Dexlansoprazole
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| 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  |
| ATC code | A02BC06 |
| PubChem | CID 9578005 |
| ChemSpider | 7852369 |
| UNII | UYE4T5I70X  |
| KEGG | D08903 |
| ChEMBL | CHEMBL1201863 |
| Chemical data | |
| Formula | C16H14F3N3O2S |
| Mol. mass | 369.363 g/mol |
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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] Of note, lansoprazole (originally sold under the brand name Prevacid) is available as a generic and generally sold at a far lower cost than dexlansoprazole. There is no evidence that dexlansoprazole provides any clinical benefits over lansoprazole, rendering the higher price of dexlansoprazole somewhat questionable.
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Pharmacokinetics [edit]
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 theoretical 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[update], clinical relevance of this form of release has yet to be shown. Though there is no evidence that it is superior, dexlansoprazole is sold at a much higher price than generic lansoprazole.
Adverse effects [edit]
Antacid preparations such as dexlansoprazole by suppressing acid mediated break down of proteins, leads to an elevated risk of developing food and drug allergies. This happens due to undigested proteins then 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.[4]
Naming confusion [edit]
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.[5]
References [edit]
- ^ a b c FDA Approves KAPIDEX (dexlansoprazole) delayed release capsules for the Treatment of GERD
- ^ Schubert-Zsilavecz, M, Wurglics, M, Neue Arzneimittel 2009.
- ^ 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.
- ^ 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.
- ^ "KAPIDEX (dexlansoprazole) Renamed DEXILANT in U.S. to Avoid Name Confusion". Takeda. 4 March 2010.
External links [edit]
- DEXILANT (product's website)
- Takeda Pharmaceuticals (manufacturer's website)
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