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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:11 UTC
Update Date2017-10-23 19:04:01 UTC
HMDB IDHMDB0002802
Secondary Accession Numbers
  • HMDB02802
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
SynonymsNot Available
Chemical FormulaC21H28O5
Average Molecular Weight360.444
Monoisotopic Molecular Weight360.193674006
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number53-06-5
SMILESNot Available
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 KeyMFYSYFVPBJMHGN-ZPOLXVRWSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Physiological effect

Health effect:

  Health condition:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

  Organ and components:

    Endocrine gland:

  Cell and elements:

    Cell:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

Role

Industrial application:

Biological role:

  Molecular messenger:

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 PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kf-2910000000-da435cee921dd7b9f8e6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05ai-5879000000-d8ce750671bf51b487e2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0f79-2918800000-ab308a6a5023c34bc22fView in MoNA
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
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03di-3940000000-16be8720b1c49cea9b06View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-0009000000-6c22c083c2dfab97a299View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-0109000000-48c96b3d1471c5cd6171View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-002r-0914000000-2466a9146383b4265e42View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000i-0900000000-214430a00501054cc774View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-059j-1900000000-0e23516e07f0baf74c79View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0abj-1900000000-ad0282ab7188d9ec3dc1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0aba-3900000000-e36e464b157b3e6159f1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4j-5900000000-fe9092d76099e1e70a4eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0aou-6900000000-1b218b97a890ac7e8f45View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03fr-0049000000-3bd424d473bdadd2b9b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-0039000000-fd181dfb87e1cbb8ab6fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-0049000000-7633496a1a53bda21707View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-0009000000-59db5e627634e4be3907View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-0009000000-9781e204df305d722d2dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-0009000000-0b5e40226163a1a334dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0009000000-946472abc72d41b1633cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003u-0149000000-efb3f94efcbdfc468859View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5j-2392000000-d014016e46f2ae8b1bd1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-1c4a8c3698ff1bfa2bd9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-2029000000-82b546174619108311f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-8093000000-47f7996c84edb1324aadView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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/PathwhizKEGG
11-beta-hydroxylase deficiency (CYP11B1)Pw000551Pw000551 greyscalePw000551 simpleNot Available
17-alpha-hydroxylase deficiency (CYP17)Pw000542Pw000542 greyscalePw000542 simpleNot Available
21-hydroxylase deficiency (CYP21)Pw000552Pw000552 greyscalePw000552 simpleNot Available
3-Beta-Hydroxysteroid Dehydrogenase DeficiencyPw000695Pw000695 greyscalePw000695 simpleNot Available
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase DeficiencyPw000177Pw000177 greyscalePw000177 simpleNot Available
Displaying entries 1 - 5 of 11 in total
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 Quantified Adult (>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. [PubMed: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. [PubMed: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
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:16899581 ]
  6. Weigand A, Hinzpeter B, Schicha H: [Deterioration of endocrine ophthalmology after radioiodine therapy in Graves' disease?]. Nuklearmedizin. 1998;37(7):234-8. [PubMed: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. [PubMed: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. [PubMed:15734867 ]
  9. Pepe GJ, Albrecht ED: Regulation of the primate fetal adrenal cortex. Endocr Rev. 1990 Feb;11(1):151-76. [PubMed:2180686 ]
  10. Boman HG: Innate immunity and the normal microflora. Immunol Rev. 2000 Feb;173:5-16. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:16079253 ]
  14. Ferrari P, Bianchetti M, Frey FJ: Juvenile hypertension, the role of genetically altered steroid metabolism. Horm Res. 2001;55(5):213-23. [PubMed: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. [PubMed: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. [PubMed: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