LANSOPRAZOLE

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 Search

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
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2002/21-428lbl.pdf
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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Potassium-transporting ATPase 30 Target ID: CHEMBL2095173 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11693467	Inhibitor 8146

Conditions

Condition	Modality	Highest Phase	Product
Active duodenal ulcer 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2002/21-428lbl.pdf	Primary	Approved 8307	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
Gastric ulcer 61 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2002/21-428lbl.pdf	Primary	Approved 8307	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
Gastroesophageal reflux disease 61 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2002/21-428lbl.pdf	Primary	Approved 8307	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

C_max

Value	Dose	Co-administered	Analyte	Population
1705 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021566s005lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021566s005lbl.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.3 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021566s005lbl.pdf	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

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:6375	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6375
ChemicalBook	CB6396972	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6396972
MolPort	MolPort-003-666-508	https://www.molport.com/shop/molecule-link/MolPort-003-666-508
Selleck Chemicals	Lansoprazole	http://www.selleckchem.com/products/Lansoprazole.html
eMolecules	902018	https://www.emolecules.com/cgi-bin/more?vid=902018

PubMed

Title	Date	PubMed
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	10383532
Peptic ulcer recurrence during maintenance therapy with H2-receptor antagonist following first-line therapy with proton pump inhibitor.	2000	11085491
Fluorometric screening for metabolism-based drug--drug interactions.	2000 Jul-Aug	11274899
How do we offer clinical relief to patients with gastro-oesophageal reflux disease?	2000 Jun	10929891
Lansoprazole in the treatment of gastro-oesophageal reflux disease in childhood.	2000 Nov	11142573
The rates of common adverse events reported during treatment with proton pump inhibitors used in general practice in England: cohort studies.	2000 Oct	11012560
Proton pump inhibitors versus H2-antagonists: a meta-analysis of their efficacy in treating bleeding peptic ulcer.	2001 Jul	11421865
Pharmacokinetic differences between lansoprazole enantiomers and contribution of cytochrome P450 isoforms to enantioselective metabolism of lansoprazole in dogs.	2001 Mar	11256484
Evaluation of the cost-effectiveness of Helicobacter pylori eradication triple therapy vs. conventional therapy for ulcers in Japan.	2001 Nov	11683692
A systematic gene expression screen of Caenorhabditis elegans cytochrome P450 genes reveals CYP35 as strongly xenobiotic inducible.	2001 Nov 15	11697852
Effect of hypergastrinemia on pancreatic carcinogenesis.	2002 Apr	11975934
Acute manic psychosis induced by triple therapy for H. pylori.	2002 Jan-Feb	11841141
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	11906479
Time-dependent transcriptional induction of CYP1A1, CYP1A2 and CYP1B1 mRNAs by H+/K+ -ATPase inhibitors and other xenobiotics.	2003 Feb	12623754
Formulation study for lansoprazole fast-disintegrating tablet. III. Design of rapidly disintegrating tablets.	2003 Oct	14519914
Lansoprazole increases testosterone metabolism and clearance in male Sprague-Dawley rats: implications for Leydig cell carcinogenesis.	2003 Oct 15	14550749
Drug-induced tubulo-interstitial nephritis secondary to proton pump inhibitors: experience from a single UK renal unit.	2004 Jun	15004262
Lansoprazole-tacrolimus interaction in Japanese transplant recipient with CYP2C19 polymorphism.	2004 May	15010519
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
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	15943850
Management of symptoms in step-down therapy of gastroesophageal reflux disease.	2005 Sep	16105122
Beyond gastric acid reduction: proton pump inhibitors induce heme oxygenase-1 in gastric and endothelial cells.	2006 Jul 7	16712795
Myopathy including polymyositis: a likely class adverse effect of proton pump inhibitors?	2006 Jun	16758264
Helicobacter pylori infection with a duodenal ulcer in a 6-year-old boy.	2006 Oct	17106182
Protective effects of proton pump inhibitors against indomethacin-induced lesions in the rat small intestine.	2007 Jan	17151854
Long-term management of gastroesophageal reflux disease with pantoprazole.	2007 Jun	18360632
Gastroprotective effect of mangiferin, a xanthonoid from Mangifera indica, against gastric injury induced by ethanol and indomethacin in rodents.	2007 Oct	17918041
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	18375387
Hypersensitivity to proton pump inhibitors: lansoprazole-induced Kounis syndrome.	2009 May 29	18378022

Patents

Sample Use Guides

In Vivo Use Guide

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

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Name

Type

Language

LANSOPRAZOLE

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