CORTISONE ACETATE

US Previously Marketed

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 Search

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
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/009866s98_105lbl.pdf
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
Glucocorticoid receptor 172 Target ID: CHEMBL2034 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15705660	Agonist 2678

Conditions

Condition	Modality	Highest Phase	Product
Severe or incapacitating allergic conditions 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/009866s98_105lbl.pdf	Primary	Approved 8429	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 -4.63363211E11
Rheumatic diseases 30 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/009866s98_105lbl.pdf	Primary	Approved 8429	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 -4.63363211E11
Primary adrenocortical insufficiency 7 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/009866s98_105lbl.pdf	Primary	Approved 8429	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 -4.63363211E11

C_max

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

T_1/2

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

F_unbound

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

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:16962	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16962
ChemicalBook	CB6413305	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6413305
MolPort	MolPort-002-529-087	https://www.molport.com/shop/molecule-link/MolPort-002-529-087
ZINC	ZINC000004083557	http://zinc15.docking.org/substances/ZINC000004083557
eMolecules	29503844	https://www.emolecules.com/cgi-bin/more?vid=29503844
eMolecules	493549	https://www.emolecules.com/cgi-bin/more?vid=493549

PubMed

Title	Date	PubMed
Activities of 11beta-hydroxysteroid dehydrogenase 2 in different regions of the intestinal tract of pigs.	2001	11573149
Chemotherapy-related hemolytic-uremic syndrome following treatment of a carcinoma of the nasopharynx.	2001	11528253
15-ketodihydro-PGF2 alpha, progesterone and cortisol profiles in heifers after induction of parturition by injection of dexamethasone.	2001	11455895
Male-female differences in rat hypothalamic-pituitary-adrenal axis responses to nicotine stimulation.	2001 Apr	11403996
Dieterich's disease: avascular necrosis of the metacarpal head: a case report.	2001 Apr	11383299
[A woman with Addison's disease and a bump on the neck].	2001 Apr 20	11402756
Regression of neovascular iris vessels by intravitreal injection of crystalline cortisone.	2001 Aug	11558812
Guidance by ultrasound of intra-articular injections in the knee and hip joints.	2001 Aug	11520164
Efficacy of nonoperative treatment for lateral epicondylitis.	2001 Aug	11520020
Expression and putative role of 11 beta-hydroxysteroid dehydrogenase isozymes within the human eye.	2001 Aug	11481269
Course of placental 11beta-hydroxysteroid dehydrogenase type 2 and 15-hydroxyprostaglandin dehydrogenase mRNA expression during human gestation.	2001 Aug	11454515
[Idiopathic thrombocytopenia during pregnancy. The risk in connection with umbilical blood sampling is probably greater than the benefit].	2001 Aug 8	11526659
Increased ACTH levels do not alter renal 11beta-hydroxysteroid dehydrogenase type 2 gene expression in the sheep.	2001 Feb	11403098
Lack of mutations of type 1 11beta-hydroxysteroid dehydrogenase gene in patients with abdominal obesity.	2001 Feb-May	11428721
[Present status of studies on pulmonary aspergillosis--special reference to the pathogenesis and progression].	2001 Jan	11400689
Intravitreal injection of crystalline cortisone as treatment of pre-phthisical ocular hypotony.	2001 Jul	11561798
Serum cortisol/cortisone ratio after Synacthen stimulation.	2001 Jul	11522281
[Usefulness and necessity of unsynchronized photosolotherapy and bath-PUVA--two variants of balneophototherapy--in funded ambulatory health care].	2001 Jul	11512224
Lipoid congenital adrenal hyperplasia (CAH): patient report and a mini-review.	2001 Jul	11491137
Percutaneous conchotome muscle biopsy. A useful diagnostic and assessment tool.	2001 Jul	11469467
Effects of growth hormone replacement on cortisol metabolism in hypopituitary patients treated with cortisone acetate.	2001 Jul	11465341
Response of amoeboid and differentiating ramified microglia to glucocorticoids in postnatal rats: a lectin histochemical and ultrastructural study.	2001 Jul	11448515
'Pseudo-aldosteronism' induced by intravenous glycyrrhizin treatment of chronic hepatitis C patients.	2001 Jul	11446888
Modulation of cortisol metabolism by the growth hormone receptor antagonist pegvisomant in patients with acromegaly.	2001 Jul	11443156
Assessing systemic 11beta-hydroxysteroid dehydrogenase with serum cortisone/cortisol ratios in healthy subjects and patients with diabetes mellitus and chronic renal failure.	2001 Jul	11436185
Dehydroepiandrosterone replacement in addison's disease.	2001 Jul	11435018
Glucocorticoid induction of the glaucoma gene MYOC in human and monkey trabecular meshwork cells and tissues.	2001 Jul	11431441
11 Beta-hydroxysteroid dehydrogenase type 1 is induced in human monocytes upon differentiation to macrophages.	2001 Jul 1	11418628
Outpatient laparoscopic adrenalectomy in patients with Conn's syndrome.	2001 Jun	11591947
Activation of the hypothalamic-pituitary-adrenal axis in obesity: cause or consequence?	2001 Jun	11527096
Effect of naloxone therapy on depersonalization: a pilot study.	2001 Jun	11448093
Shock wave therapy for chronic proximal plantar fasciitis.	2001 Jun	11400894
Expression of 11 beta-hydroxysteroid dehydrogenase isoenzymes in the human pituitary: induction of the type 2 enzyme in corticotropinomas and other pituitary tumors.	2001 Jun	11397878
Modulation of 11beta-hydroxysteroid dehydrogenase isozymes by proinflammatory cytokines in osteoblasts: an autocrine switch from glucocorticoid inactivation to activation.	2001 Jun	11393780
Cortisol metabolism and the role of 11beta-hydroxysteroid dehydrogenase.	2001 Mar	11469811
Disorders of mineralocorticoid synthesis.	2001 Mar	11469810
M. tuberculosis: immunology and vaccination.	2001 Mar	11405535
Induction of 11beta-hydroxysteroid dehydrogenase type 1 but not -2 in human aortic smooth muscle cells by inflammatory stimuli.	2001 May	11377976
Witness to a miracle: the initial cortisone trial: an interview with Richard Freyberg, MD. Interview by Mary Ellen Warner.	2001 May	11357799
Aqueous chromatography utilizing pH-/temperature-responsive polymer stationary phases to separate ionic bioactive compounds.	2001 May 1	11354486
Oxidized glucocorticoids counteract glucocorticoid-induced apoptosis in murine thymocytes in vitro.	2001 May 18	11411790
The 11beta hydroxysteroid dehydrogenase 2 exists as an inactive dimer.	2001 Nov	11576624
Effect of glucocorticoid excess on the cortisol/cortisone ratio.	2001 Nov	11576621
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	11576618
The immune haemolytic anaemias: a century of exciting progress in understanding.	2001 Sep	11564063
Glucocorticoid metabolism and adrenocortical reactivity to ACTH in myotonic dystrophy.	2001 Sep	11549662
[Chronic respiratory failure and osteoporosis: a difficult problem to unravel].	2001 Sep	11547239
Intraocular injection of crystalline cortisone as adjunctive treatment of diabetic macular edema.	2001 Sep	11530068
Impaired antifungal effector activity but not inflammatory cell recruitment in interleukin-6-deficient mice with invasive pulmonary aspergillosis.	2001 Sep 1	11494166
Determination of natural corticosteroids in urine samples from sportsmen.	2001 Sep 15	11585134

Patents

Sample Use Guides

In Vivo Use Guide

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

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

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

Common Name

English

CORTISONE ACETICUM

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