Dexlansoprazole

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Dexlansoprazole
Dexlansoprazole.svg
(R)-lansoprazole-from-xtal-3D-bs-17.png
Clinical data
Trade names Kapidex, Dexilant, others
AHFS/Drugs.com Monograph
MedlinePlus a695020
License data
Routes of
administration 		By mouth
Drug class Proton pump inhibitor
ATC code
Legal status
Legal status
Pharmacokinetic data
Excretion 50% renal and 47% in the feces [2]
Identifiers
  • (R)-(+)-2-([3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl)-1H-benzo[d]imidazole
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEMBL
ECHA InfoCard 100.215.667 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C16H14F3N3O2S
Molar mass 369.36 g·mol−1
3D model (JSmol)
  • n1c2ccccc2[nH]c1[S@](=O)Cc3nccc(c3C)OCC(F)(F)F
  • 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 X mark.svgN
  • Key:MJIHNNLFOKEZEW-RUZDIDTESA-N X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Dexlansoprazole, is a medication which reduces stomach acid. [3] It is used to treat gastroesophageal reflux disease. [3] Effectiveness is similar to other proton pump inhibitors (PPIs). [4] It is taken by mouth. [3]

Contents

Common side effects include diarrhea, abdominal pain, and nausea. [3] Serious side effects may include osteoporosis, low blood magnesium, Clostridium difficile infection, anaphylaxis, and pneumonia. [3] Use in pregnancy and breastfeeding is of unclear safety. [5] It works by blocking H+/K+-ATPase in the parietal cells of the stomach. [3]

Dexlansoprazole was approved for medical use in the United States in 2009. [3] In Canada in 2016, it was the most expensive PPI available. [4] In 2020, it was the 263rd most commonly prescribed medication in the United States, with more than 1 million prescriptions. [6] [7]

Medical use

Dexlansoprazole is used to heal and maintain healing of erosive esophagitis and to treat heartburn associated with gastroesophageal reflux disease (GERD). [2] It lasts longer than lansoprazole, to which it is chemically related, and needs to be taken less often. [8] There is no good evidence that it works better than other PPIs. [4]

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. [2]

Serious side effects are rare but may include allergic reactions, severe stomach pain, or persistent diarrhea.

Mechanism of action

Like lansoprazole, dexlansoprazole permanently binds to the proton pump and blocks it, preventing the formation of gastric acid. [8]

Chemistry

Dexlansoprazole is the (R)-(+)-enantiomer of lansoprazole, which is a racemic mixture of its (R)-(+) and (S)-(−)-enantiomers. [8] 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. [8]

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. [8] 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. [9] [10]

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. [8]

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. [11] It is also available in Bangladesh for the first time as Dexlan by IBN SINA Pharmaceuticals Ltd. in April 2014 and after them DEXILEND by Ziska Pharmaceuticals Ltd., Desopra by Alco Pharma, Delanix by Incepta Pharmaceuticals, Dexogut by Popular Pharmaceuticals Ltd. also introduced it in BD market. In 2020 many other Pharmaceuticals have launched Dexlansoprazole.

Related Research Articles

<span class="mw-page-title-main">Antacid</span> Substance that relieves stomach problems

An antacid is a substance that neutralizes stomach acidity and is used to relieve heartburn, indigestion, or an upset stomach. Some antacids have been used in the treatment of constipation and diarrhea. Marketed antacids contain salts of aluminum, calcium, magnesium, or sodium. Some preparations contain a combination of two salts, such as magnesium carbonate and aluminum hydroxide.

<span class="mw-page-title-main">Proton-pump inhibitor</span> Class of drugs for reducing stomach acid

Proton-pump inhibitors (PPIs) are a class of medications that cause a profound and prolonged reduction of stomach acid production. They do so by irreversibly inhibiting the stomach's H+/K+ ATPase proton pump.

<span class="mw-page-title-main">Gastroesophageal reflux disease</span> Medical condition

Gastroesophageal reflux disease (GERD) or gastro-oesophageal reflux disease (GORD) is a chronic upper gastrointestinal disease in which stomach content persistently and regularly flows up into the esophagus, resulting in symptoms and/or complications. Symptoms include dental corrosion, dysphagia, heartburn, odynophagia, regurgitation, non-cardiac chest pain, extraesophageal symptoms such as chronic cough, hoarseness, reflux-induced laryngitis, or asthma. In the long term, and when not treated, complications such as esophagitis, esophageal stricture, and Barrett's esophagus may arise.

<span class="mw-page-title-main">Omeprazole</span> Medication to treat gastroesophageal reflux disease and other conditions

Omeprazole, sold under the brand names Prilosec and Losec, among others, is a medication used in the treatment of gastroesophageal reflux disease (GERD), peptic ulcer disease, and Zollinger–Ellison syndrome. It is also used to prevent upper gastrointestinal bleeding in people who are at high risk. Omeprazole is a proton-pump inhibitor (PPI) and its effectiveness is similar to that of other PPIs. It can be taken by mouth or by injection into a vein. It is also available in the fixed-dose combination medication omeprazole/sodium bicarbonate as Zegerid and as Konvomep.

<span class="mw-page-title-main">Naproxen</span> Nonsteroidal anti-inflammatory drug (NSAID) used to treat pain

Naproxen, sold under the brand name Aleve among others, is a nonsteroidal anti-inflammatory drug (NSAID) used to treat pain, menstrual cramps, inflammatory diseases such as rheumatoid arthritis, gout and fever. It is taken orally. It is available in immediate and delayed release formulations. Onset of effects is within an hour and lasts for up to twelve hours.

<span class="mw-page-title-main">Pantoprazole</span> Stomach acid suppressing medication

Pantoprazole, sold under the brand name Protonix, among others, is a proton pump inhibitor used for the treatment of stomach ulcers, short-term treatment of erosive esophagitis due to gastroesophageal reflux disease (GERD), maintenance of healing of erosive esophagitis, and pathological hypersecretory conditions including Zollinger–Ellison syndrome. It may also be used along with other medications to eliminate Helicobacter pylori. Effectiveness is similar to other proton pump inhibitors (PPIs). It is available by mouth and by injection into a vein.

<span class="mw-page-title-main">Famotidine</span> Medication that reduces stomach acid

Famotidine, sold under the brand name Pepcid among others, is a histamine H2 receptor antagonist medication that decreases stomach acid production. It is used to treat peptic ulcer disease, gastroesophageal reflux disease, and Zollinger-Ellison syndrome. It is taken by mouth or by injection into a vein. It begins working within an hour.

<span class="mw-page-title-main">Esomeprazole</span> Medication which reduces stomach acid

Esomeprazole, sold under the brand name Nexium [or Neksium] among others, is a medication which reduces stomach acid. It is used to treat gastroesophageal reflux disease, peptic ulcer disease, and Zollinger–Ellison syndrome. Its effectiveness is similar to that of other proton pump inhibitors (PPIs). It is taken by mouth or injection into a vein.

<span class="mw-page-title-main">Rabeprazole</span> Stomach acid suppressing medication

Rabeprazole, sold under the brand name Aciphex, among others, is a medication that decreases stomach acid. It is used to treat peptic ulcer disease, gastroesophageal reflux disease, and excess stomach acid production such as in Zollinger–Ellison syndrome. It may also be used in combination with other medications to treat Helicobacter pylori. Effectiveness is similar to other proton pump inhibitors (PPIs). It is taken by mouth.

<span class="mw-page-title-main">Achlorhydria</span> Medical condition

Achlorhydria and hypochlorhydria refer to states where the production of hydrochloric acid in gastric secretions of the stomach and other digestive organs is absent or low, respectively. It is associated with various other medical problems.

<span class="mw-page-title-main">Nizatidine</span> Chemical compound

Nizatidine is a histamine H2 receptor antagonist that inhibits stomach acid production, and is commonly used in the treatment of peptic ulcer disease and gastroesophageal reflux disease.

<span class="mw-page-title-main">Lansoprazole</span> Stomach acid suppressing medication

Lansoprazole, sold under the brand name Prevacid among others, is a medication which reduces stomach acid. It is a proton pump inhibitor (PPI), used to treat peptic ulcer disease, gastroesophageal reflux disease, and Zollinger–Ellison syndrome. Its effectiveness is similar to that of other PPIs. It is taken by mouth. Onset is over a few hours and effects last up to a couple of days.

<span class="mw-page-title-main">Oxybutynin</span> Medication for overactive bladder

Oxybutynin, sold as under the brand name Ditropan among others, is an anticholinergic drug primarily used to treat overactive bladder. It is widely considered a first-line therapy for overactive bladder due to its well-studied side effect profile, broad applicability, and continued efficacy over long periods of time. It works similar to tolterodine, darifenacin, and solifenacin, although it is usually preferred over these medications. It is sometimes used off-label for treatment of hyperhidrosis, or excessive sweating. It has also been used off-label to treat bed wetting in children, but this use has declined, as it is most likely ineffective in this role. It is taken by mouth or applied to the skin.

Proton pump inhibitors (PPIs) block the gastric hydrogen potassium ATPase (H+/K+ ATPase) and inhibit gastric acid secretion. These drugs have emerged as the treatment of choice for acid-related diseases, including gastroesophageal reflux disease (GERD) and peptic ulcer disease. PPIs also can bind to other types of proton pumps such as those that occur in cancer cells and are finding applications in the reduction of cancer cell acid efflux and reduction of chemotherapy drug resistance.

<span class="mw-page-title-main">Ilaprazole</span> Stomach acid suppressing medication

Ilaprazole is a proton pump inhibitor (PPI) used in the treatment of dyspepsia, peptic ulcer disease (PUD), gastroesophageal reflux disease (GORD/GERD) and duodenal ulcer.

<span class="mw-page-title-main">Cabozantinib</span> Chemical compound

Cabozantinib, sold under the brand names Cometriq and Cabometyx among others, is an anti-cancer medication used to treat medullary thyroid cancer, renal cell carcinoma, and hepatocellular carcinoma. It is a small molecule inhibitor of the tyrosine kinases c-Met and VEGFR2, and also inhibits AXL and RET. It was discovered and developed by Exelixis Inc.

There are several classes of drugs for acid-related disorders, such as dyspepsia, peptic ulcer disease (PUD), gastroesophageal reflux disease (GORD/GERD), or laryngopharyngeal reflux.

Naproxen/esomeprazole, sold under the brand name Vimovo, is a pain reliever medication in the form of a tablet for oral consumption, containing naproxen, a nonsteroidal anti-inflammatory drug (NSAID), and a delayed release formulation of esomeprazole, a stomach acid–reducing proton-pump inhibitor (PPI). It is produced by AstraZeneca. Vimovo is US Food and Drug Administration approved for use against osteoarthritis, rheumatoid arthritis, and ankylosing spondylitis. It is intended to decrease the risk of gastric ulcers from treatment with NSAIDs.

<span class="mw-page-title-main">Azeloprazole</span> Chemical compound

Azeloprazole is a drug under investigation for acid-related medical conditions responsive to suppressing the production of stomach acid. It is considered a member of the proton pump inhibitor class of medications.

<span class="mw-page-title-main">Acid peptic diseases</span> Overview of the acid peptic diseases of the stomach and gastrointestinal tract

Acid peptic diseases, such as peptic ulcers, Zollinger-Ellison syndrome, and gastroesophageal reflux disease, are caused by distinct but overlapping pathogenic mechanisms involving acid effects on mucosal defense. Acid reflux damages the esophageal mucosa and may also cause laryngeal tissue injury, leading to the development of pulmonary symptoms.

References

  1. ↑ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA . Retrieved 22 October 2023.
  2. 1 2 3 Product Information: DEXILANT delayed release oral capsules, dexlansoprazole delayed release oral capsules. Takeda Pharmaceuticals, Inc., Deerfield, IL, 2010. Revised: September 2012
  3. 1 2 3 4 5 6 7 "Dexlansoprazole Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 3 March 2019.
  4. 1 2 3 "[99] Comparative effectiveness of proton pump inhibitors | Therapeutics Initiative". 28 June 2016. Retrieved 14 July 2016.
  5. ↑ "Dexlansoprazole Use During Pregnancy". Drugs.com. Retrieved 3 March 2019.
  6. ↑ "The Top 300 of 2020". ClinCalc. Retrieved 7 October 2022.
  7. ↑ "Dexlansoprazole - Drug Usage Statistics". ClinCalc. Retrieved 7 October 2022.
  8. 1 2 3 4 5 6 Behm BW, Peura DA (August 2011). "Dexlansoprazole MR for the management of gastroesophageal reflux disease". Expert Review of Gastroenterology & Hepatology. 5 (4): 439–45. doi:10.1586/egh.11.37. PMID   21780890. S2CID   39848854.
  9. ↑ FDA Approves KAPIDEX (dexlansoprazole) delayed release capsules for the Treatment of GERD
  10. ↑ Metz DC, Vakily M, Dixit T, Mulford D (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". Alimentary Pharmacology & Therapeutics. 29 (9): 928–37. doi: 10.1111/j.1365-2036.2009.03984.x . PMID   19298580. S2CID   29286087.
  11. ↑ "KAPIDEX (dexlansoprazole) Renamed DEXILANT in U.S. to Avoid Name Confusion". Takeda. 4 March 2010.
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