Vonoprazan

Chemical compound

US DailyMed: Vonoprazan

Routes of
administrationBy mouthDrug classPotassium-competitive acid blockerATC code

A02BC08 (WHO)

US: ℞-only^[1]
In general: ℞ (Prescription only)

Pharmacokinetic dataBioavailabilityUnknownProtein binding80%MetabolismLiver, by cytochrome P450 (3A4, 2B6, 2C19, 2D6)Elimination half-life7.7 hDuration of action> 24 hExcretionKidneyIdentifiersCAS Number

881681-00-1
as fumarate: 1260141-27-2

PubChem CID

15981397
as fumarate: 45375887

DrugBank

DB11739

ChemSpider

13112797

UNII

1R5L3J156G
as fumarate: 4QW3X4AMLB

KEGG

D11784
as fumarate: D10466

ChEBI

CHEBI:136048

ChEMBL

ChEMBL2079130
as fumarate: ChEMBL2064032

PDB ligand

HKT (PDBe, RCSB PDB)

CompTox Dashboard (EPA)

DTXSID20236869

Chemical and physical dataFormulaC₁₇H₁₆FN₃O₂SMolar mass345.39 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

Fc1ccccc1-c2cc(CNC)cn2S(=O)(=O)c3cccnc3

InChI

InChI=InChI=1S/C17H16FN3O2S/c1-19-10-13-9-17(15-6-2-3-7-16(15)18)21(12-13)24(22,23)14-5-4-8-20-11-14/h2-9,11-12,19H,10H2,1H3
Key:BFDBKMOZYNOTPK-UHFFFAOYSA-N

Vonoprazan, sold under the brand name Voquezna among others, is a first-in-class potassium-competitive acid blocker medication.^[2] Vonoprazan is used in form of the fumarate for the treatment of gastroduodenal ulcer (including some drug-induced peptic ulcers) and reflux esophagitis, and can be combined with antibiotics for the eradication of Helicobacter pylori.^[2] It is a potassium-competitive acid blocker.^[1]

It was approved in Japan in February 2015,^[3]^[4] and in Russia in April 2021.^[5] Vonoprazan was approved for medical use in the United States in November 2023.^[1]^[6] Co-packaged combinations of vonoprazan with amoxicillin and vonoprazan with amoxicillin and clarithromycin are available.^[7]^[8]

Medical uses

Vonoprazan is indicated for healing of all grades of erosive esophagitis and relief of heartburn associated with erosive esophagitis in adults; to maintain healing of all grades of erosive esophagitis and relief of heartburn associated with erosive esophagitis in adults; in combination with amoxicillin and clarithromycin for the treatment of Helicobacter pylori (H. pylori) infection in adults; in combination with amoxicillin for the treatment of H. pylori infection in adults.^[1]^[7]^[9]

Society and culture

Names

Vonoprazan is the international nonproprietary name (INN).^[10]

References

^ ^a ^b ^c ^d "Voquezna- vonoprazan fumarate tablet". DailyMed. 8 November 2023. Retrieved 20 November 2023.
^ ^a ^b Echizen H (April 2016). "The First-in-Class Potassium-Competitive Acid Blocker, Vonoprazan Fumarate: Pharmacokinetic and Pharmacodynamic Considerations". Clinical Pharmacokinetics. 55 (4): 409–418. doi:10.1007/s40262-015-0326-7. PMID 26369775. S2CID 5984975.
^ Garnock-Jones KP (2015). "Vonoprazan: first global approval". Drugs. 75 (4): 439–43. doi:10.1007/s40265-015-0368-z. PMID 25744862. S2CID 43293048.
^ "Takecab Now Available for the Treatment of Acid-related Diseases in Japan". Takeda Pharmaceuticals (Press release). 26 February 2015. Archived from the original on 26 October 2023. Retrieved 20 November 2023.
^ "Russian State Register of Medicines. Vocinti (vonoprazan) Film-Coated Tablets. Full Prescribing Information". grls.rosminzdrav.ru (in Russian). Takeda Pharmaceutical Company Limited. Archived from the original on 18 February 2023. Retrieved 18 February 2023.
^ "Phathom Pharmaceuticals Announces Commercial Availability of Voquezna (vonoprazan) Tablets, a Powerful First-In-Class PCAB for the Treatment of Erosive GERD and Relief of Associated Heartburn". GlobeNewswire (Press release). Phathom Pharmaceuticals. 28 November 2023. Retrieved 26 January 2024.
^ ^a ^b "Voquezna Dual Pak- vonoprazan fumarate and amoxicillin kit; Voquezna Triple Pak- vonoprazan fumarate, amoxicillin and clarithromycin kit". DailyMed. 21 June 2022. Archived from the original on 3 July 2022. Retrieved 3 July 2022.
^ "Phathom Pharmaceuticals Announces FDA Approval of Voquezna Triple Pak (vonoprazan, amoxicillin, clarithromycin) and Voquezna Dual Pak (vonoprazan, amoxicillin) for the Treatment of H. pylori Infection in Adults" (Press release). Phathom Pharmaceuticals. 3 May 2022. Archived from the original on 10 May 2022. Retrieved 9 May 2022 – via GlobeNewswire.
^ "Drug Approval Package: Voquezna". U.S. Food and Drug Administration (FDA). 8 June 2022. Retrieved 3 February 2024.
^ World Health Organization (2012). "International nonproprietary names for pharmaceutical substances (INN): recommended INN: list 68". WHO Drug Information. 26 (3). hdl:10665/109813.

External links

Clinical trial number NCT04124926 for "Efficacy and Safety of Vonoprazan Compared to Lansoprazole in Participants With Erosive Esophagitis" at ClinicalTrials.gov
Clinical trial number NCT04167670 for "Efficacy and Safety of Vonoprazan Compared to Lansoprazole in Participants With Helicobacter Pylori Infection" at ClinicalTrials.gov