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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
Structure of Cortisone acetate

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

HIDE SMILES / InChI

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

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
SOLU-CORTEF

Approved Use

Treatment 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 Date

1955
Primary
SOLU-CORTEF

Approved Use

Treatment 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 Date

1955
Primary
SOLU-CORTEF

Approved Use

When 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 Date

1955
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
4109 nM × h
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

Funbound

ValueDoseCo-administeredAnalytePopulation
16.2%
CORTISONE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: MALE
food status: UNKNOWN
PubMed

PubMed

TitleDatePubMed
The excretion of free cortisol, cortisone, cortisol sulfate and cortisone sulfate in peripheral vascular disease, diabetes mellitus and hyperthyroidism.
1978 Nov
Innate immunity and the normal microflora.
2000 Feb
Fetal endocrine signals and preterm labor.
2001
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
Diagnosis of adrenal cortical dysfunction by liquid chromatography-tandem mass spectrometry.
2001 Apr
Light and electron microscopy localization of the 11beta-hydroxysteroid dehydrogenase type I enzyme in the rat.
2001 Apr
[Idiopathic thrombocytopenia during pregnancy. The risk in connection with umbilical blood sampling is probably greater than the benefit].
2001 Aug 8
Plasma cortisol, cortisone and urinary glucocorticoid metabolites in preterm infants.
2001 Feb
Use of salivary biomarkers in biobehavioral research: cotton-based sample collection methods can interfere with salivary immunoassay results.
2001 Feb
[Serious life events and congenital malformations. A national study with a complete follow-up].
2001 Feb 19
[Microbiological and immunological monitoring in polyarticular rheumatoid arthritis after total joint replacement].
2001 Feb 9
[Present status of studies on pulmonary aspergillosis--special reference to the pathogenesis and progression].
2001 Jan
Neuroendocrine consequences of very early weaning in swine.
2001 Jan
Human cervical tissue metabolizes the tobacco-specific nitrosamine, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, via alpha-hydroxylation and carbonyl reduction pathways.
2001 Jan
[Usefulness and necessity of unsynchronized photosolotherapy and bath-PUVA--two variants of balneophototherapy--in funded ambulatory health care].
2001 Jul
Assessing systemic 11beta-hydroxysteroid dehydrogenase with serum cortisone/cortisol ratios in healthy subjects and patients with diabetes mellitus and chronic renal failure.
2001 Jul
Glucocorticoid induction of the glaucoma gene MYOC in human and monkey trabecular meshwork cells and tissues.
2001 Jul
Functional expression, characterization, and purification of the catalytic domain of human 11-beta -hydroxysteroid dehydrogenase type 1.
2001 Jun 15
Cortisol metabolism and the role of 11beta-hydroxysteroid dehydrogenase.
2001 Mar
Defective cortisone 11-oxoreductase activity?
2001 Mar
Tissue-specific dysregulation of cortisol metabolism in human obesity.
2001 Mar
Decreased gene expression of 11beta-hydroxysteroid dehydrogenase type 2 and 15-hydroxyprostaglandin dehydrogenase in human placenta of patients with preeclampsia.
2001 Mar
A mutation in the cofactor-binding domain of 11beta-hydroxysteroid dehydrogenase type 2 associated with mineralocorticoid hypertension.
2001 Mar
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
Oxidized glucocorticoids counteract glucocorticoid-induced apoptosis in murine thymocytes in vitro.
2001 May 18
Calcium inhibits human placental 11beta-hydroxysteroid dehydrogenase type 2 activity.
2001 May 18
Effect of glucocorticoid excess on the cortisol/cortisone ratio.
2001 Nov
Determination of natural corticosteroids in urine samples from sportsmen.
2001 Sep 15
Patents

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
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 Mon Mar 31 17:49:52 GMT 2025
Edited
by admin
on Mon Mar 31 17:49:52 GMT 2025
Record UNII
883WKN7W8X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Cortisone acetate
EP   MART.   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
Common Name English
CORTISONE ACETICUM
HPUS  
Preferred Name English
CORTISONE ACETATE [JAN]
Common Name English
CORTISONE ACETATE [EP MONOGRAPH]
Common Name English
CORTISONE ACETATE [ORANGE BOOK]
Common Name English
Cortisone acetate [WHO-DD]
Common Name English
17,21-Dihydroxypregn-4-ene-3,11,20-trione 21-acetate
Systematic Name English
CORTISONE ACETATE [VANDF]
Common Name English
CORTISONE ACETATE [USP MONOGRAPH]
Common Name English
HYDROCORTISONE ACETATE IMPURITY D [EP IMPURITY]
Common Name English
CORTISONE 21-ACETATE [MI]
Common Name English
CORTONE
Brand Name English
CORTISONE ACETATE [MART.]
Common Name English
CORTISONE ACETATE [USP-RS]
Common Name English
CORTISONE 21-ACETATE
MI  
Common Name English
NSC-49420
Code English
PREGN-4-ENE-3,11,20-TRIONE, 21-(ACETYLOXY)-17-HYDROXY-
Systematic Name English
CORTISONE ACETICUM [HPUS]
Common Name English
17-HYDROXY-3,11,20-TRIOXOPREGN-4-EN-21-YL ACETATE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C521
Created by admin on Mon Mar 31 17:49:52 GMT 2025 , Edited by admin on Mon Mar 31 17:49:52 GMT 2025
Code System Code Type Description
DAILYMED
883WKN7W8X
Created by admin on Mon Mar 31 17:49:52 GMT 2025 , Edited by admin on Mon Mar 31 17:49:52 GMT 2025
PRIMARY
DRUG CENTRAL
734
Created by admin on Mon Mar 31 17:49:52 GMT 2025 , Edited by admin on Mon Mar 31 17:49:52 GMT 2025
PRIMARY
EVMPD
SUB01467MIG
Created by admin on Mon Mar 31 17:49:52 GMT 2025 , Edited by admin on Mon Mar 31 17:49:52 GMT 2025
PRIMARY
MERCK INDEX
m3795
Created by admin on Mon Mar 31 17:49:52 GMT 2025 , Edited by admin on Mon Mar 31 17:49:52 GMT 2025
PRIMARY Merck Index
CAS
50-04-4
Created by admin on Mon Mar 31 17:49:52 GMT 2025 , Edited by admin on Mon Mar 31 17:49:52 GMT 2025
PRIMARY
NCI_THESAURUS
C1058
Created by admin on Mon Mar 31 17:49:52 GMT 2025 , Edited by admin on Mon Mar 31 17:49:52 GMT 2025
PRIMARY
FDA UNII
883WKN7W8X
Created by admin on Mon Mar 31 17:49:52 GMT 2025 , Edited by admin on Mon Mar 31 17:49:52 GMT 2025
PRIMARY
MESH
C015087
Created by admin on Mon Mar 31 17:49:52 GMT 2025 , Edited by admin on Mon Mar 31 17:49:52 GMT 2025
PRIMARY
ChEMBL
CHEMBL1650
Created by admin on Mon Mar 31 17:49:52 GMT 2025 , Edited by admin on Mon Mar 31 17:49:52 GMT 2025
PRIMARY
EPA CompTox
DTXSID0022858
Created by admin on Mon Mar 31 17:49:52 GMT 2025 , Edited by admin on Mon Mar 31 17:49:52 GMT 2025
PRIMARY
NSC
49420
Created by admin on Mon Mar 31 17:49:52 GMT 2025 , Edited by admin on Mon Mar 31 17:49:52 GMT 2025
PRIMARY
DRUG BANK
DB01380
Created by admin on Mon Mar 31 17:49:52 GMT 2025 , Edited by admin on Mon Mar 31 17:49:52 GMT 2025
PRIMARY
PUBCHEM
5745
Created by admin on Mon Mar 31 17:49:52 GMT 2025 , Edited by admin on Mon Mar 31 17:49:52 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-006-5
Created by admin on Mon Mar 31 17:49:52 GMT 2025 , Edited by admin on Mon Mar 31 17:49:52 GMT 2025
PRIMARY
RS_ITEM_NUM
1150003
Created by admin on Mon Mar 31 17:49:52 GMT 2025 , Edited by admin on Mon Mar 31 17:49:52 GMT 2025
PRIMARY
SMS_ID
100000087965
Created by admin on Mon Mar 31 17:49:52 GMT 2025 , Edited by admin on Mon Mar 31 17:49:52 GMT 2025
PRIMARY
RXCUI
21655
Created by admin on Mon Mar 31 17:49:52 GMT 2025 , Edited by admin on Mon Mar 31 17:49:52 GMT 2025
PRIMARY RxNorm
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY