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Identification
NameCortisone acetate
Accession NumberDB01380
TypeSmall Molecule
GroupsApproved
Description

Cortisone acetate is a steroid hormone that has both glucocoriticoid and mineral corticoid activities. Corticosteroids are used to provide relief for inflamed areas of the body. They lessen swelling, redness, itching, and allergic reactions. They are often used as part of the treatment for a number of different diseases, such as severe allergies or skin problems, asthma, or arthritis. Endogenous glucocorticoids and some synthetic corticoids have high affinity to the protein transcortin (also called CBG, corticosteroid-binding protein), whereas all of them bind albumin. Glucocorticoids also bind to the cytosolic glucocorticoid receptor.

Structure
Thumb
Synonyms
Cortisyl
Cortone acetate
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Cortisone Acetate Tab 25mgtablet25 mgoralValeant Canada Lp Valeant Canada S.E.C.1973-12-31Not applicableCanada
Cortone Sus 50mg/mlsuspension50 mgintramuscularMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1951-12-311999-08-06Canada
Cortone Tab 25mgtablet25 mgoralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1954-12-312002-07-29Canada
Cortone Tab 5mgtablet5 mgoralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1951-12-312002-07-29Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Cortisone Acetatetablet25 mg/1oralWest ward Pharmaceutical Corp1972-06-13Not applicableUs
Cortisone Acetatetablet25 mg/1oralGolden State Medical Supply, Inc.1972-06-13Not applicableUs
Cortisone Acetatetablet25 mg/1oralHikma Pharmaceutical2013-08-26Not applicableUs
Cortisone Acetatetablet25 mg/1oralWest ward Pharmaceutical Corp2013-08-22Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
Cortone Acetate MSD
Brand mixturesNot Available
SaltsNot Available
Categories
UNII883WKN7W8X
CAS number50-04-4
WeightAverage: 402.4807
Monoisotopic: 402.204238692
Chemical FormulaC23H30O6
InChI KeyInChIKey=ITRJWOMZKQRYTA-RFZYENFJSA-N
InChI
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
IUPAC Name
2-[(1S,2R,10S,11S,14R,15S)-14-hydroxy-2,15-dimethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]-2-oxoethyl acetate
SMILES
[H][C@@]12CC[C@](O)(C(=O)COC(C)=O)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassPregnane steroids
Direct ParentGluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 20-oxosteroid
  • 17-hydroxysteroid
  • Oxosteroid
  • 11-oxosteroid
  • Hydroxysteroid
  • 3-oxosteroid
  • 3-oxo-delta-4-steroid
  • Delta-4-steroid
  • Alpha-acyloxy ketone
  • Cyclohexanone
  • Acetate salt
  • Tertiary alcohol
  • Cyclic alcohol
  • Alpha-hydroxy ketone
  • Cyclic ketone
  • Ketone
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
  • C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C08173 )
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030120 )
Pharmacology
IndicationFor the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses. Also used to treat endocrine (hormonal) disorders (adrenal insufficiency, Addisons disease). It is also used to treat many immune and allergic disorders.
PharmacodynamicsAs a glucocorticoid agent, cortisone acetate changes genetic transcription levels causing varied metabolic effects and a modified immune response to varied stimuli. lucocorticoids suppress cell-mediated immunity. They act by inhibiting genes that code for the cytokines IL-1, IL-2, IL-3, IL-4, IL-5, IL-6, IL-8 and TNF-alpha, the most important of which is the IL-2. Reduced cytokine production limits T cell proliferation. Glucocorticoids also suppress humoral immunity, causing B cells to express lower amounts of IL-2 and IL-2 receptors. This diminishes both B cell clonal expansion and antibody synthesis. The diminished amounts of IL-2 also leads to fewer T lymphocyte cells being activated.
Mechanism of actionCortisone 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. The anti-inflammatory actions of corticosteroids are thought to involve lipocortins, phospholipase A2 inhibitory proteins which, through inhibition arachidonic acid, control the biosynthesis of prostaglandins and leukotrienes. Specifically glucocorticoids induce lipocortin-1 (annexin-1) synthesis, which then binds to cell membranes preventing the phospholipase A2 from coming into contact with its substrate arachidonic acid. This leads to diminished eicosanoid production. The cyclooxygenase (both COX-1 and COX-2) expression is also suppressed, potentiating the effect. In other words, the two main products in inflammation Prostaglandins and Leukotrienes are inhibited by the action of Glucocorticoids. Glucocorticoids also stimulate the lipocortin-1 escaping to the extracellular space, where it binds to the leukocyte membrane receptors and inhibits various inflammatory events: epithelial adhesion, emigration, chemotaxis, phagocytosis, respiratory burst and the release of various inflammatory mediators (lysosomal enzymes, cytokines, tissue plasminogen activator, chemokines etc.) from neutrophils, macrophages and mastocytes. Additionally the immune system is suppressed by corticosteroids due to a decrease in the function of the lymphatic system, a reduction in immunoglobulin and complement concentrations, the precipitation of lymphocytopenia, and interference with antigen-antibody binding.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationCorticosteroids are metabolized primarily in the liver and are then excreted by the kidneys. Some of the topical corticosteroids and their metabolites are also excreted into the bile.
Half lifeNot Available
ClearanceNot Available
ToxicitySide effects include inhibition of bone formation, suppression of calcium absorption, delayed wound healing and hyperglycemia.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.983
Blood Brain Barrier+0.9851
Caco-2 permeable-0.6606
P-glycoprotein substrateSubstrate0.7382
P-glycoprotein inhibitor IInhibitor0.7341
P-glycoprotein inhibitor IIInhibitor0.5925
Renal organic cation transporterNon-inhibitor0.7452
CYP450 2C9 substrateNon-substrate0.8551
CYP450 2D6 substrateNon-substrate0.9294
CYP450 3A4 substrateSubstrate0.7841
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9556
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8588
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9246
Ames testNon AMES toxic0.9409
CarcinogenicityNon-carcinogens0.9551
BiodegradationNot ready biodegradable0.9354
Rat acute toxicity2.1280 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9599
hERG inhibition (predictor II)Non-inhibitor0.6638
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Tabletoral25 mg/1
Tabletoral25 mg
Suspensionintramuscular50 mg
Tabletoral5 mg
Prices
Unit descriptionCostUnit
Cortisone acetate powder24.18USD g
Cortisone Acetate 25 mg Tablet0.47USD tablet
Cortisone 25 mg tablet0.46USD tablet
Cortaid 1% cream0.21USD g
CVS Pharmacy cortisone 1% cream0.18USD g
CVS Pharmacy anti-itch 1% cream0.13USD g
Hydrocortisone 0.5% cream0.11USD g
Medi-cortisone 1% cream0.1USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point227-229Reichstein,T.; US. Patent 2,403,683; July 9, 1946. Gallagher,T.F.; US. Patent 2,447,325; August 17,1948; assigned to Research Corporation. Sarett, L.H.; U.S. Patent 2,541,104; February 13, 1951; assigned to Merck & Co., Inc.
water solubility20 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP2.10HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0278 mg/mLALOGPS
logP2.35ALOGPS
logP2.1ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)12.6ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area97.74 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity105.63 m3·mol-1ChemAxon
Polarizability43.25 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

Reichstein,T.; US. Patent 2,403,683; July 9, 1946.
Gallagher,T.F.; US. Patent 2,447,325; August 17,1948; assigned to Research Corporation.
Sarett, L.H.; U.S. Patent 2,541,104; February 13, 1951; assigned to Merck & Co., Inc.

General ReferencesNot Available
External Links
ATC CodesH02AB10S01BA03
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (74.3 KB)
Interactions
Drug Interactions
Drug
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Cortisone acetate.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Cortisone acetate.
AldesleukinCortisone acetate may decrease the antineoplastic activities of Aldesleukin.
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Cortisone acetate.
Aluminum hydroxideThe bioavailability of Cortisone acetate can be decreased when combined with Aluminum hydroxide.
Amphotericin BCortisone acetate may increase the hypokalemic activities of Amphotericin B.
AprepitantThe serum concentration of Cortisone acetate can be increased when it is combined with Aprepitant.
Atracurium besylateAtracurium besylate may increase the adverse neuromuscular activities of Cortisone acetate.
Benzoic AcidThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Cortisone acetate.
CalcitriolThe therapeutic efficacy of Calcitriol can be decreased when used in combination with Cortisone acetate.
Calcium carbonateThe bioavailability of Cortisone acetate can be decreased when combined with Calcium carbonate.
CanagliflozinThe therapeutic efficacy of Canagliflozin can be decreased when used in combination with Cortisone acetate.
CapromabCortisone acetate may decrease effectiveness of Capromab as a diagnostic agent.
CeritinibCortisone acetate may increase the hyperglycemic activities of Ceritinib.
ChlorotrianiseneThe serum concentration of Cortisone acetate can be increased when it is combined with Chlorotrianisene.
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Cortisone acetate.
ColesevelamColesevelam can cause a decrease in the absorption of Cortisone acetate resulting in a reduced serum concentration and potentially a decrease in efficacy.
Corticorelin ovine triflutateThe therapeutic efficacy of Corticorelin can be decreased when used in combination with Cortisone acetate.
DeferasiroxThe risk or severity of adverse effects can be increased when Cortisone acetate is combined with Deferasirox.
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Cortisone acetate.
DesmopressinThe risk or severity of adverse effects can be increased when Cortisone acetate is combined with Desmopressin.
DihydrotestosteroneCortisone acetate may increase the fluid retaining activities of Dihydrotestosterone.
FosaprepitantThe serum concentration of Cortisone acetate can be increased when it is combined with Fosaprepitant.
GliclazideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Cortisone acetate.
GlimepirideThe therapeutic efficacy of Glimepiride can be decreased when used in combination with Cortisone acetate.
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Cortisone acetate.
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Cortisone acetate.
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Cortisone acetate.
IcosapentThe risk or severity of adverse effects can be increased when Cortisone acetate is combined with Icosapent.
IndacaterolIndacaterol may increase the hypokalemic activities of Cortisone acetate.
Insulin AspartThe therapeutic efficacy of Insulin Aspart can be decreased when used in combination with Cortisone acetate.
Insulin DetemirThe therapeutic efficacy of Insulin Detemir can be decreased when used in combination with Cortisone acetate.
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be decreased when used in combination with Cortisone acetate.
Insulin GlulisineThe therapeutic efficacy of Insulin Glulisine can be decreased when used in combination with Cortisone acetate.
Insulin HumanThe therapeutic efficacy of Insulin Regular can be decreased when used in combination with Cortisone acetate.
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be decreased when used in combination with Cortisone acetate.
IsoniazidThe serum concentration of Isoniazid can be decreased when it is combined with Cortisone acetate.
LeflunomideThe risk or severity of adverse effects can be increased when Cortisone acetate is combined with Leflunomide.
LinagliptinThe therapeutic efficacy of Linagliptin can be decreased when used in combination with Cortisone acetate.
Magnesium oxideThe bioavailability of Cortisone acetate can be decreased when combined with Magnesium oxide.
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Cortisone acetate.
MifepristoneThe therapeutic efficacy of Cortisone acetate can be decreased when used in combination with Mifepristone.
MitotaneThe serum concentration of Cortisone acetate can be decreased when it is combined with Mitotane.
NatalizumabThe risk or severity of adverse effects can be increased when Cortisone acetate is combined with Natalizumab.
NelfinavirThe serum concentration of Cortisone acetate can be increased when it is combined with Nelfinavir.
NicorandilThe risk or severity of adverse effects can be increased when Cortisone acetate is combined with Nicorandil.
OxandroloneCortisone acetate may increase the fluid retaining activities of Oxandrolone.
PhenytoinThe serum concentration of Cortisone acetate can be decreased when it is combined with Phenytoin.
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Cortisone acetate.
RepaglinideThe therapeutic efficacy of Repaglinide can be decreased when used in combination with Cortisone acetate.
RoflumilastRoflumilast may increase the immunosuppressive activities of Cortisone acetate.
SaxagliptinThe therapeutic efficacy of Saxagliptin can be decreased when used in combination with Cortisone acetate.
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Cortisone acetate.
Somatropin recombinantThe therapeutic efficacy of Cortisone acetate can be decreased when used in combination with Somatropin recombinant.
SparfloxacinThe risk or severity of adverse effects can be increased when Cortisone acetate is combined with Sparfloxacin.
TacrineThe risk or severity of adverse effects can be increased when Cortisone acetate is combined with Tacrine.
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with Cortisone acetate.
TelaprevirThe serum concentration of Telaprevir can be decreased when it is combined with Cortisone acetate.
TesamorelinThe serum concentration of the active metabolites of Cortisone acetate can be reduced when Cortisone acetate is used in combination with Tesamorelin resulting in a loss in efficacy.
TestosteroneCortisone acetate may increase the fluid retaining activities of Testosterone.
TofacitinibCortisone acetate may increase the immunosuppressive activities of Tofacitinib.
TolbutamideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Cortisone acetate.
TorasemideCortisone acetate may increase the hypokalemic activities of Torasemide.
TrastuzumabTrastuzumab may increase the neutropenic activities of Cortisone acetate.
TrichlormethiazideCortisone acetate may increase the hypokalemic activities of Trichlormethiazide.
VildagliptinThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Cortisone acetate.
WarfarinCortisone acetate may increase the anticoagulant activities of Warfarin.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modulator of other transcription factors. Affects inflammatory responses, cellular proliferation and differentiation in target tissues. Could act as a coactivator for STAT5-dependent transcription upon grow...
Gene Name:
NR3C1
Uniprot ID:
P04150
Molecular Weight:
85658.57 Da
References
  1. Grossman R, Yehuda R, Golier J, McEwen B, Harvey P, Maria NS: Cognitive effects of intravenous hydrocortisone in subjects with PTSD and healthy control subjects. Ann N Y Acad Sci. 2006 Jul;1071:410-21. [PubMed:16891588 ]
  2. Rautanen A, Eriksson JG, Kere J, Andersson S, Osmond C, Tienari P, Sairanen H, Barker DJ, Phillips DI, Forsen T, Kajantie E: Associations of body size at birth with late-life cortisol concentrations and glucose tolerance are modified by haplotypes of the glucocorticoid receptor gene. J Clin Endocrinol Metab. 2006 Nov;91(11):4544-51. Epub 2006 Aug 8. [PubMed:16895953 ]
  3. Hammer F, Stewart PM: Cortisol metabolism in hypertension. Best Pract Res Clin Endocrinol Metab. 2006 Sep;20(3):337-53. [PubMed:16980198 ]
  4. Shaw JR, Gabor K, Hand E, Lankowski A, Durant L, Thibodeau R, Stanton CR, Barnaby R, Coutermarsh B, Karlson KH, Sato JD, Hamilton JW, Stanton BA: Role of glucocorticoid receptor in acclimation of killifish (Fundulus heteroclitus) to seawater and effects of arsenic. Am J Physiol Regul Integr Comp Physiol. 2007 Feb;292(2):R1052-60. Epub 2006 Oct 12. [PubMed:17038445 ]
  5. Sher L: Combined dexamethasone suppression-corticotropin-releasing hormone stimulation test in studies of depression, alcoholism, and suicidal behavior. ScientificWorldJournal. 2006 Oct 31;6:1398-404. [PubMed:17086345 ]
  6. Schlechte JA, Ginsberg BH, Sherman BM: Regulation of the glucocorticoid receptor in human lymphocytes. J Steroid Biochem. 1982 Jan;16(1):69-74. [PubMed:7062741 ]
  7. Schlechte JA, Sherman BM: Decreased glucocorticoid receptor binding in adrenal insufficiency. J Clin Endocrinol Metab. 1982 Jan;54(1):145-9. [PubMed:7054210 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Ekins S, Bravi G, Wikel JH, Wrighton SA: Three-dimensional-quantitative structure activity relationship analysis of cytochrome P-450 3A4 substrates. J Pharmacol Exp Ther. 1999 Oct;291(1):424-33. [PubMed:10490933 ]
  3. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Comments
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Drug created on July 06, 2007 14:32 / Updated on August 19, 2016 10:26