Dexlansoprazole

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Cat Number

API0232158

CAS Number

138530-94-6

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CAS Number

138530-94-6

EINECS

688-930-9

Storage

Store at room temperature

Synonyms

Kapidex; dexilant; Dexilant Solutab; r-lansoprazole; TAK-390

Molecular Formula

C16H14F3N3O2S

Molecular Weight

369.4

Smiles

CC1=C(C=CN=C1C[S@@](=O)C2=NC3=CC=CC=C3N2)OCC(F)(F)F

Appearance

White to brownish powder

Melting Point

66-68°C

Boiling Point

555.8±60.0°C at 760 mmHg (Predicted)

Relative Density

1.50±0.1 (Predicted)

General Description

Dexlansoprazole is the (R)-enantiomer of lansoprazole, a proton pump inhibitor (PPI) that blocks gastric acid secretion. The molecule contains a chiral sulfur atom; the single enantiomer provides more predictable pharmacokinetics than the racemate. Its chemical structure includes a benzimidazole core linked to a pyridine ring with a trifluoroethoxy substituent.

Mechanism of Action

Dexlansoprazole is a prodrug that is converted to the active sulfenamide in the acidic canaliculi of parietal cells. The sulfenamide forms covalent disulfide bonds with the cysteine residues of the gastric H+/K+ ATPase (proton pump), irreversibly inactivating the enzyme. This blocks the final step of gastric acid secretion, regardless of secretagogue stimulus. The R-enantiomer has a longer plasma half-life and different binding kinetics compared to the S-isomer.

Application

Dexlansoprazole is indicated for the treatment of erosive esophagitis (healing and maintenance), gastroesophageal reflux disease (GERD), and symptomatic non-erosive GERD. Its unique delayed-release formulation uses two types of enteric-coated granules to produce a bimodal plasma concentration profile, providing both early and late acid suppression. The single enantiomer does not offer clinical superiority over racemic lansoprazole but allows a once-daily dosing strategy.

In a phase I open‑label crossover study (healthy adults), dexlansoprazole 30 mg orally disintegrating tablet (ODT) was bioequivalent to the 30 mg delayed‑release capsule based on peak concentration and AUC (90% CIs within 0.80‑1.25). Intragastric pH parameters (mean pH and percentage of time pH>4) were also equivalent. Adverse events (headache most common) occurred in 23% (ODT) and 28% (capsule). Once‑daily ODT provides equivalent exposure and acid suppression to the capsule, with similar tolerability.

Fig. 1 Pharmacodynamic evaluation of dexlansoprazole orally disintegrating tablet and capsule (day 5). (Kukulka M, et al., 2016)

References

Kukulka M, et al. Pharmacokinetics and pharmacodynamics of an orally disintegrating tablet formulation of dexlansoprazole. Ther Adv Gastroenterol. 2016;9(6):759-769.

In a randomized trial (202 patients with H. pylori infection), 7‑day concomitant therapy with dexlansoprazole MR (60 mg once daily) plus clarithromycin, amoxicillin, metronidazole (DACM) achieved eradication rates of 86.1% (ITT) and 90.6% (PP), non‑inferior to lansoprazole‑based concomitant therapy (LACM: 90.1% ITT, 92.6% PP). Adverse event rates were similar (11.5% vs. 10.2%). Dexlansoprazole MR‑based concomitant therapy is an effective first‑line H. pylori regimen.

Fig. 2 Schematic flowchart of study design. (Tai WC, et al., 2019)

References

Tai WC, et al. A comparison between dexlansoprazole modified release-based and lansoprazole-based nonbismuth quadruple (concomitant) therapy for first-line Helicobacter pylori eradication: a prospective randomized trial. Infect Drug Resist. 2019;12:2923-2931.

Does Dexlansoprazole require protection from moisture and light during storage?

Yes, it is highly sensitive to moisture and light. Hydrolysis and photodegradation lead to loss of the benzimidazole ring. Store in tightly sealed, light-resistant containers with desiccant.

What is the recommended storage temperature for Dexlansoprazole?

Store at controlled room temperature (15-25°C). Avoid temperatures above 30°C, which accelerate racemization and formation of sulfone impurities.

Is Dexlansoprazole stable in delayed-release capsule formulations?

Yes, when formulated with enteric coatings and moisture-protective packaging.

How is the impurity lansoprazole sulfone (oxidation product) monitored?

This degradation product is quantified using a stability-indicating chiral HPLC method, ensuring it remains within ICH limits.