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Details

Stereochemistry ACHIRAL
Molecular Formula C17H16FN3O2S
Molecular Weight 345.393
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VONOPRAZAN

SMILES

CNCc1cc(-c2ccccc2F)n(c1)S(=O)(=O)c3cccnc3

InChI

InChIKey=BFDBKMOZYNOTPK-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C17H16FN3O2S
Molecular Weight 345.393
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25744862| https://www.ncbi.nlm.nih.gov/pubmed/20624992

Vonoprazan (Vonoprazan fumarate or TAK-438) under brand name Takecab, discovered by Takeda, is a new medicine for treating acid-related diseases with a novel mechanism of action called potassium-competitive acid blockers (P-CABs) which competitively inhibits the binding of potassium ions to H+,K+-ATPase (also known as the proton pump) in the final step of gastric acid secretion in gastric parietal cells. The drug is approved in Japan for the treatment of acid-related diseases, including gastric ulcer, duodenal ulcer, reflux esophagitis and Adjunct to Helicobacter pylori eradication in the case of Helicobacter pylori gastritis.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.003 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
TAKECAB

Approved Use

Unknown
Curative
TAKECAB

Approved Use

Unknown
Curative
TAKECAB

Approved Use

Unknown
Primary
TAKECAB

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
1-[5-(2-Fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]-N-methylmethanamine monofumarate (TAK-438), a novel and potent potassium-competitive acid blocker for the treatment of acid-related diseases.
2010 Oct
Patents

Sample Use Guides

Orally at 20 mg once daily for the treatment of gastroduodenal ulcer, at 20 and 10 mg once daily for the treatment and secondary prevention of reflux esophagitis, respectively, at 10 mg once daily for the secondary prevention of low-dose aspirin- or non-steroidal anti-inflammatory drug-induced peptic ulcer, and at 20 mg twice daily in combination with clarithromycin and amoxicillin for the eradication of Helicobacter pylori.
Route of Administration: Oral
TAK-438 (Vonoprazan) inhibited H(+),K(+)-ATPase activity in porcine gastric microsomes with IC(50) values of 0.019 μM at pH 6.5. The inhibitory activity of TAK-438 was unaffected by ambient pH. The inhibition by TAK-438 was reversible and achieved in a K(+)-competitive manner.
Substance Class Chemical
Created
by admin
on Sat Jun 26 15:48:14 UTC 2021
Edited
by admin
on Sat Jun 26 15:48:14 UTC 2021
Record UNII
1R5L3J156G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VONOPRAZAN
INN   WHO-DD  
USAN   INN  
Official Name English
VONOPRAZAN [INN]
Common Name English
1H-PYRROLE-3-METHANAMINE, 5-(2-FLUOROPHENYL)-N-METHYL-1-(3-PYRIDINYLSULFONYL)-
Systematic Name English
VONOPRAZAN [WHO-DD]
Common Name English
1-(5-(2-FLUOROPHENYL)-1-(PYRIDINE-3-SULFONYL)-1H-PYRROL-3-YL)-N-METHYLMETHANAMINE
Systematic Name English
VONOPRAZAN [USAN]
Common Name English
VONOPRAZAN [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29701
Created by admin on Sat Jun 26 15:48:14 UTC 2021 , Edited by admin on Sat Jun 26 15:48:14 UTC 2021
NCI_THESAURUS C29723
Created by admin on Sat Jun 26 15:48:14 UTC 2021 , Edited by admin on Sat Jun 26 15:48:14 UTC 2021
Code System Code Type Description
PUBCHEM
15981397
Created by admin on Sat Jun 26 15:48:14 UTC 2021 , Edited by admin on Sat Jun 26 15:48:14 UTC 2021
PRIMARY
MERCK INDEX
M11860
Created by admin on Sat Jun 26 15:48:14 UTC 2021 , Edited by admin on Sat Jun 26 15:48:14 UTC 2021
PRIMARY
INN
9535
Created by admin on Sat Jun 26 15:48:14 UTC 2021 , Edited by admin on Sat Jun 26 15:48:14 UTC 2021
PRIMARY
DRUG CENTRAL
4993
Created by admin on Sat Jun 26 15:48:14 UTC 2021 , Edited by admin on Sat Jun 26 15:48:14 UTC 2021
PRIMARY
FDA UNII
1R5L3J156G
Created by admin on Sat Jun 26 15:48:14 UTC 2021 , Edited by admin on Sat Jun 26 15:48:14 UTC 2021
PRIMARY
WIKIPEDIA
Vonoprazan
Created by admin on Sat Jun 26 15:48:14 UTC 2021 , Edited by admin on Sat Jun 26 15:48:14 UTC 2021
PRIMARY
NCI_THESAURUS
C152911
Created by admin on Sat Jun 26 15:48:14 UTC 2021 , Edited by admin on Sat Jun 26 15:48:14 UTC 2021
PRIMARY
CAS
881681-00-1
Created by admin on Sat Jun 26 15:48:14 UTC 2021 , Edited by admin on Sat Jun 26 15:48:14 UTC 2021
PRIMARY
EPA CompTox
881681-00-1
Created by admin on Sat Jun 26 15:48:14 UTC 2021 , Edited by admin on Sat Jun 26 15:48:14 UTC 2021
PRIMARY
DRUG BANK
DB11739
Created by admin on Sat Jun 26 15:48:14 UTC 2021 , Edited by admin on Sat Jun 26 15:48:14 UTC 2021
PRIMARY
Related Record Type Details
BINDER->LIGAND
SALT/SOLVATE -> PARENT
CUMULATIVE EXCRETION
URINE
METABOLIC ENZYME -> SUBSTRATE
MAJOR
EXCRETED UNCHANGED
URINE
TARGET -> INHIBITOR
reversible and potassium-competitive manner with a potency of inhibition approximately 350 times higher than the proton pump inhibitor, lansoprazole.
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC