Lansoprazole

Lansoprazole

Systematic (IUPAC) name
(RS)-2-([3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl)-1H-benzo[d]imidazole
Clinical data
Trade names	Prevacid
AHFS/Drugs.com	monograph
MedlinePlus	a695020
Licence data	US FDA:link
Pregnancy cat.	B3(AU) B(US)
Legal status	OTC (US) Rx Only
Routes	Oral, IV
Pharmacokinetic data
Bioavailability	80% or more
Protein binding	97%
Metabolism	Hepatic (CYP3A4- and CYP2C19-mediated)
Half-life	1–1.5 hours
Excretion	Renal and fecal
Identifiers
CAS number	103577-45-3 Y
ATC code	A02BC03
PubChem	CID 3883
DrugBank	APRD00077
ChemSpider	3746 Y
UNII	0K5C5T2QPG Y
KEGG	D00355 Y
ChEBI	CHEBI:6375 Y
ChEMBL	CHEMBL480 Y
Chemical data
Formula	C16H14F3N3O2S
Mol. mass	369.363 g/mol
SMILES	eMolecules & PubChem
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
N(what is this?)  (verify)

Lansoprazole ( /lænˈsoʊprəzoʊl/ lan-soh-prə-zohl; INN) is a proton-pump inhibitor (PPI) which prevents the stomach from producing gastric acid. It is manufactured by a number of companies worldwide under several brand names (some brand names include: Prevacid, Helicid, Zoton, Inhibitol, Monolitum). It was first approved by the U.S. Food and Drug Administration (FDA) in 1995.^[1]

Prevacid patent protection expired on November 10, 2009.^[2][3] As a result, prescription Lansoprazole is now available in the form of a generic drug. As of November 12, 2009 (2009 -11-12)^[update], Lansoprazole is available over-the-counter (OTC) in the U.S. in a 15 mg dose marketed by Novartis as Prevacid 24HR.^[4][5][6]

Main article: Proton-pump inhibitor

Lansoprazole is a proton-pump inhibitor (PPI) in the same pharmacologic class as omeprazole. Lansoprazole has been marketed for many years and is one of several PPIs available.^[7] Lansoprazole is a racemate [1:1-mixture of the enantiomers dexlansoprazole (Kapidex) and levolansoprazole].^[8] Dexlanprantazole is an enantiomerically pure active ingredient of a commercial drug as a result of the 'enantiomeric shift'.

Lansoprazole's plasma elimination half-life is not proportional to the duration of the drug's effects to the person (i.e. gastric acid suppression). The mean plasma elimination half-life is 1.5 hours,^[9] and the effects of the drug last for over 24 hours after it has been used for 1 day or more.^[10] Lansoprazole, 30 mg administered nasogastrically, effectively controls intragastric pH and is an alternative to i.v. pantoprazole in patients who are unable to swallow solid dosage formulations.^[11]

Indications

Lansoprazole is indicated for:

• Treatment of ulcers of the stomach and duodenum, and NSAID-induced ulcers
• Treatment of gastroesophageal reflux disease (GERD) (also known as acid reflux disease)
• Treatment of Zollinger-Ellison Syndrome
• Adjunctive treatment of Helicobacter pylori infection, alongside antibiotics

Drug interactions

• PPIs reduce absorption of antifungals (itraconazole and ketoconazole) ^[12] and possibly increase Digoxin in plasma
• Increases plasma concentrations of Cilostazol (risk of toxicity)
• Absorption of lansoprazole possibly reduced by:
  • sucralfate
  • ampicillin
  • bisacodyl
  • delavirdine
  • fluvoxamine
  • iron salts
  • voriconazole
  • aminophylline and theophylline
  • astemizole

Using Prevacid for Treating H. Pylori Infections Treatment to kill Helicobacter pylori (H. pylori) involves using two other drugs besides Prevacid. This treatment is known as "triple therapy." Triple therapy to kill H. pylori involves taking Prevacid 30 mg twice a day, plus amoxicillin 1,000 mg (twice daily) and clarithromycin 500 mg (twice daily). All three medications are taken for 10 or 14 days.

Side effects

• 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)
• Severe: Gastro-intestinal disturbances (such as nausea 1.3%, abdominal pain 2.1%, diarrhea 3.8%).^[9]

Proton-pump inhibitors may be associated with a greater risk of hip fractures,^[15] Clostridium difficile-associated diarrhea.^[16] Patients are frequently administered the drugs in intensive care as a protective measure against ulcers, but this use is also associated with a 30% increase in occurrence of pneumonia.^[17]

Brand names

Prevacid 30 mg

The drug is sold under several brand names, including:^[1]

• Agopton (Germany)
• Digest (Indonesia)
• Duogast (Syria)
• Gastrolan (Indonesia)
• Lanciprol (Greece)
• Lansazol (Jordan)
• Lansobene (Austria)
• Lansoloc (South Africa)
• Lansoprazol (Denmark)
• Lansoptol (Hungary)
• Lansor (Turkey)
• Lansox (Italy)
• Lanston LFDT (South Korea)
• Lenzo (India)
• Lanzol (India)
• Lanzotec (Jordan)
• Lanzul (Slovenia)
• Lanton (Israel)
• Lanzo (Sweden)
• Lanzor (France, South Africa)
• Lanzostad (Lithuania, Latvia, Estonia)
• Laprazol (Greece)
• Limpidex (Italy)
• Monolitum (Spain)
• Ogast and OgastORO (France)
• Ogastro (Mexico)
• Prevacid (U.S. and Canada)
• Prosogan and Prosogan FD (Indonesia)
• pro-ulco (Spain)
• Refluxon (Hungary)
• SOLOX (New Zealand)
• Takepron (Japan)
• Zolt (Finland)
• Zoton (Italy, Ireland, Australia, UK)
• ZOMEL (Ireland)

Lansoprazole is also available as a generic drug in the US, UK, Canada, Belgium, Finland,^[18] France, Colombia, Italy, Sweden,^[19] and Mexico.^{[citation needed]}

References

1. ^ ^{a b} Mosby's Drug Consult: Lansoprazole
2. ^ Prevacid drug patents
3. ^ Teva to release Prevacid version when patent expires
4. ^ "Novartis launches Prevacid 24HR over-the-counter for full 24-hour frequent heartburn treatment" (PDF) (Press release). November 12, 2009. http://www.prevacid24hr.com/pdfs/News%20media%20release%20-%20Prevacid24HR%20Launch%20-%20November%202009.pdf. Retrieved 2009-11-13. 
5. ^ "Prevacid 24HR Patient Package Insert" (PDF). November 12, 2009. http://www.prevacid24hr.com/pdfs/PackageInsert.pdf. Retrieved 2009-11-13. 
6. ^ "Novartis launches Prevacid 24HR over-the-counter for full 24-hour frequent heartburn treatment" (Press release). November 12, 2009. http://www.novartis.com/newsroom/media-releases/en/2009/1354451.shtml. Retrieved 2009-11-13. 
7. ^ http://www.patient.co.uk/showdoc/30002943/
8. ^ http://www.mainecarepdl.org/index.pl/genpharmfiles/memos-and-mailings/pharmacy-benefit-update-summer-fall-2009.pdf
9. ^ ^{a b} "Prevacid Pharmacology, Pharmacokinetics, Studies, Metabolism". RxList.com. 2007. http://www.rxlist.com/cgi/generic/lansop_cp.htm. Retrieved 2007-04-14. 
10. ^ "Prevacid 24HR Fact Sheet" (PDF). November 12, 2009. http://www.prevacid24hr.com/pdfs/Prevacid24HR_Product_Fact_Sheet.pdf. Retrieved 2009-11-13. 
11. ^ Effects on 24-Hour Intragastric pHFreston M.D., Ph.D., James; Yi-Lin Chiu, Ph.D., Wei-Jian Pan, Ph.D., Nancy Lukasik, B.S.N., and Jörg Täubel, M.D., A.F.P.M. (2001). "Effects on 24-Hour Intragastric pH: A Comparison of Lansoprazole Administered Nasogastrically in Apple Juice and Pantoprazole Administered Intravenously". American Journal of Gastroenterology 96 (7): 2058–2065. doi:10.1111/j.1572-0241.2001.03939.x. ISSN 0002-9270. OCLC 440925790. PMID 11467632. 
12. ^ Antimicrob Agents Chemother. 1991 September; 35(9): 1765–1771. Effects of ranitidine and sucralfate on ketoconazole bioavailability. S C Piscitelli, T F Goss, J H Wilton, D T D'Andrea, H Goldstein, and J J Schentag [1]
13. ^ K C Singhal & S Z Rahman, Lansoprazole Induced Adverse Effects on the Skin, Indian Medical Gazette, July 2001, Vol. CXXXV. N0. 7: 223-225
14. ^ Sterry W, Assaf C (2007). "Erythroderma". In Bolognia JL. Dermatology. St. Louis: Mosby. p. 154. ISBN 1-4160-2999-0. .
15. ^ Yang YX, Lewis JD, Epstein S, Metz DC (December 2006). "Long-term proton pump inhibitor therapy and risk of hip fracture". JAMA 296 (24): 2947–53. doi:10.1001/jama.296.24.2947. PMID 17190895. 
16. ^ "Proton pump inhibitors and Clostridium difficile". Bandolier. 2003. http://www.medicine.ox.ac.uk/bandolier/booth/Pharmacy/PPIcdiff.html. Retrieved 2007-07-13. 
17. ^ Herzig SJ, Howell MD, Ngo LH, Marcantonio ER (May 2009). "Acid-suppressive medication use and the risk for hospital-acquired pneumonia". JAMA 301 (20): 2120–8. doi:10.1001/jama.2009.722. PMID 19470989. 
18. ^ "Vastaavat tuotteet - hintavertailu" (in Finnish). http://www.terveyskirjasto.fi/terveysportti/geneerinen.substituutio?p_ryhma=0000130030. 
19. ^ "FASS.se, accessed 2010-02-13" (in Swedish). http://www.fass.se/LIF/produktfakta/substance_products.jsp?substanceId=IDE4POFNUB4MJVERT1. 

External links

• Prevacid official website Takeda Pharmaceuticals North America
• Prevacid 24HR official website Novartis Consumer Health
• Prevpac official website Takeda Pharmaceuticals North America
• U.S. National Library of Medicine: Drug Information Portal - Lansoprazole