LANSOPRAZOLE

Search structure
Trade Names:
Synonyms:
Status: Approved (1995)
Entry Type: Small molecule
Molecule Category: Parent
ATC: A02BC03
UNII: 0K5C5T2QPG

Structure
InChI Key MJIHNNLFOKEZEW-UHFFFAOYSA-N
Smile Cc1c(OCC(F)(F)F)ccnc1C[S+]([O-])c1nc2ccccc2[nH]1
InChI
InChI=1S/C16H14F3N3O2S/c1-10-13(20-7-6-14(10)24-9-16(17,18)19)8-25(23)15-21-11-4-2-3-5-12(11)22-15/h2-7H,8-9H2,1H3,(H,21,22)

Physicochemical Descriptors

Property Name Value
Molecular Formula C16H14F3N3O2S
Molecular Weight 369.37
AlogP 3.52
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 5.0
Polar Surface Area 67.87
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 25.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Potassium-transporting ATPase inhibitor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 1 Cytochrome P450 family 1A Cytochrome P450 1A2
- 6460 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C19
- 336.7-13400 - - 86
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C8
- 5750 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- 19200 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2D Cytochrome P450 2D6
- 2900-5314.8 - - -
Enzyme Hydrolase
- 51000-51000 - - 5.66-6.43
Enzyme Isomerase
- 760 - - -
Enzyme Oxidoreductase
- 8200 - - -
Enzyme Phosphatase
- 434 - - -
Enzyme Protease Serine protease Serine protease PA clan Serine protease S1A subfamily
- - - - 5.66-6.43
Enzyme Transferase
- 46700-124000 - 1700-5300 98.98-103.13
Enzyme
- 46700-124000 - 1700-5300 98.98-103.13
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- - - - -46.91-6.18
Epigenetic regulator Reader Bromodomain
- 5900 - - -
Epigenetic regulator Reader Methyl-lysine/arginine binding protein WDR domain
- 5900 - - -
Epigenetic regulator Reader Plant homeodomain
- 5900 - - -
Epigenetic regulator Writer Protein methyltransferase
- 5900 - - -
Ion channel Other ion channel Phospholemman family
- 39810.72 - - -
Other cytosolic protein
- - - 2.5 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 23.3-100.47
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 62800 - - -
Transporter Primary active transporter ATP-binding cassette ABCG subfamily
- 14400 - - -
Transporter Primary active transporter P-type ATPase Hydrogen potassium ATPase
- 398.11 - - -
Transporter Primary active transporter P-type ATPase Sodium potassium ATPase
- 39810.72 - - -
Unclassified protein
- - - - 7.279

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Lymphoma 3 D008223 ClinicalTrials
Diabetes Mellitus, Type 1 3 D003922 ClinicalTrials
Esophagitis, Peptic 3 D004942 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Gout 3 D006073 ClinicalTrials
Gastritis 3 D005756 ClinicalTrials
Idiopathic Pulmonary Fibrosis 3 D054990 ClinicalTrials
Helicobacter Infections 3 D016481 ClinicalTrials
Osteoarthritis 3 D010003 ClinicalTrials
Premature Birth 2 D047928 ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-Cell 2 D015451 ClinicalTrials
Eosinophilic Esophagitis 2 D057765 ClinicalTrials
Pseudomyxoma Peritonei 2 D011553 ClinicalTrials
Rectal Neoplasms 2 D012004 ClinicalTrials
Uterine Cervical Neoplasms 2 D002583 ClinicalTrials
Endometrial Neoplasms 2 D016889 ClinicalTrials
Cystic Fibrosis 1 D003550 ClinicalTrials
Laryngopharyngeal Reflux 1 D057045 ClinicalTrials
Pain 1 D010146 ClinicalTrials
Neoplasms 1 D009369 ClinicalTrials

Related Entries

MCS

Scaffolds

Mixture
Mixture

Side Effects from Label

Side effects Relative Frequency (%) Labels
Nervous system disorders Headache
Nervous system disorders Headache 14.9
Gastrointestinal disorders Pharyngitis 14.5
Nervous system disorders Headache 9.9
Gastrointestinal disorders Pharyngitis 9.9
Gastrointestinal disorders Pharyngitis 9.6
Gastrointestinal disorders Abdominal pain 9.0
Gastrointestinal disorders Diarrhoea 9.0
Gastrointestinal disorders Gastrointestinal pain 9.0
Gastrointestinal disorders Abdominal pain 8.8
Gastrointestinal disorders Gastrointestinal pain 8.8
Gastrointestinal disorders Diarrhoea 8.0
Gastrointestinal disorders Diarrhoea 7.6
Gastrointestinal disorders Abdominal pain 7.0
Gastrointestinal disorders Diarrhoea 7.0
Gastrointestinal disorders Gastrointestinal pain 7.0
Nervous system disorders Headache 7.0
Nervous system disorders Headache 6.45
Infections and infestations Rhinitis 6.4
Gastrointestinal disorders Diarrhoea 6.36
Nervous system disorders Headache 6.0
Gastrointestinal disorders Diarrhoea 5.7
Gastrointestinal disorders Abdominal pain
Skin and subcutaneous tissue disorders Dermatitis
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Gastrointestinal pain
General disorders and administration site conditions Pain
Gastrointestinal disorders Pharyngitis
Skin and subcutaneous tissue disorders Rash
Gastrointestinal disorders Diarrhoea 5.1
Gastrointestinal disorders Abdominal pain 5.07
Gastrointestinal disorders Gastrointestinal pain 5.07
Gastrointestinal disorders Abdominal pain 5.0
Gastrointestinal disorders Constipation 5.0
Gastrointestinal disorders Dysgeusia 5.0
Gastrointestinal disorders Gastrointestinal pain 5.0
Gastrointestinal disorders Diarrhoea 4.8
Gastrointestinal disorders Diarrhoea 4.7
Gastrointestinal disorders Diarrhoea 4.02
Gastrointestinal disorders Abdominal pain 4.0
Gastrointestinal disorders Gastrointestinal pain 4.0
Gastrointestinal disorders Diarrhoea 3.8
Gastrointestinal disorders Diarrhoea 3.6
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Abdominal pain 3.5
Gastrointestinal disorders Gastrointestinal pain
Gastrointestinal disorders Gastrointestinal pain 3.5
Gastrointestinal disorders Diarrhoea 3.3
Gastrointestinal disorders Nausea 3.3
Gastrointestinal disorders Abdominal pain 3.23
Skin and subcutaneous tissue disorders Dermatitis 3.23
Gastrointestinal disorders Diarrhoea 3.23
Gastrointestinal disorders Gastrointestinal pain 3.23
Nervous system disorders Paraesthesia 3.23
Skin and subcutaneous tissue disorders Rash 3.23
Eye disorders Visual impairment 3.23
Gastrointestinal disorders Diarrhoea 3.2
Cardiac disorders Dizziness 3.0
Nervous system disorders Headache 3.0
Gastrointestinal disorders Nausea 3.0
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Nausea 2.9
Infections and infestations Upper respiratory tract infection 2.9
Gastrointestinal disorders Nausea 2.8
Gastrointestinal disorders Abdominal pain 2.6
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Flatulence 2.6
Gastrointestinal disorders Gastrointestinal pain 2.6
Gastrointestinal disorders Nausea
Gastrointestinal disorders Oesophagitis 2.5
Gastrointestinal disorders Diarrhoea
Investigations Laboratory test abnormal 2.3
General disorders and administration site conditions Pain 2.3
Gastrointestinal disorders Vomiting 2.2
Gastrointestinal disorders Abdominal pain 2.1
Gastrointestinal disorders Gastritis 2.1
Gastrointestinal disorders Gastrointestinal pain 2.1
Infections and infestations Upper respiratory tract infection 1.9
Gastrointestinal disorders Nausea 1.8
Gastrointestinal disorders Abdominal pain 1.77
Gastrointestinal disorders Gastrointestinal pain 1.77
Infections and infestations Upper respiratory tract infection 1.7
General disorders and administration site conditions Pain 1.61
Gastrointestinal disorders Flatulence 1.6
Gastrointestinal disorders Vomiting 1.6
Nervous system disorders Headache 1.5
Gastrointestinal disorders Flatulence 1.4
Gastrointestinal disorders Nausea 1.4
Gastrointestinal disorders Vomiting 1.4
Gastrointestinal disorders Flatulence 1.3
Gastrointestinal disorders Nausea
Gastrointestinal disorders Nausea 1.3
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Constipation 1.2
Gastrointestinal disorders Flatulence 1.2
Gastrointestinal disorders Gastrointestinal pain
Gastrointestinal disorders Nausea
Skin and subcutaneous tissue disorders Dermatitis 1.15
Gastrointestinal disorders Pharyngitis 1.15
Skin and subcutaneous tissue disorders Rash 1.15
General disorders and administration site conditions Asthenia 1.1
Cardiac disorders Dizziness 1.1
Nervous system disorders Headache 1.1
Gastrointestinal disorders Vomiting 1.1
Gastrointestinal disorders Abdominal pain 1.0
Investigations Alanine aminotransferase increased 1.0
Gastrointestinal disorders Constipation 1.0
Blood and lymphatic system disorders Eosinophilia 1.0
Gastrointestinal disorders Gastrointestinal pain 1.0
Nervous system disorders Headache 1.0
General disorders and administration site conditions Injection site pain 1.0
General disorders and administration site conditions Injection site reaction 1.0
Gastrointestinal disorders Nausea 1.0
Infections and infestations Upper respiratory tract infection
Infections and infestations Upper respiratory tract infection 0.8
Gastrointestinal disorders Vomiting
Gastrointestinal disorders Diarrhoea 0.7
Gastrointestinal disorders Flatulence
Gastrointestinal disorders Constipation

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Renal and urinary disorders
50.96
Injury, poisoning and procedural complications
8.96
General disorders and administration site conditions
6.03
Gastrointestinal disorders
5.58
Vascular disorders
3.4
Nervous system disorders
2.73
Metabolism and nutrition disorders
2.44
Skin and subcutaneous tissue disorders
2.29

Cross References

Resources Reference
CAS NUMBER 103577-45-3
ChEBI 6375
ChEMBL CHEMBL480
DrugBank DB00448
DrugCentral 1547
EPA CompTox DTXSID4023200
FDA SRS 0K5C5T2QPG
Human Metabolome Database HMDB0005008
Guide to Pharmacology 7208
KEGG D00355
PharmGKB PA450180
PubChem 3883
SureChEMBL SCHEMBL22365
ZINC ZINC03830986
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