Dexlansoprazole

Dexlansoprazole
Dexlansoprazole
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. B(US)
Legal status ℞-only (US)
Routes Oral
Identifiers
CAS number 138530-94-6 YesY
ATC code None
UNII UYE4T5I70X N
KEGG D08903 YesY
ChEMBL CHEMBL1201863 N
Chemical data
Formula C16H14F3N3O2S 
Mol. mass 369.363 g/mol
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

Dexlansoprazole (INN, trade names Kapidex, Dexilant) is a proton pump inhibitor that is marketed by Takeda Pharmaceuticals. Chemically, it is an enantiomer of lansoprazole. The compound was launched in the US for use in the treatment and maintenance of patients with erosive oesophagitis and non-erosive gastro-oesophageal reflux disease (GERD or GORD).[1] Dexlansoprazole was approved by the U.S. Food and Drug Administration (FDA) on January 30, 2009.[1]

Contents

Pharmacokinetics

After racemic lansoprazole is applied orally, 80% of the circulating drug is dexlansoprazole. Moreover, both enantiomers have a similar effect on the proton pump.[2] Consequently, the main advantage of Kapidex is not the enantiopure substance, but the pharmaceutical formulation.

Kapidex is based on a dual release technology, with the first quick release producing a plasma peak concentration about one hour after application, and the second retarded release producing another peak about four hours later.[1][3] As of November 2009, clinical relevance of this form of release has yet to be shown.

Naming confusion

Since Kapidex was approved in January 2009, there have 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. On March 4, 2010, the FDA has approved a name change for Kapidex to avoid confusion with the two other medications. Effective in late April 2010, Takeda Pharmaceuticals North America began marketing Kapidex under the new name Dexilant.[4]

References

  1. ^ a b c FDA Approves KAPIDEX (dexlansoprazole) delayed release capsules for the Treatment of GERD
  2. ^ Schubert-Zsilavecz, M, Wurglics, M, Neue Arzneimittel 2009.
  3. ^ 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. 
  4. ^ "KAPIDEX (dexlansoprazole) Renamed DEXILANT in U.S. to Avoid Name Confusion". Takeda. 4 March 2010. http://www.takeda.com/press/article_35868.html. 

External links

v · d · eDrugs for acid related disorders: Drugs for peptic ulcer and GERD/GORD (A02B)
H2 antagonists ("-tidine")
Cimetidine • Famotidine • Lafutidine • Loxtidine • Niperotidine • Nizatidine • Ranitidine • Roxatidine
Prostaglandins (E)/analogues ("-prost-")
Proton-pump inhibitors ("-prazole")
Dexlansoprazole • Esomeprazole • Lansoprazole • Omeprazole • Pantoprazole • Rabeprazole • Tenatoprazole
Other
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M: DIG

anat(t, g, p)/phys/devp/enzy

noco/cong/tumr, sysi/epon

proc, drug(A2A/2B/3/4/5/6/7/14/16), blte


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