Chemical Component Summary

Name1-[5-(2-fluorophenyl)-1-pyridin-3-ylsulfonyl-pyrrol-3-yl]-~{N}-methyl-methanamine
SynonymsVonoprazan
Identifiers1-[5-(2-fluorophenyl)-1-pyridin-3-ylsulfonyl-pyrrol-3-yl]-~{N}-methyl-methanamine
FormulaC17 H16 F N3 O2 S
Molecular Weight345.391
TypeNON-POLYMER
Isomeric SMILESCNCc1cc(n(c1)S(=O)(=O)c2cccnc2)c3ccccc3F
InChIInChI=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
InChIKeyBFDBKMOZYNOTPK-UHFFFAOYSA-N

Chemical Details

Formal Charge0
Atom Count40
Chiral Atom Count0
Bond Count42
Aromatic Bond Count17

Drug Info: DrugBank

DrugBank IDDB11739 
NameVonoprazan
Groups
  • approved
  • investigational
DescriptionVonoprazan is a potassium-competitive acid blocker (PCAB) that inhibits H<sup>+</sup>, K<sup>+</sup>-ATPase-mediated gastric acid secretion. PCABs represent an alternative to proton-pump inhibitors for the treatment of acid-related disorders. Unlike proton-pump inhibitors, PCABs are not affected by CYP2C19 genetic polymorphisms and do not require acid-resistant formulations.[A253702] Furthermore, vonoprazan is 350-times more potent than the proton-pump inhibitor [lansoprazole], thanks to its ability to accumulate in the gastric corpus mucosa, specifically in the parietal cells.[A253707] In February 2015, vonoprazan was first marketed in Japan for the treatment of acid-related disorders and as an adjunct to _Helicobacter pylori_ (_H. pylori_) eradication.[A253702] In May 2022, the FDA approved the use of vonoprazan in a co-packaged product containing amoxicillin and clarithromycin for the treatment of _H. pylori_ infection.[L41695] Studies have shown that the concomitant use of vonoprazan, amoxicillin, and clarithromycin leads to an _H. pylori_ eradication rate of approximately 90%.[A253742]
Synonyms
  • Vonoprazan
  • 1-[5-(2-fluorophenyl)-1-pyridin-3-ylsulfonylpyrrol-3-yl]-N-methylmethanamine
Brand Names
  • Voquezna Triple Pak
  • Voquezna
  • Voquezna Dual Pak
IndicationVonoprazan, in combination with amoxicillin and clarithromycin in a co-packaged product, is indicated for the treatment of _Helicobacter pylori_ (_H. pylori_) infection in adults. Another co-packaged product with only vonoprazan and amoxicillin is also indicated for the treatment of _H. pylori_ infection in adults.[L41695]
Categories
  • Alimentary Tract and Metabolism
  • Amides
  • Cytochrome P-450 CYP2B6 Substrates
  • Cytochrome P-450 CYP2C19 Inhibitors
  • Cytochrome P-450 CYP2C19 inhibitors (strength unknown)
ATC-Code
  • A02BD14
  • A02BD15
  • A02BC08
CAS number881681-00-1

Drug Targets

NameTarget SequencePharmacological ActionActions
Hydrogen potassium ATPaseMGKAENYELYSVELGPGPGGDMAAKMSKKKKAGGGGGKRKEKLENMKKEM...unknowninhibitor
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate
Cytochrome P450 3A5MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...unknownsubstrate
Cytochrome P450 2B6MELSVLLFLALLTGLLLLLVQRHPNTHDRLPPGPRPLPLLGNLLQMDRRG...unknownsubstrate
Cytochrome P450 2C19MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDV...unknownsubstrate,inhibitor
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL2079130
PubChem 15981397
ChEMBL CHEMBL2079130
ChEBI CHEBI:136048