cortisone

General Material Information

Preferred name	cortisone
Trivial Name	Cortisone
Short Description	17a,21-dihydroxy-4-pregnene-3,11,20-trione
Formula	C21 H28 O5
CAS Number	53-06-5
ECHA Number	200-162-4
FDA UNII	V27W9254FZ
Nikkaji Number	J4.139D
Beilstein Number	1356062
MDL	MFCD00003610
Bio Activity Summary	External link
NMR Predictor	External link
Synonyms	adrenalex cortadren cortandren cortisal cortisate cortistal cortivite cortone 17a,21-dihydroxy-4-pregnene-3,11,20-trione 17,21-dihydroxypregn-4-ene-3,11,20-trione 17a,21-dihydroxypregn-4-ene-3,11,20-trione 17a- hydroxy-11-dehydrocorticosterone (1S,10S,11S,15S,2R,14R)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0.0]heptadec-6-ene-5,17-dione (8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxy-acetyl)-10,13-dimethyl-1,6,7,8,9,10,12,13,14,15,16,17-dodecahydro-2H-cyclopenta[a]phenanthrene-3,11-dione (8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,11-dione (8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-7,8,9,10,12,13,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,11(2H,6H)-dione incortin kendall's compound kortison pregn-4-ene-3,11,20-trione, 17,21-dihydroxy- 4-pregnene-17a,21-diol-3,11,20-trione D4-pregnene-17a,21-diol-3,11,20-trione reichstein's substance Fa scheroson stie-cort wintersteiner's compound F (8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,11-dione 17,21-Dihydroxypregn-4-ene-3,11,20-trione Compound E (cortisone) Cortogen 11-Dehydro-17-hydroxycorticosterone 17α,21-Dihydroxy-4-pregnene-3,11,20-trione 17-Hydroxy-11-dehydrocorticosterone 17α-Hydroxy-11-dehydrocorticosterone KE Kendall's compound E Pregn-4-en-17α,21-diol-3,11,20-trione Δ4-Pregnene-17α,21-diol-3,11,20-trione 17α,21β-Dihydroxy-4-pregnene-3,11,20-trione NSC 9703 14: PN: US20220380460 SEQID: 15 claimed sequence MeSH ID: D003348

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Literature & References

	(8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,11-dione
NIST Chemistry WebBook:	Search Inchi
Pubchem (cid):	222786
Pubchem (sid):	134971011

Publications by PubMed
LC-MS/MS Method for the Simultaneous Determination of Free Urinary Steroids.
Development and validation of a high-resolution mass-spectrometry-based method to study the long-term stability of natural and synthetic glucocorticoids in faeces.
Identification of novel 11β-HSD1 inhibitors by combined ligand- and structure-based virtual screening.
High cortisol and cortisone levels are associated with breast milk dioxin concentrations in Vietnamese women.
The postprandial rise in plasma cortisol in men is mediated by macronutrient-specific stimulation of adrenal and extra-adrenal cortisol production.
Rooibos influences glucocorticoid levels and steroid ratios in vivo and in vitro: a natural approach in the management of stress and metabolic disorders?
Food protein-induced enterocolitis syndrome, from practice to theory.
[Establishment of chronic constraint stress animal model and its application in the study of hyperglycemia].
Glucocorticoids and microbiota regulate ontogeny of intestinal fucosyltransferase 2 requisite for gut homeostasis.
A validated analytical method to study the long-term stability of natural and synthetic glucocorticoids in livestock urine using ultra-high performance liquid chromatography coupled to Orbitrap-high resolution mass spectrometry.
Combined food intake and exercise unmask different hormonal responses in lean and obese children.
Fast and multiresidue determination of twenty glucocorticoids in bovine milk using ultra high performance liquid chromatography-tandem mass spectrometry.
Effects of Lactobacillus helveticus on murine behavior are dependent on diet and genotype and correlate with alterations in the gut microbiome.
11β Hydroxysteroid dehydrogenase type 2 and dietary acid load are independently associated with blood pressure in healthy children and adolescents.
Sub-therapeutic treatments of bulls with dexamethasone: direct and indirect markers of treatment.
A field survey on the presence of prednisolone and prednisone in urine samples from untreated cows.
Developmental stress has sex-specific effects on nestling growth and adult metabolic rates but no effect on adult body size or body composition in song sparrows.
Prednisolone and prednisone neo-formation in bovine urine after sampling.
Detection and quantitative analysis of 21 veterinary drugs in river water using high-pressure liquid chromatography coupled to tandem mass spectrometry.
Is cortisol a modulator of interferon tau action in the endometrium during early pregnancy in cattle?
A gene variant of 11β-hydroxysteroid dehydrogenase type 1 is associated with obesity in children.
[Detection of glucocorticoids by pressurized capillary electrochromatography with ultra-violet detection and its application in hair analysis].
Attenuation of the cortisol response to stress in female rainbow trout chronically exposed to dietary selenomethionine.
Grapefruit juice and licorice increase cortisol availability in patients with Addison's disease.
Pistacia lentiscus resin regulates intestinal damage and inflammation in trinitrobenzene sulfonic acid-induced colitis.
Corticosteroid hormone receptors and prereceptors as new biomarkers of the illegal use of glucocorticoids in meat production.
Urine metabolomics analysis for adrenal incidentaloma activity detection and biomarker discovery.
Investigation of the origin of prednisolone in cow urine.
Is glycyrrhizin sensitivity increased in anorexia nervosa and should licorice be avoided? Case report and review of the literature.
Contribution of central SGK-1 to the acute phase responses of mice to social isolation.
Repeated measurements of 11β-HSD-1 activity in subcutaneous adipose tissue from lean, abdominally obese, and type 2 diabetes subjects--no change following a mixed meal.
New in vitro dermal absorption database and the prediction of dermal absorption under finite conditions for risk assessment purposes.
Investigation on possible transformations of cortisol, cortisone and cortisol glucuronide in bovine faecal matter using liquid chromatography-mass spectrometry.
Licorice: a sweet alternative to prevent hyperkalemia in dialysis patients?
Efficacious 11beta-hydroxysteroid dehydrogenase type I inhibitors in the diet-induced obesity mouse model.
Glycyrrhetinic acid food supplementation lowers serum potassium concentration in chronic hemodialysis patients.
Omental adipose tissue type 1 11 beta-hydroxysteroid dehydrogenase oxoreductase activity, body fat distribution, and metabolic alterations in women.
Validation of a solid-phase extraction and ultra-performance liquid chromatographic tandem mass spectrometric method for the detection of 16 glucocorticoids in pig tissues.
Food restriction induces long-lasting recovery of spatial memory deficits following global ischemia in delayed matching and non-matching-to-sample radial arm maze tasks.
11beta-HSD1, inflammation, metabolic disease and age-related cognitive (dys)function.
Effect of nutrient ingestion on total-body and splanchnic cortisol production in humans.
Why is 11beta-hydroxysteroid dehydrogenase type 1 facing the endoplasmic reticulum lumen? Physiological relevance of the membrane topology of 11beta-HSD1.
Increased cortisol bioavailability, abdominal obesity, and the metabolic syndrome in obese women.
Effect of central administration of carnosine and its constituents on behaviors in chicks.
Binding of perfluorinated fatty acids to serum proteins.
Neurochemical and behavioral alterations elicited by a chronic intermittent stressor regimen: implications for allostatic load.
Shock wave therapy for chronic proximal plantar fasciitis.
Neuroendocrine consequences of very early weaning in swine.
A population physiologically based pharmacokinetic/pharmacodynamic model for the inhibition of 11-beta-hydroxysteroid dehydrogenase activity by glycyrrhetic acid.
Methotrexate use in rheumatoid arthritis. A Clinician's perspective.
Decreased type 2 corticotropin-releasing hormone receptor mRNA expression in the ventromedial hypothalamus during repeated immobilization stress.
Food as a trigger in asthma.
Influence of sampling on steroid hormone patterns of beef from bulls and steers.
Characterisation of glucocorticoid receptors in peripheral blood leukocytes of Carp, Cyprinus carpio L.
[Updates on the earlier treatments for atopic dermatitis].
Corticotropin releasing factor receptor type II (CRF2) messenger ribonucleic acid levels in the hypothalamic ventromedial nucleus of the infant rat are reduced by maternal deprivation.
A putative cortisol receptor in the rainbow trout erythrocyte: stress prevents starvation-induced increases in specific binding of cortisol
Pulmonary pathohistological changes in mice in experimental infection with Pneumocystis carinii.
Reproducibility of the dose-response curve of steroid-induced cleft palate in mice.
Factors affecting circulating growth hormone binding protein in chickens.
Plasma cortisol concentrations in dogs given cortisone or placebo by mouth.
Glycyrrhizic acid in liquorice--evaluation of health hazard.
Effect of chronic intravenous injection of steroid hormones on body weight and composition of female rats.
Etiology and treatment of fluid retention (hydrops) in Ménière's syndrome.
Steroid research at Syntex: "the pill" and cortisone.
Steroids and "the pill": early steroid research at Searle.
A reexamination of the effects of intracerebroventricular glucocorticoids in adrenalectomized rats.
Determination of cholesterol and cortisone absorption in polyurethane. I. Methodology using size-exclusion chromatography and dual detection.
Cortisone effects on growth, food efficiency, and in vitro growth hormone release.
[Experimental listeriosis in chickens: microbiological and anatomo-histopathological studies and health and hygiene considerations].
Diaphragm atrophy and weakness in cortisone-treated rats.
In vitro dissolution profile of water-insoluble drug dosage forms in the presence of surfactants.
[Polyserositic syndromes and/or sectorial dysventilation with platelet activation induced by immunoallergic etiopathogenesis].
Rats stunted by high-dose glucocorticoid treatment are capable of undergoing catch-up growth after fasting.
Analysis of prednisolone acetate and related corticoids in swine plasma by reversed-phase high-performance liquid chromatography.
Liquid chromatographic determination and identification tests for dexamethasone in bulk drugs and elixirs: collaborative study.
Enterovirus replication in porcine ileal explants.
Adrenalectomy and steroid treatment in obese (ob/ob) and diabetic (db/db) mice.
Effect of neuropeptide Y on ingestive behaviors in the rat.
Central nervous system control of hyperphagia in hypothalamic obesity: dependence on adrenal glucocorticoids.
Increase in pulsatile secretion of growth hormone during failure of catch-up growth following glucocorticoid-induced growth inhibition.
Effects of natural androgens and corticosteroids on gonad differentiation in the rainbow trout, Salmo gairdneri.
Vegan regimen with reduced medication in the treatment of bronchial asthma.
Decreased resistance to mycobacterial infection in mice fed a trichothecene compound (T-2 toxin).
Accumulation of glycoprotein gonadotropin in the pituitary of juvenile rainbow trout in response to androgens and C21-steroids, including 11-steroids.
Adrenalectomy and food restriction in the genetically obese (ob/ob) mouse.
Studies on the pathogenesis of staphylococcal osteomyelitis in chickens. I. Effect of stress on experimentally induced osteomyelitis.
Effect of cortisol on some nutritional and biochemical parameters in pregnant rats and their foetuses.
Inhibition by hypophysectomy of the hyperphagia and obesity following gold thioglucose.
Gold thioglucose-induced hypothalamic damage, hyperphagia, and obesity: dependence on the adrenal gland.
Plasma cortisol concentrations after oral substitution of cortisone in the fasting and non-fasting state.
Cytotoxic leukocyte reaction.
The effects of hypophysectomy and continuous food restriction, begun at ages 70 and 400 days, on collagen aging, proteinuria, incidence of pathology and longevity in the male rat.
Growth and food intake of prematurely weaned rats: effect of cortisone and thyroxine injection during the suckling period.
Development of sucrase activity: effect of maternal hormonal status and fetal programming of jejuno-ileal differences.
[Induction of tyrosine aminotransferase (EC 2.5.1.5) by nicotinamide in rat liver (author's transl)].
Gold thioglucose obesity syndrome.
[Effect of cortisone acetate on acid secretion induced by histamine, pentagastrin, gastrin and food in dogs].
The role of ACTH and adrenal glucocorticoids in the salt appetite of wild rabbits (Oryctolagus cuniculus (L)).
[Irreversible degradation rate of free essential amino acids in vivo].
Letter: Cleft-palate teratogens.
Ulcerative colitis. Selected clinical, diagnostic and therapeutic aspects. II.
Hypoglycemia in infancy and childhood. I.
Significance of cleft palate induced by chemicals in the rat and mouse.
Effect of diet and tryptophan on hepatic polyribosomal disaggregation due to actinomycin D.
Yam--a valuable source of food and drugs.
A rationale for the treatment of symptoms in allergic diseases.
Effects of ACTH and corticosteroids in the regulation of food and water intake.
[Effect of some azo dyes on certain pathways of anaerobic metabolism].
The effects of feeding and various hormones on the glucose tolerance of the sand rat (Psammomys obesus).
Effects of desiccated thyroid, propylthiouracil, vitamin B12 and caloric restriction on somatic growth, food intake and dentinogenesis in cortisone-treated immature albino rats.
INDUCTION OF OVULATION.
RELATIONSHIP OF FOOD INTAKE TO THE EFFECT OF CORTISONE ACETATE ON SKIN WOUND HEALING.
EFFECT OF CORTISONE, AMPUTATION, AND FOOD RESTRICTION ON GROWTH OF RAT MAXILLARY INCISORS.
MANAGEMENT OF CHILDHOOD ASTHMA. THE IMPORTANCE OF VIGOROUS THERAPY.
Effect of bacterial endotoxin on metabolism. II Protein-carbohydrate balance following cortisone. Inhibition of intestinal absorption and adrenal response to ACTH.
Thyroid function in experimental streptococcal pneumonia in the rat.
The effect of diuretics on the water excretion of protein deficient rats.
Nutritional deficiency due to age and physiologic stress; its control by food and hormones.
Relation of sodium, potassium, and chloride intake to cortisone action during food restriction.
CORTISONE and food consumption.
The effect of cortisone on the food consumption of pregnant mice.
Thyroid-cortisone antagonism in rats as measured by growth, organ weights and food utilization.
Induction of arterial hypertension in normal and adrenalectomized rats given cortisone acetate.
[Corticoid excretion in urine in normal and pathological conditions; corticoid excretion in urine in different salt contents of food].

Other Information

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KEGG (GenomeNet):	C00762
HMDB (The Human Metabolome Database):	HMDB02802
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Export Tariff Code:	2937.21.0010
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Suppliers

BOC Sciences	Glentham Life Sciences
Sigma-Aldrich: Sigma	Glentham Life Sciences Ltd

PhysChem Properties

Material listed in food chemical codex	No
Molecular weight	360.45016479492
Flash Point TCC Value	311.2 °C TCC
logP (o/w)	1.47
Solubility
water, 280 mg/L @ 25 °C (exp)	Yes
water, 297.4 mg/L @ 25 °C (est)	Yes

Safety Information

Safety information

Preferred SDS: View

Hazards identification

Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements

Pictogram

Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
pharmaceuticals / chemical synthisis
Recommendation for cortisone usage levels up to:
	not for fragrance use.

Recommendation for cortisone flavor usage levels up to:
	not for flavor use.

Safety references

EPI System: View

ClinicalTrials.gov:search

Daily Med:search

AIDS Citations:Search

Cancer Citations:Search

Toxicology Citations:Search

EPA ACToR:Toxicology Data

EPA Substance Registry Services (SRS):Registry

Laboratory Chemical Safety Summary :222786

National Institute of Allergy and Infectious Diseases:Data

WGK Germany:3

(8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,11-dione

Chemidplus:0000053065

RTECS:GM9020000 for cas# 53-06-5