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

Molecular Formula	C22H23FN4
Molecular Weight	362.4432
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

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

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 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Gastritis 46 Sources: https://business.highbeam.com/436989/article-1G1-151758768/revaprazan-yuhan-registered-south-korea	Primary		Approved 8583	Revanex Approved Use treatment of gastritis Launch Date 2006
Non-erosive reflux disease 2 Sources: https://clinicaltrials.gov/ct2/show/NCT01750437	Primary		Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
364.58 ng/mL CLINICAL TRIAL https://www.sciencedirect.com/science/article/abs/pii/S0149291812004316	200 mg 1 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	REVAPRAZAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
328.23 ng/mL CLINICAL TRIAL https://www.sciencedirect.com/science/article/abs/pii/S0149291812004316	200 mg 1 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	REVAPRAZAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
271.2 μg/L CLINICAL TRIAL https://link.springer.com/article/10.1007%2Fs10337-011-1951-4	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	REVAPRAZAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
450.8 μg/L CLINICAL TRIAL https://link.springer.com/article/10.1007%2Fs10337-011-1951-4	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	REVAPRAZAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
93.7 pg/mL CLINICAL TRIAL https://doi.org/10.1111/apt.16121	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	REVAPRAZAN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
162.2 pg/mL CLINICAL TRIAL https://doi.org/10.1111/apt.16121	200 mg 1 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	REVAPRAZAN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
2573.95 ng × h/mL CLINICAL TRIAL https://www.sciencedirect.com/science/article/abs/pii/S0149291812004316	200 mg 1 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	REVAPRAZAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2370.49 ng × h/mL CLINICAL TRIAL https://www.sciencedirect.com/science/article/abs/pii/S0149291812004316	200 mg 1 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	REVAPRAZAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1851.8 μg × h/L CLINICAL TRIAL https://link.springer.com/article/10.1007%2Fs10337-011-1951-4	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	REVAPRAZAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3239.5 μg × h/L CLINICAL TRIAL https://link.springer.com/article/10.1007%2Fs10337-011-1951-4	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	REVAPRAZAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1315.4 pg × h/mL CLINICAL TRIAL https://doi.org/10.1111/apt.16121	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	REVAPRAZAN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2126.8 pg × h/mL CLINICAL TRIAL https://doi.org/10.1111/apt.16121	200 mg 1 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	REVAPRAZAN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
2 h CLINICAL TRIAL https://www.sciencedirect.com/science/article/abs/pii/S0149291812004316	200 mg 1 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	REVAPRAZAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2 h CLINICAL TRIAL https://www.sciencedirect.com/science/article/abs/pii/S0149291812004316	200 mg 1 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	REVAPRAZAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
10.3 h CLINICAL TRIAL https://link.springer.com/article/10.1007%2Fs10337-011-1951-4	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	REVAPRAZAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
12.6 h CLINICAL TRIAL https://link.springer.com/article/10.1007%2Fs10337-011-1951-4	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	REVAPRAZAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
300 mg 1 times / day multiple, oral Highest studied dose Dose: 300 mg, 1 times / day Route: oral Route: multiple Dose: 300 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14681344/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/14681344/	Sources: https://pubmed.ncbi.nlm.nih.gov/14681344/
200 mg 1 times / day multiple, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/22858177/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/22858177/	Sources: https://pubmed.ncbi.nlm.nih.gov/22858177/

PubMed

Title	Date	PubMed
Potassium-competitive acid blockers: Advanced therapeutic option for acid-related diseases.	2016-12	27514776
Clinical trial: inhibitory effect of revaprazan on gastric acid secretion in healthy male subjects.	2010-10	20880169
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.	2009-02	18981288
Pharmacokinetic and pharmacodynamic evaluation of a novel proton pump inhibitor, YH1885, in healthy volunteers.	2004-01	14681344
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.	2001-01	11124230
Determination of a new proton pump inhibitor, YH1885, in human plasma and urine by high-performance liquid chromatography.	1997-08-29	9323554

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:30:57 GMT 2025` Edited by `admin` on `Mon Mar 31 18:30:57 GMT 2025`
Record UNII	4DQ6T10R64
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SB-641257 HYDROCHLORIDE

Preferred Name

English

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-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