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
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)
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 |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/22950496
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.
CNS Activity
Originator
Sources: http://www.takeda.com/company/history/1985.html
Curator's Comment: # Takeda
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2095173 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11693467 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | PREVACID Approved UseUse •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 Date1.0306656E12 |
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Primary | PREVACID Approved UseUse •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 Date1.0306656E12 |
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Primary | PREVACID Approved UseUse •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 Date1.0306656E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Title | Date | PubMed |
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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 |
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Peptic ulcer recurrence during maintenance therapy with H2-receptor antagonist following first-line therapy with proton pump inhibitor. | 2000 |
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Fluorometric screening for metabolism-based drug--drug interactions. | 2000 Jul-Aug |
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How do we offer clinical relief to patients with gastro-oesophageal reflux disease? | 2000 Jun |
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Lansoprazole in the treatment of gastro-oesophageal reflux disease in childhood. | 2000 Nov |
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The rates of common adverse events reported during treatment with proton pump inhibitors used in general practice in England: cohort studies. | 2000 Oct |
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Proton pump inhibitors versus H2-antagonists: a meta-analysis of their efficacy in treating bleeding peptic ulcer. | 2001 Jul |
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Pharmacokinetic differences between lansoprazole enantiomers and contribution of cytochrome P450 isoforms to enantioselective metabolism of lansoprazole in dogs. | 2001 Mar |
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Evaluation of the cost-effectiveness of Helicobacter pylori eradication triple therapy vs. conventional therapy for ulcers in Japan. | 2001 Nov |
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A systematic gene expression screen of Caenorhabditis elegans cytochrome P450 genes reveals CYP35 as strongly xenobiotic inducible. | 2001 Nov 15 |
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Effect of hypergastrinemia on pancreatic carcinogenesis. | 2002 Apr |
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Acute manic psychosis induced by triple therapy for H. pylori. | 2002 Jan-Feb |
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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 |
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Time-dependent transcriptional induction of CYP1A1, CYP1A2 and CYP1B1 mRNAs by H+/K+ -ATPase inhibitors and other xenobiotics. | 2003 Feb |
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Formulation study for lansoprazole fast-disintegrating tablet. III. Design of rapidly disintegrating tablets. | 2003 Oct |
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Lansoprazole increases testosterone metabolism and clearance in male Sprague-Dawley rats: implications for Leydig cell carcinogenesis. | 2003 Oct 15 |
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Drug-induced tubulo-interstitial nephritis secondary to proton pump inhibitors: experience from a single UK renal unit. | 2004 Jun |
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Lansoprazole-tacrolimus interaction in Japanese transplant recipient with CYP2C19 polymorphism. | 2004 May |
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Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
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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 |
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Management of symptoms in step-down therapy of gastroesophageal reflux disease. | 2005 Sep |
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Beyond gastric acid reduction: proton pump inhibitors induce heme oxygenase-1 in gastric and endothelial cells. | 2006 Jul 7 |
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Myopathy including polymyositis: a likely class adverse effect of proton pump inhibitors? | 2006 Jun |
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Helicobacter pylori infection with a duodenal ulcer in a 6-year-old boy. | 2006 Oct |
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Protective effects of proton pump inhibitors against indomethacin-induced lesions in the rat small intestine. | 2007 Jan |
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Long-term management of gastroesophageal reflux disease with pantoprazole. | 2007 Jun |
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Gastroprotective effect of mangiferin, a xanthonoid from Mangifera indica, against gastric injury induced by ethanol and indomethacin in rodents. | 2007 Oct |
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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 |
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Hypersensitivity to proton pump inhibitors: lansoprazole-induced Kounis syndrome. | 2009 May 29 |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9184356
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
Edited
Fri Dec 16 17:38:34 UTC 2022
by
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on
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Record UNII |
0K5C5T2QPG
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Record Status |
Validated (UNII)
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Record Version |
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WHO-ATC |
A02BC03
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WHO-VATC |
QA02BD07
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LIVERTOX |
NBK548452
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WHO-VATC |
QA02BD03
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A02BD03
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WHO-VATC |
QA02BD02
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A02BD02
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WHO-ATC |
A02BD10
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A02BD07
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NCI_THESAURUS |
C29723
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WHO-VATC |
QA02BC03
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FDA ORPHAN DRUG |
446014
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WHO-ATC |
A02BC53
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NDF-RT |
N0000000147
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NDF-RT |
N0000175525
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FDA ORPHAN DRUG |
264508
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WHO-ATC |
A02BD09
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M6683
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PRIMARY | Merck Index | ||
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0K5C5T2QPG
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PRIMARY | |||
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17128
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1356916
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N0000009724
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PRIMARY | Inhibition Gastric Acid Secretion [PE] | ||
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3883
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1547
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103577-45-3
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6397
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7208
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DB00448
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C29150
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LANSOPRAZOLE
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C058687
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758638
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7204
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Lansoprazole
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DTXSID4023200
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0K5C5T2QPG
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SUB08403MIG
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CHEMBL480
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AA-78
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6375
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Related Record | Type | Details | ||
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METABOLIC ENZYME -> INDUCER | |||
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ENANTIOMER -> RACEMATE | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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DEGRADENT -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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SALT/SOLVATE -> PARENT | |||
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ENANTIOMER -> RACEMATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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BINDER->LIGAND |
BINDING
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TARGET -> INHIBITOR | |||
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DEGRADENT -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PRODRUG | |||
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METABOLITE ACTIVE -> PRODRUG | |||
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METABOLITE ACTIVE -> PRODRUG | |||
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METABOLITE -> PARENT |
These metabolites have very little or no antisecretory activity.
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METABOLITE -> PARENT |
Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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With Hepatic impairment PHARMACOKINETIC PHARMACOKINETIC |
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