Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C23H30O6 |
Molecular Weight | 402.4807 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(=O)OCC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3C(=O)C[C@]12C
InChI
InChIKey=ITRJWOMZKQRYTA-RFZYENFJSA-N
InChI=1S/C23H30O6/c1-13(24)29-12-19(27)23(28)9-7-17-16-5-4-14-10-15(25)6-8-21(14,2)20(16)18(26)11-22(17,23)3/h10,16-17,20,28H,4-9,11-12H2,1-3H3/t16-,17-,20+,21-,22-,23-/m0/s1
Molecular Formula | C23H30O6 |
Molecular Weight | 402.4807 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including:
http://www.wikidoc.org/index.php/Cortisone | https://www.drugs.com/pro/cortisone-acetate.html | https://www.ncbi.nlm.nih.gov/pubmed/2811372 | https://www.ncbi.nlm.nih.gov/pubmed/7358829 | https://books.google.com/books?id=Q1voCAAAQBAJ&pg=PA113&lpg=PA113&dq=CORTISONE+SULFATE&source=bl&ots=-bwZTb4Fzh&sig=4gjBk9MhoF8OrL-7I5c06Fr32A8&hl=en&sa=X&ved=0ahUKEwiblMuT9pfVAhXK4SYKHXKKB6wQ6AEITTAG#v=onepage&q=CORTISONE%20SULFATE&f=false | http://www.google.com.pg/patents/US20120135924 | http://www.google.com.pg/patents/US20120128785 | https://www.google.com/patents/US4450151
Curator's Comment: description was created based on several sources, including:
http://www.wikidoc.org/index.php/Cortisone | https://www.drugs.com/pro/cortisone-acetate.html | https://www.ncbi.nlm.nih.gov/pubmed/2811372 | https://www.ncbi.nlm.nih.gov/pubmed/7358829 | https://books.google.com/books?id=Q1voCAAAQBAJ&pg=PA113&lpg=PA113&dq=CORTISONE+SULFATE&source=bl&ots=-bwZTb4Fzh&sig=4gjBk9MhoF8OrL-7I5c06Fr32A8&hl=en&sa=X&ved=0ahUKEwiblMuT9pfVAhXK4SYKHXKKB6wQ6AEITTAG#v=onepage&q=CORTISONE%20SULFATE&f=false | http://www.google.com.pg/patents/US20120135924 | http://www.google.com.pg/patents/US20120128785 | https://www.google.com/patents/US4450151
Cortisone is a hormone that is FDA approved for the treatment of primary and secondary adrenocortical deficiency, rheumatic disorders, psoriasis, exfoliative dermatitis, bronchial asthma, allergic conjunctivitis, hemolytic anemia, enteritis, tuberculosis, trichnosis. Cortisone acetate binds to the cytosolic glucocorticoid receptor. After binding the receptor, the newly formed receptor-ligand complex translocates itself into the cell nucleus, where it binds to many glucocorticoid response elements (GRE) in the promoter region of the target genes. The DNA bound receptor then interacts with basic transcription factors, causing the increase in expression of specific target genes. Common adverse reactions include convulsions, increased intracranial pressure with papilledema, vertigo, headache, psychic disturbances, hirsuitism, glaucoma, exophthalmos. Aminoglutethimide may lead to a loss of corticosteroid-induced adrenal suppression. Co-administration of corticosteroids and warfarin usually results in inhibition of response to warfarin, although there have been some conflicting reports. Cortisone is a natural steroid hormone. Its sulfate analog has been detected in in umbilical vein blood fetus plasma between 19 and 32 weeks of gestation with a significant increase at 29-30 weeks and in amniotic fluid. Base on the experiments with rats it was suggested that cortisone sulfate in mammals could be hydrolyzed enzymatically liberating sulfate ions from cortisone. Cortisone sulfate has been proposed for use as one of the glycosaminoglycan compound materials in a cartilage prosthesis and biological nasal bridge implant manufacture as well as auxiliary agent in powder aerosol composition for use in baby powder, dry shampoo, water-eczema remedy and antiperspirant.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2034 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15705660 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | SOLU-CORTEF Approved UseTreatment of the Allergic states, Dermatologic diseases, Endocrine disorders, Gastrointestinal diseases, Hematologic disorders, Neoplastic diseases, Rheumatic disorders, Respiratory diseases, Renal diseases, Ophthalmic diseases, Nervous System Launch Date1955 |
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Primary | SOLU-CORTEF Approved UseTreatment of the Allergic states, Dermatologic diseases, Endocrine disorders, Gastrointestinal diseases, Hematologic disorders, Neoplastic diseases, Rheumatic disorders, Respiratory diseases, Renal diseases, Ophthalmic diseases, Nervous System. Launch Date1955 |
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Primary | SOLU-CORTEF Approved UseWhen oral therapy is not feasible, and the strength, dosage form, and route of administration of the drug reasonably lend the preparation to the treatment of the condition, the intravenous or intramusculat use of SOLU-CORTEF Sterile Powder is indicated as follows: Primary or secondary adrenocortical insufficiency (hydrocortisone or cortisone is the drug of choice). Launch Date1955 |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4109 nM × h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/6691888 |
44.8 mg 1 times / day steady-state, oral dose: 44.8 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CORTISONE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
16.2% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7195404/ |
CORTISONE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: MALE food status: UNKNOWN |
PubMed
Title | Date | PubMed |
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The excretion of free cortisol, cortisone, cortisol sulfate and cortisone sulfate in peripheral vascular disease, diabetes mellitus and hyperthyroidism. | 1978 Nov |
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Innate immunity and the normal microflora. | 2000 Feb |
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Fetal endocrine signals and preterm labor. | 2001 |
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High levels of mRNA encoding IL-4 in unstimulated peripheral blood mononuclear cells from tuberculosis patients revealed by quantitative nested reverse transcriptase-polymerase chain reaction; correlations with serum IgE levels. | 2001 |
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Diagnosis of adrenal cortical dysfunction by liquid chromatography-tandem mass spectrometry. | 2001 Apr |
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Light and electron microscopy localization of the 11beta-hydroxysteroid dehydrogenase type I enzyme in the rat. | 2001 Apr |
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[Idiopathic thrombocytopenia during pregnancy. The risk in connection with umbilical blood sampling is probably greater than the benefit]. | 2001 Aug 8 |
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Plasma cortisol, cortisone and urinary glucocorticoid metabolites in preterm infants. | 2001 Feb |
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Use of salivary biomarkers in biobehavioral research: cotton-based sample collection methods can interfere with salivary immunoassay results. | 2001 Feb |
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[Serious life events and congenital malformations. A national study with a complete follow-up]. | 2001 Feb 19 |
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[Microbiological and immunological monitoring in polyarticular rheumatoid arthritis after total joint replacement]. | 2001 Feb 9 |
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[Present status of studies on pulmonary aspergillosis--special reference to the pathogenesis and progression]. | 2001 Jan |
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Neuroendocrine consequences of very early weaning in swine. | 2001 Jan |
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Human cervical tissue metabolizes the tobacco-specific nitrosamine, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, via alpha-hydroxylation and carbonyl reduction pathways. | 2001 Jan |
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[Usefulness and necessity of unsynchronized photosolotherapy and bath-PUVA--two variants of balneophototherapy--in funded ambulatory health care]. | 2001 Jul |
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Assessing systemic 11beta-hydroxysteroid dehydrogenase with serum cortisone/cortisol ratios in healthy subjects and patients with diabetes mellitus and chronic renal failure. | 2001 Jul |
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Glucocorticoid induction of the glaucoma gene MYOC in human and monkey trabecular meshwork cells and tissues. | 2001 Jul |
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Functional expression, characterization, and purification of the catalytic domain of human 11-beta -hydroxysteroid dehydrogenase type 1. | 2001 Jun 15 |
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Cortisol metabolism and the role of 11beta-hydroxysteroid dehydrogenase. | 2001 Mar |
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Defective cortisone 11-oxoreductase activity? | 2001 Mar |
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Tissue-specific dysregulation of cortisol metabolism in human obesity. | 2001 Mar |
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Decreased gene expression of 11beta-hydroxysteroid dehydrogenase type 2 and 15-hydroxyprostaglandin dehydrogenase in human placenta of patients with preeclampsia. | 2001 Mar |
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A mutation in the cofactor-binding domain of 11beta-hydroxysteroid dehydrogenase type 2 associated with mineralocorticoid hypertension. | 2001 Mar |
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Regulation of glucocorticoid receptor alpha and beta isoforms and type I 11beta-hydroxysteroid dehydrogenase expression in human skeletal muscle cells: a key role in the pathogenesis of insulin resistance? | 2001 May |
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Oxidized glucocorticoids counteract glucocorticoid-induced apoptosis in murine thymocytes in vitro. | 2001 May 18 |
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Calcium inhibits human placental 11beta-hydroxysteroid dehydrogenase type 2 activity. | 2001 May 18 |
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Effect of glucocorticoid excess on the cortisol/cortisone ratio. | 2001 Nov |
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Determination of natural corticosteroids in urine samples from sportsmen. | 2001 Sep 15 |
Sample Use Guides
Therapy is initiated by administering hydrocortisone sterile powder intravenously over a period of 30 seconds (e.g., 100 mg) to 10 minutes (e.g., 500 mg or more). In general, high dose corticosteroid therapy should be continued only until the patient’s condition has stabilized, usually not beyond 48 to 72 hours.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/13035752
With the highest concentration of cortisone that can be used under these conditions (owing to the limitation of solubility), namely 10 ug/ml., it is only possible to kill about 50 % of the lymphocytes in 46 hr; and, by extrapolation of the curve, that a concentration of about 10 mg/ml. would be required to kill 99 % of them.
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:49:52 GMT 2025
by
admin
on
Mon Mar 31 17:49:52 GMT 2025
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Record UNII |
883WKN7W8X
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Record Status |
Validated (UNII)
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NCI_THESAURUS |
C521
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50-04-4
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |
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