U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

[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

HIDE SMILES / InChI

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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
477 nM
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

AUC

ValueDoseCo-administeredAnalytePopulation
1211 nM × h
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
23 min
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

Funbound

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

PubMed

TitleDatePubMed
Chemotherapy-related hemolytic-uremic syndrome following treatment of a carcinoma of the nasopharynx.
2001
15-ketodihydro-PGF2 alpha, progesterone and cortisol profiles in heifers after induction of parturition by injection of dexamethasone.
2001
Dieterich's disease: avascular necrosis of the metacarpal head: a case report.
2001 Apr
20beta-Hydroxysteroid dehydrogenase of the Japanese eel ovary: its cellular localization and changes in the enzymatic activity during sexual maturation.
2001 Apr
Diagnosis of adrenal cortical dysfunction by liquid chromatography-tandem mass spectrometry.
2001 Apr
Adrenal nodules in patients with congenital adrenal hyperplasia due to 21-hydroxylase deficiency: regression after adequate hormonal control.
2001 Apr
Cervical intramedullar schistosomiasis as a rare cause of acute tetraparesis.
2001 Apr
Apparent mineralocorticoid excess.
2001 Apr
Intravitreal injection of crystalline cortisone as adjunctive treatment of proliferative diabetic retinopathy.
2001 Apr
Expression of 11 beta-hydroxysteroid dehydrogenase isozymes and corticosteroid hormone receptors in primary cultures of human trophoblast and placental bed biopsies.
2001 Apr
[A woman with Addison's disease and a bump on the neck].
2001 Apr 20
Guidance by ultrasound of intra-articular injections in the knee and hip joints.
2001 Aug
Efficacy of nonoperative treatment for lateral epicondylitis.
2001 Aug
Course of placental 11beta-hydroxysteroid dehydrogenase type 2 and 15-hydroxyprostaglandin dehydrogenase mRNA expression during human gestation.
2001 Aug
[Idiopathic thrombocytopenia during pregnancy. The risk in connection with umbilical blood sampling is probably greater than the benefit].
2001 Aug 8
Increased ACTH levels do not alter renal 11beta-hydroxysteroid dehydrogenase type 2 gene expression in the sheep.
2001 Feb
Ontogeny of 11beta-hydroxysteroid dehydrogenase: activity in the placenta, kidney, colon of fetal rats and rabbits.
2001 Feb
Intravitreal injection of crystalline cortisone as treatment of pre-phthisical ocular hypotony.
2001 Jul
Serum cortisol/cortisone ratio after Synacthen stimulation.
2001 Jul
Percutaneous conchotome muscle biopsy. A useful diagnostic and assessment tool.
2001 Jul
Response of amoeboid and differentiating ramified microglia to glucocorticoids in postnatal rats: a lectin histochemical and ultrastructural study.
2001 Jul
'Pseudo-aldosteronism' induced by intravenous glycyrrhizin treatment of chronic hepatitis C patients.
2001 Jul
Modulation of cortisol metabolism by the growth hormone receptor antagonist pegvisomant in patients with acromegaly.
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
Dehydroepiandrosterone replacement in addison's disease.
2001 Jul
11 Beta-hydroxysteroid dehydrogenase type 1 is induced in human monocytes upon differentiation to macrophages.
2001 Jul 1
Outpatient laparoscopic adrenalectomy in patients with Conn's syndrome.
2001 Jun
Activation of the hypothalamic-pituitary-adrenal axis in obesity: cause or consequence?
2001 Jun
Effect of naloxone therapy on depersonalization: a pilot study.
2001 Jun
Shock wave therapy for chronic proximal plantar fasciitis.
2001 Jun
Modulation of 11beta-hydroxysteroid dehydrogenase isozymes by proinflammatory cytokines in osteoblasts: an autocrine switch from glucocorticoid inactivation to activation.
2001 Jun
Short term respiratory effects of acute exposure to chlorine due to a swimming pool accident.
2001 Jun
Functional expression, characterization, and purification of the catalytic domain of human 11-beta -hydroxysteroid dehydrogenase type 1.
2001 Jun 15
M. tuberculosis: immunology and vaccination.
2001 Mar
New ideas for medical treatment of congenital adrenal hyperplasia.
2001 Mar
Cortisol-secreting adrenal adenomas express 11beta-hydroxysteroid dehydrogenase type-2 gene yet possess low 11beta-HSD2 activity.
2001 Mar
[Reducing the need for cortisone. Does eucalyptus oil work in asthma? (interview by Brigitte Moreano].
2001 Mar 29
Witness to a miracle: the initial cortisone trial: an interview with Richard Freyberg, MD. Interview by Mary Ellen Warner.
2001 May
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
Regulation of expression of 11beta-hydroxysteroid dehydrogenase type 1 in adipose tissue: tissue-specific induction by cytokines.
2001 May
Aqueous chromatography utilizing pH-/temperature-responsive polymer stationary phases to separate ionic bioactive compounds.
2001 May 1
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
The 11beta hydroxysteroid dehydrogenase 2 exists as an inactive dimer.
2001 Nov
Effect of glucocorticoid excess on the cortisol/cortisone ratio.
2001 Nov
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
Intraocular injection of crystalline cortisone as adjunctive treatment of diabetic macular edema.
2001 Sep
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
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.
Name Type Language
CORTISONE ACETATE
EP   MART.   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
Common 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
CORTISONE ACETICUM
HPUS  
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 Fri Dec 15 15:11:55 GMT 2023 , Edited by admin on Fri Dec 15 15:11:55 GMT 2023
Code System Code Type Description
DAILYMED
883WKN7W8X
Created by admin on Fri Dec 15 15:11:55 GMT 2023 , Edited by admin on Fri Dec 15 15:11:55 GMT 2023
PRIMARY
DRUG CENTRAL
734
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PRIMARY
EVMPD
SUB01467MIG
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PRIMARY
MERCK INDEX
m3795
Created by admin on Fri Dec 15 15:11:55 GMT 2023 , Edited by admin on Fri Dec 15 15:11:55 GMT 2023
PRIMARY Merck Index
CAS
50-04-4
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PRIMARY
NCI_THESAURUS
C1058
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PRIMARY
FDA UNII
883WKN7W8X
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PRIMARY
MESH
C015087
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PRIMARY
ChEMBL
CHEMBL1650
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PRIMARY
EPA CompTox
DTXSID0022858
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PRIMARY
NSC
49420
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PRIMARY
DRUG BANK
DB01380
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PRIMARY
PUBCHEM
5745
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PRIMARY
ECHA (EC/EINECS)
200-006-5
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PRIMARY
RS_ITEM_NUM
1150003
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PRIMARY
SMS_ID
100000087965
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PRIMARY
RXCUI
21655
Created by admin on Fri Dec 15 15:11:55 GMT 2023 , Edited by admin on Fri Dec 15 15:11:55 GMT 2023
PRIMARY RxNorm