Dexlansoprazole

Dexlansoprazole

245px
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 category	US: B (No risk in non-human studies)
Legal status	US: ℞-only
Routes of administration	Oral
Pharmacokinetic data
Excretion	50% renal and 47% in the feces
Identifiers
CAS Number	138530-94-6 Y
ATC code	A02BC06 (WHO)
PubChem	CID: 9578005
IUPHAR/BPS	5487
ChemSpider	7852369 N
UNII	UYE4T5I70X N
KEGG	D08903 Y
ChEMBL	CHEMBL1201863 N
Chemical data
Formula	C16H14F3N3O2S
Molecular mass	369.363 g/mol
SMILES O=S(Cc1nccc(OCC(F)(F)F)c1C)c1nc2ccccc2[nH]1
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)/t25-/m1/s1 N Key:MJIHNNLFOKEZEW-RUZDIDTESA-N N
NY (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

Dexlansoprazole is used to heal and maintain healing of erosive esophagitis and to treat heartburn associated with gastroesophageal reflux disease (GERD). 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.

Adverse effects

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

Mechanism of action

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

Chemistry

Dexlansoprazole is the (R)-(+)-enantiomer of lansoprazole, which is a racemic mixture of its (R)-(+) and (S)-(−)-enantiomers. 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.

Pharmacokinetics

Dexlansoprazole ((R)-(+)-lansoprazole) has the same binding affinity to the proton pump as the (S)-enantiomer, but is associated with a three- to five-fold greater area under the plasma drug concentration time curve (AUC) compared with (S)-lansoprazole. 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. As of November 2009, clinical relevance of this form of release has yet to be shown.

History

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

Since Kapidex was approved in 2009, there were been reports of dispensing errors because of confusion with the drugs Casodex (bicalutamide) and Kadian (morphine), 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.