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Details

Stereochemistry ACHIRAL
Molecular Formula C17H16FN3O2S.C4H4O4
Molecular Weight 461.463
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of VONOPRAZAN FUMARATE

SMILES

OC(=O)\C=C\C(O)=O.CNCC1=CN(C(=C1)C2=C(F)C=CC=C2)S(=O)(=O)C3=CC=CN=C3

InChI

InChIKey=ROGSHYHKHPCCJW-WLHGVMLRSA-N
InChI=1S/C17H16FN3O2S.C4H4O4/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;5-3(6)1-2-4(7)8/h2-9,11-12,19H,10H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1+

HIDE SMILES / InChI

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula C17H16FN3O2S
Molecular Weight 345.391
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Primary TargetPharmacologyConditionPotency
0.003 µM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
TAKECAB
Curative
TAKECAB
Curative
TAKECAB
Primary
TAKECAB

PubMed

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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
Record UNII
4QW3X4AMLB
Record Status Validated (UNII)
Record Version