Dexlansoprazole

Dexlansoprazole

Clinical data
Trade names	Kapidex, Dexilant, others
AHFS/Drugs.com	Monograph
MedlinePlus	a695020
License data	US DailyMed: Dexlansoprazole
Routes of administration	By mouth
Drug class	Proton-pump inhibitor
ATC code	A02BC06 (WHO)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Excretion	50% renal and 47% in the feces
Identifiers
IUPAC name (R)-(+)-2-([3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl)-1H-benzo[d]imidazole
CAS Number	138530-94-6 Y
PubChem CID	9578005
IUPHAR/BPS	5487
ChemSpider	7852369 N
UNII	UYE4T5I70X
KEGG	D08903 Y
ChEMBL	ChEMBL1201863 N
E number	{{#property:P628}}
CompTox Dashboard (EPA)	{{#property:P3117}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C16H14F3N3O2S
Molar mass	369.36 g·mol−1
3D model (JSmol)	Interactive image
SMILES n1c2ccccc2[nH]c1[S@](=O)Cc3nccc(c3C)OCC(F)(F)F
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, is a medication which reduces stomach acid. It is used to treat gastroesophageal reflux disease. Effectiveness is similar to other proton pump inhibitors (PPIs). It is taken by mouth.

Common side effects include diarrhea, abdominal pain, and nausea. Serious side effects may include osteoporosis, low blood magnesium, Clostridioides difficile infection, anaphylaxis, and pneumonia. Use in pregnancy and breastfeeding is of unclear safety. It works by blocking H⁺/K⁺-ATPase in the parietal cells of the stomach.

Dexlansoprazole was approved for medical use in the United States in 2009. In Canada in 2016, it was the most expensive Proton-pump inhibitor (PPI) available. In 2022, it was the 186th most commonly prescribed medication in the United States, with more than 2 million prescriptions.

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. There is no good evidence that it works better than other PPIs.

Adverse effects

The most significant adverse reactions (≥2%) reported in clinical trials were diarrhea, abdominal pain, bloating, 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 delayed release producing another peak about four hours later.

History

Dexlansoprazole was approved in the United States in 2009, in Canada in 2010, and in Mexico in 2011.

Society and culture

Since Kapidex was approved in 2009, there have 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.