VONOPRAZAN FUMARATE

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 Search

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

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

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.takeda.com/news/2015/20150226_6922.html
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

Primary Target	Pharmacology	Condition	Potency
Potassium-transporting ATPase 31 Target ID: CHEMBL2095173 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20624992	Blocker 537		0.003 µM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Gastric ulcer 67 Sources: https://www.takeda.com/news/2015/20150226_6922.html	Curative	Approved 8429	TAKECAB Approved Use Unknown
Duodenal ulcer 42 Sources: https://www.takeda.com/news/2015/20150226_6922.html	Curative	Approved 8429	TAKECAB Approved Use Unknown
Reflux esophagitis 3 Sources: https://www.takeda.com/news/2015/20150226_6922.html	Curative	Approved 8429	TAKECAB Approved Use Unknown
Helicobacter pylori gastritis 3 Sources: https://www.takeda.com/news/2015/20150226_6922.html	Primary	Approved 8429	TAKECAB Approved Use Unknown

PubMed

Title	Date	PubMed
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	20624992

Patents

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 Created by `admin` on `Sat Dec 16 01:55:11 GMT 2023` Edited by `admin` on `Sat Dec 16 01:55:11 GMT 2023`
Record UNII	4QW3X4AMLB
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

VONOPRAZAN FUMARATE

Common Name

English

TAK-438

Code

English

VOCINTI

Brand Name

English

VONOPRAZAN MONOFUMARATE

Common Name

English

VONOPRAZAN FUMARATE [JAN]

Common Name

English

VOQUEZNA

Brand Name

English

1H-PYRROLE-3-METHANAMINE, 5-(2-FLUOROPHENYL)-N-METHYL-1-(3-PYRIDINYLSULFONYL)-, (2E)-2-BUTENEDIOATE (1:1)

Systematic Name

English

TAKECAB

Brand Name

English

TAK 438

Common Name

English

VONOPRAZAN FUMARATE [MI]

Common Name

English

TAK-438 MONOFUMARATE

Code

English

Vonoprazan fumarate [WHO-DD]

Common Name

English

Code System Code Type Description

RXCUI

2604576