLatinINN
SaltsNot Available
Brand names
NameCompany
AgoptonTakeda
BamaliteNot Available
LansolocCipla Medpro
LanzolCipla
LanzopralPharma Investi
LanzopranRanbaxy
LimpidexSigma-Tau
MonolitumSalvat
OgastTakeda
OgastroAbbott
OpirenAlmirall
PrevacidNovartis
Prevacid 24HRNovartis
Prevacid IVNovartis
Prevacid SolutabNovartis
ProsoganTakeda
TakepronTakeda
UlpaxHormona
ZoprolToprak
ZotonPfizer
Brand mixturesNot Available
Categories
CAS number103577-45-3
WeightAverage: 369.361
Monoisotopic: 369.075882012
Chemical FormulaC16H14F3N3O2S
InChI KeyInChIKey=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)
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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassBenzimidazoles
SubclassSulfinylbenzimidazoles
Direct parentSulfinylbenzimidazoles
Alternative parentsAlkyl Aryl Ethers; Pyridines and Derivatives; Benzene and Substituted Derivatives; Imidazoles; Sulfoxides; Polyamines; Alkyl Fluorides; Organofluorides
Substituentsalkyl aryl ether; benzene; pyridine; azole; imidazole; sulfoxide; ether; polyamine; organofluoride; organohalogen; alkyl halide; alkyl fluoride; organonitrogen compound
Classification descriptionThis compound belongs to the sulfinylbenzimidazoles. These are polycyclic aromatic compounds containing a sulfinyl group attached at the position 2 of a benzimidazole moiety.
Pharmacology
IndicationFor the treatment of acid-reflux disorders (GERD), peptic ulcer disease, H. pylori eradication, and prevention of gastroinetestinal bleeds with NSAID use.
PharmacodynamicsLansoprazole, 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 actionLansoprazole 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.
AbsorptionThe 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 distributionNot Available
Protein binding97%
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<sup>+</sup>,K<sup>+</sup>)-ATPase within the parietal cell canaliculus, but are not present in the systemic circulation.

SubstrateEnzymesProduct
Lansoprazole
5-HydroxylansoprazoleDetails
Lansoprazole
Lansoprazole sulfoneDetails
Route of eliminationFollowing 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 life1.5 (± 1.0) hours
ClearanceNot Available
ToxicitySymptoms of overdose include abdominal pain, nausea and diarrhea.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated Effects
Interacting Gene/EnzymeSNP RS IDAllele nameDefining changeEffectReference(s)
Cytochrome P450 2C19
Gene symbol: CYP2C19
UniProt: P33261
rs4244285 CYP2C19*2A Allele, homozygotePoor metabolizer, lower dose requirement, improved drug efficacy9867757
Cytochrome P450 2C19
Gene symbol: CYP2C19
UniProt: P33261
rs4986893 CYP2C19*3A Allele, homozygotePoor metabolizer, lower dose requirement, improved drug efficacy9867757
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9972
Blood Brain Barrier + 0.7007
Caco-2 permeable + 0.8866
P-glycoprotein substrate Non-substrate 0.547
P-glycoprotein inhibitor I Inhibitor 0.5357
P-glycoprotein inhibitor II Non-inhibitor 0.8692
Renal organic cation transporter Inhibitor 0.5521
CYP450 2C9 substrate Non-substrate 0.7826
CYP450 2D6 substrate Non-substrate 0.8659
CYP450 3A4 substrate Substrate 0.6771
CYP450 1A2 substrate Inhibitor 0.9106
CYP450 2C9 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Inhibitor 0.8932
CYP450 2C19 substrate Inhibitor 0.8993
CYP450 3A4 substrate Inhibitor 0.7959
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8768
Ames test Non AMES toxic 0.5858
Carcinogenicity Non-carcinogens 0.7944
Biodegradation Not ready biodegradable 1.0
Rat acute toxicity 1.8997 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8777
hERG inhibition (predictor II) Non-inhibitor 0.8734
Pharmacoeconomics
Manufacturers
  • Matrix laboratories ltd
  • Teva pharmaceuticals usa
  • Takeda pharmaceuticals north america inc
  • Novartis consumer health inc
  • Sandoz inc
Packagers
Dosage forms
FormRouteStrength
Capsule, delayed releaseOral
Tablet, delayed releaseOral
Prices
Unit descriptionCostUnit
Prevacid SoluTab 100 15 mg Dispersible Tablet Box620.65USDbox
Prevacid NapraPAC 84 15-500 mg Kit Box175.8USDbox
Prevpac Miscellaneous32.02USDea
Prevpac patient pack28.22USDeach
Lansoprazole 100% powder27.54USDg
Prevacid iv 30 mg vial27.31USDvial
Prevacid dr 15 mg capsule6.25USDcapsule
Prevacid SoluTab 30 mg Dispersible Tablet6.21USDdispersible tablet
Prevacid 15 mg capsule dr6.0USDcapsule
Prevacid 30 mg capsule dr6.0USDcapsule
Prevacid dr 30 mg capsule5.91USDcapsule
Lansoprazole 15 mg Delayed Release Capsule5.9USDcapsule
Lansoprazole 30 mg Delayed Release Capsule5.9USDcapsule
Prevacid 15 mg solutab5.73USDtablet
Prevacid 30 mg solutab5.73USDtablet
Lansoprazole dr 15 mg capsule5.67USDcapsule
Lansoprazole dr 30 mg capsule5.67USDcapsule
Prevacid 30 mg Delayed Release Capsule4.45USDcapsule
Prevacid 15 mg Delayed Release Capsule4.32USDcapsule
Apo-Lansoprazole 15 mg Delayed Release Capsule1.17USDcapsule
Apo-Lansoprazole 30 mg Delayed Release Capsule1.17USDcapsule
Novo-Lansoprazole 15 mg Delayed Release Capsule1.17USDcapsule
Novo-Lansoprazole 30 mg Delayed Release Capsule1.17USDcapsule
Prevacid 24hr dr 15 mg capsule0.86USDcapsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States73968412002-02-172022-02-17
United States46280981992-11-102009-11-10
Canada24190672008-12-232021-08-17
Canada13270101994-02-152011-02-15
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point178-182 °CNot Available
water solubility0.97 mg/LNot Available
logP1.9Not Available
Predicted Properties
PropertyValueSource
water solubility2.50e-01 g/lALOGPS
logP2.84ALOGPS
logP3.03ChemAxon
logS-3.2ALOGPS
pKa (strongest acidic)9.35ChemAxon
pKa (strongest basic)4.16ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count1ChemAxon
polar surface area67.87ChemAxon
rotatable bond count6ChemAxon
refractivity87.61ChemAxon
polarizability34.59ChemAxon
number of rings3ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleYesChemAxon
Spectra
Spectra
References
Synthesis Reference

Clarke Slemon, Bob Macel, “Preparation of omeprazole and lansoprazole.” U.S. Patent US5374730, issued December, 1986.

US5374730
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00355
PubChem Compound3883
PubChem Substance46508975
ChemSpider3746
ChEBI6375
ChEMBLCHEMBL480
Therapeutic Targets DatabaseDAP000725
PharmGKBPA450180
Drug Product Database2165503
RxListhttp://www.rxlist.com/cgi/generic/lansop.htm
Drugs.comhttp://www.drugs.com/lansoprazole.html
WikipediaLansoprazole
ATC CodesA02BC03
AHFS Codes
  • 56:28.36
PDB EntriesNot Available
FDA labelshow(114 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AtazanavirThis gastric pH modifier decreases the levels/effects of atazanavir
BosutinibConcomitant lansoprazole (PPI) decreased bosutinib Cmax by 46% and AUC by 26% compared to bosutinib alone. Consider using short-acting antacids or H2 blockers instead of PPIs to avoid a reduction in bosutinib exposure. Separate antacid or H2 blocker dosing and BOSULIF dosing by more than 2 hours.
CefditorenProton 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.
ClopidogrelLansoprazole 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.
EnoxacinLansoprazole may decrease the absorption of enoxacin.
IndinavirOmeprazole decreases the absorption of indinavir
ItraconazoleThe proton pump inhibitor, lansoprazole, may decrease the absorption of itraconazole.
KetoconazoleThe proton pump inhibitor, lansoprazole, may decrease the absorption of ketoconazole.
PrasugrelLansoprazole is a CYP2C19 substrate which decreases AUC and Cmax of prasugrel. Despite these decreases, there was no significant reduction of inhibition of platelet aggregation.
RilpivirineProton-pump inhibitors increase gastric pH which causes a decrease in the exposure of rilpivirine thus reducing efficacy.
SucralfateSucralfate 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.

1. Potassium-transporting ATPase alpha chain 1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Potassium-transporting ATPase alpha chain 1 P20648 Details

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

1. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor inducer

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C19 P33261 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor inducer

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Cytochrome P450 1A1 P04798 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Cytochrome P450 1B1 Q16678 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C18 P33260 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C8 P10632 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Cytochrome P450 4A11 Q02928 Details

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

1. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
ATP-binding cassette sub-family G member 2 Q9UNQ0 Details

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 January 10, 2014 19:52