Lansoprazole

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Lansoprazole
Lansoprazole.svg
Lansoprazole 3D.png
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.
Legal status
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 YesY
ATC code A02BC03
PubChem CID 3883
DrugBank DB00448
ChemSpider 3746 YesY
UNII 0K5C5T2QPG YesY
KEGG D00355 YesY
ChEBI CHEBI:6375 YesY
ChEMBL CHEMBL480 YesY
Chemical data
Formula C16H14F3N3O2S 
Mol. mass 369.363 g/mol
 YesY (what is this?)  (verify)

Lansoprazole (/lænˈsprəzl/ lan-SOH-prə-zohl; INN) is a proton-pump inhibitor (PPI) which inhibits the stomach's production of gastric acids. It is manufactured by a number of companies worldwide under several brand names. In the United States it was first approved by the Food and Drug Administration (FDA) in 1995.[1] Prevacid patent protection expired on November 10, 2009.[2][3] Since 2009 Lansoprazole has been available over the counter (OTC) in the U.S. in a 15 mg dose marketed by Novartis as Prevacid 24HR.[4][5][6] In Australia, it is marketed by Pfizer as Zoton.

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 (Dexilant, formerly named Kapidex) and levolansoprazole.[8] Dexlansoprazole 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[edit]

Lansoprazole is indicated for:

Drug interactions[edit]

Lansoprazole interacts with several other drugs, either due to its own nature or as a proton pump inhibitor.[12]

Side effects[edit]

Side effects of proton pump inhibitors in general[14] and lansoprazole in particular[15] may include:

Proton-pump inhibitors may be associated with a greater risk of hip fractures[18] and Clostridium difficile-associated diarrhea.[19] Antacid preparations such as lansoprazole suppress acid-mediated breakdown of proteins, leading to an elevated risk of developing food and drug allergies. This happens due to undigested proteins passing into the gastrointestinal tract where sensitisation occurs. It is unclear whether this risk occurs with only long-term use or with short-term use as well.[20] 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.[21]

Brand names[edit]

Prevacid 30 mg

Lansoprazole is available as a generic drug in the US, Russian Federation, UK, Canada, Belgium,Brazil, Finland,[22] France, Colombia, Italy, Sweden,[23] and Mexico.[citation needed]

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

  • Agopton (Germany)
  • LANSOPAZ (NEPAL)
  • Digest (Indonesia)
  • Duogast (Syria)
  • GERD (Pakistan)
  • Gastrolan (Indonesia)
  • Gastrovex (Malaysia)
  • 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, Ireland)
  • Lanzopran (Australia)
  • Lanzotec (Jordan)
  • Lanzul (Romania/Slovenia)
  • Lanton (Israel)
  • Lantrea (Poland)
  • Lanzap (Romania)
  • Lanzo (Sweden)
  • Lanzopral (Argentina, Chile, Peru, Venezuela [2])
  • Lanzor (France, South Africa)
  • Lanzostad (Lithuania, Latvia, Estonia)
  • Laprazol (Greece)
  • Levant (Romania)
  • Limpidex (Italy)
  • Monolitum (Spain)
  • Ogast and OgastORO (France)
  • Ogastro (Mexico)
  • Prazol (Brazil)
  • Prevacid (US. and Canada)
  • Prevacid 24HR(US)
  • Prosogan and Prosogan FD (Indonesia)
  • pro-ulco (Spain)
  • Refluxon (Hungary)
  • Sabax (Serbia)
  • SOLOX (New Zealand)[24]
  • Takepron (Japan)
  • Zolt (Finland)
  • Zoton (Italy, Ireland, Australia, UK)
  • ZOMEL (Ireland)

Synthesis[edit]

Lansoprazole (AG-1749) synthesis:[25]

References[edit]

  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. Retrieved November 13, 2009. 
  5. ^ a b "Prevacid 24HR Patient Package Insert" (PDF). November 12, 2009. Retrieved November 13, 2009. 
  6. ^ "Novartis launches Prevacid 24HR over-the-counter for full 24-hour frequent heartburn treatment" (Press release). November 12, 2009. Retrieved November 13, 2009. 
  7. ^ http://www.patient.co.uk/showdoc/30002943/
  8. ^ "Pharmacy Benefit Update". Retrieved 2 July 2014. 
  9. ^ a b "Prevacid Pharmacology, Pharmacokinetics, Studies, Metabolism". RxList.com. 2007. Retrieved April 14, 2007. 
  10. ^ "Prevacid 24HR Fact Sheet" (PDF). November 12, 2009. Retrieved November 13, 2009. 
  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. ^ British National Formulary (Free registration required) Lansoprazole interactions
  13. ^ 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]
  14. ^ British National Formulary (Free registration required) 1.3.5 Proton pump inhibitors
  15. ^ British National Formulary (Free registration required) Lansoprazole
  16. ^ K C Singhal & S Z Rahman, Lansoprazole Induced Adverse Effects on the Skin, Indian Medical Gazette, July 2001, Vol. CXXXV. N0. 7: 223-225
  17. ^ Sterry W, Assaf C (2007). "Erythroderma". In Bolognia JL. Dermatology. St. Louis: Mosby. p. 154. ISBN 1-4160-2999-0. .
  18. ^ 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. 
  19. ^ "Proton pump inhibitors and Clostridium difficile". Bandolier. 2003. Retrieved July 13, 2007. 
  20. ^ Pali-Schöll I, Jensen-Jarolim E (April 2011). "Anti-acid medication as a risk factor for food allergy". Allergy 66 (4): 469–77. doi:10.1111/j.1398-9995.2010.02511.x. PMID 21121928. 
  21. ^ 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. 
  22. ^ "Vastaavat tuotteet - hintavertailu" (in Finnish). 
  23. ^ "FASS.se, accessed 2010-02-13" (in Swedish). 
  24. ^ "Lansoprazole -- Pharmaceutical Schedule". Pharmaceutical Management Agency. Retrieved 19 June 2014. 
  25. ^ Kubo, K.; Oda, K.; Kaneko, T.; Satoh, H.; Nohara, A. (1990). "Synthesis of 2-(((4-fluoroalkoxy-2-pyridyl)methyl)sulfinyl)-1H-benzimidazoles as antiulcer agents". Chemical & Pharmaceutical Bulletin 38 (10): 2853. doi:10.1248/cpb.38.2853.  edit

External links[edit]