Identification

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Name
Lansoprazole
Accession Number
DB00448  (APRD00077)
Type
Small Molecule
Groups
Approved, Investigational
Description

Lansoprazole marketed under the brand Prevacid, is a proton pump inhibitor (PPI) and is structurally classified as a substituted benzimidazole.4 It reduces gastric acid secretion by targeting gastric H,K-ATPase pumps and is thus effective at promoting healing in ulcerative diseases, and treating gastroesophageal reflux disease (GERD) along with other pathologies caused by excessive acid secretion.2

Structure
Thumb
Synonyms
  • Lansoprazol
  • Lansoprazole
  • Lansoprazolum
External IDs
A 65006 / A-65006 / AG 1749 / AG-1749
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
LansoprazoleCapsule, delayed release15 mg/1OralRebel Distributors2009-11-11Not applicableUs
LansoprazoleCapsule, delayed release15 mgOralPharmascience Inc2015-01-13Not applicableCanada
LansoprazoleCapsule, delayed release pellets30 mg/1OralApace Packaging, Llc2016-07-14Not applicableUs
LansoprazoleCapsule, delayed release30 mgOralPharmascience Inc2015-02-11Not applicableCanada
LansoprazoleCapsule, delayed release pellets15 mg/1OralApace Packaging, Llc2016-07-14Not applicableUs
LansoprazoleCapsule, delayed release30 mgOralPro Doc Limitee2011-06-07Not applicableCanada
LansoprazoleCapsule, delayed release30 mgOralSivem Pharmaceuticals Ulc2013-10-23Not applicableCanada
LansoprazoleCapsule, delayed release30 mgOralSanis Health Inc2010-11-22Not applicableCanada
LansoprazoleCapsule, delayed release30 mg/1OralRebel Distributors2009-11-11Not applicableUs
LansoprazoleCapsule, delayed release15 mgOralSivem Pharmaceuticals Ulc2012-06-11Not applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-lansoprazoleCapsule, delayed releaseOralApotex Corporation2009-06-03Not applicableCanada
Apo-lansoprazoleCapsule, delayed releaseOralApotex Corporation2009-06-03Not applicableCanada
Dom-lansoprazoleCapsule, delayed releaseOralDominion Pharmacal2014-07-08Not applicableCanada
Dom-lansoprazoleCapsule, delayed releaseOralDominion PharmacalNot applicableNot applicableCanada
LansoprazoleCapsule, delayed release30 mg/1OralPhysicians Total Care, Inc.2009-11-17Not applicableUs54868 608620180907 15195 in9pg6
LansoprazoleCapsule, delayed release30 mg/1OralA-S Medication Solutions2014-12-15Not applicableUs
LansoprazoleCapsule, delayed release pellets30 mg/1Oralbryant ranch prepack2013-08-23Not applicableUs
LansoprazoleTablet, orally disintegrating, delayed release30 mg/1OralCardinal Health2018-03-08Not applicableUs
LansoprazoleCapsule, delayed release pellets30 mg/1OralQuality Care Products, LLC2019-11-08Not applicableUs
LansoprazoleCapsule, delayed release15 mg/1Oralbryant ranch prepack2010-10-15Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Basic Care LansoprazoleTablet, orally disintegrating, delayed release15 mg/1OralL. Perrigo Company2018-12-29Not applicableUs
Basic Care LansoprazoleCapsule, delayed release15 mg/1OralL. Perrigo Company2017-09-03Not applicableUs
Berkley and Jensen LansoprazoleCapsule, delayed release15 mg/1OralBJWC2012-05-22Not applicableUs
CareOne Acid ReducerCapsule, delayed release15 mg/1OralAmerican Sales Company2016-10-14Not applicableUs
CareOne LansoprazoleCapsule, delayed release15 mg/1OralAmerican Sales Company2012-05-242018-07-10Us
Dg Health LansoprazoleCapsule, delayed release15 mg/1OralDOLGENCORP, LLC2012-05-21Not applicableUs
Equaline LansoprazoleCapsule, delayed release15 mg/1OralSUPERVALU INC2012-05-21Not applicableUs
Equate LansoprazoleTablet, orally disintegrating, delayed release15 mg/1OralWAL-MART STORES INC2019-03-19Not applicableUs
Equate Lansoprazole Delayed ReleaseCapsule, delayed release15 mg/1OralWAL-MART STORES INC2014-05-05Not applicableUs
Exchange Select LansoprazoleCapsule, delayed release15 mg/1OralArmy + Air Force Exchange Service2012-06-11Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Apo-lansoprazole-amoxicillin-clarithromycinLansoprazole (30 mg) + Amoxicillin (500 mg) + Clarithromycin (500 mg)Capsule; Capsule, delayed release; Kit; TabletOralApotex Corporation2018-08-03Not applicableCanada
Hp-pacLansoprazole (30 mg) + Amoxicillin (500 mg) + Clarithromycin (500 mg)Capsule; Capsule, delayed release; Kit; TabletOralTakeda1998-08-18Not applicableCanada
Lansoprazole, Amoxicillin and ClarithromycinLansoprazole (30 mg/1) + Amoxycillin trihydrate (500 mg/1) + Clarithromycin (500 mg/1)KitOralSandoz Inc2014-03-04Not applicableUs
Lansoprazole, Amoxicillin and ClarithromycinLansoprazole (30 mg/1) + Amoxycillin trihydrate (500 mg/1) + Clarithromycin (500 mg/1)KitOralPrasco Laboratories2015-03-032021-02-28Us
Lansoprazole, Amoxicillin, and ClarithromycinLansoprazole (30 mg/1) + Amoxycillin trihydrate (500 mg/1) + Clarithromycin (500 mg/1)KitOralTeva2013-09-092015-04-30Us00093 8055 14 nlmimage10 c2386123
Lansoprazole, Amoxicillin, ClarithromycinLansoprazole (30 mg/1) + Amoxycillin trihydrate (500 mg/1) + Clarithromycin (500 mg/1)KitOralRising Health, Llc2016-10-14Not applicableUs57237 00120180913 8702 1lfom9c
Prevacid NaprapacLansoprazole (15 mg/1) + Naproxen (500 mg/1)KitOralTakeda2003-11-142008-06-30Us
PREVACID NapraPAC 250Lansoprazole + NaproxenKitOralTap Pharmaceutical Products Inc.2006-11-302006-11-30Us
PREVACID NapraPAC 375Lansoprazole + NaproxenKitOralTap Pharmaceutical Products Inc.2006-11-302006-11-30Us
PREVACID NapraPAC 500Lansoprazole + NaproxenKitOralTap Pharmaceutical Products Inc.2006-11-302006-11-30Us
International/Other Brands
Agopton (Takeda) / Bamalite / Lansoloc (Cipla Medpro) / Lanzol (Cipla) / Lanzopral (Pharma Investi) / Lanzopran (Ranbaxy) / Limpidex (Sigma-Tau) / Monolitum (Salvat) / Ogast (Takeda) / Ogastro (Abbott) / Opiren (Almirall) / Prevacid 24HR (Novartis) / Prosogan (Takeda) / Takepron (Takeda) / Ulpax (Hormona) / Zoprol (Toprak) / Zoton (Pfizer)
Categories
UNII
0K5C5T2QPG
CAS number
103577-45-3
Weight
Average: 369.361
Monoisotopic: 369.075882012
Chemical Formula
C16H14F3N3O2S
InChI Key
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]methanesulfinyl}-1H-1,3-benzodiazole
SMILES
CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1

Pharmacology

Indication

Lansoprazole is used to reduce gastric acid secretion and is approved for short term treatment of active gastric ulcers, active duodenal ulcers, erosive reflux oesophagitis, symptomatic gastroesophageal reflux disease, and non-steroidal anti-inflammatory drug (NSAID) induced gastric and duodenal ulcers. 14Label It may be used in the maintenance and healing of several gastric conditions including duodenal ulcers, NSAID related gastric ulcers, and erosive esophagitis.Label Lansoprazole prevents recurrence of gastric ulcers in patients who have a documented history of gastric ulcers who also use NSAIDs chronically. Label Predictably, it is also useful in the management of hypersecretory conditions including Zollinger-Ellison syndrome. Label Lansoprazole is effective at eradicating H. pylori when used in conjunction with amoxicillin and clarithromycin (triple therapy) or with amoxicillin alone (dual therapy). Label

Associated Conditions
Pharmacodynamics

Lansoprazole decreases gastric acid secretion by targeting H+,K+-ATPase, which is the enzyme that catalyzes the final step in the acid secretion pathway in parietal cells. 6 Conveniently, lansoprazole administered any time of day is able to inhibit both daytime and nocturnal acid secretion.6 The result is that lansoprazole is effective at healing duodenal ulcers, reduces ulcer-related pain, and offers relief from symptoms of heartburn 6 Lansoprazole also reduces pepsin secretion, making it a useful treatment option for hypersecretory conditions such as Zollinger-Ellison syndrome.76[F4352]

Mechanism of action

As a PPI, lansoprazole is a prodrug and requires protonation via an acidic environment to become activated. 3 Once protonated, lansoprazole is able to react with cysteine residues, specifically Cys813 and Cys321, on parietal H+,K+-ATPase resulting in stable disulfides. 35 PPI's in general are able to provide prolonged inhibition of acid secretion due to their ability to bind covalently to their targets. 3

TargetActionsOrganism
APotassium-transporting ATPase alpha chain 1
inhibitor
Humans
UMicrotubule-associated protein tauNot AvailableHumans
Additional Data Available
Adverse Effects

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Contraindications

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Absorption

The oral bioavailability of lansoprazole is reported to be 80-90%2 and the peak plasma concentration(Cmax) is achieved about 1.7 hours after oral dosing.Label Food reduces the absorption of lansoprazole (both Cmax and AUC are reduced by 50-70%); therefore, patients should be instructed to take lansoprazole before meals.Label

Volume of distribution

The apparent volume of distribution of lansoprazole is 0.4 L/kg. 3

Protein binding

97% of lansoprazole is plasma protein bound. Label

Metabolism

Lansoprazole is predominantly metabolized in the liver by CYP3A4 and CYP2C19. 3 The resulting major metabolites are 5-hydroxy lansoprazole and the sulfone derivative of lansoprazole. 3Label

Route of elimination

A reported 14-23% of a lansoprazole is eliminated in the urine with this percentage range including both conjugated and unconjugated hydroxylated metabolites. 6

Half life

One source reports the half life of lansoprazole to be 0.9 - 1.6 hours2, while another source cites 0.9 - 2.1 hours3. The general consensus is that lansoprazole has a short half life and is approximately 2 hours or less. Label These numbers may be misleading since it suggests that lansoprazole has a short duration of action when in practice, lansoprazole can effectively inhibit acid secretion for ~24 hours due to it's mechanism of action. Label

Clearance

The reported clearance of lansoprazole is 400-650 mL/min. 3

Toxicity

The most commonly reported adverse events occurring more frequently in lansoprazole treated patients compared to placebo include abdominal pain, constipation, diarrhea, and nausea.Label There is a case report of toxic epidermal necrolysis (TEN), which is a rare but very serious cutaneous reaction, caused by lansoprazole.8 The previously healthy patient presented with symptoms of TEN 15 days after starting lansoprazole to manage peptic disease.8 Although the use of PPI's is rarely associated with TEN, causation should be considered if a patient presents with TEN shortly after newly commencing a PPI.8

In a single case report, a patient ingested 600 mg of lansoprazole and did not experience any adverse effects or symptoms of overdose.Label Overall, lansoprazole is well tolerated with relatively few adverse effects.

Lansoprazole is classified as Pregnancy Category B.Label Although there are animal studies that suggest lansoprazole does not cause harm to the fetus, there is still a paucity of human data. Hence, lansoprazole should only be administered to pregnant women if other options with more safety data have been exhausted.

It is unknown if lansoprazole is excreted in human breast milk.Label It is worth mentioning that lansoprazole has been used safely in infants, and is therefore likely safe to use during breastfeeding.9

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Lansoprazole Metabolism PathwayDrug metabolism
Lansoprazole Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 2C19CYP2C19*2(A;A)A Allele, homozygoteEffect Directly StudiedPatients with this genotype have reduced metabolism of lansoprazole.Details
Cytochrome P450 2C19CYP2C19*3(A;A)A Allele, homozygoteEffect Directly StudiedPatients with this genotype have reduced metabolism of lansoprazole.Details
Multidrug resistance protein 1---(C;T)C Allele, heterozygoteEffect Directly StudiedPatients with this genotype have increased plasma concentration of lansoprazole.Details
Cytochrome P450 2C19CYP2C19*2ANot Available681G>AEffect InferredPoor metabolizer, lower dose requirement, improved drug efficacyDetails
Cytochrome P450 2C19CYP2C19*2BNot Available681G>AEffect InferredPoor metabolizer, lower dose requirement, improved drug efficacyDetails
Cytochrome P450 2C19CYP2C19*4Not Available1A>GEffect InferredPoor metabolizer, lower dose requirement, improved drug efficacyDetails
Cytochrome P450 2C19CYP2C19*5Not Available1297C>TEffect InferredPoor metabolizer, lower dose requirement, improved drug efficacyDetails
Cytochrome P450 2C19CYP2C19*6Not Available395G>AEffect InferredPoor metabolizer, lower dose requirement, improved drug efficacyDetails
Cytochrome P450 2C19CYP2C19*7Not Available19294T>AEffect InferredPoor metabolizer, lower dose requirement, improved drug efficacyDetails
Cytochrome P450 2C19CYP2C19*22Not Available557G>C / 991A>GEffect InferredPoor metabolizer, lower dose requirement, improved drug efficacyDetails
Cytochrome P450 2C19CYP2C19*24Not Available99C>T / 991A>G  … show all Effect InferredPoor metabolizer, lower dose requirement, improved drug efficacyDetails
Cytochrome P450 2C19CYP2C19*35Not Available12662A>GEffect InferredPoor metabolizer, lower dose requirement, improved drug efficacyDetails

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be increased when combined with Lansoprazole.
(S)-WarfarinThe metabolism of (S)-Warfarin can be increased when combined with Lansoprazole.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be increased when combined with Lansoprazole.
4-MethoxyamphetamineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Lansoprazole.
5-methoxy-N,N-dimethyltryptamineThe metabolism of 5-methoxy-N,N-dimethyltryptamine can be decreased when combined with Lansoprazole.
9-aminocamptothecinThe metabolism of 9-aminocamptothecin can be increased when combined with Lansoprazole.
AbataceptThe metabolism of Lansoprazole can be increased when combined with Abatacept.
AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with Lansoprazole.
AbirateroneThe metabolism of Lansoprazole can be decreased when combined with Abiraterone.
AcenocoumarolThe metabolism of Acenocoumarol can be increased when combined with Lansoprazole.
Additional Data Available
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    Extended Description

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  • Severity
    Severity

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Food Interactions
  • Avoid alcohol.
  • Take before a meal. Take 30-60 minutes before meals.
  • Take with or without food. Food reduces bioavailability, but not to a clinically significant extent.

References

Synthesis Reference

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

US5374730
General 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:11693467]
  2. Shin JM, Sachs G: Pharmacology of proton pump inhibitors. Curr Gastroenterol Rep. 2008 Dec;10(6):528-34. [PubMed:19006606]
  3. Shin JM, Kim N: Pharmacokinetics and pharmacodynamics of the proton pump inhibitors. J Neurogastroenterol Motil. 2013 Jan;19(1):25-35. doi: 10.5056/jnm.2013.19.1.25. Epub 2013 Jan 8. [PubMed:23350044]
  4. Gremse DA: Lansoprazole: pharmacokinetics, pharmacodynamics and clinical uses. Expert Opin Pharmacother. 2001 Oct;2(10):1663-70. doi: 10.1517/14656566.2.10.1663 . [PubMed:11825309]
  5. Bosnjak T, Solberg R, Hemati PD, Jafari A, Kassem M, Johansen HT: Lansoprazole inhibits the cysteine protease legumain by binding to the active site. Basic Clin Pharmacol Toxicol. 2019 Mar 27. doi: 10.1111/bcpt.13230. [PubMed:30916878]
  6. 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. [PubMed:1382017]
  7. Hirschowitz BI, Simmons JL, Johnson LF, Mohnen J: Risk factors for esophagitis in extreme acid hypersecretors with and without Zollinger-Ellison syndrome. Clin Gastroenterol Hepatol. 2004 Mar;2(3):220-9. [PubMed:15017606]
  8. Fracaroli TS, Miranda LQ, Sodre JL, Chaves M, Gripp A: Toxic epidermal necrolysis induced by lansoprazole. An Bras Dermatol. 2013 Jan-Feb;88(1):117-20. [PubMed:23539016]
  9. Lansoprazole - Drugs and Lactation Database [Link]
External Links
Human Metabolome Database
HMDB0005008
KEGG Drug
D00355
PubChem Compound
3883
PubChem Substance
46508975
ChemSpider
3746
BindingDB
47032
RxNav
17128
ChEBI
6375
ChEMBL
CHEMBL480
Therapeutic Targets Database
DAP000725
PharmGKB
PA450180
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Lansoprazole
ATC Codes
A02BC03 — LansoprazoleA02BD07 — Lansoprazole, amoxicillin and clarithromycinA02BD02 — Lansoprazole, tetracycline and metronidazoleA02BD09 — Lansoprazole, clarithromycin and tinidazoleA02BD10 — Lansoprazole, amoxicillin and levofloxacinA02BD03 — Lansoprazole, amoxicillin and metronidazoleA02BC53 — Lansoprazole, combinations
AHFS Codes
  • 56:28.36 — Proton-pump Inhibitors
FDA label
Download (508 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHealthy Volunteers5
1CompletedBasic ScienceHealthy Volunteers3
1CompletedOtherHealthy Volunteers1
1CompletedTreatmentCystic Fibrosis (CF)1
1CompletedTreatmentEffect of Drugs / Safety Issues2
1CompletedTreatmentGastro-esophageal Reflux Disease (GERD)2
1CompletedTreatmentHealthy Volunteers3
1CompletedTreatmentHelicobacter Pylori1
1CompletedTreatmentLaryngopharyngeal Reflux1
1CompletedTreatmentNeoplasms, Advanced or Metastatic1
1TerminatedOtherHealthy Volunteers1
1TerminatedTreatmentHealthy Volunteers1
1Unknown StatusNot AvailableEndothelial Dysfunction1
1, 2CompletedTreatmentGastroesophageal Reflux / Infants, Premature1
1, 2CompletedTreatmentPain, Fracture, Sprain1
1, 2Unknown StatusTreatmentDyspepsia / Gastro-esophageal Reflux Disease (GERD) / Heartburn1
2CompletedTreatmentChronic Lymphocytic Leukaemia (CLL)1
2CompletedTreatmentEsophagitis1
2CompletedTreatmentEsophagitis / Reflux1
2CompletedTreatmentGastrointestinal Reflux / Preterm, Infant1
2CompletedTreatmentGouty Arthritis / Moderate Renal Impairment1
2CompletedTreatmentHeartburn1
2CompletedTreatmentOesophagitis, Eosinophilic1
2Not Yet RecruitingTreatmentBreast Cancer1
2RecruitingTreatmentAppendiceal Neoplasms / Pseudomyxoma Peritonei1
2RecruitingTreatmentCervical Cancers / Endometrial Cancer / Uterine Malignancies1
2RecruitingTreatmentGastric Diffuse Large B-cell Lymphoma1
2TerminatedTreatmentDiabetes, Autoimmune / Type 1 Diabetes Mellitus1
2Unknown StatusTreatmentType 1 Diabetes Mellitus1
2WithdrawnTreatmentBreast Cancer1
2, 3TerminatedTreatmentAsthma / Gastroesophageal Reflux1
2, 3Unknown StatusPreventionHearing loss or impairment1
3CompletedPreventionDuodenal Ulcer / Gastric Ulcer4
3CompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)4
3CompletedTreatmentDuodenal Ulcer2
3CompletedTreatmentDuodenal Ulcer / Gastric Ulcer1
3CompletedTreatmentErosive Esophagitis (EE)4
3CompletedTreatmentErosive Esophagitis (EE) / Gastro-esophageal Reflux Disease (GERD)1
3CompletedTreatmentFrequent Heartburn1
3CompletedTreatmentGastric Ulcer2
3CompletedTreatmentGastro-esophageal Reflux Disease (GERD)1
3CompletedTreatmentGouty Arthritis1
3CompletedTreatmentHeartburn1
3CompletedTreatmentHuman Experimentation1
3CompletedTreatmentLarynx Disease1
3CompletedTreatmentOptimization of Second Line Treatment Protocol for H Pylori Eradication1
3CompletedTreatmentOsteoarthritis (OA) / Peptic Ulcer1
3CompletedTreatmentPeptic Esophagitis / Reflux Esophagitis (RE)2
3RecruitingTreatmentAnti-Ulcer Agents / Digestive System Diseases / Enzyme Inhibitors / Gastric Ulcer / Gastrointestinal Agents / Gastrointestinal Diseases / Lansoprazole / Molecular Mechanisms of Pharmacological Action / Peptic Ulcer / Proton Pump Inhibitors1
3RecruitingTreatmentAsthma / Gastroesophageal Reflux1
3RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)2
3RecruitingTreatmentErosive Esophagitis (EE)1
3RecruitingTreatmentHealed erosive esophagitis1
3TerminatedPreventionBleeding / Malignant Neoplasm of Stomach1
3TerminatedTreatmentDuodenal Ulcer / Gastric Ulcer1
3TerminatedTreatmentErosive Esophagitis (EE)1
3Unknown StatusTreatmentDuodenal Ulcer / Gastric Ulcer / Gastritis / Helicobacter Infections1
3Unknown StatusTreatmentGastro-esophageal Reflux Disease (GERD)1
3Unknown StatusTreatmentPeptic Ulcer1
3WithdrawnTreatmentType 1 Diabetes Mellitus1
4Active Not RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori) / Gastrointestinal Ulcer Haemorrhage1
4Active Not RecruitingTreatmentErosive Esophagitis (EE)1
4CompletedNot AvailableHealthy Volunteers1
4CompletedBasic ScienceHealthy Volunteers1
4CompletedDiagnosticBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
4CompletedPreventionPeptic Ulcer1
4CompletedPreventionPulmonary Aspiration of Gastric Contents1
4CompletedPreventionRespiratory Failure1
4CompletedTreatmentAcid Regurgitation / Heartburn / Nausea / Upper Abdominal Pain1
4CompletedTreatmentArrhythmia1
4CompletedTreatmentAsthma1
4CompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)3
4CompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori) / Chronic Idiopathic Thrombocytopenic Purpura1
4CompletedTreatmentDyspepsia / Gastritis / Peptic Ulcer1
4CompletedTreatmentDyspepsia / Peptic Ulcer1
4CompletedTreatmentEpigastric Pain Syndrome / Functional Dyspepsia / Post Prandial Distress Syndrome1
4CompletedTreatmentErosive Esophagitis (EE)2
4CompletedTreatmentEsophagus, Barrett1
4CompletedTreatmentFunctional Dyspepsia / Peptic Ulcer1
4CompletedTreatmentFunctional Dyspepsia / Scarred Peptic Ulcer1
4CompletedTreatmentGastric Ulcer1
4CompletedTreatmentGastro-esophageal Reflux Disease (GERD)2
4CompletedTreatmentGastro-esophageal Reflux Disease (GERD) / Heartburn1
4CompletedTreatmentGastroesophageal Reflux3
4CompletedTreatmentGastroesophageal Reflux / Larynx Disease1
4CompletedTreatmentHealthy Volunteers1
4CompletedTreatmentHelicobacter Infection1
4CompletedTreatmentHelicobacter Pylori Treatment Failure1
4CompletedTreatmentMultiple Endocrine Neoplasia / Zollinger-Ellison Syndrome1
4CompletedTreatmentOtitis Media With Effusion1
4CompletedTreatmentReflux Esophagitis (RE)1
4Enrolling by InvitationTreatmentGastro-esophageal Reflux Disease (GERD)1
4Not Yet RecruitingScreeningCardiovascular Events / Gastro-esophageal Reflux Disease (GERD) / Safety Issues1
4Not Yet RecruitingTreatmentHelicobacter Pylori1
4TerminatedDiagnosticGastro-esophageal Reflux Disease (GERD) / Oesophagitis, Eosinophilic1
4TerminatedPreventionPatients Undergoing Elective Coronary Artery Bypass Graft1
4TerminatedTreatmentDysphonia / Pediatric Dysphonia1
4TerminatedTreatmentFunctional Dyspepsia1
4TerminatedTreatmentLaryngopharyngeal Reflux1
4Unknown StatusTreatmentAsthma1
4Unknown StatusTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori) / Functional Dyspepsia1
4Unknown StatusTreatmentCoronary Stenting1
4Unknown StatusTreatmentEradication Rate for Helicobacter1
4Unknown StatusTreatmentEradication Rates of the Two Regimens1
4Unknown StatusTreatmentGastro-esophageal Reflux Disease (GERD) / Nasal Obstruction / Rhinitis1
4Unknown StatusTreatmentPost-Tonsillectomy Activity / Post-Tonsillectomy Hydration / Post-Tonsillectomy Pain1
4Unknown StatusTreatmentUlcers1
4WithdrawnTreatmentGastroesophageal Reflux1
4WithdrawnTreatmentLaryngopharyngeal Reflux1
4WithdrawnTreatmentUpper Gastrointestinal Hemorrhage1
Not AvailableCompletedNot AvailableAcute Stress Ulcer and Acute Gastric Mucosal Lesions1
Not AvailableCompletedNot AvailableCommunity Acquired Pneumonia (CAP) / Gastro-esophageal Reflux Disease (GERD)1
Not AvailableCompletedNot AvailableGastric Ulcer, Duodenal Ulcer, Acute Stress Gastritis, and Acute Gastric Mucosal Lesions1
Not AvailableCompletedNot AvailableGastric or Duodenal Ulcers2
Not AvailableCompletedNot AvailableGastroesophageal Reflux Disease With Dyspepsia Symptoms1
Not AvailableCompletedNot AvailableHelicobacter Infections1
Not AvailableCompletedNot AvailablePeriodontitis, Chronic1
Not AvailableCompletedDiagnosticNeuroendocrine Carcinoma (Carcinoid)1
Not AvailableCompletedSupportive CareGlomerulonephritis / Glomerulonephritis membranous / Nephrotic Syndrome1
Not AvailableCompletedTreatmentAnti Platelet Effects1
Not AvailableCompletedTreatmentAsthma1
Not AvailableCompletedTreatmentGastro-esophageal Reflux Disease (GERD)1
Not AvailableCompletedTreatmentGastroesophageal Reflux / Polyps, Nasal1
Not AvailableCompletedTreatmentOtitis Media With Effusion1
Not AvailableCompletedTreatmentPeptic ulcer haemorrhage1
Not AvailableNot Yet RecruitingNot AvailableGastro-esophageal Reflux Disease (GERD)1
Not AvailableRecruitingDiagnosticGastroesophageal Reflux / Non-erosive Reflux Disease (NERD)1
Not AvailableRecruitingTreatmentAortic Root Dilatation / Aortic Valve Disorder / Coronary Artery Disease / Diseases of Mitral Valve / Surgery, Cardiac / Tricuspid valve disease1
Not AvailableRecruitingTreatmentCompare the Response Rate of Atypical GERD After PPI Therapy1
Not AvailableTerminatedNot AvailableGastro-esophageal Reflux Disease (GERD) / Gastroesophageal Reflux1
Not AvailableUnknown StatusPreventionPeptic Ulcer / Ulcer Complications1
Not AvailableUnknown StatusTreatmentLaryngopharyngeal Reflux1
Not AvailableWithdrawnTreatmentGastro-esophageal Reflux Disease (GERD) / Head and Neck Carcinoma / Oropharyngeal Cancers1
Not AvailableWithdrawnTreatmentGastroesophageal Reflux / OSAS (Obstructive Sleep Apneas Syndrome)1

Pharmacoeconomics

Manufacturers
  • Matrix laboratories ltd
  • Teva pharmaceuticals usa
  • Takeda pharmaceuticals north america inc
  • Novartis consumer health inc
  • Sandoz inc
Packagers
  • Abbott Laboratories Ltd.
  • Advanced Pharmaceutical Services Inc.
  • AQ Pharmaceuticals Inc.
  • A-S Medication Solutions LLC
  • Cardinal Health
  • Caremark LLC
  • Direct Pharmaceuticals Inc.
  • Dispensing Solutions
  • H.J. Harkins Co. Inc.
  • Heartland Repack Services LLC
  • Innoviant Pharmacy Inc.
  • Inventia Healthcare Pvt Ltd.
  • Lake Erie Medical and Surgical Supply
  • Mckesson Corp.
  • Medisca Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Novartis AG
  • Nucare Pharmaceuticals Inc.
  • Patheon Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Promex Medical Inc.
  • Redpharm Drug
  • Resource Optimization and Innovation LLC
  • Sandoz
  • Southwood Pharmaceuticals
  • Stat Rx Usa
  • Takeda Pharmaceutical Co. Ltd.
  • TAP Pharmaceuticals
  • Teva Pharmaceutical Industries Ltd.
  • UDL Laboratories
  • Va Cmop Dallas
  • Vangard Labs Inc.
Dosage forms
FormRouteStrength
KitNot applicable0.9 g/0.9g
Capsule; capsule, delayed release; kit; tabletOral
CapsuleOral15 mg/1
Capsule, delayed releaseOral15 mg/1
Capsule, delayed release pelletsOral15 mg/1
Capsule, delayed release pelletsOral30 mg/1
PowderNot applicable1 g/1g
Tablet, orally disintegrating, delayed releaseOral30 mg/1
Capsule, delayed releaseOral15 mg
Capsule, delayed releaseOral30 mg
Capsule, delayed releaseOral30 mg/1
InjectionIntravenous30 mg/5mL
SuspensionOral15 mg/1
SuspensionOral30 mg/1
Tablet, orally disintegratingOral15 mg/1
Tablet, orally disintegratingOral30 mg/1
Tablet, orally disintegrating, delayed releaseOral15 mg/1
Tablet, delayed releaseOral
Injection, powder, for solutionIntravenous30 mg/5mL
KitOral
Capsule, delayed releaseOral
Prices
Unit descriptionCostUnit
Prevacid SoluTab 100 15 mg Dispersible Tablet Box620.65USD box
Prevacid NapraPAC 84 15-500 mg Kit Box175.8USD box
Prevpac Miscellaneous32.02USD ea
Prevpac patient pack28.22USD each
Lansoprazole 100% powder27.54USD g
Prevacid iv 30 mg vial27.31USD vial
Prevacid dr 15 mg capsule6.25USD capsule
Prevacid SoluTab 30 mg Dispersible Tablet6.21USD dispersible tablet
Prevacid 15 mg capsule dr6.0USD capsule
Prevacid 30 mg capsule dr6.0USD capsule
Prevacid dr 30 mg capsule5.91USD capsule
Lansoprazole 15 mg Delayed Release Capsule5.9USD capsule
Lansoprazole 30 mg Delayed Release Capsule5.9USD capsule
Prevacid 15 mg solutab5.73USD tablet
Prevacid 30 mg solutab5.73USD tablet
Lansoprazole dr 15 mg capsule5.67USD capsule
Lansoprazole dr 30 mg capsule5.67USD capsule
Prevacid 30 mg Delayed Release Capsule4.45USD capsule
Prevacid 15 mg Delayed Release Capsule4.32USD capsule
Apo-Lansoprazole 15 mg Delayed Release Capsule1.17USD capsule
Apo-Lansoprazole 30 mg Delayed Release Capsule1.17USD capsule
Novo-Lansoprazole 15 mg Delayed Release Capsule1.17USD capsule
Novo-Lansoprazole 30 mg Delayed Release Capsule1.17USD capsule
Prevacid 24hr dr 15 mg capsule0.86USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US4628098No1986-12-092009-11-10Us
CA2419067No2008-12-232021-08-17Canada
CA1327010No1994-02-152011-02-15Canada
US7399485Yes2008-07-152018-11-26Us
US6328994Yes2001-12-112019-11-17Us
US7875292Yes2011-01-252019-11-17Us
US7431942Yes2008-10-072019-11-17Us
US7396841Yes2008-07-082022-02-17Us
US9901546Yes2018-02-272019-11-17Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)178-182 °Chttps://www.chemicalbook.com/ChemicalProductProperty_US_CB6396972.aspx
water solubility0.97 mg/LFDA Label
Predicted Properties
PropertyValueSource
Water Solubility0.25 mg/mLALOGPS
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 Area67.87 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity87.61 m3·mol-1ChemAxon
Polarizability34.59 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9972
Blood Brain Barrier+0.7007
Caco-2 permeable+0.8866
P-glycoprotein substrateNon-substrate0.547
P-glycoprotein inhibitor IInhibitor0.5357
P-glycoprotein inhibitor IINon-inhibitor0.8692
Renal organic cation transporterInhibitor0.5521
CYP450 2C9 substrateNon-substrate0.7826
CYP450 2D6 substrateNon-substrate0.8659
CYP450 3A4 substrateSubstrate0.6771
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorInhibitor0.8993
CYP450 3A4 inhibitorInhibitor0.7959
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8768
Ames testNon AMES toxic0.5858
CarcinogenicityNon-carcinogens0.7944
BiodegradationNot ready biodegradable1.0
Rat acute toxicity1.8997 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8777
hERG inhibition (predictor II)Non-inhibitor0.8734
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-0udi-0090000000-502b719a981f262577ba
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-0uxr-0890000000-2734547f6dc584ba4877
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-053i-0930000000-94e6e179919ee803d567
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-03di-0900000000-1676d647709a023eb1d8
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-03di-0900000000-95a3126e9d69aa2812d6
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-03di-0900000000-0bb1e54ec8c7d6bb5746
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-03di-0900000000-52d969183040eb21720c
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-03di-0900000000-bba914a2bd85fb3b0823
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-02u0-0900000000-10a04626464fa2bcd6f9
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-014i-2900000000-14157d06ad23e343435e
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-02t9-8900000000-025e7246e314127a8422
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-03xr-9300000000-6a804721218ef90d3f61
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-0290000000-a108432755e4f5916f6e
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-0390000000-b8a59093f6b667fae5e4
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0fs9-0790000000-a2f5e86f6faaab508112
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00li-0940000000-cc60a0c246e3fc1399d6
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0pvr-0910000000-3c73fbb04b031d6b077d
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-1900000000-731f4b8d7ac3ecfe924e
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-6900000000-9474d5b5b8646c57c023
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0aor-9400000000-1533765e29fdaabcfcfe
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-066s-9200000000-1a1318476ca6543b3482
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0006-0339000000-30ca3e1162573d0632eb
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0udi-2590000000-3562d6bdd29198e5bf3e
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as sulfinylbenzimidazoles. These are polycyclic aromatic compounds containing a sulfinyl group attached at the position 2 of a benzimidazole moiety.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzimidazoles
Sub Class
Sulfinylbenzimidazoles
Direct Parent
Sulfinylbenzimidazoles
Alternative Parents
Methylpyridines / Alkyl aryl ethers / Benzenoids / Imidazoles / Heteroaromatic compounds / Sulfoxides / Sulfinyl compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds
show 4 more
Substituents
Sulfinylbenzimidazole / Alkyl aryl ether / Methylpyridine / Pyridine / Benzenoid / Azole / Imidazole / Heteroaromatic compound / Sulfoxide / Azacycle
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
sulfoxide, pyridines, benzimidazoles (CHEBI:6375)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Sodium:potassium-exchanging atpase activity
Specific Function
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.
Gene Name
ATP4A
Uniprot ID
P20648
Uniprot Name
Potassium-transporting ATPase alpha chain 1
Molecular Weight
114117.74 Da
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:11693467]
  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:9279507]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Structural constituent of cytoskeleton
Specific Function
Promotes microtubule assembly and stability, and might be involved in the establishment and maintenance of neuronal polarity. The C-terminus binds axonal microtubules while the N-terminus binds neu...
Gene Name
MAPT
Uniprot ID
P10636
Uniprot Name
Microtubule-associated protein tau
Molecular Weight
78927.025 Da
References
  1. Rojo LE, Alzate-Morales J, Saavedra IN, Davies P, Maccioni RB: Selective interaction of lansoprazole and astemizole with tau polymers: potential new clinical use in diagnosis of Alzheimer's disease. J Alzheimers Dis. 2010;19(2):573-89. doi: 10.3233/JAD-2010-1262. [PubMed:20110603]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Vitamin d 24-hydroxylase activity
Specific Function
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 un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Curi-Pedrosa R, Daujat M, Pichard L, Ourlin JC, Clair P, Gervot L, Lesca P, Domergue J, Joyeux H, Fourtanier G, et al.: Omeprazole and lansoprazole are mixed inducers of CYP1A and CYP3A in human hepatocytes in primary culture. J Pharmacol Exp Ther. 1994 Apr;269(1):384-92. [PubMed:8169844]
  2. Krusekopf S, Roots I, Hildebrandt AG, Kleeberg U: 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. [PubMed:12623754]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Oxygen binding
Specific Function
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 un...
Gene Name
CYP1B1
Uniprot ID
Q16678
Uniprot Name
Cytochrome P450 1B1
Molecular Weight
60845.33 Da
References
  1. Krusekopf S, Roots I, Hildebrandt AG, Kleeberg U: 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. [PubMed:12623754]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Curator comments
Very minor contribution to metabolism and not relevant at therapeutic concentrations.
General Function
Steroid hydroxylase activity
Specific Function
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 un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Pearce RE, Rodrigues AD, Goldstein JA, Parkinson A: Identification of the human P450 enzymes involved in lansoprazole metabolism. J Pharmacol Exp Ther. 1996 May;277(2):805-16. [PubMed:8627562]
  2. Pichard L, Curi-Pedrosa R, Bonfils C, Jacqz-Aigrain E, Domergue J, Joyeux H, Cosme J, Guengerich FP, Maurel P: Oxidative metabolism of lansoprazole by human liver cytochromes P450. Mol Pharmacol. 1995 Feb;47(2):410-8. [PubMed:7870052]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Inducer
Curator comments
Very minor contribution to metabolism and not relevant at therapeutic concentrations. R-lansoprazole acts as a steroespecific inducer of the enzyme but the degree of activation varies depending on the substrate. All data supporting this enzyme action are in vitro,
General Function
Steroid hydroxylase activity
Specific Function
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 un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
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:19515014]
  2. Liu KH, Kim MJ, Jung WM, Kang W, Cha IJ, Shin JG: Lansoprazole enantiomer activates human liver microsomal CYP2C9 catalytic activity in a stereospecific and substrate-specific manner. Drug Metab Dispos. 2005 Feb;33(2):209-13. doi: 10.1124/dmd.104.001438. Epub 2004 Nov 10. [PubMed:15537834]
  3. Li XQ, Andersson TB, Ahlstrom M, Weidolf L: Comparison of inhibitory effects of the proton pump-inhibiting drugs omeprazole, esomeprazole, lansoprazole, pantoprazole, and rabeprazole on human cytochrome P450 activities. Drug Metab Dispos. 2004 Aug;32(8):821-7. [PubMed:15258107]
  4. Liu KH, Kim MJ, Shon JH, Moon YS, Seol SY, Kang W, Cha IJ, Shin JG: Stereoselective inhibition of cytochrome P450 forms by lansoprazole and omeprazole in vitro. Xenobiotica. 2005 Jan;35(1):27-38. doi: 10.1080/00498250400026472 . [PubMed:15788366]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
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 un...
Gene Name
CYP2C18
Uniprot ID
P33260
Uniprot Name
Cytochrome P450 2C18
Molecular Weight
55710.075 Da
References
  1. Pichard L, Curi-Pedrosa R, Bonfils C, Jacqz-Aigrain E, Domergue J, Joyeux H, Cosme J, Guengerich FP, Maurel P: Oxidative metabolism of lansoprazole by human liver cytochromes P450. Mol Pharmacol. 1995 Feb;47(2):410-8. [PubMed:7870052]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
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...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Ko JW, Sukhova N, Thacker D, Chen P, Flockhart DA: Evaluation of omeprazole and lansoprazole as inhibitors of cytochrome P450 isoforms. Drug Metab Dispos. 1997 Jul;25(7):853-62. [PubMed:9224780]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Kim KA, Kim MJ, Park JY, Shon JH, Yoon YR, Lee SS, Liu KH, Chun JH, Hyun MH, Shin JG: Stereoselective metabolism of lansoprazole by human liver cytochrome P450 enzymes. Drug Metab Dispos. 2003 Oct;31(10):1227-34. doi: 10.1124/dmd.31.10.1227. [PubMed:12975331]
  2. Curi-Pedrosa R, Daujat M, Pichard L, Ourlin JC, Clair P, Gervot L, Lesca P, Domergue J, Joyeux H, Fourtanier G, et al.: Omeprazole and lansoprazole are mixed inducers of CYP1A and CYP3A in human hepatocytes in primary culture. J Pharmacol Exp Ther. 1994 Apr;269(1):384-92. [PubMed:8169844]
  3. Masubuchi N, Li AP, Okazaki O: 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. [PubMed:9744552]
  4. Pearce RE, Rodrigues AD, Goldstein JA, Parkinson A: Identification of the human P450 enzymes involved in lansoprazole metabolism. J Pharmacol Exp Ther. 1996 May;277(2):805-16. [PubMed:8627562]
  5. Ko JW, Sukhova N, Thacker D, Chen P, Flockhart DA: Evaluation of omeprazole and lansoprazole as inhibitors of cytochrome P450 isoforms. Drug Metab Dispos. 1997 Jul;25(7):853-62. [PubMed:9224780]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Curator comments
Higher affinity for S-lansoprazole but contributes to the metabolism of R-lansoprazole as well. This affinity is also proportional to the potency of each molecule as an inhibitor of the enzyme.
General Function
Steroid hydroxylase activity
Specific Function
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 im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Pearce RE, Rodrigues AD, Goldstein JA, Parkinson A: Identification of the human P450 enzymes involved in lansoprazole metabolism. J Pharmacol Exp Ther. 1996 May;277(2):805-16. [PubMed:8627562]
  2. Kim KA, Kim MJ, Park JY, Shon JH, Yoon YR, Lee SS, Liu KH, Chun JH, Hyun MH, Shin JG: Stereoselective metabolism of lansoprazole by human liver cytochrome P450 enzymes. Drug Metab Dispos. 2003 Oct;31(10):1227-34. doi: 10.1124/dmd.31.10.1227. [PubMed:12975331]
  3. Liu KH, Kim MJ, Shon JH, Moon YS, Seol SY, Kang W, Cha IJ, Shin JG: Stereoselective inhibition of cytochrome P450 forms by lansoprazole and omeprazole in vitro. Xenobiotica. 2005 Jan;35(1):27-38. doi: 10.1080/00498250400026472 . [PubMed:15788366]
  4. Li XQ, Andersson TB, Ahlstrom M, Weidolf L: Comparison of inhibitory effects of the proton pump-inhibiting drugs omeprazole, esomeprazole, lansoprazole, pantoprazole, and rabeprazole on human cytochrome P450 activities. Drug Metab Dispos. 2004 Aug;32(8):821-7. [PubMed:15258107]
  5. Kita T, Sakaeda T, Baba T, Aoyama N, Kakumoto M, Kurimoto Y, Kawahara Y, Okamura N, Kirita S, Kasuga M, Okumura K: Different contribution of CYP2C19 in the in vitro metabolism of three proton pump inhibitors. Biol Pharm Bull. 2003 Mar;26(3):386-90. [PubMed:12612455]
  6. Yasui-Furukori N, Saito M, Uno T, Takahata T, Sugawara K, Tateishi T: Effects of fluvoxamine on lansoprazole pharmacokinetics in relation to CYP2C19 genotypes. J Clin Pharmacol. 2004 Nov;44(11):1223-9. doi: 10.1177/0091270004269015. [PubMed:15496639]
  7. Ko JW, Sukhova N, Thacker D, Chen P, Flockhart DA: Evaluation of omeprazole and lansoprazole as inhibitors of cytochrome P450 isoforms. Drug Metab Dispos. 1997 Jul;25(7):853-62. [PubMed:9224780]
  8. Shin JM, Kim N: Pharmacokinetics and pharmacodynamics of the proton pump inhibitors. J Neurogastroenterol Motil. 2013 Jan;19(1):25-35. doi: 10.5056/jnm.2013.19.1.25. Epub 2013 Jan 8. [PubMed:23350044]
  9. Flockhart Table of Drug Interactions [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
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. doi: 10.1111/j.1365-2125.2008.03303.x. Epub 2008 Nov 17. [PubMed:19076159]
  2. Delayed Elimination of Methotrexate Associated with Co-Administration of Proton Pump Inhibitors [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
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:11770010]
  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. doi: 10.1007/s00228-009-0625-8. Epub 2009 Feb 24. [PubMed:19238367]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. Hamada Y, Ikemura K, Iwamoto T, Okuda M: Stereoselective Inhibition of Renal Basolateral Human Organic Anion Transporter 3 by Lansoprazole Enantiomers. Pharmacology. 2018;101(3-4):176-183. doi: 10.1159/000485920. Epub 2018 Jan 19. [PubMed:29353278]
  2. Proton Pump Inhibitors Inhibit Methotrexate Transport by Renal Basolateral Organic Anion Transporter hOAT3 [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Secondary active organic cation transmembrane transporter activity
Specific Function
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
Molecular Weight
61153.345 Da
References
  1. Nies AT, Hofmann U, Resch C, Schaeffeler E, Rius M, Schwab M: Proton pump inhibitors inhibit metformin uptake by organic cation transporters (OCTs). PLoS One. 2011;6(7):e22163. doi: 10.1371/journal.pone.0022163. Epub 2011 Jul 14. [PubMed:21779389]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Quaternary ammonium group transmembrane transporter activity
Specific Function
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
Molecular Weight
62579.99 Da
References
  1. Nies AT, Hofmann U, Resch C, Schaeffeler E, Rius M, Schwab M: Proton pump inhibitors inhibit metformin uptake by organic cation transporters (OCTs). PLoS One. 2011;6(7):e22163. doi: 10.1371/journal.pone.0022163. Epub 2011 Jul 14. [PubMed:21779389]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Toxin transporter activity
Specific Function
Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain.
Gene Name
SLC22A3
Uniprot ID
O75751
Uniprot Name
Solute carrier family 22 member 3
Molecular Weight
61279.485 Da
References
  1. Nies AT, Hofmann U, Resch C, Schaeffeler E, Rius M, Schwab M: Proton pump inhibitors inhibit metformin uptake by organic cation transporters (OCTs). PLoS One. 2011;6(7):e22163. doi: 10.1371/journal.pone.0022163. Epub 2011 Jul 14. [PubMed:21779389]

Drug created on June 13, 2005 07:24 / Updated on February 25, 2020 00:04