U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C16H14F3N3O2S
Molecular Weight 369.361
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LANSOPRAZOLE

SMILES

CC1=C(C[S+]([O-])C2=NC3=C(N2)C=CC=C3)N=CC=C1OCC(F)(F)F

InChI

InChIKey=MJIHNNLFOKEZEW-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C16H14F3N3O2S
Molecular Weight 369.361
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/22950496

Lansoprazole is a proton pump inhibitor, which prevents the stomach from producing acid. Lansoprazole has been marketed for many years and is one of several proton-pump inhibitors (PPI's). It was used for the treatment of acid-reflux disorders (GERD), peptic ulcer disease, H. pylori eradication, and prevention of gastrointestinal bleeds with NSAID use. Lansoprazole belongs to a class of ant secretory compounds, the substituted benzimidazoles, that do not exhibit anticholinergic or histamine H2-receptor antagonist properties, but that 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. Lansoprazole is extensively metabolized in the liver. 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. 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.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PREVACID

Approved Use

Use •treats frequent heartburn (occurs 2 or more days a week) •not intended for immediate relief of heartburn; this drug may take 1 to 4 days for full effect

Launch Date

1.0306656E12
Primary
PREVACID

Approved Use

Use •treats frequent heartburn (occurs 2 or more days a week) •not intended for immediate relief of heartburn; this drug may take 1 to 4 days for full effect

Launch Date

1.0306656E12
Primary
PREVACID

Approved Use

Use •treats frequent heartburn (occurs 2 or more days a week) •not intended for immediate relief of heartburn; this drug may take 1 to 4 days for full effect

Launch Date

1.0306656E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1705 ng/mL
30 mg single, intravenous
dose: 30 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
LANSOPRAZOLE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
3192 ng × h/mL
30 mg single, intravenous
dose: 30 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
LANSOPRAZOLE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.3 h
30 mg single, intravenous
dose: 30 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
LANSOPRAZOLE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
PubMed

PubMed

TitleDatePubMed
Double-blind comparison of lansoprazole 15 mg, lansoprazole 30 mg and placebo as maintenance therapy in patients with healed duodenal ulcers resistant to H2-receptor antagonists.
1999 Jul
Peptic ulcer recurrence during maintenance therapy with H2-receptor antagonist following first-line therapy with proton pump inhibitor.
2000
Fluorometric screening for metabolism-based drug--drug interactions.
2000 Jul-Aug
How do we offer clinical relief to patients with gastro-oesophageal reflux disease?
2000 Jun
Lansoprazole in the treatment of gastro-oesophageal reflux disease in childhood.
2000 Nov
The rates of common adverse events reported during treatment with proton pump inhibitors used in general practice in England: cohort studies.
2000 Oct
Proton pump inhibitors versus H2-antagonists: a meta-analysis of their efficacy in treating bleeding peptic ulcer.
2001 Jul
Pharmacokinetic differences between lansoprazole enantiomers and contribution of cytochrome P450 isoforms to enantioselective metabolism of lansoprazole in dogs.
2001 Mar
Evaluation of the cost-effectiveness of Helicobacter pylori eradication triple therapy vs. conventional therapy for ulcers in Japan.
2001 Nov
A systematic gene expression screen of Caenorhabditis elegans cytochrome P450 genes reveals CYP35 as strongly xenobiotic inducible.
2001 Nov 15
Effect of hypergastrinemia on pancreatic carcinogenesis.
2002 Apr
Acute manic psychosis induced by triple therapy for H. pylori.
2002 Jan-Feb
A comparative study on the activity of lansoprazole, omeprazole and PD-136450 on acidified ethanol- and indomethacin-induced gastric lesions in the rat.
2002 Mar
Time-dependent transcriptional induction of CYP1A1, CYP1A2 and CYP1B1 mRNAs by H+/K+ -ATPase inhibitors and other xenobiotics.
2003 Feb
Formulation study for lansoprazole fast-disintegrating tablet. III. Design of rapidly disintegrating tablets.
2003 Oct
Lansoprazole increases testosterone metabolism and clearance in male Sprague-Dawley rats: implications for Leydig cell carcinogenesis.
2003 Oct 15
Drug-induced tubulo-interstitial nephritis secondary to proton pump inhibitors: experience from a single UK renal unit.
2004 Jun
Lansoprazole-tacrolimus interaction in Japanese transplant recipient with CYP2C19 polymorphism.
2004 May
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Preventive therapy for non-steroidal anti-inflammatory drug-induced ulcers in Japanese patients with rheumatoid arthritis: the current situation and a prospective controlled-study of the preventive effects of lansoprazole or famotidine.
2005 Jun
Management of symptoms in step-down therapy of gastroesophageal reflux disease.
2005 Sep
Beyond gastric acid reduction: proton pump inhibitors induce heme oxygenase-1 in gastric and endothelial cells.
2006 Jul 7
Myopathy including polymyositis: a likely class adverse effect of proton pump inhibitors?
2006 Jun
Helicobacter pylori infection with a duodenal ulcer in a 6-year-old boy.
2006 Oct
Protective effects of proton pump inhibitors against indomethacin-induced lesions in the rat small intestine.
2007 Jan
Long-term management of gastroesophageal reflux disease with pantoprazole.
2007 Jun
Gastroprotective effect of mangiferin, a xanthonoid from Mangifera indica, against gastric injury induced by ethanol and indomethacin in rodents.
2007 Oct
Lansoprazole protects and heals gastric mucosa from non-steroidal anti-inflammatory drug (NSAID)-induced gastropathy by inhibiting mitochondrial as well as Fas-mediated death pathways with concurrent induction of mucosal cell renewal.
2008 May 23
Hypersensitivity to proton pump inhibitors: lansoprazole-induced Kounis syndrome.
2009 May 29
Patents

Sample Use Guides

Duodenal Ulcers: 15 mg Once daily for 4 weeks Gastroesophageal Reflux: 30 mg Once daily for up to 8 weeks
Route of Administration: Oral
In Vitro Use Guide
Lansoprazole is a gastric parietal cell proton pump inhibitor that is also active against Helicobacter pylori in vitro. The antimicrobial activity of lansoprazole and of its sulfenamide, a rearrangement product occurring spontaneously in acid environments, was studied by determining the MICs and MBCs for 11 cytotoxic and eight non-cytotoxic H. pylori strains and by measuring the rapidity of bacterial killing. The MIC90 and MBC90 were 2.5 mg/L and 10 mg/L, respectively, both for lansoprazole and for its sulfenamide.
Substance Class Chemical
Created
by admin
on Fri Dec 16 17:38:34 UTC 2022
Edited
by admin
on Fri Dec 16 17:38:34 UTC 2022
Record UNII
0K5C5T2QPG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LANSOPRAZOLE
EP   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
LANSOPRAZOLE [MI]
Common Name English
LANZOR
Brand Name English
AG-1749
Code English
LANSOPRAZOLE [ORANGE BOOK]
Common Name English
2-[[[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]benzimidazole
Systematic Name English
LANSOPRAZOLE COMPONENT OF PREVPAC
Common Name English
LANSOPRAZOLE [USP MONOGRAPH]
Common Name English
PREVACID
Brand Name English
PREVPAC COMPONENT LANSOPRAZOLE
Brand Name English
TAKEPRON
Brand Name English
2-(((3-METHYL-4-(2,2,2-TRIFLUOROETHOXY)PYRIDIN-2-YL)METHYL)SULFINYL)-1H-BENZIMIDAZOLE
Systematic Name English
Lansoprazole [WHO-DD]
Common Name English
A-65006
Code English
LANSOPRAZOLE [EP MONOGRAPH]
Common Name English
LANZOPRAZOLE
Common Name English
AGOPTON
Brand Name English
lansoprazole [INN]
Common Name English
(±)-LANSOPRAZOLE
Common Name English
PREVONCO
Brand Name English
NSC-758638
Code English
LANSOX
Brand Name English
LANSOPRAZOLE [USP-RS]
Common Name English
LIMPIDEX
Brand Name English
LANSOPRAZOLE [HSDB]
Common Name English
LANSOPRAZOLE [JAN]
Common Name English
LANSOPRAZOLE [MART.]
Common Name English
1H-BENZIMIDAZOLE, 2-(((3-METHYL-4-(2,2,2-TRIFLUOROETHOXY)-2-PYRIDINYL)METHYL)SULFINYL)-
Systematic Name English
OGAST
Brand Name English
ZOTON
Brand Name English
OGASTORO
Brand Name English
LANSOPRAZOLE [VANDF]
Common Name English
LANSOPRAZOLE [USAN]
Common Name English
Classification Tree Code System Code
WHO-ATC A02BC03
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
WHO-VATC QA02BD07
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
LIVERTOX NBK548452
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
WHO-VATC QA02BD03
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
WHO-ATC A02BD03
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
WHO-VATC QA02BD02
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
WHO-ATC A02BD02
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
WHO-ATC A02BD10
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
WHO-ATC A02BD07
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
NCI_THESAURUS C29723
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
WHO-VATC QA02BC03
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
FDA ORPHAN DRUG 446014
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
WHO-ATC A02BC53
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
NDF-RT N0000000147
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
NDF-RT N0000175525
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
FDA ORPHAN DRUG 264508
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
WHO-ATC A02BD09
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
Code System Code Type Description
MERCK INDEX
M6683
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
PRIMARY Merck Index
DAILYMED
0K5C5T2QPG
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
PRIMARY
RXCUI
17128
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
PRIMARY RxNorm
RS_ITEM_NUM
1356916
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
PRIMARY
NDF-RT
N0000009724
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
PRIMARY Inhibition Gastric Acid Secretion [PE]
PUBCHEM
3883
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
PRIMARY
DRUG CENTRAL
1547
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
PRIMARY
CAS
103577-45-3
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
PRIMARY
INN
6397
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
PRIMARY
IUPHAR
7208
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
PRIMARY
DRUG BANK
DB00448
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
PRIMARY
NCI_THESAURUS
C29150
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
PRIMARY
WIKIPEDIA
LANSOPRAZOLE
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
PRIMARY
MESH
C058687
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
PRIMARY
NSC
758638
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
PRIMARY
HSDB
7204
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
PRIMARY
LACTMED
Lansoprazole
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
PRIMARY
EPA CompTox
DTXSID4023200
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
PRIMARY
FDA UNII
0K5C5T2QPG
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
PRIMARY
EVMPD
SUB08403MIG
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
PRIMARY
ChEMBL
CHEMBL480
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
PRIMARY
USAN
AA-78
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
PRIMARY
CHEBI
6375
Created by admin on Fri Dec 16 17:38:35 UTC 2022 , Edited by admin on Fri Dec 16 17:38:35 UTC 2022
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> INDUCER
ENANTIOMER -> RACEMATE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
DEGRADENT -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
METABOLIC ENZYME -> SUBSTRATE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
BINDER->LIGAND
BINDING
TARGET -> INHIBITOR
DEGRADENT -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG
METABOLITE ACTIVE -> PRODRUG
METABOLITE ACTIVE -> PRODRUG
METABOLITE -> PARENT
These metabolites have very little or no antisecretory activity.
METABOLITE -> PARENT
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC With Hepatic impairment
PHARMACOKINETIC
Elderly
PHARMACOKINETIC