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Details

Stereochemistry RACEMIC
Molecular Formula C22H23FN4
Molecular Weight 362.444
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of REVAPRAZAN

SMILES

Cc1c(C)nc(Nc2ccc(cc2)F)nc1N3CCc4ccccc4C3C

InChI

InChIKey=LECZXZOBEZITCL-UHFFFAOYSA-N
InChI=1S/C22H23FN4/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)

HIDE SMILES / InChI
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P05023|||Q9UJ20
Gene ID: 476
Gene Symbol: ATP1A1
Target Organism: Homo sapiens (Human)
Conditions
PubMed

PubMed

TitleDatePubMed
Determination of a new proton pump inhibitor, YH1885, in human plasma and urine by high-performance liquid chromatography.
1997 Aug 29
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
Pharmacokinetic and pharmacodynamic evaluation of a novel proton pump inhibitor, YH1885, in healthy volunteers.
2004 Jan
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
Clinical trial: inhibitory effect of revaprazan on gastric acid secretion in healthy male subjects.
2010 Oct
Potassium-competitive acid blockers: Advanced therapeutic option for acid-related diseases.
2016 Dec
Patents

Sample Use Guides

33.3 - 100 mg YH1885L (Revaprazan) for 4 weeks in patients with non-erosive reflux disease(NERD)
Route of Administration: Oral
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
INN   MART.   MI   WHO-DD  
INN  
Official Name English
SB-641257
Code English
REVAPRAZAN [MART.]
Common Name English
REVAPRAZAN [WHO-DD]
Common Name English
REVAPRAZAN [MI]
Common Name English
YH-1885 FREE BASE
Code English
4-(3,4-DIHYDRO-1-METHYL-2(1H)-ISOQUINOLINYL)-N-(4-FLUOROPHENYL)-5,6-DIMETHYL-2-PYRIMIDINAMINE
Systematic Name English
N-(4-FLUOROPHENYL)-5,6-DIMETHYL-4-(1-METHYL-3,4-DIHYDROISOQUINOLIN-2(1H)-YL)PYRIMIDIN-2-AMINE, (+/-)-
Systematic Name English
N-(4-FLUOROPHENYL)-5,6-DIMETHYL-4-((1RS)-1-METHYL-3,4-DIHYDROISOQUINOLIN-2(1H)-YL)PYRIMIDIN-2-AMINE
Systematic Name English
REVAPRAZAN [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29701
Created by admin on Sat Jun 26 09:04:53 UTC 2021 , Edited by admin on Sat Jun 26 09:04:53 UTC 2021
Code System Code Type Description
DRUG CENTRAL
3525
Created by admin on Sat Jun 26 09:04:53 UTC 2021 , Edited by admin on Sat Jun 26 09:04:53 UTC 2021
PRIMARY
FDA UNII
5P184180P5
Created by admin on Sat Jun 26 09:04:53 UTC 2021 , Edited by admin on Sat Jun 26 09:04:53 UTC 2021
PRIMARY
MERCK INDEX
M9561
Created by admin on Sat Jun 26 09:04:53 UTC 2021 , Edited by admin on Sat Jun 26 09:04:53 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL1618279
Created by admin on Sat Jun 26 09:04:53 UTC 2021 , Edited by admin on Sat Jun 26 09:04:53 UTC 2021
PRIMARY
PUBCHEM
204104
Created by admin on Sat Jun 26 09:04:53 UTC 2021 , Edited by admin on Sat Jun 26 09:04:53 UTC 2021
PRIMARY
NCI_THESAURUS
C76489
Created by admin on Sat Jun 26 09:04:53 UTC 2021 , Edited by admin on Sat Jun 26 09:04:53 UTC 2021
PRIMARY
EVMPD
SUB32092
Created by admin on Sat Jun 26 09:04:53 UTC 2021 , Edited by admin on Sat Jun 26 09:04:53 UTC 2021
PRIMARY
INN
8415
Created by admin on Sat Jun 26 09:04:53 UTC 2021 , Edited by admin on Sat Jun 26 09:04:53 UTC 2021
PRIMARY
CAS
199463-33-7
Created by admin on Sat Jun 26 09:04:53 UTC 2021 , Edited by admin on Sat Jun 26 09:04:53 UTC 2021
PRIMARY
WIKIPEDIA
Revaprazan
Created by admin on Sat Jun 26 09:04:53 UTC 2021 , Edited by admin on Sat Jun 26 09:04:53 UTC 2021
PRIMARY