Lansoprazole

Lansoprazole, sold under the brand name Prevacid among others, is a medication which reduces stomach acid.^[3] It is a proton pump inhibitor (PPI), used to treat peptic ulcer disease, gastroesophageal reflux disease, and Zollinger–Ellison syndrome.^[4] Its effectiveness is similar to that of other PPIs.^[5] It is taken by mouth.^[3] Onset is over a few hours and effects last up to a couple of days.^[3]

Lansoprazole

Clinical data
Pronunciation	/lænˈsoʊprəzoʊl/ lan-SOH-prə-zohl
Trade names	Prevacid, others
Other names	AG 1749
AHFS/Drugs.com	Monograph
MedlinePlus	a695020
License data	US DailyMed: Lansoprazole
Pregnancy category	AU: B3[1]
Routes of administration	By mouth, intravenous
Drug class	Proton pump inhibitor
ATC code	A02BC03 (WHO)
Legal status
Legal status	AU: S2, S3, & S4 UK: POM (Prescription only) US: OTC / Rx-only[2]
Pharmacokinetic data
Bioavailability	80% or more
Protein binding	97%
Metabolism	Liver (CYP3A4- and CYP2C19-mediated)
Elimination half-life	1.0–1.5 hours
Excretion	Kidney and fecal
Identifiers
IUPAC name 2-{[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methanesulfinyl}-1H-benzimidazole
CAS Number	103577-45-3 Y
PubChem CID	3883
IUPHAR/BPS	7208
DrugBank	DB00448 Y
ChemSpider	3746 Y
UNII	0K5C5T2QPG
KEGG	D00355 Y
ChEBI	CHEBI:6375 Y
ChEMBL	ChEMBL480 Y
CompTox Dashboard (EPA)	DTXSID4023200
ECHA InfoCard	100.173.220
Chemical and physical data
Formula	C16H14F3N3O2S
Molar mass	369.36 g·mol−1
3D model (JSmol)	Interactive image
Chirality	Racemic mixture
Melting point	178 °C (352 °F) (decomposes)
SMILES FC(F)(F)COc1ccnc(c1C)CS(=O)c2[nH]c3ccccc3n2
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) Y Key:MJIHNNLFOKEZEW-UHFFFAOYSA-N Y
(verify)

Common side effects include constipation, abdominal pain, and nausea.^[3][2] Serious side effects may include osteoporosis, low blood magnesium, Clostridioides difficile infection, and pneumonia.^[3][2] Use in pregnancy and breastfeeding is of unclear safety.^[1] It works by blocking H⁺/K⁺-ATPase in the parietal cells of the stomach.^[3]

Lansoprazole was patented in 1984 and came into medical use in 1992.^[6] It is available as a generic medication.^[4] In 2022, it was the 224th most commonly prescribed medication in the United States, with more than 1 million prescriptions.^[7][8]

Medical uses

Lansoprazole is used for treatment of:^[2]

• Ulcers of the stomach and duodenum, and NSAID-induced ulcers
• Helicobacter pylori infection, alongside antibiotics (adjunctive treatment), treatment to kill H. pylori causing ulcers or other problems involves using two other drugs besides lansoprazole known as "triple therapy", and involves taking twice daily for 10 or 14 days lansoprazole, amoxicillin, and clarithromycin
• Gastroesophageal reflux disease
• Zollinger–Ellison syndrome^[9]

There is no good evidence that it works better than other PPIs.^[5]

Side effects

Side effects of PPIs in general^[10] and lansoprazole in particular^[11] may include:^[2]

• Common: diarrhea, abdominal pain^[12]
• Infrequent: dry mouth, insomnia, drowsiness, blurred vision, rash, pruritus
• Rarely and very rarely: taste disturbance, liver dysfunction, peripheral oedema, hypersensitivity reactions (including bronchospasm, urinary, angioedema, anaphylaxis), photosensitivity, fever, sweating, depression, interstitial nephritis, blood disorders (including leukopenia, leukocytosis, pancytopenia, thrombocytopenia), arthralgia, myalgia, skin reactions^[13] including (erythroderma,^[14] Stevens–Johnson syndrome, toxic epidermal necrolysis, bullous eruption)

PPIs may be associated with a greater risk of hip fractures and Clostridioides difficile-associated diarrhea.^[2]: 22

Interactions

Lansoprazole interacts with several other drugs, either due to its nature or as a PPI.^[15]

• PPIs reduce absorption of antifungals (itraconazole and ketoconazole) ^[16] and possibly increase digoxin in plasma
• Increases plasma concentrations of cilostazol (risk of toxicity)

Lansoprazole possibly interacts with, among other drugs:

• sucralfate
• ampicillin
• bisacodyl
• clopidogrel
• delavirdine
• fluvoxamine
• iron salts
• voriconazole
• aminophylline and theophylline
• astemizole

Chemistry

It is a racemic 1:1 mixture of the enantiomers dexlansoprazole and levolansoprazole.^[17] Dexlansoprazole is an enantiomerically pure active ingredient of a commercial drug as a result of the enantiomeric shift. Lansoprazole's plasma elimination half-life (1.5 h) is not proportional to the duration of the drug's effects to the person (i.e., gastric acid suppression).^[18]

History

Main article: Discovery and development of proton pump inhibitors

Lansoprazole was originally synthesized at Takeda and was given the development name AG 1749.^[19] Takeda patented it in 1984 and the drug was launched in 1991.^[20] In the United States, it was approved for medical use in 1995.^[21]

Society and culture

Prevacid 30 mg

Patents

Patent protection of the lansoprazole molecule expired on 10 November 2009,^[22][23] and generic formulations became available under many brand names in many countries.^[24] Some formulations may not be available in generic form.^[25]

Availability

Since 2009, lansoprazole has been available over the counter (OTC) in the U.S. as Prevacid 24HR^[26][27] and as Lansoprazole 24HR.^[28] In Australia, it is marketed by Pfizer as Zoton.^[29]

Research

In vitro experiments have shown that lansoprazole binds to the pathogenic form of tau protein.^[30] As of 2015^[update] laboratory studies were underway on analogs of lansoprazole to explore their use as potential PET imaging agents for diagnosing tauopathies including Alzheimer's disease.^[30]