OMEPRAZOLE

Search structure
Trade Names:
Synonyms:
Status: Approved (1989)
Entry Type: Small molecule
Molecule Category: Parent Prodrug
ATC: A02BC01
UNII: KG60484QX9

Structure
InChI Key SUBDBMMJDZJVOS-UHFFFAOYSA-N
Smile COc1ccc2[nH]c([S+]([O-])Cc3ncc(C)c(OC)c3C)nc2c1
InChI
InChI=1S/C17H19N3O3S/c1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)

Physicochemical Descriptors

Property Name Value
Molecular Formula C17H19N3O3S
Molecular Weight 345.42
AlogP 2.9
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 5.0
Polar Surface Area 77.1
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 24.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Potassium-transporting ATPase inhibitor FDA PubMed PubMed PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C19
- 35000 - - 93-93
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- - - 45000 -
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- 77983 - - -
Enzyme Hydrolase
- 250-22400 - - 100
Enzyme Transferase
- 29600 - 3400 -
Enzyme
- 250-22400 - 3400 93-93
Epigenetic regulator Reader Bromodomain
- 1700 - - -
Epigenetic regulator Reader Plant homeodomain
- 1700 - - -
Epigenetic regulator Writer Protein methyltransferase
- 1700 - - -
Ion channel Other ion channel Phospholemman family
- 31623 - - -
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) GRP-related receptor
14000 - - - -
Other nuclear protein
- 1700 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 11
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 89000-97200 - - -
Transporter Primary active transporter P-type ATPase Hydrogen potassium ATPase
- 250-22400 - - 100
Transporter Primary active transporter P-type ATPase Sodium potassium ATPase
- 31623 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Gastrointestinal Hemorrhage 3 D006471 ClinicalTrials
Hemorrhage 3 D006470 ClinicalTrials
Helicobacter Infections 3 D016481 ClinicalTrials
Esophagitis, Peptic 3 D004942 ClinicalTrials
Exocrine Pancreatic Insufficiency 3 D010188 ClinicalTrials
Stomach Neoplasms 3 D013274 ClinicalTrials
Dyspepsia 3 D004415 ClinicalTrials
Cough 3 D003371 ClinicalTrials
Diabetes Mellitus, Type 1 3 D003922 ClinicalTrials
Cysticercosis 3 D003551 ClinicalTrials
Multiple Sclerosis, Relapsing-Remitting 3 D020529 ClinicalTrials
Spondylitis, Ankylosing 3 D013167 ClinicalTrials
Pain 3 D010146 ClinicalTrials
Osteoarthritis 3 D010003 ClinicalTrials
Barrett Esophagus 3 D001471 ClinicalTrials
Wounds and Injuries 3 D014947 ClinicalTrials
Ulcer 2 D014456 ClinicalTrials
Idiopathic Pulmonary Fibrosis 2 D054990 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Carcinoma, Squamous Cell 2 D002294 ClinicalTrials
Lymphoma, B-Cell, Marginal Zone 2 D018442 ClinicalTrials
Lymphoma 2 D008223 ClinicalTrials
Head and Neck Neoplasms 2 D006258 ClinicalTrials
Zollinger-Ellison Syndrome 2 D015043 ClinicalTrials
Colorectal Neoplasms 2 D015179 ClinicalTrials
Granuloma 2 D006099 ClinicalTrials
Cystic Fibrosis 2 D003550 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 2 D064129 ClinicalTrials
Squamous Intraepithelial Lesions 2 D000081483 ClinicalTrials
Squamous Cell Carcinoma of Head and Neck 2 D000077195 ClinicalTrials
Gastrinoma 2 D015408 ClinicalTrials
Psoriasis 1 D011565 ClinicalTrials
Neoplasms 1 D009369 ClinicalTrials
HIV Infections 1 D015658 ClinicalTrials
Diabetes Mellitus 1 D003920 ClinicalTrials
Melanoma 1 D008545 ClinicalTrials
Crohn Disease 1 D003424 ClinicalTrials
Clostridium Infections 1 D003015 ClinicalTrials
Pulmonary Disease, Chronic Obstructive 1 D029424 ClinicalTrials
Muscular Atrophy, Spinal 1 D009134 ClinicalTrials
Chronic Pain 1 D059350 ClinicalTrials
Glaucoma 1 D005901 ClinicalTrials
Diabetes Mellitus, Type 2 1 D003924 ClinicalTrials
Central Serous Chorioretinopathy 1 D056833 ClinicalTrials
Laryngomalacia 1 D055092 ClinicalTrials
Neoplasms 1 D009369 ClinicalTrials
Dermatitis, Atopic 1 D003876 ClinicalTrials
Mitochondrial Diseases 1 D028361 ClinicalTrials
Erectile Dysfunction 1 D007172 ClinicalTrials
Carcinoma, Medullary 1 D018276 ClinicalTrials
Hepatitis C 1 D006526 ClinicalTrials
Child Development Disorders, Pervasive 1 D002659 ClinicalTrials
HIV Infections 1 D015658 ClinicalTrials
Colitis, Ulcerative 1 D003093 ClinicalTrials
Arthritis, Rheumatoid 1 D001172 ClinicalTrials
Hepatitis C, Chronic 1 D019698 ClinicalTrials
Anemia 1 D000740 ClinicalTrials
Communicable Diseases 1 D003141 ClinicalTrials
Alzheimer Disease 1 D000544 ClinicalTrials
Pancreatic Neoplasms 0 D010190 ClinicalTrials

Related Entries

MCS

Scaffolds

UNKNOWN
Mixture
Mixture
Mixture
Mixture

Side Effects from Label

Side effects Relative Frequency (%) Labels
Gastrointestinal disorders Gastrooesophageal reflux disease 56.0
Gastrointestinal disorders Gastrooesophageal reflux disease 44.0
Gastrointestinal disorders Diarrhoea 28.0
Gastrointestinal disorders Dysgeusia 15.0
Gastrointestinal disorders Diarrhoea 14.0
Gastrointestinal disorders Diarrhoea 13.0
Nervous system disorders Headache 10.9
Gastrointestinal disorders Flatulence 10.3
Gastrointestinal disorders Dysgeusia 10.0
Gastrointestinal disorders Diarrhoea 9.2
Nervous system disorders Headache 8.1
Nervous system disorders Headache 7.0
Nervous system disorders Headache 6.9
Gastrointestinal disorders Dysgeusia 6.6
Gastrointestinal disorders Nausea 6.4
Nervous system disorders Headache
Investigations Alanine aminotransferase increased 6.0
Nervous system disorders Headache 6.0
Gastrointestinal disorders Abdominal pain 5.8
Gastrointestinal disorders Gastrointestinal pain 5.8
Gastrointestinal disorders Abdominal pain 5.2
Gastrointestinal disorders Gastrointestinal pain 5.2
Investigations Aspartate aminotransferase increased 5.0
Gastrointestinal disorders Flatulence 5.0
Nervous system disorders Headache 5.0
Gastrointestinal disorders Nausea 5.0
Gastrointestinal disorders Vomiting
Gastrointestinal disorders Diarrhoea 4.3
Gastrointestinal disorders Duodenal ulcer haemorrhage 4.27
General disorders and administration site conditions Injection site reaction 4.27
Gastrointestinal disorders Duodenal ulcer haemorrhage
Gastrointestinal disorders Flatulence 4.0
Gastrointestinal disorders Nausea 4.0
Gastrointestinal disorders Diarrhoea 3.9
Gastrointestinal disorders Dry mouth 3.9
Gastrointestinal disorders Abdominal pain 3.8
Gastrointestinal disorders Gastrointestinal pain 3.8
Nervous system disorders Headache 3.8
Gastrointestinal disorders Abdominal pain 3.7
Gastrointestinal disorders Diarrhoea 3.7
Gastrointestinal disorders Gastrointestinal pain 3.7
Investigations Body temperature increased 3.47
Gastrointestinal disorders Vomiting 3.2
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Gastrointestinal pain
Gastrointestinal disorders Nausea
Gastrointestinal disorders Dyspepsia 3.0
Gastrointestinal disorders Nausea 3.0
Investigations Body temperature increased
Gastrointestinal disorders Diarrhoea 2.8
Cardiac disorders Dizziness 2.8
Ear and labyrinth disorders Vertigo 2.8
Gastrointestinal disorders Abdominal pain 2.7
Gastrointestinal disorders Flatulence 2.7
Gastrointestinal disorders Gastrointestinal pain 2.7
Nervous system disorders Headache 2.6
Gastrointestinal disorders Constipation 2.5
Gastrointestinal disorders Flatulence 2.3
Gastrointestinal disorders Abdominal pain 2.1
Gastrointestinal disorders Gastrointestinal pain 2.1
Gastrointestinal disorders Abdominal pain 2.0
Gastrointestinal disorders Diarrhoea 2.0
Gastrointestinal disorders Dry mouth 2.0
Gastrointestinal disorders Gastrointestinal pain 2.0
Gastrointestinal disorders Nausea 2.0
Infections and infestations Rhinitis 2.0
Gastrointestinal disorders Tongue discolouration 2.0
Ear and labyrinth disorders Vertigo 2.0
Nervous system disorders Headache 1.9
Gastrointestinal disorders Regurgitation 1.9
Nervous system disorders Somnolence 1.9
Infections and infestations Upper respiratory tract infection 1.9
Gastrointestinal disorders Abdominal pain 1.7
Gastrointestinal disorders Gastrointestinal pain 1.7
General disorders and administration site conditions Injection site reaction 1.7
Gastrointestinal disorders Constipation 1.5
Respiratory, thoracic and mediastinal disorders Cough 1.5
Skin and subcutaneous tissue disorders Dermatitis 1.5
Cardiac disorders Dizziness 1.5
Skin and subcutaneous tissue disorders Rash 1.5
General disorders and administration site conditions Asthenia 1.3
Gastrointestinal disorders Constipation 1.3
Musculoskeletal and connective tissue disorders Back pain 1.1
Respiratory, thoracic and mediastinal disorders Cough 1.1
Skin and subcutaneous tissue disorders Pruritus 1.1
Ear and labyrinth disorders Vertigo 1.1
Respiratory, thoracic and mediastinal disorders Cough 1.07
Cardiac disorders Dizziness 1.07
Gastrointestinal disorders Abdominal pain 1.0
Gastrointestinal disorders Abdominal pain upper 1.0
Investigations Alanine aminotransferase increased 1.0
General disorders and administration site conditions Asthenia 1.0
Gastrointestinal disorders Eructation 1.0
General disorders and administration site conditions Fatigue 1.0
Gastrointestinal disorders Gastrointestinal pain 1.0
Gastrointestinal disorders Glossitis 1.0
Infections and infestations Influenza 1.0
Gastrointestinal disorders Pharyngitis 1.0
Gastrointestinal disorders Regurgitation 1.0
Respiratory, thoracic and mediastinal disorders Tachypnoea 1.0
Cardiac disorders Dizziness
General disorders and administration site conditions Injection site reaction
Musculoskeletal and connective tissue disorders Back pain 0.5
Respiratory, thoracic and mediastinal disorders Cough

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Gastrointestinal disorders
13.58
General disorders and administration site conditions
11.17
Nervous system disorders
10.0
Metabolism and nutrition disorders
6.44
Injury, poisoning and procedural complications
6.24
Musculoskeletal and connective tissue disorders
6.23
Psychiatric disorders
6.15
Skin and subcutaneous tissue disorders
5.67
Respiratory, thoracic and mediastinal disorders
4.81
Vascular disorders
4.67
Cardiac disorders
4.27
Investigations
3.81
Renal and urinary disorders
2.84
Immune system disorders
2.74
Infections and infestations
2.26

Cross References

Resources Reference
CAS NUMBER 73590-58-6
ChEBI 77260
ChEMBL CHEMBL1503
DrugBank DB00338
DrugCentral 1990
EPA CompTox DTXSID6021080
FDA SRS KG60484QX9
Human Metabolome Database HMDB0001913
Guide to Pharmacology 4279
KEGG C07324
PharmGKB PA450704
PubChem 4594
SureChEMBL SCHEMBL1191
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