Dexlansoprazole

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Dexlansoprazole
Dexlansoprazole structure.svg
Systematic (IUPAC) name
(R)-(+)2-([3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl)-1H-benzo[d]imidazole
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a695020
Licence data US FDA:link
Pregnancy cat.
Legal status
Routes Oral
Pharmacokinetic data
Excretion 50% renal and 47% in the feces[1]
Identifiers
CAS number 138530-94-6 YesY
ATC code A02BC06
PubChem CID 9578005
ChemSpider 7852369 N
UNII UYE4T5I70X N
KEGG D08903 YesY
ChEMBL CHEMBL1201863 N
Chemical data
Formula C16H14F3N3O2S 
Mol. mass 369.363 g/mol
 N (what is this?)  (verify)

Dexlansoprazole (INN, trade names Kapidex, Dexilant) is a proton pump inhibitor that is marketed by Takeda Pharmaceuticals for the treatment of erosive esophagitis and gastro-oesophageal reflux disease.

Medical use[edit]

Dexlansoprazole is used to heal and maintain healing of erosive esophagitis and to treat heartburn associated with gastroesophageal reflux disease (GERD).[1] It lasts longer than lansoprazole, to which it is chemically related, and needs to be taken less often, making it possible to better control gastric acid.[2]

Adverse effects[edit]

The most significant adverse reactions (≥2%) reported in clinical trials were diarrhea, abdominal pain, nausea, upper respiratory tract infection, vomiting, and flatulence.[1]

Mechanism of action[edit]

Like lansoprazole, dexlansoprazole permanently binds to the proton pump and blocks it, preventing the formation of gastric acid.[2]

Chemistry[edit]

Dexlansoprazole is the R-enantiomer of lansoprazole, which is a racemic mixture of its R- and S-enantiomers.[2] The Takeda drug has a dual release pharmaceutical formulation, with two types of granules of dexlansoprazole, each with a coating that dissolves at a different pH level.[2]

Pharmacokinetics[edit]

Dexlansoprazole has the same binding affinity to the proton pump as the S-enantiomer, but is associated witha three- to five-fold greater area under the plasma drug concentration time curve (AUC) compared with S -lansoprazole.[2] With its dual release pharmaceutical formulation, the first quick release produces a plasma peak concentration about one hour after application, with a second retarded release producing another peak about four hours later.[3][4] As of November 2009, clinical relevance of this form of release has yet to be shown.

History[edit]

Dexlansoprazole was approved by the U.S. Food and Drug Administration (FDA) in 2009, and was approved in in Canada in 2010 and in Mexico in 2011.[2]

Since Kapidex was approved in 2009, there were been reports of dispensing errors because of confusion with the drugs Casodex (bicalutamide) and Kadian (morphine sulfate), which have very different uses from Kapidex and from each other. In 2010, the FDA approved a name change for Kapidex to avoid confusion with the two other medications and Takeda began marketing it under the new name Dexilant.[5]

References[edit]

  1. ^ a b c Product Information: DEXILANT(R) delayed release oral capsules, dexlansoprazole delayed release oral capsules. Takeda Pharmaceuticals America, Inc., Deerfield, IL, 2010. Revised: September 2012
  2. ^ a b c d e f Behm BW, Peura DA. Dexlansoprazole MR for the management of gastroesophageal reflux disease. Expert Rev Gastroenterol Hepatol. 2011 Aug;5(4):439-45. PMID 21780890
  3. ^ FDA Approves KAPIDEX (dexlansoprazole) delayed release capsules for the Treatment of GERD
  4. ^ Metz, DC; Vakily, M; Dixit, T; Mulford, D (1 May 2009). "Review article: dual delayed release formulation of dexlansoprazole MR, a novel approach to overcome the limitations of conventional single release proton pump inhibitor therapy". Aliment Pharmacol Ther 29 (9): 928–37. doi:10.1111/j.1365-2036.2009.03984.x. PMID 19298580. 
  5. ^ "KAPIDEX (dexlansoprazole) Renamed DEXILANT in U.S. to Avoid Name Confusion". Takeda. 4 March 2010.