Tegoprazan Chemical Properties

Boiling point:

596.5±50.0 °C(Predicted)

Density 

1.371±0.06 g/cm3(Predicted)

storage temp. 

Store at -20°C

solubility 

DMSO: soluble

form 

A solid

pka

9.73±0.30(Predicted)

color 

Off-white to light yellow

InChI

InChI=1S/C20H19F2N3O3/c1-10-23-14-6-11(20(26)25(2)3)7-17(19(14)24-10)28-15-4-5-27-16-9-12(21)8-13(22)18(15)16/h6-9,15H,4-5H2,1-3H3,(H,23,24)/t15-/m0/s1

InChIKey

CLIQCDHNPDMGSL-HNNXBMFYSA-N

SMILES

C1(C)NC2=C(O[C@@H]3C4=C(F)C=C(F)C=C4OCC3)C=C(C(N(C)C)=O)C=C2N=1

Tegoprazan Usage And Synthesis

Drug Approval

Tegoprazan was approved by the Ministry of Food and Drug Safety (MFDS) for marketing in July 2018 for the treatment of gastroesophageal reflux disease and erosive esophagitis. Tegoprazan was originally developed by Pfizer. In 2008, it was licensed to RaQualiaPharma (separated from Pfizer) for joint development. In 2014, Tegoprazan was licensed to CJHealthCare by RaQualiaPharma. Finally, CJHealthCare was successfully developed and marketed in Korea. The drug was first marketed in South Korea.

Medical efficacy

Tegoprazan is medicine for treating gastroesophageal reflux disease and erosive esophagitis. Proton pump hydrogen ion/potassium ion exchange ATPase is the main pharmacological target for the treatment of gastric acid-related diseases. Potassium-competitive acid blocker (P-CAB) can inhibit gastric acid secretion by competitively binding to K+ with H+/K+-ATPase. Research finds that Tegoprazan is such a potassium-competitive acid blocker and is considered to be the most advanced drug for treating gastroesophageal reflux disease, because proton pump inhibitors are the most commonly used drugs for treating gastroesophageal reflux disease.

Description

Tegoprazan: a novel potassium-competitive acid blocker.
Tegoprazan is a novel potassium-competitive acid blocker (P-CAB) showing promising in vitro and in vivo animal pharmacology activities; clinical studies showed favourable tolerability and safety as well as potent and long-lasting efficacy. P-CABs represent a new class of drugs; they exhibit rapid and effective anti-secretory activity by competitively and reversibly binding with H+/K+-ATPase on the parietal cell. Unlike conventional Proton pump inhibitors (PPIs), tegoprazan offers a rapid onset of action and full effect from the first dose as it can immediately inhibit proton pumps.10 Furthermore, since P-CABs do not require activation in the presence of gastric acid, they can be administered regardless of meals. Therefore, P-CABs are expected to have improved NAB control, overcoming the limitations of current PPIs[1].

Uses

Tegoprazan is used for remedying and treating nocturnal acid breakthrough symptoms, such as GERD, ulcer, Barrett''s esophagus, and heartburn.

Pharmacokinetics

A dose-dependent increase was observed in the plasma drug concentrations (observed as average Cmax: 383, 970, and 1,859 ng/mL), whereas the AUClast was 2,469, 5,385, and 11,512 ng?hr/mL for the 50, 100, and 200 mg tegoprazan groups, respectively. The time to reach the maximum plasma concentration was between 1.42 and 1.84 hours for tegoprazan (range of dose group medians)[1].

Side effects

Common side effects reported with Tegoprazan use include gastrointestinal disturbances such as nausea, vomiting, diarrhea, and abdominal pain. These symptoms are generally mild to moderate and often resolve on their own without the need for medical intervention. However, persistent or severe gastrointestinal symptoms should be reported to a healthcare provider.

in vivo

References

[1] Sungpil Han. “Comparison of Pharmacodynamics between Tegoprazan and Dexlansoprazole Regarding Nocturnal Acid Breakthrough: A Randomized Crossover Study.” Gut and Liver 17 1 (2023): 92–99.

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