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Compound Detail

CHEMBL1219

RABEPRAZOLE
💊 Approved Drug
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💊 Approved Drug
COCCCOc1ccnc(C[S+]([O-])c2nc3ccccc3[nH]2)c1C

Basic Information

ChEMBL ID CHEMBL1219
Name RABEPRAZOLE
Phase Approved
Structure Type MOL
InChI Key YREYEVIYCVEVJK-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

E-3810 (PPI) E3810 Eraloc Ly-307640 LY307640 Pariprazole Rabeprazol Rabeprazole
17
Targets
24
Activities
2
Assay Types
8
PK Parameters
20
Publications
8
Known Names
13
Indications

Molecular Properties

359.4
MW (Da)
2.99
ALogP
5
HBA
1
HBD
83.1
PSA (Ų)
0.49
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1999
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -prazole
USAN Year 1995

Extended Properties

Molecular Formula C18H21N3O3S
MW 359.45
Aromatic Rings 3
Heavy Atoms 25
NP-Likeness -0.57

Indications

Gastroesophageal Reflux Peptic Ulcer Duodenal Ulcer Gastrointestinal Hemorrhage Helicobacter Infections Dyspepsia Amyotrophic Lateral Sclerosis Cholangiocarcinoma Communicable Diseases Hematologic Neoplasms Lymphoma Neoplasms Neoplasms

ATC Classification

A02BC04
rabeprazole
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: DRUGS FOR ACID RELATED DISORDERS
A02BC54
rabeprazole, combinations
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: DRUGS FOR ACID RELATED DISORDERS

Activity Summary

IC50 20 meas. best 7.74
Ki 4 meas. best 6.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Giardia intestinalis
CHEMBL612652
IC50 7.74 7.74 18.1 1
Entamoeba histolytica
CHEMBL612853
IC50 7.62 7.62 23.7 1
Trichomonas vaginalis
CHEMBL612884
IC50 6.98 6.98 105.7 2
Urease subunit alpha/Urease subunit beta
CHEMBL3885651
IC50 6.54 6.54 290.0 1
Unchecked
CHEMBL612545
IC50 6.52 6.08 300.0 2
Histone-lysine N-methyltransferase 2A/WDR5
CHEMBL3883320
IC50 6.31 6.31 490.0 1
D(3) dopamine receptor
CHEMBL234
Ki 6.1 6.1 790.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 6.1 6.1 793.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
IC50 5.76 5.76 1737.0 1
Adenosine receptor A3
CHEMBL256
Ki 5.74 5.74 1820.0 1
D(3) dopamine receptor
CHEMBL234
IC50 5.63 5.63 2326.0 1
NAD(+) hydrolase SARM1
CHEMBL4523350
IC50 5.5 5.49 3200.0 2
Adenosine receptor A3
CHEMBL256
IC50 5.49 5.49 3219.0 1
Cytosolic endo-beta-N-acetylglucosaminidase
CHEMBL5172
IC50 5.35 5.35 4470.0 1
Fatty acid synthase
CHEMBL4158
Ki 5.23 5.23 5900.0 1
Plasmodium falciparum
CHEMBL364
IC50 5.16 5.16 7000.0 1
NON-PROTEIN TARGET
CHEMBL3879801
IC50 5.1 5.1 7880.0 1
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
IC50 5.07 5.07 8500.0 1
Insulin-degrading enzyme
CHEMBL1293287
IC50 4.96 4.96 11000.0 1
N(G),N(G)-dimethylarginine dimethylaminohydrolase 1
CHEMBL6036
IC50 4.28 4.28 53000.0 1
Fatty acid synthase
CHEMBL4158
IC50 4.28 4.28 52000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 4.0 mL.min-1.kg-1 Homo sapiens
CL 4.0 mL.min-1.kg-1 Homo sapiens
CL 4.0 mL.min-1.kg-1 Homo sapiens
CL 4.0 mL.min-1.kg-1 Homo sapiens
Fu 0.037 - Homo sapiens
Fu 0.037 - Homo sapiens
MRT 0.92 hr Homo sapiens
T1/2 1.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Giardia intestinalis IC50 = 18.1 nM 7.74 Antiprotozoan activity against Giardia intestinalis IMSS:0989:1 trophozoites com... 22047694
Entamoeba histolytica IC50 = 23.7 nM 7.62 Antiprotozoan activity against Entamoeba histolytica HM1-IMSS trophozoites compo... 22047694
Trichomonas vaginalis IC50 = 105.7 nM 6.98 Antiprotozoan activity against Trichomonas vaginalis GT3 trophozoites compound t... 22047694
Trichomonas vaginalis IC50 = 105.7 nM 6.98 Anti-Trichomonas activity against Trichomonas vaginalis JT assessed as reduction... 29175675
Urease subunit alpha/Urease subunit beta IC50 = 290.0 nM 6.54 Inhibition of Helicobacter pylori ATCC 43504 urease assessed as amount of ammoni... 27524377
Unchecked IC50 = 300.0 nM 6.52 Inhibition of Trichomonas vaginalis uridine nucleoside ribohydrolase using 5-flu... 24468412
Histone-lysine N-methyltransferase 2A/WDR5 IC50 = 490.0 nM 6.31 Inhibition of MLL1-WDR5 interaction in human MV4-11 cells assessed as reduction ... 31923859
D(3) dopamine receptor Ki = 790.0 nM 6.1 DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) -
Alpha-2B adrenergic receptor Ki = 793.0 nM 6.1 DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin... -
Alpha-2B adrenergic receptor IC50 = 1737.0 nM 5.76 DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin... -
Adenosine receptor A3 Ki = 1820.0 nM 5.74 DRUGMATRIX: Adenosine A3 radioligand binding (ligand: AB-MECA) -
Unchecked IC50 = 2285.0 nM 5.64 DRUGMATRIX: Phosphodiesterase PDE3 enzyme inhibition (substrate: [3H]cAMP + cAMP... -
D(3) dopamine receptor IC50 = 2326.0 nM 5.63 DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) -
NAD(+) hydrolase SARM1 IC50 = 3200.0 nM 5.5 Inhibition of StrepTag-tagged human SARM1 TIR (561 to 724 residues) expressed in... -
Adenosine receptor A3 IC50 = 3219.0 nM 5.49 DRUGMATRIX: Adenosine A3 radioligand binding (ligand: AB-MECA) -
NAD(+) hydrolase SARM1 IC50 = 3300.0 nM 5.48 Inhibition of StrepTag-tagged human SARM1 TIR (561 to 724 residues) expressed in... -
Cytosolic endo-beta-N-acetylglucosaminidase IC50 = 4470.0 nM 5.35 Inhibition of recombinant human C-MYC/DDK-tagged ENGase expressed in HEK293T cel... 28512024
Fatty acid synthase Ki = 5900.0 nM 5.23 Inhibition of purified recombinant FASN TE activity (unknown origin) using 4-MUH... 25513712
Plasmodium falciparum IC50 = 7000.0 nM 5.16 Antimicrobial activity against Plasmodium falciparum 20185316
NON-PROTEIN TARGET IC50 = 7880.0 nM 5.1 Inhibition of survival of human BxPC3 cells after 10 to 14 days by crystal viole... 25513712

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 270
31923859 10.1016/j.ejmech.2019.112027 MV4-11 14
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
20070106 10.1021/jm901371v Homo sapiens 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
31923859 10.1016/j.ejmech.2019.112027 Histone-lysine N-methyltransferase 2A/WDR5 7
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 4
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 4
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
38665828 10.1039/d3md00455d HT-22 4
19188389 10.1128/aac.00049-09 Helicobacter pylori 4
18426954 10.1124/dmd.108.020479 ADMET 4
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 4
38665828 10.1039/d3md00455d PC-12 4
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 3
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 3
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 3
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 3

Data from ChEMBL 36 via Core Engine