DEXAMETHASONE

Search structure
Trade Names:
Synonyms:
Status: Approved (1958)
Entry Type: Small molecule
Molecule Category: Parent
ATC: A01AC02
UNII: 7S5I7G3JQL

Structure
InChI Key UREBDLICKHMUKA-CXSFZGCWSA-N
Smile C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O)C(=O)CO
InChI
InChI=1S/C22H29FO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,17+,19+,20+,21+,22+/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C22H29FO5
Molecular Weight 392.47
AlogP 1.9
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 28.0

Pharmacology

Action Mechanism of Action Reference
AGONIST Glucocorticoid receptor agonist PubMed PubMed PubMed
Primary Target
Glucocorticoid receptor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Auxiliary transport protein Fatty acid binding protein family
- - - 22100-41300 -
Enzyme Protease Serine protease Serine protease SC clan Serine protease S33 family
- - - - 59
Secreted protein
- - - - 50
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
2600 - - - -
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
0-17 1-21 2-19 1-6 7-21
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
- 33-40 - 0-7 30
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
- 440 - 561-778 -
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
- 81283 - 1410 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 34-104
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC47 family of multidrug and toxin extrusion transporters
- - - - 30
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- - - - 0

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Neoplasms 4 D009369 ClinicalTrials
Bursitis 4 D002062 ClinicalTrials
Pemphigus 4 D010392 ClinicalTrials
Macular Edema 4 D008269 ClinicalTrials
Psoriasis 4 D011565 ClinicalTrials
Adrenal Hyperplasia, Congenital 4 D000312 ClinicalTrials
Eye Diseases 4 D005128 ClinicalTrials
Meniere Disease 3 D008575 ClinicalTrials
Multiple Myeloma 3 D009101 ClinicalTrials
Pain 3 D010146 ClinicalTrials
Prostatic Neoplasms 3 D011471 ClinicalTrials
Bronchiolitis 3 D001988 ClinicalTrials
Cataract 3 D002386 ClinicalTrials
Anemia, Sickle Cell 3 D000755 ClinicalTrials
Liver Cirrhosis 3 D008103 ClinicalTrials
HELLP Syndrome 3 D017359 ClinicalTrials
Postoperative Nausea and Vomiting 3 D020250 ClinicalTrials
Respiratory Distress Syndrome 3 D012128 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 3 D054198 ClinicalTrials
Ovarian Neoplasms 3 D010051 ClinicalTrials
Hernias, Diaphragmatic, Congenital 3 D065630 ClinicalTrials
Urinary Tract Infections 3 D014552 ClinicalTrials
Migraine Disorders 3 D008881 ClinicalTrials
Lymphoma, Mantle-Cell 3 D020522 ClinicalTrials
Ovarian Hyperstimulation Syndrome 3 D016471 ClinicalTrials
Hypersensitivity 3 D006967 ClinicalTrials
Pelvic Organ Prolapse 3 D056887 ClinicalTrials
Wounds and Injuries 3 D014947 ClinicalTrials
Leukemia, Biphenotypic, Acute 3 D015456 ClinicalTrials
Lymphoma, Follicular 3 D008224 ClinicalTrials
Carcinoma, Hepatocellular 3 D006528 ClinicalTrials
Hodgkin Disease 3 D006689 ClinicalTrials
Myelodysplastic Syndromes 3 D009190 ClinicalTrials
Leukemia, Biphenotypic, Acute 3 D015456 ClinicalTrials
Leukemia, Myeloid, Acute 3 D015470 ClinicalTrials
Leukemia, Promyelocytic, Acute 3 D015473 ClinicalTrials
Colorectal Neoplasms 3 D015179 ClinicalTrials
Lymphoma, Large B-Cell, Diffuse 3 D016403 ClinicalTrials
Glaucoma 3 D005901 ClinicalTrials
Prostatic Neoplasms 3 D011471 ClinicalTrials
Sarcoma 3 D012509 ClinicalTrials
Small Cell Lung Carcinoma 3 D055752 ClinicalTrials
Deafness 3 D003638 ClinicalTrials
Malaria 3 D008288 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 3 D002289 ClinicalTrials
Smoldering Multiple Myeloma 3 D000075122 ClinicalTrials
Renal Insufficiency, Chronic 3 D051436 ClinicalTrials
Vaginosis, Bacterial 3 D016585 ClinicalTrials
Glomerulosclerosis, Focal Segmental 3 D005923 ClinicalTrials
Otitis Media 3 D010033 ClinicalTrials
Lymphoma, Non-Hodgkin 3 D008228 ClinicalTrials
Plasmacytoma 3 D010954 ClinicalTrials
Nausea 3 D009325 ClinicalTrials
Nausea 3 D009325 ClinicalTrials
Cysticercosis 3 D003551 ClinicalTrials
Uveitis, Anterior 3 D014606 ClinicalTrials
Vitreoretinopathy, Proliferative 3 D018630 ClinicalTrials
Rhinitis, Allergic, Perennial 3 D012221 ClinicalTrials
Precursor T-Cell Lymphoblastic Leukemia-Lymphoma 3 D054218 ClinicalTrials
Amyloidosis 3 D000686 ClinicalTrials
Sarcoma 3 D012509 ClinicalTrials
Deglutition Disorders 3 D003680 ClinicalTrials
Postoperative Nausea and Vomiting 3 D020250 ClinicalTrials
Nausea 3 D009325 ClinicalTrials
Headache 3 D006261 ClinicalTrials
Encephalitis, Herpes Simplex 3 D020803 ClinicalTrials
Amyloidosis 3 D000686 ClinicalTrials
Bronchopulmonary Dysplasia 3 D001997 ClinicalTrials
Amyloidosis, Familial 3 D028226 ClinicalTrials
Lichen Planus, Oral 3 D017676 ClinicalTrials
Conjunctivitis, Viral 3 D003236 ClinicalTrials
Neuralgia 3 D009437 ClinicalTrials
Waldenstrom Macroglobulinemia 3 D008258 ClinicalTrials
Knee Injuries 3 D007718 ClinicalTrials
Blepharitis 3 D001762 ClinicalTrials
Otitis Externa 3 D010032 ClinicalTrials
Strabismus 3 D013285 ClinicalTrials
Back Pain 3 D001416 ClinicalTrials
Fatigue 3 D005221 ClinicalTrials
Leukemia, Erythroblastic, Acute 3 D004915 ClinicalTrials
Leukemia, Monocytic, Acute 3 D007948 ClinicalTrials
Leukemia, Myelomonocytic, Acute 3 D015479 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Leukemia, Megakaryoblastic, Acute 3 D007947 ClinicalTrials
Leukemia, Myeloid, Acute 3 D015470 ClinicalTrials
Anemia, Refractory 3 D000753 ClinicalTrials
Anemia, Refractory, with Excess of Blasts 3 D000754 ClinicalTrials
Ovarian Neoplasms 3 D010051 ClinicalTrials
Anemia 3 D000740 ClinicalTrials
Pneumonia, Viral 3 D011024 ClinicalTrials
Leukemia, Myelomonocytic, Chronic 3 D015477 ClinicalTrials
Colorectal Neoplasms 3 D015179 ClinicalTrials
Vomiting 3 D014839 ClinicalTrials
Chronic Pain 3 D059350 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 3 D054198 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 3 D054198 ClinicalTrials
Nephrosis 3 D009401 ClinicalTrials
Dermatitis 3 D003872 ClinicalTrials
Ovarian Neoplasms 3 D010051 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 3 D064129 ClinicalTrials
Hodgkin Disease 3 D006689 ClinicalTrials
Graft vs Host Disease 3 D006086 ClinicalTrials
Lymphohistiocytosis, Hemophagocytic 3 D051359 ClinicalTrials
Specific Language Disorder 3 D000080888 ClinicalTrials
Leukemia, Biphenotypic, Acute 3 D015456 ClinicalTrials
Granuloma, Lethal Midline 3 D006103 ClinicalTrials
Precursor T-Cell Lymphoblastic Leukemia-Lymphoma 3 D054218 ClinicalTrials
Atrioventricular Block 3 D054537 ClinicalTrials
Leiomyoma 3 D007889 ClinicalTrials
Lymphoma, Follicular 3 D008224 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Respiratory Distress Syndrome 3 D012128 ClinicalTrials
Mastoiditis 3 D008417 ClinicalTrials
Genital Neoplasms, Female 3 D005833 ClinicalTrials
Radiculopathy 2 D011843 ClinicalTrials
Burkitt Lymphoma 2 D002051 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Dyspnea 2 D004417 ClinicalTrials
Intestinal Obstruction 2 D007415 ClinicalTrials
Tonsillitis 2 D014069 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Neck Pain 2 D019547 ClinicalTrials
Fasciitis, Plantar 2 D036981 ClinicalTrials
Cholangiocarcinoma 2 D018281 ClinicalTrials
Histiocytosis, Sinus 2 D015618 ClinicalTrials
Tuberculosis 2 D014376 ClinicalTrials
Hematologic Neoplasms 2 D019337 ClinicalTrials
Breast Carcinoma In Situ 2 D000071960 ClinicalTrials
Sciatica 2 D012585 ClinicalTrials
Stomach Neoplasms 2 D013274 ClinicalTrials
Liposarcoma, Myxoid 2 D018208 ClinicalTrials
Urinary Bladder Neoplasms 2 D001749 ClinicalTrials
Wet Macular Degeneration 2 D057135 ClinicalTrials
Mesothelioma 2 D008654 ClinicalTrials
Brain Neoplasms 2 D001932 ClinicalTrials
Urinary Bladder Neoplasms 2 D001749 ClinicalTrials
Gout 2 D006073 ClinicalTrials
Pulmonary Fibrosis 2 D011658 ClinicalTrials
Glomerulonephritis 2 D005921 ClinicalTrials
Liver Neoplasms 2 D008113 ClinicalTrials
Neoplasm Metastasis 2 D009362 ClinicalTrials
Endocrine Gland Neoplasms 2 D004701 ClinicalTrials
Carcinoma, Squamous Cell 2 D002294 ClinicalTrials
Red-Cell Aplasia, Pure 2 D012010 ClinicalTrials
Endometrial Neoplasms 2 D016889 ClinicalTrials
Kidney Diseases 2 D007674 ClinicalTrials
Premature Birth 2 D047928 ClinicalTrials
Purpura, Thrombotic Thrombocytopenic 2 D011697 ClinicalTrials
Carcinoma, Renal Cell 2 D002292 ClinicalTrials
Respiratory Tract Diseases 2 D012140 ClinicalTrials
Castleman Disease 2 D005871 ClinicalTrials
Cholangiocarcinoma 2 D018281 ClinicalTrials
Macular Degeneration 2 D008268 ClinicalTrials
Hematologic Neoplasms 2 D019337 ClinicalTrials
Pancreatic Neoplasms 2 D010190 ClinicalTrials
Lymphoma, Large-Cell, Anaplastic 2 D017728 ClinicalTrials
Mouth Neoplasms 2 D009062 ClinicalTrials
Leukemia, T-Cell 2 D015458 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Toxoplasmosis, Cerebral 2 D016781 ClinicalTrials
Hemorrhage 2 D006470 ClinicalTrials
Lymphoma, T-Cell, Peripheral 2 D016411 ClinicalTrials
Hearing Loss 2 D034381 ClinicalTrials
Nasopharyngeal Neoplasms 2 D009303 ClinicalTrials
Leukemia, Lymphoid 2 D007945 ClinicalTrials
Carcinoma, Squamous Cell 2 D002294 ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-Cell 2 D015451 ClinicalTrials
Leukemia, Plasma Cell 2 D007952 ClinicalTrials
Nervous System Diseases 2 D009422 ClinicalTrials
Lichen Planus 2 D008010 ClinicalTrials
Xerostomia 2 D014987 ClinicalTrials
Appendicitis 2 D001064 ClinicalTrials
Meningitis, Cryptococcal 2 D016919 ClinicalTrials
Blast Crisis 2 D001752 ClinicalTrials
Leptospirosis 2 D007922 ClinicalTrials
Rectal Neoplasms 2 D012004 ClinicalTrials
Histiocytosis, Langerhans-Cell 2 D006646 ClinicalTrials
Dry Eye Syndromes 2 D015352 ClinicalTrials
Purpura, Schoenlein-Henoch 2 D011695 ClinicalTrials
Uveitis, Intermediate 2 D015867 ClinicalTrials
Intracranial Hypertension 2 D019586 ClinicalTrials
POEMS Syndrome 2 D016878 ClinicalTrials
Meningitis 2 D008581 ClinicalTrials
Hearing Loss, Sensorineural 2 D006319 ClinicalTrials
Melanoma 2 D008545 ClinicalTrials
Hematoma, Subdural, Intracranial 2 D046648 ClinicalTrials
Leukemia-Lymphoma, Adult T-Cell 2 D015459 ClinicalTrials
Retinal Vein Occlusion 2 D012170 ClinicalTrials
Scleritis 1 D015423 ClinicalTrials
Rheumatic Diseases 1 D012216 ClinicalTrials
Osteoarthritis, Knee 1 D020370 ClinicalTrials
Lacrimal Apparatus Diseases 1 D007766 ClinicalTrials
Esophageal Neoplasms 1 D004938 ClinicalTrials
Lung Neoplasms 1 D008175 ClinicalTrials
Lymphoma, T-Cell, Cutaneous 1 D016410 ClinicalTrials
Brain Edema 1 D001929 ClinicalTrials
Rotator Cuff Injuries 1 D000070636 ClinicalTrials
Head and Neck Neoplasms 1 D006258 ClinicalTrials
Graves Disease 1 D006111 ClinicalTrials
Aortic Coarctation 1 D001017 ClinicalTrials
Adrenal Insufficiency 1 D000309 ClinicalTrials
Heart Failure 1 D006333 ClinicalTrials
Vitiligo 1 D014820 ClinicalTrials
Meningeal Carcinomatosis 1 D055756 ClinicalTrials
Radius Fractures 0 D011885 ClinicalTrials
Tooth Diseases 0 D014076 ClinicalTrials
Hypertension 0 D006973 ClinicalTrials

Related Entries

MCS

Scaffolds

Salt
UNKNOWN
Salt
UNKNOWN
UNKNOWN
Mixture
Mixture
Mixture

Side Effects from Label

Side effects Relative Frequency (%) Labels
Investigations Intraocular pressure increased 35.5
Eye disorders Conjunctival haemorrhage 30.3
Investigations Intraocular pressure increased 25.2
Investigations Intraocular pressure increased 25.0
Investigations Intraocular pressure increased 24.0
Eye disorders Conjunctival haemorrhage 22.5
Eye disorders Conjunctival haemorrhage 21.7
Eye disorders Conjunctival haemorrhage 15.9
Eye disorders Conjunctival haemorrhage 14.7
Eye disorders Conjunctival haemorrhage 13.4
Vascular disorders Hypertension 12.7
Eye disorders Cataract 11.8
Eye disorders Visual acuity reduced 8.64
Eye disorders Eye pain 8.05
Eye disorders Conjunctival hyperaemia 6.64
Vascular disorders Hypertension 6.4
Eye disorders Conjunctivitis 5.86
Eye disorders Conjunctival hyperaemia 5.42
Eye disorders Eye pain 5.22
Eye disorders Vitreous floaters 4.94
Investigations Intraocular pressure increased 4.88
Eye disorders Cataract 4.83
Eye disorders Conjunctival oedema 4.63
Eye disorders Dry eye 4.63
Eye disorders Ocular hypertension 4.63
Eye disorders Vitreous detachment 4.32
Eye disorders Visual acuity reduced 3.96
Nervous system disorders Headache 3.82
Eye disorders Vitreous opacities 3.4
Eye disorders Retinal aneurysm 3.09
Eye disorders Conjunctivitis 2.44
Eye disorders Vitreous detachment 2.44
Nervous system disorders Headache 2.41
Eye disorders Vitreous detachment 2.41
Eye disorders Corneal erosion 2.16
General disorders and administration site conditions Sensation of foreign body 2.16
Eye disorders Dry eye 2.13
Eye disorders Cataract 2.01
Investigations Intraocular pressure increased 2.01
Eye disorders Anterior chamber inflammation 1.85
Eye disorders Keratitis 1.85
Eye disorders Vitreous floaters 1.83
Eye disorders Vitreous detachment 1.61
Eye disorders Eyelid ptosis 1.54
Eye disorders Retinal tear 1.54
Eye disorders Retinal aneurysm 1.52
Eye disorders Glaucoma 1.23
Eye disorders Conjunctival oedema 1.22
General disorders and administration site conditions Sensation of foreign body 1.22
Eye disorders Corneal erosion 0.915
Eye disorders Keratitis 0.915
Eye disorders Vitreous opacities 0.915
Eye disorders Eyelid ptosis 0.61
Eye disorders Retinal tear 0.61
Eye disorders Ocular hypertension 0.602
Eye disorders Glaucoma 0.305

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Blood and lymphatic system disorders
12.08
Infections and infestations
9.95
General disorders and administration site conditions
9.68
Nervous system disorders
8.31
Respiratory, thoracic and mediastinal disorders
7.3
Gastrointestinal disorders
7.24
Vascular disorders
5.38
Metabolism and nutrition disorders
4.24
Injury, poisoning and procedural complications
4.22
Investigations
3.87
Cardiac disorders
3.81
Eye disorders
3.75
Psychiatric disorders
3.7
Musculoskeletal and connective tissue disorders
3.09
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
2.88
Skin and subcutaneous tissue disorders
2.68
Renal and urinary disorders
2.13

Cross References

Resources Reference
CAS NUMBER 50-02-2
ChEBI 41879
ChEMBL CHEMBL384467
DrugBank DB01234
DrugCentral 824
EPA CompTox DTXSID3020384
FDA SRS 7S5I7G3JQL
Human Metabolome Database HMDB0015364
Guide to Pharmacology 3447
KEGG C15643
PDB DEX
PharmGKB PA449247
PubChem 5743
SureChEMBL SCHEMBL3774
ZINC ZINC000003875332
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