Lansoprazole
 | |
-lansoprazole-from-xtal-3D-bs-17.png) | |
| Clinical data | |
|---|---|
| Pronunciation | /lænˈsoʊprəzoʊl/ lan-SOH-prə-zohl |
| Trade names | Prevacid, others |
| Other names | AG 1749 |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a695020 |
| License data |
|
| Pregnancy category |
|
| Routes of administration | By mouth, intravenous |
| Drug class | Proton pump inhibitor |
| ATC code | |
| Legal status | |
| Legal status | |
| 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 | |
| |
| CAS Number | |
| PubChem CID | |
| IUPHAR/BPS | |
| DrugBank | |
| ChemSpider | |
| UNII | |
| KEGG | |
| ChEBI | |
| ChEMBL | |
| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.173.220 |
| Chemical and physical data | |
| Formula | C16H14F3N3O2S |
| Molar mass | 369.36 g·mol−1 |
| 3D model (JSmol) | |
| Chirality | Racemic mixture |
| Melting point | 178 °C (352 °F) (decomposes) |
| |
| |
| (verify) | |
Lansoprazole, sold under the brand name Prevacid among others, is a medication which reduces stomach acid.[4] It is a proton pump inhibitor (PPI), used to treat peptic ulcer disease, gastroesophageal reflux disease, and Zollinger–Ellison syndrome.[5] Its effectiveness is similar to that of other PPIs.[6] It is taken by mouth.[4] Onset is over a few hours and effects last up to a couple of days.[4]
Common side effects include constipation, abdominal pain, and nausea.[4][3] Serious side effects may include osteoporosis, low blood magnesium, Clostridioides difficile infection, and pneumonia.[4][3] Use in pregnancy and breastfeeding is of unclear safety.[1] It works by blocking H /K -ATPase in the parietal cells of the stomach.[4]
Lansoprazole was patented in 1984 and came into medical use in 1992.[7] It is available as a generic medication.[5] In 2021, it was the 216th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[8][9]
Medical uses
[edit]Lansoprazole is used for treatment of:[3]
- 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[10]
There is no good evidence that it works better than other PPIs.[6]
Side effects
[edit]Side effects of PPIs in general[11] and lansoprazole in particular[12] may include:[3]
- Common: diarrhea, abdominal pain[13]
- 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[14] including (erythroderma,[15] Stevens–Johnson syndrome, toxic epidermal necrolysis, bullous eruption)
PPIs may be associated with a greater risk of hip fractures and Clostridioides difficile-associated diarrhea.[3]: 22
Interactions
[edit]Lansoprazole interacts with several other drugs, either due to its nature or as a PPI.[16]
- PPIs reduce absorption of antifungals (itraconazole and ketoconazole) [17] 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
[edit]It is a racemic 1:1 mixture of the enantiomers dexlansoprazole and levolansoprazole.[18] 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).[19]
History
[edit]Lansoprazole was originally synthesized at Takeda and was given the development name AG 1749.[20] Takeda patented it in 1984 and the drug launched in 1991.[21] In the United States, it was approved for medical use in 1995.[22]
Society and culture
[edit]
Patents
[edit]Patent protection of the lansoprazole molecule expired on 10 November 2009,[23][24] and generic formulations became available under many brand names in many countries.[25] Some formulations may not be available in generic form.[26]
Availability
[edit]Since 2009, lansoprazole has been available over the counter (OTC) in the U.S. as Prevacid 24HR[27][28] and as Lansoprazole 24HR.[29] In Australia, it is marketed by Pfizer as Zoton.[30]
Research
[edit]In vitro experiments have shown that lansoprazole binds to the pathogenic form of tau protein.[31] 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.[31]
References
[edit]- ^ a b "Lansoprazole Use During Pregnancy". Drugs.com. Retrieved 3 March 2019.
- ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
- ^ a b c d e f "Lansoprazole capsule, delayed release pellets". DailyMed. U.S. National Library of Medicine. 11 October 2016. Retrieved 31 December 2019.
- ^ a b c d e f "Lansoprazole Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 3 March 2019.
- ^ a b British national formulary: BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 79–80. ISBN 9780857113382.
- ^ a b "Comparative effectiveness of proton pump inhibitors". Therapeutics Initiative. Dept of Anesthesiology, Pharmacology & Therapeutics, Faculty of Medicine, University of British Columbia. 28 June 2016. Retrieved 14 July 2016.
- ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 445. ISBN 9783527607495.
- ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
- ^ "Lansoprazole - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
- ^ Hirschowitz BI, Mohnen J, Shaw S (August 1996). "Long-term treatment with lansoprazole for patients with Zollinger-Ellison syndrome". Alimentary Pharmacology & Therapeutics. 10 (4): 507–522. doi:10.1046/j.1365-2036.1996.10152000.x. PMID 8853754. S2CID 10668517.
- ^ "1.3.5 Proton pump inhibitors". British National Formulary. Archived from the original on 21 February 2020. Retrieved 1 February 2012.
- ^ "Lansoprazole". British National Formulary. Archived from the original on 21 February 2020. Retrieved 1 February 2012.
- ^ "Prevacid (Lansoprazole) Drug Information: Side Effects and Drug Interactions - Prescribing Information". RxList. Retrieved 9 February 2016.
- ^ Salloum A, Nasr D, Maalouf D (April 2021). "Dermatologic adverse reactions to proton-pump inhibitors: A synthetized review". Journal of Cosmetic Dermatology. 20 (4): 1073–1079. doi:10.1111/jocd.13763. PMID 33031621. S2CID 222236157.
- ^ Sterry W, Assaf C (2007). "Erythroderma". In Bolognia JL (ed.). Dermatology. St. Louis: Mosby. p. 154. ISBN 978-1-4160-2999-1..
- ^ "Lansoprazole interactions". British National Formulary. Archived from the original on 28 August 2021. Retrieved 1 February 2012.
- ^ Piscitelli SC, Goss TF, Wilton JH, D'Andrea DT, Goldstein H, Schentag JJ (September 1991). "Effects of ranitidine and sucralfate on ketoconazole bioavailability". Antimicrobial Agents and Chemotherapy. 35 (9): 1765–1771. doi:10.1128/aac.35.9.1765. PMC 245265. PMID 1952845.
- ^ "Pharmacy Benefit Update". Archived from the original on 14 July 2014. Retrieved 2 July 2014.
- ^ "Prevacid Pharmacology, Pharmacokinetics, Studies, Metabolism". RxList.com. 2007. Archived from the original on 16 August 2000. Retrieved 14 April 2007.
- ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 102. ISBN 9783527607495.
- ^ Chorghade MS (2006). Drug Discovery and Development, Volume 1: Drug Discovery. John Wiley & Sons. p. 201. ISBN 9780471780090.
- ^ "Lansoprazole". Mosby's Drug Consult. Archived from the original on 8 February 2009.
- ^ "Prevacid Drug Profile". Drugpatentwatch.com. Retrieved 30 April 2020.
- ^ Witkowski W (7 November 2008). "Teva to release Prevacid version when patent expires". Market Watch. Dow Jones.
- ^ "International availability of lansoprazole". Drugs.com. Retrieved 3 February 2015.
- ^ "Generic lansoprazole". Drugs.com. Retrieved 20 November 2023.
- ^ "Prevacid 24 HR- lansoprazole capsule, delayed release". DailyMed. U.S. National Library of Medicine. 7 August 2019. Retrieved 31 December 2019.
- ^ "Prevacid 24 HR- lansoprazole capsule, delayed release". DailyMed. U.S. National Library of Medicine. 11 December 2019. Retrieved 31 December 2019.
- ^ "Lansoprazole 24 HR- lansoprazole capsule, delayed release". DailyMed. U.S. National Library of Medicine. 21 December 2017. Retrieved 31 December 2019.
- ^ "Zoton FasTabs". NPS MedicineWise. 2 September 2019. Retrieved 24 April 2022.
- ^ a b Villemagne VL, Fodero-Tavoletti MT, Masters CL, Rowe CC (January 2015). "Tau imaging: early progress and future directions". The Lancet. Neurology. 14 (1): 114–124. doi:10.1016/s1474-4422(14)70252-2. PMID 25496902. S2CID 10502833.
