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Record Information
Version3.6
Creation Date2006-05-22 15:12:11 UTC
Update Date2016-05-20 16:38:37 UTC
HMDB IDHMDB02802
Secondary Accession NumbersNone
Metabolite Identification
Common NameCortisone
DescriptionCortisone is a naturally occurring glucocorticoid. It has been used in replacement therapy for adrenal insufficiency and as an anti-inflammatory agent. Cortisone itself is inactive. It is converted in the liver to the active metabolite hydrocortisone. (From Martindale, The Extra Pharmacopoeia, 30th ed, p726) -- Pubchem; Cortisone is a hormone. Chemically it is a corticosteroid with formula C21H28O5 and IUPAC name 17-hydroxy-11-dehydrocorticosterone. It is closely related to corticosterone. -- Wikipedia; One of cortisone's effects on the body, and a potentially harmful side effect when administered clinically, is the suppression of the immune system. This is an explanation for the apparent correlation between high stress and sickness. -- Wikipedia.
Structure
Thumb
Synonyms
ValueSource
11-dehydro-17-HydroxycorticosteroneChEBI
17-Hydroxy-11-dehydrocorticosteroneChEBI
17alpha,21-Dihydroxy-4-pregnene-3,11,20-trioneChEBI
4-Pregnene-17alpha,21-diol-3,11,20-trioneChEBI
CortisonChEBI
Delta(4)-Pregnene-17alpha,21-diol-3,11,20-trioneChEBI
Kendall's compound eChEBI
KortisonChEBI
Pregn-4-en-17alpha,21-diol-3,11,20-trioneChEBI
Reichstein's substance faChEBI
Wintersteiner's compound FChEBI
17a,21-Dihydroxy-4-pregnene-3,11,20-trioneGenerator
17α,21-dihydroxy-4-pregnene-3,11,20-trioneGenerator
4-Pregnene-17a,21-diol-3,11,20-trioneGenerator
4-Pregnene-17α,21-diol-3,11,20-trioneGenerator
delta(4)-Pregnene-17a,21-diol-3,11,20-trioneGenerator
δ(4)-pregnene-17α,21-diol-3,11,20-trioneGenerator
Pregn-4-en-17a,21-diol-3,11,20-trioneGenerator
Pregn-4-en-17α,21-diol-3,11,20-trioneGenerator
δ(4)-pregnene-17a,21-diol-3,11,20-trioneGenerator
AndresonHMDB
Anusol HCHMDB
Balneol-HCHMDB
beta-HCHMDB
ColocortHMDB
Compound eHMDB
CorlinHMDB
CortadrenHMDB
CortandrenHMDB
CortefHMDB
Cortef acetateHMDB
CortisalHMDB
CortisateHMDB
Cortisone acetateHMDB
CortistalHMDB
CortiviteHMDB
CortogenHMDB
CortoneHMDB
CortrilHMDB
DermacortHMDB
DricortHMDB
FlexicortHMDB
FlorinefHMDB
Fludrocortisone acetateHMDB
GlycortHMDB
Hemsol-HCHMDB
Hi-corHMDB
IncortinHMDB
Kendall'S compoundHMDB
LocoidHMDB
Locoid lipocreamHMDB
Micort-HCHMDB
Nogenic HCHMDB
Orabase hcaHMDB
PandelHMDB
Prestwick_132HMDB
Reichstein faHMDB
ScherosonHMDB
Solu-cortefHMDB
Stie-cortHMDB
TexacortHMDB
WestcortHMDB
Chemical FormulaC21H28O5
Average Molecular Weight360.444
Monoisotopic Molecular Weight360.193674006
IUPAC Name(1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,17-dione
Traditional Namecortisone
CAS Registry Number53-06-5
SMILES
[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C21H28O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h9,14-15,18,22,26H,3-8,10-11H2,1-2H3/t14-,15-,18+,19-,20-,21-/m0/s1
InChI KeyInChIKey=MFYSYFVPBJMHGN-ZPOLXVRWSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassHydroxysteroids
Direct Parent21-hydroxysteroids
Alternative Parents
Substituents
  • 21-hydroxysteroid
  • Progestogin-skeleton
  • Pregnane-skeleton
  • 20-oxosteroid
  • 17-hydroxysteroid
  • Oxosteroid
  • 11-oxosteroid
  • 3-oxosteroid
  • 3-oxo-delta-4-steroid
  • Delta-4-steroid
  • Cyclohexanone
  • Tertiary alcohol
  • Cyclic alcohol
  • Alpha-hydroxy ketone
  • Cyclic ketone
  • Ketone
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point222 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.28 mg/mL at 25 °CNot Available
LogP1.47HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.14 mg/mLALOGPS
logP1.98ALOGPS
logP1.66ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)12.58ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity96.47 m3·mol-1ChemAxon
Polarizability38.78 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0009000000-5d34de066e82cc9f0a41View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-0900000000-24ec04976da03c3f9c77View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fdo-4900000000-d0880bfc6f3d80e4aa72View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Muscle
  • Myelin
  • Nerve Cells
  • Placenta
  • Stratum Corneum
  • Testes
  • Thyroid Gland
Pathways
NameSMPDB LinkKEGG Link
11-beta-hydroxylase deficiency (CYP11B1)SMP00575Not Available
17-alpha-hydroxylase deficiency (CYP17)SMP00566Not Available
21-hydroxylase deficiency (CYP21)SMP00576Not Available
3-Beta-Hydroxysteroid Dehydrogenase DeficiencySMP00718Not Available
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase DeficiencySMP00373Not Available
Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia due to 17 Alpha-hydroxylase DeficiencySMP00372Not Available
Apparent mineralocorticoid excess syndromeSMP00717Not Available
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAHSMP00371Not Available
Corticosterone methyl oxidase I deficiency (CMO I)SMP00577Not Available
Corticosterone methyl oxidase II deficiency - CMO IISMP00578Not Available
SteroidogenesisSMP00130map00140
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0411 (0.0222 - 0.0750) uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.0380 (0.0222 - 0.0750) uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.0624 +/- 0.009 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.011 +/- 0.001 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot ApplicableAdult (>18 years old)Femaleovarian cancer details
BloodDetected and Quantified0.0466 +/- 0.0071 uMAdult (>18 years old)BothDepersonalization syndrome details
UrineDetected and Quantified0.0042 +/- 0.0011 umol/mmol creatinineAdult (>18 years old)Both
Systemic lupus erythematosus (SLE)
details
UrineDetected and Quantified0.014 +/- 0.0013 umol/mmol creatinineAdult (>18 years old)Both
Systemic lupus erythematosus (SLE)
details
UrineDetected and Quantified0.0039 +/- 0.0012 umol/mmol creatinineAdult (>18 years old)Both
Rheumatoid arthritis
details
UrineDetected and Quantified0.0070 +/- 0.0014 umol/mmol creatinineAdult (>18 years old)Both
Rheumatoid arthritis
details
Associated Disorders and Diseases
Disease References
Depersonalization disorder
  1. Nuller YL, Morozova MG, Kushnir ON, Hamper N: Effect of naloxone therapy on depersonalization: a pilot study. J Psychopharmacol. 2001 Jun;15(2):93-5. [11448093 ]
Rheumatoid arthritis
  1. Straub RH, Weidler C, Demmel B, Herrmann M, Kees F, Schmidt M, Scholmerich J, Schedel J: Renal clearance and daily excretion of cortisol and adrenal androgens in patients with rheumatoid arthritis and systemic lupus erythematosus. Ann Rheum Dis. 2004 Aug;63(8):961-8. [15249323 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023065
KNApSAcK IDNot Available
Chemspider ID193441
KEGG Compound IDC00762
BioCyc IDCORTISONE
BiGG ID35911
Wikipedia LinkCortisone
NuGOwiki LinkHMDB02802
Metagene LinkHMDB02802
METLIN ID271
PubChem Compound222786
PDB IDNot Available
ChEBI ID16962
References
Synthesis ReferenceGanis, Frank M.; Axelrod, Leonard R.; Miller, Leon L. The metabolism of hydrocortisone by kidney tissue in vitro. Journal of Biological Chemistry (1956), 218 841-8.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Bolt RJ, Van Weissenbruch MM, Popp-Snijders C, Sweep FG, Lafeber HN, Delemarre-van de Waal HA: Maturity of the adrenal cortex in very preterm infants is related to gestational age. Pediatr Res. 2002 Sep;52(3):405-10. [12193676 ]
  2. AvRuskin TW, Krishnan N, Juan CS: Congenital adrenal hypoplasia and male pseudohermaphroditism due to DAX1 mutation, SF1 mutation or neither: a patient report. J Pediatr Endocrinol Metab. 2004 Aug;17(8):1125-32. [15379426 ]
  3. Zuber M, Miesel R, Brandl B: A patient with a high titer of antinuclear antibody and a functioning adrenal tumour. Clin Rheumatol. 1995 Jan;14(1):100-3. [7743733 ]
  4. Edwin B, Raeder I, Trondsen E, Kaaresen R, Buanes T: Outpatient laparoscopic adrenalectomy in patients with Conn's syndrome. Surg Endosc. 2001 Jun;15(6):589-91. Epub 2001 Mar 13. [11591947 ]
  5. Onyimba CU, Vijapurapu N, Curnow SJ, Khosla P, Stewart PM, Murray PI, Walker EA, Rauz S: Characterisation of the prereceptor regulation of glucocorticoids in the anterior segment of the rabbit eye. J Endocrinol. 2006 Aug;190(2):483-93. [16899581 ]
  6. Weigand A, Hinzpeter B, Schicha H: [Deterioration of endocrine ophthalmology after radioiodine therapy in Graves' disease?] Nuklearmedizin. 1998;37(7):234-8. [9830613 ]
  7. Mark PJ, Waddell BJ: P-glycoprotein restricts access of cortisol and dexamethasone to the glucocorticoid receptor in placental BeWo cells. Endocrinology. 2006 Nov;147(11):5147-52. Epub 2006 Jul 27. [16873536 ]
  8. Sandeep TC, Andrew R, Homer NZ, Andrews RC, Smith K, Walker BR: Increased in vivo regeneration of cortisol in adipose tissue in human obesity and effects of the 11beta-hydroxysteroid dehydrogenase type 1 inhibitor carbenoxolone. Diabetes. 2005 Mar;54(3):872-9. [15734867 ]
  9. Pepe GJ, Albrecht ED: Regulation of the primate fetal adrenal cortex. Endocr Rev. 1990 Feb;11(1):151-76. [2180686 ]
  10. Boman HG: Innate immunity and the normal microflora. Immunol Rev. 2000 Feb;173:5-16. [10719663 ]
  11. Andrew R, Westerbacka J, Wahren J, Yki-Jarvinen H, Walker BR: The contribution of visceral adipose tissue to splanchnic cortisol production in healthy humans. Diabetes. 2005 May;54(5):1364-70. [15855321 ]
  12. Sharma KK, Lindqvist A, Zhou XJ, Auchus RJ, Penning TM, Andersson S: Deoxycorticosterone inactivation by AKR1C3 in human mineralocorticoid target tissues. Mol Cell Endocrinol. 2006 Mar 27;248(1-2):79-86. Epub 2005 Dec 5. [16337083 ]
  13. Draper N, Stewart PM: 11beta-hydroxysteroid dehydrogenase and the pre-receptor regulation of corticosteroid hormone action. J Endocrinol. 2005 Aug;186(2):251-71. [16079253 ]
  14. Ferrari P, Bianchetti M, Frey FJ: Juvenile hypertension, the role of genetically altered steroid metabolism. Horm Res. 2001;55(5):213-23. [11740142 ]
  15. Stormer FC, Reistad R, Alexander J: Glycyrrhizic acid in liquorice--evaluation of health hazard. Food Chem Toxicol. 1993 Apr;31(4):303-12. [8386690 ]
  16. Jiang JQ, Wang DS, Senthilkumaran B, Kobayashi T, Kobayashi HK, Yamaguchi A, Ge W, Young G, Nagahama Y: Isolation, characterization and expression of 11beta-hydroxysteroid dehydrogenase type 2 cDNAs from the testes of Japanese eel (Anguilla japonica) and Nile tilapia (Oreochromis niloticus). J Mol Endocrinol. 2003 Oct;31(2):305-15. [14519098 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7-alpha,12-alpha-dihydroxy-4-cholesten-3-one and 7-alpha-hydroxy-4-cholesten-3-one can also act as substrates.
Gene Name:
AKR1D1
Uniprot ID:
P51857
Molecular weight:
32889.38
Reactions
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione + NADP → Cortisonedetails
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione + NADP → Cortisone + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the conversion of cortisol to the inactive metabolite cortisone. Modulates intracellular glucocorticoid levels, thus protecting the nonselective mineralocorticoid receptor from occupation by glucocorticoids.
Gene Name:
HSD11B2
Uniprot ID:
P80365
Molecular weight:
44126.06
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes reversibly the conversion of cortisol to the inactive metabolite cortisone. Catalyzes reversibly the conversion of 7-ketocholesterol to 7-beta-hydroxycholesterol. In intact cells, the reaction runs only in one direction, from 7-ketocholesterol to 7-beta-hydroxycholesterol (By similarity).
Gene Name:
HSD11B1
Uniprot ID:
P28845
Molecular weight:
32400.665
Reactions
Hydrocortisone + NADP → Cortisone + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Displays NADPH-dependent dicarbonyl reductase activity in vitro with 3,4-Hexanedione, 2,3-Heptanedione and 1-Phenyl-1,2- propanedione as substrates. No reductase activity is displayed in vitro with steroids, retinoids and sugars as substrates. May inhibit cell replication
Gene Name:
DHRS2
Uniprot ID:
Q13268
Molecular weight:
27438.4