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
[H][C@@]12CC[C@](O)(C(=O)COC(C)=O)[C@@]1(C)CC(=O)[C@@]3([H])[C@@]2([H])CCC4=CC(=O)CC[C@]34C
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 |
---|---|---|---|
Target ID: CHEMBL2034 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15705660 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
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 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
477 nM EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8284505 |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
CORTISONE plasma | Canis lupus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1211 nM × h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8284505 |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
CORTISONE plasma | Canis lupus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
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 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
23 min EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8284505 |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
CORTISONE plasma | Canis lupus population: HEALTHY age: ADULT sex: 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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Activities of 11beta-hydroxysteroid dehydrogenase 2 in different regions of the intestinal tract of pigs. | 2001 |
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Chemotherapy-related hemolytic-uremic syndrome following treatment of a carcinoma of the nasopharynx. | 2001 |
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Fetal endocrine signals and preterm labor. | 2001 |
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Male-female differences in rat hypothalamic-pituitary-adrenal axis responses to nicotine stimulation. | 2001 Apr |
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Dieterich's disease: avascular necrosis of the metacarpal head: a case report. | 2001 Apr |
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20beta-Hydroxysteroid dehydrogenase of the Japanese eel ovary: its cellular localization and changes in the enzymatic activity during sexual maturation. | 2001 Apr |
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Adrenal nodules in patients with congenital adrenal hyperplasia due to 21-hydroxylase deficiency: regression after adequate hormonal control. | 2001 Apr |
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Adrenocortical response and cortisone replacement in systemic inflammatory response syndrome. | 2001 Apr |
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Cervical intramedullar schistosomiasis as a rare cause of acute tetraparesis. | 2001 Apr |
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Apparent mineralocorticoid excess. | 2001 Apr |
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Intravitreal injection of crystalline cortisone as adjunctive treatment of proliferative diabetic retinopathy. | 2001 Apr |
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Expression of 11 beta-hydroxysteroid dehydrogenase isozymes and corticosteroid hormone receptors in primary cultures of human trophoblast and placental bed biopsies. | 2001 Apr |
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The adrenal and the metabolic syndrome. | 2001 Apr |
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The effect of structural QSAR parameters on skin penetration. | 2001 Apr 17 |
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[A woman with Addison's disease and a bump on the neck]. | 2001 Apr 20 |
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Peroxisome proliferator-activated receptor-gamma ligands inhibit adipocyte 11beta -hydroxysteroid dehydrogenase type 1 expression and activity. | 2001 Apr 20 |
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Expression and putative role of 11 beta-hydroxysteroid dehydrogenase isozymes within the human eye. | 2001 Aug |
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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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Increased ACTH levels do not alter renal 11beta-hydroxysteroid dehydrogenase type 2 gene expression in the sheep. | 2001 Feb |
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Ontogeny of 11beta-hydroxysteroid dehydrogenase: activity in the placenta, kidney, colon of fetal rats and rabbits. | 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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Lack of mutations of type 1 11beta-hydroxysteroid dehydrogenase gene in patients with abdominal obesity. | 2001 Feb-May |
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Serum cortisol/cortisone ratio after Synacthen stimulation. | 2001 Jul |
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Effects of growth hormone replacement on cortisol metabolism in hypopituitary patients treated with cortisone acetate. | 2001 Jul |
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The intracellular localization of the mineralocorticoid receptor is regulated by 11beta-hydroxysteroid dehydrogenase type 2. | 2001 Jul 27 |
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Outpatient laparoscopic adrenalectomy in patients with Conn's syndrome. | 2001 Jun |
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Activation of the hypothalamic-pituitary-adrenal axis in obesity: cause or consequence? | 2001 Jun |
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Effect of naloxone therapy on depersonalization: a pilot study. | 2001 Jun |
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Modulation of 11beta-hydroxysteroid dehydrogenase isozymes by proinflammatory cytokines in osteoblasts: an autocrine switch from glucocorticoid inactivation to activation. | 2001 Jun |
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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 |
|
M. tuberculosis: immunology and vaccination. | 2001 Mar |
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New ideas for medical treatment of congenital adrenal hyperplasia. | 2001 Mar |
|
[Polycystic ovary syndrome of extra-ovarian origin. Review]. | 2001 Mar |
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Cortisol-secreting adrenal adenomas express 11beta-hydroxysteroid dehydrogenase type-2 gene yet possess low 11beta-HSD2 activity. | 2001 Mar |
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Defective cortisone 11-oxoreductase activity? | 2001 Mar |
|
Tissue-specific dysregulation of cortisol metabolism in human obesity. | 2001 Mar |
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[Reducing the need for cortisone. Does eucalyptus oil work in asthma? (interview by Brigitte Moreano]. | 2001 Mar 29 |
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Witness to a miracle: the initial cortisone trial: an interview with Richard Freyberg, MD. Interview by Mary Ellen Warner. | 2001 May |
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Twenty-four-hour pattern of cortisol in the human fetus at term. | 2001 May |
|
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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Regulation of expression of 11beta-hydroxysteroid dehydrogenase type 1 in adipose tissue: tissue-specific induction by cytokines. | 2001 May |
|
Sarcoidosis: old and new treatments. | 2001 May |
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Aqueous chromatography utilizing pH-/temperature-responsive polymer stationary phases to separate ionic bioactive compounds. | 2001 May 1 |
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Calcium inhibits human placental 11beta-hydroxysteroid dehydrogenase type 2 activity. | 2001 May 18 |
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The 11beta hydroxysteroid dehydrogenase 2 exists as an inactive dimer. | 2001 Nov |
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Effect of glucocorticoid excess on the cortisol/cortisone ratio. | 2001 Nov |
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Hydrolysis of conjugated steroids by the combined use of beta-glucuronidase preparations from helix pomatia and ampullaria: determination of urinary cortisol and its metabolites. | 2001 Nov |
|
Impaired antifungal effector activity but not inflammatory cell recruitment in interleukin-6-deficient mice with invasive pulmonary aspergillosis. | 2001 Sep 1 |
|
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
Fri Dec 15 15:11:55 GMT 2023
by
admin
on
Fri Dec 15 15:11:55 GMT 2023
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Record UNII |
883WKN7W8X
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C521
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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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