REVAPRAZAN HYDROCHLORIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C22H23FN4.ClH
Molecular Weight	398.904
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CC1N(CCC2=C1C=CC=C2)C3=NC(NC4=CC=C(F)C=C4)=NC(C)=C3C

InChI

InChIKey=MALPZYQJEDBIAK-UHFFFAOYSA-N

InChI=1S/C22H23FN4.ClH/c1-14-15(2)24-22(25-19-10-8-18(23)9-11-19)26-21(14)27-13-12-17-6-4-5-7-20(17)16(27)3;/h4-11,16H,12-13H2,1-3H3,(H,24,25,26);1H

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20880169 | https://www.ncbi.nlm.nih.gov/pubmed/11124230 | https://www.ncbi.nlm.nih.gov/pubmed/14681344 | https://www.ncbi.nlm.nih.gov/pubmed/18981288 | https://www.drugs.com/international/revaprazan.html | https://www.ncbi.nlm.nih.gov/pubmed/27514776

Revaprazan (trade name Revanex) is a drug that reduces gastric acid secretion and is used for the treatment of gastritis and acid-related disease. It acts as an acid pump antagonist (potassium-competitive acid blocker) that reversibly inhibits H+, K+-ATPase by binding to the K+-binding site of the pump, thereby causing fewer side effects, compared with the irreversible proton pump inhibitors. Revaprazan is approved for use in Korea, but is not approved in Europe or the United States.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium/potassium-transporting ATPase subunit alpha-1 16 Target ID: P05023\|\|\|Q9UJ20 Gene ID: 476.0 Gene Symbol: ATP1A1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/18981288	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Gastritis 45 Sources: https://business.highbeam.com/436989/article-1G1-151758768/revaprazan-yuhan-registered-south-korea	Primary		Approved 8429	Revanex Approved Use treatment of gastritis Launch Date 2006
Non-erosive reflux disease 2 Sources: https://clinicaltrials.gov/ct2/show/NCT01750437	Primary		Phase II 1132	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
The transport of a reversible proton pump antagonist, 5, 6-dimethyl-2-(4-Fluorophenylamino)-4-(1-methyl-1,2,3, 4-tetrahydroisoquinoline-2-yl) pyrimidine hydrochloride (YH1885), across caco-2 cell monolayers.	2001 Jan	11124230
Pharmacokinetic and pharmacodynamic evaluation of a novel proton pump inhibitor, YH1885, in healthy volunteers.	2004 Jan	14681344
N-(2-hydroxyethyl)-N,2-dimethyl-8-{[(4R)-5-methyl-3,4-dihydro-2H-chromen-4-yl]amino}imidazo[1,2-a]pyridine-6-carboxamide (PF-03716556), a novel, potent, and selective acid pump antagonist for the treatment of gastroesophageal reflux disease.	2009 Feb	18981288
Potassium-competitive acid blockers: Advanced therapeutic option for acid-related diseases.	2016 Dec	27514776

Patents

Sample Use Guides

In Vivo Use Guide

33.3 - 100 mg YH1885L (Revaprazan) for 4 weeks in patients with non-erosive reflux disease(NERD)

Route of Administration: Oral

In Vitro Use Guide

Human colon carcinoma cell line, Caco-2. The cells were grown to confluency on a permeable polycarbonate membrane insert to permit loading of YH1885 (revaprazan) on either the apical or basolateral side of the cell monolayer. The flux across the monolayer from the apical to basolateral side was 3 to 5 times greater than that from the basolateral to apical side. The uptake of YH1885 into the Caco-2 cell monolayer was saturable and appeared to be mediated by a high-affinity transporter, with an apparent Km of 1.47+/-0.21 uM and a Vmax of 25.14+/-1.16 pmol/cm(2)/40 s.

Name

Type

Language

REVAPRAZAN HYDROCHLORIDE

Official Name

English

N-(4-FLUOROPHENYL)-5,6-DIMETHYL-4-(1-METHYL-3,4-DIHYDROISOQUINOLIN-2(1H)-YL)PYRIMIDIN-2-AMINE MONOHYDROCHLORIDE, (±)-

Systematic Name

English

(±)-N-(4-FLUOROPHENYL)-5,6-DIMETHYL-4-(1-METHYL-3,4-DIHYDROISOQUINOLIN-2(1H)-YL)PYRIMIDIN-2-AMINE MONOHYDROCHLORIDE

Systematic Name

English

2-PYRIMIDINAMINE, 4-(3,4-DIHYDRO-1-METHYL-2(1H)-ISOQUINOLINYL)-N-(4-FLUOROPHENYL)-5,6-DIMETHYL-, HYDROCHLORIDE (1:1)

Systematic Name

English

SB-641257 HYDROCHLORIDE

Code

English

SB-641257A

Code

English

Revaprazan hydrochloride [WHO-DD]

Common Name

English

YH1885

Code

English

REVAPRAZAN HCL

Common Name

English

REVAPRAZAN HYDROCHLORIDE [USAN]

Common Name

English

N-(4-Fluorophenyl)-5,6-dimethyl-4-[(1RS)-1-methyl-3,4-dihydroisoquinolin-2(1H)-yl]pyrimidin-2-amine monohydrochloride

Systematic Name

English

YH-1885

Code

English

REVAPRAZAN HYDROCHLORIDE [MART.]

Common Name

English

REVAPRAZAN HYDROCHLORIDE [MI]

Common Name

English

5,6-DIMETHYL-2-(4-FLUOROPHENYLAMINO)-4-(1-METHYL-1,2,3,4-TETRAHYDROISOQUINOLIN-2-YL)PYRIMIDINE HYDROCHLORIDE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29723