DAPAGLIFLOZIN

Search structure
Trade Names:
Synonyms:
Status: Approved (2014)
Entry Type: Small molecule
Molecule Category: Parent
ATC: A10BK01
UNII: 1ULL0QJ8UC

Structure
InChI Key JVHXJTBJCFBINQ-ADAARDCZSA-N
Smile CCOc1ccc(Cc2cc([C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)ccc2Cl)cc1
InChI
InChI=1S/C21H25ClO6/c1-2-27-15-6-3-12(4-7-15)9-14-10-13(5-8-16(14)22)21-20(26)19(25)18(24)17(11-23)28-21/h3-8,10,17-21,23-26H,2,9,11H2,1H3/t17-,18-,19+,20-,21+/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C21H25ClO6
Molecular Weight 408.88
AlogP 1.84
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 4.0
Number of Rotational Bond 6.0
Polar Surface Area 99.38
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 28.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Sodium/glucose cotransporter 2 inhibitor
Primary Target
Sodium/glucose cotransporter 2
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Transferase
- - - - 11.09-13.81
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- - - - -18--8.84
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC02 family of hexose and sugar alcohol transporters
- - - - 8
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC05 family of sodium-dependent glucose transporters
1.1-3 0.49-22 - - 69.7-103

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Non-alcoholic Fatty Liver Disease 3 D065626 ClinicalTrials
Polycystic Ovary Syndrome 3 D011085 ClinicalTrials
Atrial Fibrillation 3 D001281 ClinicalTrials
Coronary Disease 3 D003327 ClinicalTrials
Acute Kidney Injury 3 D058186 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Diabetic Retinopathy 3 D003930 ClinicalTrials
Renal Insufficiency 3 D051437 ClinicalTrials
Fatty Liver 3 D005234 ClinicalTrials
Diabetes Mellitus, Type 1 3 D003922 ClinicalTrials
Insulin Resistance 3 D007333 ClinicalTrials
Glomerulonephritis, IGA 3 D005922 ClinicalTrials
ST Elevation Myocardial Infarction 3 D000072657 ClinicalTrials
Kidney Failure, Chronic 3 D007676 ClinicalTrials
Myocardial Infarction 2 D009203 ClinicalTrials
Hypertension, Pulmonary 2 D006976 ClinicalTrials
Liver Cirrhosis 2 D008103 ClinicalTrials
Weight Loss 2 D015431 ClinicalTrials
Hyperuricemia 2 D033461 ClinicalTrials
Metabolic Syndrome 2 D024821 ClinicalTrials
Motor Activity 2 D009043 ClinicalTrials
Diabetic Nephropathies 2 D003928 ClinicalTrials
Heart Failure, Diastolic 2 D054144 ClinicalTrials
Depressive Disorder 2 D003866 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Fabry Disease 2 D000795 ClinicalTrials
Albuminuria 2 D000419 ClinicalTrials
Diabetic Neuropathies 2 D003929 ClinicalTrials
Inflammatory Bowel Diseases 2 D015212 ClinicalTrials
Amyloidosis, Familial 2 D028226 ClinicalTrials
Obesity 2 D009765 ClinicalTrials
Cystinuria 2 D003555 ClinicalTrials
Reperfusion Injury 1 D015427 ClinicalTrials
Pancreatic Neoplasms 1 D010190 ClinicalTrials
Prostatic Neoplasms 1 D011471 ClinicalTrials
Aging 1 D000375 ClinicalTrials
Myocardial Ischemia 1 D017202 ClinicalTrials
Lupus Nephritis 1 D008181 ClinicalTrials
Alzheimer Disease 1 D000544 ClinicalTrials
Brain Neoplasms 1 D001932 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 1 D064129 ClinicalTrials

Related Entries

MCS

Scaffolds

Mixture
Mixture
Mixture

Side Effects from Label

Side effects Relative Frequency (%) Labels
Infections and infestations Genital infection fungal 8.4
Infections and infestations Genital infection fungal 6.9
Infections and infestations Nasopharyngitis 6.6
Infections and infestations Nasopharyngitis 6.3
Infections and infestations Nasopharyngitis
Infections and infestations Urinary tract infection 5.7
Infections and infestations Urinary tract infection 4.3
Musculoskeletal and connective tissue disorders Back pain 4.2
Infections and infestations Urinary tract infection
Musculoskeletal and connective tissue disorders Back pain
Musculoskeletal and connective tissue disorders Back pain 3.1
Infections and infestations Genital infection fungal 2.8
Gastrointestinal disorders Nausea 2.8
Infections and infestations Genital infection fungal 2.7
Infections and infestations Influenza 2.7
Metabolism and nutrition disorders Dyslipidaemia 2.5
Gastrointestinal disorders Nausea 2.5
Gastrointestinal disorders Nausea
Infections and infestations Influenza
Infections and infestations Influenza 2.3
Gastrointestinal disorders Constipation 2.2
General disorders and administration site conditions Discomfort 2.1
Metabolism and nutrition disorders Dyslipidaemia 2.1
Musculoskeletal and connective tissue disorders Pain in extremity 2.0
Gastrointestinal disorders Constipation 1.9
Musculoskeletal and connective tissue disorders Pain in extremity 1.7
General disorders and administration site conditions Discomfort 1.6
Gastrointestinal disorders Constipation
Metabolism and nutrition disorders Dyslipidaemia
Infections and infestations Genital infection fungal
Musculoskeletal and connective tissue disorders Pain in extremity
General disorders and administration site conditions Discomfort
Investigations Blood creatinine increased 0.4
Infections and infestations Genital infection fungal
Infections and infestations Urinary tract infection 0.3
Skin and subcutaneous tissue disorders Dermatitis 0.2
Cardiac disorders Dizziness 0.2
Gastrointestinal disorders Nausea 0.2
Skin and subcutaneous tissue disorders Rash 0.2

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Metabolism and nutrition disorders
11.27
Renal and urinary disorders
8.81
Investigations
8.55
Infections and infestations
7.78
General disorders and administration site conditions
7.74
Gastrointestinal disorders
6.58
Endocrine disorders
6.44
Nervous system disorders
6.43
Vascular disorders
5.69
Injury, poisoning and procedural complications
5.37
Skin and subcutaneous tissue disorders
4.61
Cardiac disorders
3.86
Musculoskeletal and connective tissue disorders
3.15
Reproductive system and breast disorders
2.91
Respiratory, thoracic and mediastinal disorders
2.9
Psychiatric disorders
2.36

Cross References

Resources Reference
CAS NUMBER 461432-26-8
ChEBI 85078
ChEMBL CHEMBL429910
DrugBank DB06292
DrugCentral 4304
FDA SRS 1ULL0QJ8UC
Guide to Pharmacology 4594
KEGG D08897
PDB LE6
PubChem 9887712
SureChEMBL SCHEMBL157820
ZINC ZINC000003819138
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