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Lansoprazole

HCID 3883
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Basic information

CAS
103577-45-3
Standard SMILES
Cc1c(OCC(F)(F)F)ccnc1CS(=O)c1nc2ccccc2[nH]1
InChIKey
MJIHNNLFOKEZEW-UHFFFAOYSA-N
Molecular formula
C16H14F3N3O2S
Average molar mass
369.4 g/mol
Monoisotopic mass
369.07588236

Overview

Lansoprazole is a sulfoxide, a member of benzimidazoles and a member of pyridines. It has a role as an EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor and an anti-ulcer drug.

Names & identifiers

Preferred name
Lansoprazole
IUPAC
2-[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methylsulfinyl]-1H-benzimidazole
English name
Lansoprazole
Molecular formula
C16H14F3N3O2S
Molecular weight
369.36

Names & synonyms

lansoprazole103577-45-3PrevacidLimpidexAgoptonLanzorTakepronZotonPrevacid SoluTabLansoprazolLanzopralOpiren
Show more names
LANSAPRAZOLELANSOPRAZOLE, MM(CRM STANDARD)2-[3-METHYL-4-(2,2,2-TRIFLUORO-ETHOXY)-PYRIDIN-2-YLMETHANESULFINYL]-1H-BENZOIMIDAZOLE2-(((3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methyl)sulfinyl)-1H-benzo[d]imidazoleLANSOPRAZOLE, RELATED COMPOUND A2-[[[3-METHYL-4-(2,2,2-TRIFLOUROETHOXY)-2-PYRIDYL]METHYL]SULFONYL]BENZIMIDAZOLE USP STANDARDLanzPromp
LansoprazolumLansoxOgastAG-1749Prevacid IvlanzoprazolePrevOncoOgastoro

Database identifiers

CAS
103577-45-3、138530-94-6
PubChem CID
3883

Properties

Computed structural properties

XLogP
2.8
Topological polar surface area
87.1 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
8
Rotatable bonds
5
Heavy atoms
25
Formal charge
0
Complexity
480

Experimental & physicochemical properties

Drugs · 3 items

Pharmaceuticals -> Alimentary tract and metabolism -> Drugs for acid related disorders

Pharmaceuticals

Pharmaceuticals -> Used in Switzerland

LogP2.7
OdorOdorless
Color/FormWhite to brownish-white crystalline powder
Solubility · 2 items

Freely soluble in dimethylformamide; soluble in ethyl acetate, dichloromethane and acetonitrile; very slightly soluble in ether, and practically insoluble in hexane and water.

>55.4 [ug/mL] (The mean of the results at pH 7.4)

Human Drugs · 3 items

Breast Feeding; Lactation; Milk, Human; Anti-Ulcer Agents; Gastrointestinal Agents; Proton Pump Inhibitors

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Melting Point · 4 items

178-182 °C

178 to 182 °C (decomposes)

MP: approx 166 °C with decomposition. Stable when exposed to light for up to two months. The compound degrades in aqueous solution, the rate of degradation increasing with decreasing pH. At 25 °C the half-lives are approx 0.5 and 18 hrs at pH 5.0 and pH 7.0, respectively.

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 0.7% (1 of 136) of reports.

Warning

H315 (96.3%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 136 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

Hazard information

Regulatory InformationLansoprazole: Does not have an individual approval but may be used under an appropriate group standard
FDA Requirements · 1 item

The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl lansoprazole, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

Hazard Classes and Categories · 2 items

Skin Irrit. 2 (96.3%)

Skin Irrit. 2 (100%)

Safety & protection

Disposal Methods · 1 item

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Chemistry & industry

Pharmacology

ATC Code · 3 items

A02BC03

A - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

Protein Binding97% of lansoprazole is plasma protein bound.
Pharmacodynamics · 1 item

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. Conveniently, lansoprazole administered any time of day is able to inhibit both daytime and nocturnal acid secretion. The result is that lansoprazole is effective at healing duodenal ulcers, reduces ulcer-related pain, and offers relief from symptoms of heartburn Lansoprazole also reduces pepsin secretion, making it a useful treatment option for hypersecretory conditions such as Zollinger-Ellison syndrome.

Mechanism of Action · 2 items

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

Lansoprazole is a selective and irreversible proton pump inhibitor. In the acidic environment of the gastric parietal cell, lansoprazole is converted to active sulphenamide derivatives that bind to the sulfhydryl group of (H+, K+)-adenosine triphosphatase ((H+,K+)-ATPase), also known as the proton pump (H+,K+)-ATPase catalyzes the final step in the gastric acid secretion pathway. Lansoprazole's inhibition of (H+,K+)-ATPase results in inhibition of both centrally and peripherally mediated gastric acid secretion. The inhibitory effect is dose-related. Lansoprazole inhibits both basal and stimulated gastric acid secretion regardless of the stimulus.

Biological Half-Life · 2 items

One source reports the half life of lansoprazole to be 0.9 - 1.6 hours, while another source cites 0.9 - 2.1 hours. The general consensus is that lansoprazole has a short half life and is approximately 2 hours or less. 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.

Related reactions

95 records
New reaction record
HRID 16931 reaction equation
HRID 16931As reactantuspto-grants-2010_06
HRID 16932 reaction equation
HRID 16932As reactantuspto-grants-2010_06
HRID 97256 reaction equation
HRID 97256As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 103703 reaction equation
HRID 103703As productTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 113827 reaction equation
HRID 113827As productTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 116292 reaction equation
HRID 116292As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 125111 reaction equation
HRID 125111As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 148031 reaction equation
HRID 148031As productTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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DTXSID
DTXSID4023200
ChEMBL
CHEMBL480
ChEBI
CHEBI:6375
UNII
0K5C5T2QPG
EC Number
627-144-2、645-308-1

178 - 182 °C

Physical DescriptionSolid
Dissociation ConstantspKa1 = 1.1; pKa2 = 6.9; pKa3 = 12 /Estimated/
Collision Cross Section · 2 items

185.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

177.38 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
178 · 178-182°C dec.
Boiling point
555.8 · 555.8±60.0 °C(Predicted)
Density
1.5 · 1.50±0.1 g/cm3(Predicted)
storage temp.
2 · 2-8°C
solubility
Practically insoluble in water, soluble in anhydrous ethanol, very slightly soluble in acetonitrile.
pka
2.34 · pKa 2.34±0.37 (Occasionally);3.53±0.37 (Occasionally);8.48±0.30 (Occasionally)
form
powder
color
off-white
Merck
14 · 14,5362
BCS Class
2 · 2
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)
InChIKey
MJIHNNLFOKEZEW-UHFFFAOYSA-N
SMILES
C1(S(CC2=NC=CC(OCC(F)(F)F)=C2C)=O)NC2=CC=CC=C2N=1
CAS DataBase Reference
103577 · 103577-45-3(CAS DataBase Reference)
NCI Dictionary of Cancer Terms
lansoprazole; Prevacid
FDA UNII
0 K5C5T2QPG · 0K5C5T2QPG
ATC code
2 BC03,A02BC53 · A02BC03,A02BC53
UNSPSC Code
41116107 · 41116107
NACRES
77 · NA.77
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319-H335
Precautionary statements
261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xi
Risk Statements
36 · 36/37/38
Safety Statements
26 · 26-36
WGK Germany
2 · 2
RTECS
9487500 · DD9487500
HS Code
29339900 · 29339900
Storage Class
11 · 11 - Combustible Solids
Hazardous Substances Data
103577 · 103577-45-3(Hazardous Substances Data)
Toxicity
2 gm/kg · dog,LD,oral,> 2gm/kg (2000mg/kg),Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 35, Pg. 387, 1993.

Toxicology

Interactions · 5 items

Possible interactions of lansoprazole with medications known to be metabolized by the hepatic cytochrome p450 enzyme system should be considered.

... Lansoprazole, by increasing gastric pH, as the potential to affect the bioavailability of any medication whose absorption is pH-dependent. Also, lansoprazole may prevent the degradation of acid-labile drugs.

Lansoprazole causes prolonged inhibition of gastric acid secretion, and thereby my interfere with the absorption of these medications /ampicillin ester, digoxin, iron salts, ketoconazole/and other for which bioavailability is determined by gastric pH.

Lansoprazole appears to produce a dose-dependent decrease in the absorption of cyanocobalamin; this my be due to lansoprazole-induced hypochlorhydria or achlorhydria.

For more Interactions (Complete) data for LANSOPRAZOLE (9 total), please visit the HSDB record page.

Hepatotoxicity · 1 item

Despite its wide use, lansoprazole has only rarely been associated with hepatic injury. In large scale, long term trials of lansoprazole, serum ALT elevations have occurred in less than 1% of patients and at rates similar to those that occur with placebo or comparator drugs. Only a small number of cases of clinically apparent liver disease due to lansoprazole or dexlansoprazole have been published and most have been anicteric and mild. In most instances, the time to onset was within 2 to 4 weeks and the pattern of enzyme elevations was hepatocellular or mixed. Hypersensitivity reactions with fever, rash and eosinophilia have been described due to dexlansoprazole and lansoprazole, and these reactions may be accompanied by minor serum enzyme elevations and thus qualify for DRESS syndrome (drug-rash with eosinophilia and systemic symptoms). Autoantibody formation is rare. Recovery is usually rapid (within a month) and complete upon stopping lansoprazole. Recurrence on reexposures has been reported.

Milk ConcentrationsIt is not known whether lansoprazole is distributed into breast milk. However, lansoprazole or its metabolites are distributed into the milk of rats.
Human Toxicity Excerpts/HUMAN EXPOSURE STUDIES/ In one reported case of overdose, the patient consumed 600 mg of lansoprazole with no adverse reaction.
Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Lansoprazole

vLess-DILI-concern

3

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Non-Human Toxicity Excerpts · 5 items

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Duodenogastric reflux is known to cause an increased frequency of cancer in the glandular portion of the stomach in rats. Furthermore, it is debated whether inhibition of gastric acid secretion may promote gastric carcinogenesis. In the present study we examined the combined effect of gastroduodenal reflux and acid inhibition with respect to the development of gastric carcinoma in the rat. Following the construction of a gastrojejunostomy in male Wistar rats, half of them were given the proton pump inhibitor lanzoprazole for 1 year. The rats were then killed and the pH in the stomach and gastrin in blood were measured. The stomach was examined macroscopically as well as histologically. Gastrin levels at autopsy were significantly increased in treated rats compared to the control group, confirming an effect of lanzoprazole on gastric acid secretion. Body weight was significantly reduced in the treated rats. Thirty of 79 rats developed gastric cancer, and they were all adenocarcinomas of the Lauren intestinal type. Gastric cancers occurred significantly more often in lanzoprazole-treated rats (50%) compared with controls (27%). Lanzoprazole given orally enhances the carcinogenic effect of duodenogastric reflux in rats.

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Leydig cell tumors (LCTs) are frequently observed during rodent carcinogenicity studies, however, the significance of this effect to humans remains a matter of debate. Many chemicals that produce LCTs also induce hepatic cytochromes P450 (CYPs), but it is unknown whether these two phenomena are causally related. Our aim was to investigate the existence of a liver-testis axis wherein microsomal enzyme inducers enhance testosterone metabolic clearance, resulting in a drop in circulating hormone levels and a consequent hypertrophic response from the hypothalamic-pituitary-testis axis. Lansoprazole was selected as the model compound as it induces hepatic CYPs and produces LCTs in rats. Male Sprague-Dawley rats were dosed with lansoprazole (150 mg/kg/day) or vehicle for 14 days. Lansoprazole treatment produced effects on the liver consistent with an enhanced metabolic capacity, including significant increases in relative liver weights, total microsomal CYP content, individual CYP protein levels, and enhanced CYP-dependent testosterone metabolism in vitro. Following intravenous administration of 14(C)testosterone, lansoprazole-treated rats exhibited a significantly smaller area under the curve and significantly higher plasma clearance. Significant reductions in plasma and testicular testosterone levels were observed, confirming the ability of this compound to perturb androgen homeostasis. No significant changes in plasma LH, FSH, or prolactin levels were detected under our experimental conditions. Lansoprazole treatment exerted no marked effects on testicular testosterone metabolism.

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ In 2 year studies in rats receiving up to 40 times the recommended human dose, lansoprazole produced dose-related gastric enterochromaffin-life (ECL) cell hyperplasia and ECL cell carcinoids in both male and female rats. Lansoprazole also increased the incidence of intestinal metaplasia of the gastric epithelium, and produced dose-related increases in the incidence of testicular interstitial adenomas. In a 1 year toxicity study in rats receiving 13 times the recommended human dose, testicular interstitial cell adenoma also occurred in 1 of 30 rats. In a 2 year study in mice receiving up to 80 times the recommended human dose, lansoprazole produced an increased incidence of liver tumors (Hepatocellular adenomas and carcinomas), a dose-related increase in the incidence of gastric ECL cell hyperplasia, and adenomas of the rete restis in males.

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
EPA Human Health Benchmarks for Pharmaceuticals · 6 items

Lansoprazole

0.3

1.5

The recommended dose for treating frequent heartburn is 15 mg daily for 14 days.

Data used to generate the benchmarks include the following: Lowest Daily Dose (LDD): 15 mg/day, Lowest Therapeutic Dose (LTD): 0.2 mg/kg-day, and Screening Dose: 0.00006 mg/kg-day.

13-Aug-21

Regulatory information

FDA Requirements · 1 item

The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl lansoprazole, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
2
rtecs
DD9487500
hs_code
29339900
Toxicity
dog,LD,oral,> 2gm/kg (2000mg/kg),Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 35, Pg. 387, 1993.
risk_code
36/37/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi
safety_code
26-36
Storage Class
11 - Combustible Solids
Hazard statements
H315-H319-H335
Precautionary statements
P261-P264-P271-P280-P302+P352-P305+P351+P338
Hazardous Substances Data
103577-45-3(Hazardous Substances Data)

Elimination: Normal renal function: Approximately 1.5 hours. Renal function impairment: Shortened elimination half-life. Elderly patients: 1.9 to 2.9 hours. Hepatic function impairment: 3.2 to 7.2 hours.

Metabolism/Metabolites · 2 items

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

Lansoprazole is extensively metabolized in the liver to two main excretory metabolites that are inactive. In the acidic environment of the gastric parietal cell, lansoprazole is converted to two active compounds that inhibit acid secretion by (H+,K+)-ATPase within the parietal cell canaliculus, but that are not present in the systemic circulation.

FDA Pharmacological Classification · 6 items

0K5C5T2QPG

LANSOPRAZOLE

Established Pharmacologic Class [EPC] - Proton Pump Inhibitor

Mechanisms of Action [MoA] - Proton Pump Inhibitors

Physiologic Effects [PE] - Inhibition Gastric Acid Secretion

Lansoprazole is a Proton Pump Inhibitor. The mechanism of action of lansoprazole is as a Proton Pump Inhibitor. The physiologic effect of lansoprazole is by means of Inhibition Gastric Acid Secretion.

MeSH Pharmacological Classification · 2 items

Various agents with different action mechanisms used to treat or ameliorate PEPTIC ULCER or irritation of the gastrointestinal tract. This has included ANTIBIOTICS to treat HELICOBACTER INFECTIONS; HISTAMINE H2 ANTAGONISTS to reduce GASTRIC ACID secretion; and ANTACIDS for symptomatic relief.

Compounds that inhibit H(+)-K(+)-EXCHANGING ATPASE. They are used as ANTI-ULCER AGENTS and sometimes in place of HISTAMINE H2 ANTAGONISTS for GASTROESOPHAGEAL REFLUX.

Absorption, Distribution and Excretion · 6 items

The oral bioavailability of lansoprazole is reported to be 80-90% and the peak plasma concentration(Cmax) is achieved about 1.7 hours after oral dosing. 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.

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

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

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

Very high (around 97%) /protein binding/; protein binding remains constant over the concentration range of 0.05 to 5 ug/mL. In patient with renal function impairment, protein binding may be decreased by 1 to 1.5%.

Distributed in tissue, particularly gastric parietal cells. Apparent oral volume of distribution following administration of 30 mg of lansoprazole is about 0.5 L/kg.

Tissue LocationsLiver
Cellular LocationsMembrane
Metabolite PathwaysLansoprazole Action Pathway

Uses & manufacturing

Uses · 3 items

Antiulcerative

Medication

Use (kg; approx.) in Germany (2009): >750

Formulations/PreparationsTrade names: Agopton, Lansox, Lanzor, Limpidex, Ogast, Prevacid, Takepron, Zoton
General Manufacturing InformationPreparation: A. Nohara, Y. Maki, EP 174726; US 4628098 (both 1986 to Takeda)
Applications · 8 items

UsesLansoprazole is a proton pump inhibitor (PPI) similar to omeprazole that inactivates the hydrogen/potassium-stimulated ATPase pumps in parietal cells, thus inhibiting gastric acid secretion and increasing intragastric pH. It is a potent inhibitor of gastric acidity which is widely used in the therapy of gastroesophageal reflux and peptic ulcer disease. Lansoprazole is a racemic mixture of (R)- and (S)-isomers. Dexlansoprazole is an isomer of lansoprazole that has a similar spectrum of activity and toxicities. Lansoprazole therapy is associated with a low rate of transient and asymptomatic serum aminotransferase elevations and is a reported, but very rare cause of clinically apparent liver injury. Lansoprazole's plasma elimination half-life is not proportional to the duration of the drug's effects (i. e. gastric acid suppression). The plasma elimination half-life is 1. 5 hours or less, and the effects of the drug last for over 24 hours after it has been given for 5 days or more. Lansoprazole is a prescription medicine used to treat: gastroesophageal reflux disease (GERD) erosive esophagitis stomach ulcers duodenal ulcers H. Pylori infections Zollinger-Ellison syndrome

DescriptionLansoprazole is a proton pump inhibitor that inhibits the H+/K+-ATPase. It inhibits K+ and H+ accumulation in gastric microsomes in a concentration-dependent manner (IC50s = 6.3 and 7.0 μM, respectively) and inhibits H+/K+-ATPase activity by approximately 60% when used at a concentration of 10 μM. Lansoprazole inhibits the H+/K+-ATPase in parietal cells, thus inhibiting gastric acid secretion and increasing intragastric pH. It is a substituted benzimidazole that binds covalently to proton pumps, providing complete and prolonged inhibition of acid secretion. Formulations containing lansoprazole have been used as a proton pump inhibitor and in combination with antibiotics in the treatment of H. pylori infections and duodenal ulcer disease.

DescriptionLansoprazole is the second proton pump inhibitor approved as an antiulcer agent for the short term treatment of duodenal ulcer and gastroesophageal reflux disease. Like omeprazole, lansoprazole is reported to be more efficacious than the H2-antagonists in treating peptic ulcer disease.Other potential uses could be in the treatment of Zollinger-Ellison syndrome.

UsesA H+,K+-ATPase inhibitor that displays antisecretory activity

UsesFor the treatment of acid-reflux disorders (GERD), peptic ulcer disease, H. pylori eradication, and prevention of gastroinetestinal bleeds with NSAID use.

UsesTreatment of gastroesophageal reflux disease (GERD), erosive esophagitis, duodenal ulcers, Helicobacter pylori (H. pylori) infections,stomach ulcers, prevention of stomach ulcers in those people taking non-steroidal anti-inflammatory drugs (NSAIDs), such

UsesUsed as a gastric proton pump inhibitor. An antiulcerative

General DescriptionLansoprazole, 2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole(Prevacid), is a white to brownish white, odorless crystallinepowder that is practically insoluble in water.Lansoprazole is a weak base (pyridine N, pKa 3.83.) and aweak acid (benzimidazole N-H, pK 0.62). Like other PPIs,lansoprazole is essentially a prodrug that, in the acidic biophaseof the parietal cell, forms an active metabolite thatirreversibly interacts with the target ATPase of the pump.Lansoprazole must be formulated as encapsulated entericcoatedgranules for oral administration to protect the drugfrom the acidic environment of the stomach.In the fasting state, about 80% of a dose of lansoprazole(vs. 50% of omeprazole) reaches the systemic circulation,where it is 97% bound to plasma proteins. Thedrug is metabolized in the liver (sulfone and hydroxymetabolites) and excreted in bile and urine, with a plasmahalf-life of about 1.5 hours.

Upstream & downstream products

Upstream raw materials

Acetic anhydridetert-ButanolMethanol solution of sodium methoxideVanadium(V) oxideAcetic acid2,3-Lutidine2-MercaptobenzimidazoleThionyl chlorideTriphenylphosphineDiethyl azodicarboxylateTetrabutyl ammonium chlorideSodium hypochlorite

Downstream products

R-(+)-Lansoprazole2-[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methylthio-1H-benzimidazole(S)-Lansoprazole

Additional notes

DefinitionChEBI: Lansoprazole is a member of benzimidazoles, a member of pyridines and a sulfoxide. It has a role as an EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor and an anti-ulcer drug.

/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Lansoprazole at oral doses up to 150 mg/kg/day was found to have no effect on fertility and reproductive performance of male and female rats.

For more Non-Human Toxicity Excerpts (Complete) data for LANSOPRAZOLE (6 total), please visit the HSDB record page.