Compound Detail

CHEMBL1503

OMEPRAZOLE

💊 Approved Drug

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💊 Approved Drug

COc1ccc2[nH]c([S+]([O-])Cc3ncc(C)c(OC)c3C)nc2c1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL1503
Name	OMEPRAZOLE
Phase	Approved
Structure Type	MOL
InChI Key	SUBDBMMJDZJVOS-UHFFFAOYSA-N
Therapeutic	✓ Yes
Active Moiety	CHEMBL1201400

Known Names

Antra H 168/68 H-168/68 Losec Losec mups Mezzopram Mopral NSC-751450 NSC-759192 Omeprazol Omeprazole Omeprazole component of konvomep +6 more

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

345.4

MW (Da)

2.90

ALogP

HBA

HBD

83.1

PSA (Å²)

0.72

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1989
Availability	OTC
Chirality	Racemic

Routes of Administration

Oral

Flags

Natural Product Prodrug

USAN Stem	-prazole
USAN Year	1986

Extended Properties

Molecular Formula	C17H19N3O3S
MW	345.42
Aromatic Rings	3
Heavy Atoms	24
NP-Likeness	-0.69

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Potassium-transporting ATPase inhibitor	INHIBITOR	Potassium-transporting ATPase	✓	✓

Indications

Duodenal Ulcer Esophagitis Gastroesophageal Reflux Heartburn Infections Peptic Ulcer Stomach Ulcer Stomach Ulcer Barrett Esophagus Cough Cysticercosis Diabetes Mellitus, Type 1 Dyspepsia Esophagitis, Peptic Exocrine Pancreatic Insufficiency Gastrointestinal Hemorrhage Helicobacter Infections Hemorrhage Multiple Sclerosis, Relapsing-Remitting Osteoarthritis

ATC Classification

A02BC01

omeprazole

Level 1: ALIMENTARY TRACT AND METABOLISM

Level 2: DRUGS FOR ACID RELATED DISORDERS

Activity Summary

IC50 49 meas. best 7.02

EC50 2 meas. best 4.85

Ki 2 meas. best 5.47

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Giardia intestinalis CHEMBL612652	IC50	7.02	7.02	95.5	2
Trichomonas vaginalis CHEMBL612884	IC50	6.92	6.92	121.6	2
Potassium-transporting ATPase CHEMBL2095173	IC50	6.6	5.95	250.0	7
Entamoeba histolytica CHEMBL612853	IC50	6.31	6.31	492.2	1
Plasmodium berghei CHEMBL612653	IC50	6.17	6.17	680.0	1
Unchecked CHEMBL612545	IC50	6.01	5.144	980.0	5
Histone-lysine N-methyltransferase 2A/WDR5 CHEMBL3883320	IC50	5.77	5.77	1700.0	1
Cytochrome P450 2C19 CHEMBL3622	IC50	5.68	5.1975	2080.0	4
Induced myeloid leukemia cell differentiation protein Mcl-1 CHEMBL4361	IC50	5.5	5.5	3144.8	1
Fatty acid synthase CHEMBL4158	Ki	5.47	5.47	3400.0	1
Potassium-transporting ATPase CHEMBL2095228	IC50	5.42	4.86	3800.0	2
Glutathione S-transferase omega-1 CHEMBL3174	IC50	5.34	5.34	4600.0	1
Plasmodium falciparum CHEMBL364	IC50	4.88	4.5	13230.0	2
Bombesin receptor subtype-3 CHEMBL4080	EC50	4.85	4.85	14000.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	4.83	4.83	14800.0	1
SARS-CoV-2 CHEMBL4303835	EC50	4.77	4.77	17060.0	1
ATP-dependent translocase ABCB1 CHEMBL4302	IC50	4.75	4.2125	17700.0	4
Broad substrate specificity ATP-binding cassette transporter ABCG2 CHEMBL5393	IC50	4.75	4.75	17600.0	1
N(G),N(G)-dimethylarginine dimethylaminohydrolase 1 CHEMBL6036	IC50	4.7	4.7	20000.0	1
Cytosolic endo-beta-N-acetylglucosaminidase CHEMBL5172	IC50	4.6	4.6	25000.0	1
Fatty acid synthase CHEMBL4158	IC50	4.53	4.53	29600.0	1
Sodium/potassium-transporting ATPase CHEMBL2095186	IC50	4.5	4.5	31622.8	1
Cytochrome P450 2C9 CHEMBL3397	Ki	4.35	4.35	45000.0	1
Trypanosoma brucei rhodesiense CHEMBL612348	IC50	4.29	4.29	51820.0	1
Trypanosoma cruzi CHEMBL368	IC50	4.17	4.17	68320.0	1
Bile salt export pump CHEMBL6020	IC50	4.12	4.06	75000.0	2
Cytochrome P450 3A4 CHEMBL340	IC50	4.11	4.11	77983.0	1
Leishmania donovani CHEMBL367	IC50	4.04	4.04	90900.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	511.0	ng.hr.mL-1	Homo sapiens
AUC	1140.0	ng.hr.mL-1	Homo sapiens
AUC	1220.0	ng.hr.mL-1	Homo sapiens
AUC	3352.0	ng.hr.mL-1	Homo sapiens
AUC	2276.0	ng.hr.mL-1	Homo sapiens
AUC	1179.0	ng.hr.mL-1	Homo sapiens
AUC	3882.52	ng.hr.mL-1	Homo sapiens
CL	8.4	mL.min-1.kg-1	Homo sapiens
CL	8.3	mL.min-1.kg-1	Homo sapiens
CL	8.4	mL.min-1.kg-1	Homo sapiens
CL	8.4	mL.min-1.kg-1	Homo sapiens
CL	0.035	mL.min-1.g-1	Homo sapiens
CL	0.032	mL.min-1.g-1	Homo sapiens
CL	0.0077	mL.min-1.g-1	Homo sapiens
CL	0.0066	mL.min-1.g-1	Homo sapiens
CL	0.0082	mL.min-1.g-1	Homo sapiens
CL	0.0071	mL.min-1.g-1	Homo sapiens
CL	0.18	uL/min	Homo sapiens
CL	0.4	uL/min	Homo sapiens
CL	0.94	uL/min	Homo sapiens
CL	1.11	uL/min	Homo sapiens
CL	0.53	uL/min	Homo sapiens
CL	0.24	uL/min	Homo sapiens
CL	0.79	uL/min	Homo sapiens
CL	0.66	uL/min	Homo sapiens
CL	1.3	uL/min	Homo sapiens
CL	0.41	uL/min	Homo sapiens
CL	1.21	uL/min	Homo sapiens
CL	1.91	uL/min	Homo sapiens
CL	1.54	uL/min	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Giardia intestinalis	IC50	=	95.5	nM	7.02	Antiprotozoan activity against Giardia intestinalis IMSS:0989:1 trophozoites com...	22047694
Giardia intestinalis	IC50	=	95.5	nM	7.02	Giardicidal activity against Giardia intestinalis incubated for 48 hrs by hemocy...	33360795
Trichomonas vaginalis	IC50	=	121.6	nM	6.92	Antiprotozoan activity against Trichomonas vaginalis GT3 trophozoites compound t...	22047694
Trichomonas vaginalis	IC50	=	121.6	nM	6.92	Anti-Trichomonas activity against Trichomonas vaginalis JT assessed as reduction...	29175675
Potassium-transporting ATPase	IC50	=	250.0	nM	6.6	Antisecretory activity evaluated by the inhibition of 14C -AP uptake in isolated...	2842503
Potassium-transporting ATPase	IC50	=	280.0	nM	6.55	Antisecretory activity evaluated by the inhibition of 14C -AP uptake in isolated...	2842503
Potassium-transporting ATPase	IC50	=	370.0	nM	6.43	Inhibition of [14C]aminopyrine (AP) accumulation stimulated by dibutyryl cyclic ...	9022797
Entamoeba histolytica	IC50	=	492.2	nM	6.31	Antiprotozoan activity against Entamoeba histolytica HM1-IMSS trophozoites compo...	22047694
Potassium-transporting ATPase	IC50	=	501.19	nM	6.3	In vitro evaluation for the inhibition of H+/K+ ATPase at pH < 3 in the gastric ...	1313110
Plasmodium berghei	IC50	=	680.0	nM	6.17	HARVARD: Inhibition of liver stage Plasmodium berghei infection in HepG2 cells	22586124
Unchecked	IC50	=	980.0	nM	6.01	Inhibition of hydrogen potassium ATPase in goat stomach mucosal membrane assesse...	28818769
Histone-lysine N-methyltransferase 2A/WDR5	IC50	=	1700.0	nM	5.77	Inhibition of MLL1-WDR5 interaction in human MV4-11 cells assessed as reduction ...	31923859
Potassium-transporting ATPase	IC50	=	2000.0	nM	5.7	In vitro inhibitory activity against H+/K+ ATPase prepared from canine fundic mu...	2836591
Cytochrome P450 2C19	IC50	=	2080.0	nM	5.68	Inhibition of CYP2C19 in human liver microsomes using S-mephenytoin as substrate...	35609303
Unchecked	IC50	=	2300.0	nM	5.64	Inhibition of Trichomonas vaginalis uridine nucleoside ribohydrolase using 5-flu...	24468412
Cytochrome P450 2C19	IC50	=	2550.0	nM	5.59	Inhibition of CYP2C19 in human liver microsomes using S-mephenytoin as substrate...	34672559
Induced myeloid leukemia cell differentiation protein Mcl-1	IC50	=	3144.81	nM	5.5	PUBCHEM_BIOASSAY: Dose Response Confirmation for Mcl-1/Noxa Interaction Inhibito...	-
Fatty acid synthase	Ki	=	3400.0	nM	5.47	Inhibition of purified recombinant FASN TE activity (unknown origin) using 4-MUH...	25513712
Potassium-transporting ATPase	IC50	=	3800.0	nM	5.42	Inhibition of H+/K+ ATPase activity in buffered solution (pH 7.4)	9873457
Potassium-transporting ATPase	IC50	=	3800.0	nM	5.42	In vitro inhibition against H+/K+ ATPase from porcine gastric mucosal membrane v...	8558532

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885861	Rattus norvegicus	1441
-	10.6019/CHEMBL3885881	Rattus norvegicus	463
31158845	10.1038/s41586-019-1291-3	ADMET	162
21325430	10.1124/dmd.110.037549	Cytochrome P450 2C19	94
-	10.5281/zenodo.13943903	ADMET	88
19487446	10.1128/aac.00158-09	Helicobacter pylori	54
17101679	10.1128/aac.01306-05	Staphylococcus aureus	35
17045703	10.1016/j.ejmech.2006.08.016	Unchecked	23
12643921	10.1016/s0960-894x(03)00052-0	Rattus norvegicus	22
22010218	10.1124/dmd.111.042200	Liver microsome	20
16472241	10.2174/1570163043334794	Hepatotoxicity	18
19307359	10.1128/aac.01483-08	Salmonella typhimurium	17
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
8558532	10.1021/jm950610n	Potassium-transporting ATPase	9
25740159	10.1016/j.bmcl.2015.02.013	No relevant target	9
-	10.1007/s00044-012-0358-6	Rattus norvegicus	9
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
20070106	10.1021/jm901371v	Homo sapiens	8
8523404	10.1021/jm00025a008	Unchecked	6

Data from ChEMBL 36 via Core Engine