PREDNISOLONE

Search structure
Trade Names:
Synonyms:
Status: Approved (1955)
Entry Type: Small molecule
Molecule Category: Parent Metabolite
ATC: A07EA01
UNII: 9PHQ9Y1OLM

Structure
InChI Key OIGNJSKKLXVSLS-VWUMJDOOSA-N
Smile C[C@]12C[C@H](O)[C@H]3[C@@H](CCC4=CC(=O)C=C[C@@]43C)[C@@H]1CC[C@]2(O)C(=O)CO
InChI
InChI=1S/C21H28O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h5,7,9,14-16,18,22,24,26H,3-4,6,8,10-11H2,1-2H3/t14-,15-,16-,18+,19-,20-,21-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C21H28O5
Molecular Weight 360.45
AlogP 1.56
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 2.0
Polar Surface Area 94.83
Molecular species NEUTRAL
Aromatic Rings 0.0
Heavy Atoms 26.0

Pharmacology

Action Mechanism of Action Reference
AGONIST Glucocorticoid receptor agonist
Primary Target
Glucocorticoid receptor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Auxiliary transport protein Fatty acid binding protein family
- - - 2660-101000 -
Enzyme Hydrolase
- - - -
Enzyme Ligase
32 - - - -
Enzyme Protease Metallo protease Metallo protease MAM clan Metallo protease M12B subfamily
- 14.9 - - -
Enzyme Transferase
- - - - 14.7-25.57
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- - - - -1.16-1.72
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Lipid-like ligand receptor (family A GPCR) Steroid-like ligand receptor
- 251 - - -
Secreted protein
- 251 - 30.9 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 1
2.1-211 0.526-340 - 1.14-7.397 71-100
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 2
0.002-2 11-44 - 0.29-37 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 3
- 2080-27000 - - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 4
- 34000 - 2520-2762 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 2.3-79.83
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 91470 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Tennis Elbow 4 D013716 ClinicalTrials
Dermatitis, Atopic 4 D003876 ClinicalTrials
Bronchiolitis Obliterans Syndrome 3 D000092122 ClinicalTrials
Multiple Myeloma 3 D009101 ClinicalTrials
Pulmonary Disease, Chronic Obstructive 3 D029424 ClinicalTrials
Glomerulonephritis, IGA 3 D005922 ClinicalTrials
Pulpitis 3 D011671 ClinicalTrials
Idiopathic Pulmonary Fibrosis 3 D054990 ClinicalTrials
Hepatitis, Alcoholic 3 D006519 ClinicalTrials
Pericarditis 3 D010493 ClinicalTrials
Lymphoma, Follicular 3 D008224 ClinicalTrials
Carcinoma, Hepatocellular 3 D006528 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 3 D054198 ClinicalTrials
Lymphoma, Large B-Cell, Diffuse 3 D016403 ClinicalTrials
Prostatic Neoplasms 3 D011471 ClinicalTrials
Prostatic Neoplasms 3 D011471 ClinicalTrials
Kidney Diseases 3 D007674 ClinicalTrials
Mucocutaneous Lymph Node Syndrome 3 D009080 ClinicalTrials
Lupus Nephritis 3 D008181 ClinicalTrials
Lymphoma, Non-Hodgkin 3 D008228 ClinicalTrials
Aspergillosis, Allergic Bronchopulmonary 3 D001229 ClinicalTrials
Purpura, Thrombocytopenic, Idiopathic 3 D016553 ClinicalTrials
Churg-Strauss Syndrome 3 D015267 ClinicalTrials
Croup 3 D003440 ClinicalTrials
Anemia, Hemolytic, Autoimmune 3 D000744 ClinicalTrials
Hypereosinophilic Syndrome 3 D017681 ClinicalTrials
Eczema 3 D004485 ClinicalTrials
Headache 3 D006261 ClinicalTrials
Inflammation 3 D007249 ClinicalTrials
Glomerulonephritis, Membranous 3 D015433 ClinicalTrials
Anti-Neutrophil Cytoplasmic Antibody-Associated Vasculitis 3 D056648 ClinicalTrials
Polymyalgia Rheumatica 3 D011111 ClinicalTrials
Abortion, Habitual 3 D000026 ClinicalTrials
Orbital Pseudotumor 3 D016727 ClinicalTrials
Leukemia, Biphenotypic, Acute 3 D015456 ClinicalTrials
Glaucoma, Open-Angle 3 D005902 ClinicalTrials
Graves Disease 3 D006111 ClinicalTrials
Ocular Hypertension 3 D009798 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 3 D054198 ClinicalTrials
Red-Cell Aplasia, Pure 3 D012010 ClinicalTrials
Glomerulonephritis 3 D005921 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 3 D064129 ClinicalTrials
Lymphoma, Follicular 3 D008224 ClinicalTrials
Colitis 3 D003092 ClinicalTrials
Glomerulosclerosis, Focal Segmental 3 D005923 ClinicalTrials
Adrenal Insufficiency 3 D000309 ClinicalTrials
Pemphigus 3 D010392 ClinicalTrials
Eye Infections 3 D015817 ClinicalTrials
Sarcoma 3 D012509 ClinicalTrials
Endocardial Cushion Defects 3 D004694 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Prostatic Neoplasms 3 D011471 ClinicalTrials
Cataract 3 D002386 ClinicalTrials
Hypersensitivity 3 D006967 ClinicalTrials
Biliary Atresia 3 D001656 ClinicalTrials
Spasms, Infantile 3 D013036 ClinicalTrials
Purpura, Thrombotic Thrombocytopenic 3 D011697 ClinicalTrials
Stroke 3 D020521 ClinicalTrials
Takayasu Arteritis 3 D013625 ClinicalTrials
Glaucoma 3 D005901 ClinicalTrials
Graft vs Host Disease 3 D006086 ClinicalTrials
Neoplasms, Plasma Cell 3 D054219 ClinicalTrials
Infections 3 D007239 ClinicalTrials
Multiple Sclerosis, Chronic Progressive 3 D020528 ClinicalTrials
Liver Diseases, Alcoholic 3 D008108 ClinicalTrials
Hyperthyroidism 3 D006980 ClinicalTrials
Sjogren's Syndrome 2 D012859 ClinicalTrials
Osteoarthritis, Knee 2 D020370 ClinicalTrials
HIV Infections 2 D015658 ClinicalTrials
Pemphigoid, Benign Mucous Membrane 2 D010390 ClinicalTrials
Lichen Planus 2 D008010 ClinicalTrials
Stomatitis, Aphthous 2 D013281 ClinicalTrials
Uveitis 2 D014605 ClinicalTrials
Cardiomyopathies 2 D009202 ClinicalTrials
Infertility 2 D007246 ClinicalTrials
Sinusitis 2 D012852 ClinicalTrials
Immunoblastic Lymphadenopathy 2 D007119 ClinicalTrials
Giant Cell Arteritis 2 D013700 ClinicalTrials
Schizophrenia 2 D012559 ClinicalTrials
Hearing Loss, Sensorineural 2 D006319 ClinicalTrials
Diabetes Mellitus, Type 2 2 D003924 ClinicalTrials
Scleroderma, Systemic 2 D012595 ClinicalTrials
Alveolitis, Extrinsic Allergic 2 D000542 ClinicalTrials
Pituitary ACTH Hypersecretion 2 D047748 ClinicalTrials
Microscopic Polyangiitis 2 D055953 ClinicalTrials
Lymphoma, T-Cell, Peripheral 2 D016411 ClinicalTrials
Granulomatosis with Polyangiitis 2 D014890 ClinicalTrials
Renal Insufficiency, Chronic 2 D051436 ClinicalTrials
Lymphoma, Large-Cell, Anaplastic 2 D017728 ClinicalTrials
Celiac Disease 2 D002446 ClinicalTrials
Leprosy 2 D007918 ClinicalTrials
Hodgkin Disease 2 D006689 ClinicalTrials
Hemangioma 2 D006391 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Melanoma 2 D008545 ClinicalTrials
Hyperlipoproteinemia Type I 2 D008072 ClinicalTrials
Muscular Dystrophy, Duchenne 2 D020388 ClinicalTrials
Leukemia, Lymphoid 2 D007945 ClinicalTrials
Bell Palsy 1 D020330 ClinicalTrials
Lipoma 1 D008067 ClinicalTrials
Neoplasms 1 D009369 ClinicalTrials
Macular Degeneration 1 D008268 ClinicalTrials
Neoplasms 1 D009369 ClinicalTrials
Lymphohistiocytosis, Hemophagocytic 1 D051359 ClinicalTrials

Related Entries

MCS

Scaffolds

Salt
Salt
Salt
Salt
Mixture

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Infections and infestations
10.62
General disorders and administration site conditions
10.4
Nervous system disorders
7.7
Respiratory, thoracic and mediastinal disorders
6.53
Gastrointestinal disorders
6.17
Vascular disorders
5.93
Musculoskeletal and connective tissue disorders
5.42
Skin and subcutaneous tissue disorders
4.71
Injury, poisoning and procedural complications
4.62
Psychiatric disorders
4.6
Metabolism and nutrition disorders
4.47
Blood and lymphatic system disorders
4.29
Investigations
3.5
Cardiac disorders
3.42
Renal and urinary disorders
3.13
Immune system disorders
3.07
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
2.32
Pregnancy, puerperium and perinatal conditions
2.17
Eye disorders
2.07

Cross References

Resources Reference
CAS NUMBER 50-24-8
ChEBI 8378
ChEMBL CHEMBL131
DrugBank DB00860
DrugCentral 2245
EPA CompTox DTXSID9021184
FDA SRS 9PHQ9Y1OLM
Human Metabolome Database HMDB14998
Guide to Pharmacology 2866
KEGG C07369
PDB TUA
PharmGKB PA451096
PubChem 5755
SureChEMBL SCHEMBL3233
ZINC ZINC000003833821
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