METHYLPREDNISOLONE

Search structure
Trade Names:
Synonyms:
Status: Approved (1957)
Entry Type: Small molecule
Molecule Category: Parent
ATC: D07AA01
UNII: X4W7ZR7023

Structure
InChI Key VHRSUDSXCMQTMA-PJHHCJLFSA-N
Smile C[C@H]1C[C@H]2[C@@H]3CC[C@](O)(C(=O)CO)[C@@]3(C)C[C@H](O)[C@@H]2[C@@]2(C)C=CC(=O)C=C12
InChI
InChI=1S/C22H30O5/c1-12-8-14-15-5-7-22(27,18(26)11-23)21(15,3)10-17(25)19(14)20(2)6-4-13(24)9-16(12)20/h4,6,9,12,14-15,17,19,23,25,27H,5,7-8,10-11H2,1-3H3/t12-,14-,15-,17-,19+,20-,21-,22-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C22H30O5
Molecular Weight 374.48
AlogP 1.8
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 27.0

Experimental and Estimated Properties

Property Name Value Unit Method
log P (octanol-water) 1.820 - EST
Atmospheric OH Rate Constant 7.39E-11 cm3/molecule-sec EST
Melting Point 232.5 deg C EXP
Water Solubility 120 mg/L EXP

Pharmacology

Action Mechanism of Action Reference
AGONIST Glucocorticoid receptor agonist
Primary Target
Glucocorticoid receptor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- - - -
Enzyme Transferase
- - - - 30.95
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- - - - -40.44--3.84
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group I Nuclear hormone receptor subfamily 1 group I member 2
12600 - - - -
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
- 11 - 5.033 -
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
- 26680 - 17786 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 79.56
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 33030 - - -
Transporter Primary active transporter ATP-binding cassette ABCC subfamily
- 40970 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Spinal Cord Injuries 3 D013119 ClinicalTrials
Meniere Disease 3 D008575 ClinicalTrials
Graft vs Host Disease 3 D006086 ClinicalTrials
Multiple Sclerosis, Chronic Progressive 3 D020528 ClinicalTrials
Multiple Myeloma 3 D009101 ClinicalTrials
Respiratory Tract Diseases 3 D012140 ClinicalTrials
Carpal Tunnel Syndrome 3 D002349 ClinicalTrials
Urinary Tract Infections 3 D014552 ClinicalTrials
Optic Neuropathy, Ischemic 3 D018917 ClinicalTrials
Hematologic Neoplasms 3 D019337 ClinicalTrials
Kidney Diseases 3 D007674 ClinicalTrials
Purpura, Thrombocytopenic, Idiopathic 3 D016553 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 3 D054198 ClinicalTrials
Dermatomyositis 3 D003882 ClinicalTrials
Leukemia 3 D007938 ClinicalTrials
Lymphoma 3 D008223 ClinicalTrials
Scleroderma, Systemic 3 D012595 ClinicalTrials
Heart Diseases 3 D006331 ClinicalTrials
Renal Insufficiency, Chronic 3 D051436 ClinicalTrials
Glomerulonephritis, IGA 3 D005922 ClinicalTrials
Glomerulonephritis, Membranous 3 D015433 ClinicalTrials
Anti-Neutrophil Cytoplasmic Antibody-Associated Vasculitis 3 D056648 ClinicalTrials
Granulomatosis with Polyangiitis 3 D014890 ClinicalTrials
Lupus Nephritis 3 D008181 ClinicalTrials
Bell Palsy 3 D020330 ClinicalTrials
Vestibular Neuronitis 3 D020338 ClinicalTrials
Respiratory Distress Syndrome 3 D012128 ClinicalTrials
Microscopic Polyangiitis 3 D055953 ClinicalTrials
Hematoma, Subdural, Intracranial 3 D046648 ClinicalTrials
Spinal Cord Injuries 3 D013119 ClinicalTrials
Thrombocytopenia 3 D013921 ClinicalTrials
Deglutition Disorders 3 D003680 ClinicalTrials
Pain 3 D010146 ClinicalTrials
Edema 3 D004487 ClinicalTrials
Heart Arrest 3 D006323 ClinicalTrials
Leukemia, Biphenotypic, Acute 3 D015456 ClinicalTrials
Pulmonary Disease, Chronic Obstructive 3 D029424 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Optic Neuritis 3 D009902 ClinicalTrials
Pneumonia, Pneumocystis 3 D011020 ClinicalTrials
Pulpitis 3 D011671 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 3 D054198 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 3 D064129 ClinicalTrials
Graft vs Host Disease 3 D006086 ClinicalTrials
Lymphohistiocytosis, Hemophagocytic 3 D051359 ClinicalTrials
Specific Language Disorder 3 D000080888 ClinicalTrials
Hematologic Neoplasms 3 D019337 ClinicalTrials
Abdominal Pain 3 D015746 ClinicalTrials
Ischemic Stroke 3 D000083242 ClinicalTrials
Hodgkin Disease 3 D006689 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Respiratory Distress Syndrome 3 D012128 ClinicalTrials
Multiple Sclerosis, Chronic Progressive 3 D020528 ClinicalTrials
Myocarditis 3 D009205 ClinicalTrials
Macrophage Activation Syndrome 3 D055501 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 3 D054198 ClinicalTrials
Language Disorders 3 D007806 ClinicalTrials
Bronchopulmonary Dysplasia 3 D001997 ClinicalTrials
Wounds and Injuries 3 D014947 ClinicalTrials
Stroke 3 D020521 ClinicalTrials
Idiopathic Pulmonary Fibrosis 3 D054990 ClinicalTrials
Colitis 3 D003092 ClinicalTrials
Renal Insufficiency 3 D051437 ClinicalTrials
Lupus Erythematosus, Systemic 3 D008180 ClinicalTrials
Hodgkin Disease 3 D006689 ClinicalTrials
Aging 3 D000375 ClinicalTrials
Erythema Multiforme 3 D004892 ClinicalTrials
Multiple Sclerosis, Relapsing-Remitting 3 D020529 ClinicalTrials
Coronavirus Infections 2 D018352 ClinicalTrials
Nasal Polyps 2 D009298 ClinicalTrials
Neoplasms 2 D009369 ClinicalTrials
IgA Vasculitis 2 D011695 ClinicalTrials
Lymphoma, AIDS-Related 2 D016483 ClinicalTrials
Migraine Disorders 2 D008881 ClinicalTrials
Fasciitis, Plantar 2 D036981 ClinicalTrials
Amyotrophic Lateral Sclerosis 2 D000690 ClinicalTrials
Anemia, Aplastic 2 D000741 ClinicalTrials
Graves Ophthalmopathy 2 D049970 ClinicalTrials
Burkitt Lymphoma 2 D002051 ClinicalTrials
Immunoblastic Lymphadenopathy 2 D007119 ClinicalTrials
Lymphoma, T-Cell, Peripheral 2 D016411 ClinicalTrials
Myelodysplastic Syndromes 2 D009190 ClinicalTrials
Prostatic Neoplasms 2 D011471 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 2 D002289 ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-Cell 2 D015451 ClinicalTrials
Myeloproliferative Disorders 2 D009196 ClinicalTrials
Hepatitis, Alcoholic 2 D006519 ClinicalTrials
Hyperlipoproteinemia Type I 2 D008072 ClinicalTrials
Neuromyelitis Optica 2 D009471 ClinicalTrials
Lymphoproliferative Disorders 2 D008232 ClinicalTrials
Myeloproliferative Disorders 2 D009196 ClinicalTrials
Purpura, Thrombotic Thrombocytopenic 2 D011697 ClinicalTrials
Fallopian Tube Neoplasms 2 D005185 ClinicalTrials
Radiculopathy 2 D011843 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Fanconi Anemia 2 D005199 ClinicalTrials
Bronchiolitis Obliterans Syndrome 2 D000092122 ClinicalTrials
Kidney Failure, Chronic 2 D007676 ClinicalTrials
Neoplasms, Plasma Cell 2 D054219 ClinicalTrials
Sinusitis 2 D012852 ClinicalTrials
Spondylarthropathies 2 D025242 ClinicalTrials
Osteoarthritis, Knee 2 D020370 ClinicalTrials
Neoplasms 2 D009369 ClinicalTrials
Adenomatous Polyposis Coli 2 D011125 ClinicalTrials
Lymphoma, Large B-Cell, Diffuse 2 D016403 ClinicalTrials
Spasms, Infantile 2 D013036 ClinicalTrials
Melanoma 2 D008545 ClinicalTrials
Lymphoma, Large-Cell, Anaplastic 2 D017728 ClinicalTrials
Immunoglobulin G4-Related Disease 2 D000077733 ClinicalTrials
Death, Sudden, Cardiac 2 D016757 ClinicalTrials
Myelodysplastic-Myeloproliferative Diseases 2 D054437 ClinicalTrials
Blastic Plasmacytoid Dendritic Cell Neoplasm 2 D000099067 ClinicalTrials
Lymphoma, Non-Hodgkin 2 D008228 ClinicalTrials
Appendicitis 2 D001064 ClinicalTrials
Hantavirus Infections 2 D018778 ClinicalTrials
Spondylitis, Ankylosing 2 D013167 ClinicalTrials
Gangliosidoses 1 D005733 ClinicalTrials
Shoulder Pain 1 D020069 ClinicalTrials
DiGeorge Syndrome 1 D004062 ClinicalTrials
Lymphoma, Follicular 1 D008224 ClinicalTrials
Optic Nerve Diseases 1 D009901 ClinicalTrials
Frontotemporal Dementia 1 D057180 ClinicalTrials
Radius Fractures 1 D011885 ClinicalTrials
Cognitive Dysfunction 1 D060825 ClinicalTrials
Gaucher Disease 1 D005776 ClinicalTrials
Chemical and Drug Induced Liver Injury 1 D056486 ClinicalTrials
Friedreich Ataxia 1 D005621 ClinicalTrials
Parkinson Disease 1 D010300 ClinicalTrials
Hearing Loss, Noise-Induced 1 D006317 ClinicalTrials
Muscular Diseases 1 D009135 ClinicalTrials
Hyperuricemia 1 D033461 ClinicalTrials
Mucocutaneous Lymph Node Syndrome 1 D009080 ClinicalTrials
Immune System Diseases 1 D007154 ClinicalTrials
Myasthenia Gravis 1 D009157 ClinicalTrials
Intussusception 1 D007443 ClinicalTrials
Stiff-Person Syndrome 1 D016750 ClinicalTrials
Atherosclerosis 1 D050197 ClinicalTrials
Ovarian Hyperstimulation Syndrome 1 D016471 ClinicalTrials

Related Entries

MCS

Scaffolds

UNKNOWN
Salt
Salt
Mixture

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Infections and infestations
10.63
General disorders and administration site conditions
9.56
Nervous system disorders
7.15
Gastrointestinal disorders
7.06
Respiratory, thoracic and mediastinal disorders
6.1
Vascular disorders
6.07
Immune system disorders
5.57
Injury, poisoning and procedural complications
5.41
Skin and subcutaneous tissue disorders
5.37
Metabolism and nutrition disorders
4.99
Musculoskeletal and connective tissue disorders
4.82
Psychiatric disorders
4.14
Investigations
3.85
Cardiac disorders
3.39
Blood and lymphatic system disorders
2.9
Endocrine disorders
2.68
Renal and urinary disorders
2.57
Hepatobiliary disorders
2.12
Eye disorders
2.06

Cross References

Resources Reference
CAS NUMBER 83-43-2
ChEBI 6888
ChEMBL CHEMBL650
DrugBank DB00959
DrugCentral 1768
EPA CompTox DTXSID7023300
FDA SRS X4W7ZR7023
Human Metabolome Database HMDB0015094
Guide to Pharmacology 7088
PharmGKB PA450466
PubChem 6741
SureChEMBL SCHEMBL5084
ZINC ZINC000003875560
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