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Details

Stereochemistry RACEMIC
Molecular Formula C16H13F3N3O2S.Na
Molecular Weight 391.345
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LANSOPRAZOLE SODIUM

SMILES

Cc1c(CS(=O)c2nc3ccccc3[n-]2)nccc1OCC(F)(F)F.[Na+]

InChI

InChIKey=OTGPYEHFRKGRIZ-UHFFFAOYSA-N
InChI=1S/C16H13F3N3O2S.Na/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;/q-1;+1

HIDE SMILES / InChI

Molecular Formula C16H14F3N3O2S
Molecular Weight 369.3632
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
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
Prostacyclin analog prevents stress-induced expression of immediate early genes and gastric mucosal lesions in the rat stomach.
1999
Standard-dose lansoprazole is more effective than high-dose ranitidine in achieving endoscopic healing and symptom relief in patients with moderately severe reflux oesophagitis. The Dutch Lansoprazole Study Group.
1999 Dec
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
Ultrasonographic evaluation of lansoprazole-induced improvement of submucosal injury in patients with gastroesophageal reflux.
2000 Feb
Measurement of cytochrome P450 gene induction in human hepatocytes using quantitative real-time reverse transcriptase-polymerase chain reaction.
2000 Jul
Fluorometric screening for metabolism-based drug--drug interactions.
2000 Jul-Aug
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
Management of heartburn in a large, randomized, community-based study: comparison of four therapeutic strategies.
2001 Jun
High-performance liquid chromatographic assay for the simultaneous determination of lansoprazole enantiomers and metabolites in human liver microsomes.
2001 Jun 5
Pharmacokinetic differences between lansoprazole enantiomers and contribution of cytochrome P450 isoforms to enantioselective metabolism of lansoprazole in dogs.
2001 Mar
Lansoprazole-based triple therapy versus ranitidine bismuth citrate-based dual therapy in the eradication of Helicobacter pylori in patients with duodenal ulcer: a multicenter, randomized, double-dummy study.
2001 May
Reversible pheripheral edema in female patients taking proton pump inhibitors for peptic acid diseases.
2001 May
[Submicroscopic aspects of the mechanism of inhibitors of H+/K+-ATPase in gastric parietal cells].
2002
Gastroesophageal reflux in children: pathogenesis, prevalence, diagnosis, and role of proton pump inhibitors in treatment.
2002
Lansoprazole induces mucosal protection through gastrin receptor-dependent up-regulation of cyclooxygenase-2 in rats.
2002 Dec
Acute manic psychosis induced by triple therapy for H. pylori.
2002 Jan-Feb
ATPase inhibitors suppress actinomycin D-induced apoptosis in leukemia cells.
2002 Sep-Oct
Time-dependent transcriptional induction of CYP1A1, CYP1A2 and CYP1B1 mRNAs by H+/K+ -ATPase inhibitors and other xenobiotics.
2003 Feb
[New triple therapy for Helicobacter pylori infection in Japan].
2003 Jan
Safety and pharmacokinetics of oral lansoprazole in preadolescent rats exposed from weaning through sexual maturity.
2003 Jan-Feb
Does eradication of Helicobacter pylori reduce hypergastrinaemia during long term therapy with proton pump inhibitors?
2003 Mar
Lansoprazole increases testosterone metabolism and clearance in male Sprague-Dawley rats: implications for Leydig cell carcinogenesis.
2003 Oct 15
Enhanced expression of interleukin-8 and activation of nuclear factor kappa-B in endoscopy-negative gastroesophageal reflux disease.
2004 Apr
Comparison of inhibitory effects of the proton pump-inhibiting drugs omeprazole, esomeprazole, lansoprazole, pantoprazole, and rabeprazole on human cytochrome P450 activities.
2004 Aug
Aplastic anemia associated with initiation of nizatidine therapy in a hemodialysis patient.
2004 Jun
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
Lansoprazole ameliorates intestinal mucosal damage induced by ischemia-reperfusion in rats.
2004 Oct 1
Lansoprazole-associated collagenous colitis: a case report.
2005 Jul
Enhanced ghrelin secretion in rats with cysteamine-induced duodenal ulcers.
2005 Jul
Effect of concomitant dosing of famotidine with lansoprazole on gastric acid secretion in relation to CYP2C19 genotype status.
2005 Jul 1
Mechanisms of action of leptin in preventing gastric ulcer.
2005 Jul 21
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
"Proton-pump inhibitor-first" strategy versus "step-up" strategy for the acute treatment of reflux esophagitis: a cost-effectiveness analysis in Japan.
2005 Nov
Management of symptoms in step-down therapy of gastroesophageal reflux disease.
2005 Sep
Laryngopharyngeal reflux disease with nocturnal gastric acid breakthrough while on proton pump inhibitor therapy.
2006 Dec
Inlet patch of gastric mucosa in upper esophagus causing chronic cough and vocal cord dysfunction.
2006 Jan
Lansoprazole, a proton pump inhibitor, reduces the severity of indomethacin-induced rat enteritis.
2006 Jan
Sensitive determination of omeprazole and its two main metabolites in human plasma by column-switching high-performance liquid chromatography: application to pharmacokinetic study in relation to CYP2C19 genotypes.
2006 Mar 7
Suppression of proinflammatory cytokine production in macrophages by lansoprazole.
2006 Nov
Lack of pharmacokinetic interaction between omeprazole or lansoprazole and ivabradine in healthy volunteers: an open-label, randomized, crossover, pharmacokinetic interaction clinical trial.
2006 Oct
Long-term management of gastroesophageal reflux disease with pantoprazole.
2007 Jun
Gastroprotective and antioxidant effects of amiodarone on indomethacin-induced gastric ulcers in rats.
2007 Nov
Gastroprotective effect of mangiferin, a xanthonoid from Mangifera indica, against gastric injury induced by ethanol and indomethacin in rodents.
2007 Oct
Immune and Inflammatory Responses in GERD and Lansoprazole.
2007 Sep
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 Sat Jun 26 06:22:28 UTC 2021
Edited
by admin
on Sat Jun 26 06:22:28 UTC 2021
Record UNII
GV9NY1U369
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LANSOPRAZOLE SODIUM
Common Name English
1H-BENZIMIDAZOLE, 2-(((3-METHYL-4-(2,2,2-TRIFLUOROETHOXY)-2-PYRIDINYL)METHYL)SULFINYL)-, SODIUM SALT (1:1)
Common Name English
Code System Code Type Description
CAS
226904-00-3
Created by admin on Sat Jun 26 06:22:28 UTC 2021 , Edited by admin on Sat Jun 26 06:22:28 UTC 2021
PRIMARY
FDA UNII
GV9NY1U369
Created by admin on Sat Jun 26 06:22:28 UTC 2021 , Edited by admin on Sat Jun 26 06:22:28 UTC 2021
PRIMARY
EVMPD
SUB179772
Created by admin on Sat Jun 26 06:22:28 UTC 2021 , Edited by admin on Sat Jun 26 06:22:28 UTC 2021
PRIMARY
PUBCHEM
12044540
Created by admin on Sat Jun 26 06:22:28 UTC 2021 , Edited by admin on Sat Jun 26 06:22:28 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY