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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:19 UTC
HMDB IDHMDB0014773
Secondary Accession Numbers
  • HMDB14773
Metabolite Identification
Common NamePrednisone
DescriptionPrednisone is only found in individuals that have used or taken this drug. It is a synthetic anti-inflammatory glucocorticoid derived from cortisone. It is biologically inert and converted to prednisolone in the liver. [PubChem]Prednisone is a glucocorticoid receptor agonist. It is first metabolized in the liver to its active form, prednisolone. Prednisolone crosses cell membranes and binds with high affinity to specific cytoplasmic receptors. The result includes inhibition of leukocyte infiltration at the site of inflammation, interference in the function of mediators of inflammatory response, suppression of humoral immune responses, and reduction in edema or scar tissue. The antiinflammatory actions of corticosteroids are thought to involve phospholipase A2 inhibitory proteins, lipocortins, which control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes.
Structure
Data?1582753219
Synonyms
ValueSource
1,2-DehydrocortisoneChEBI
1,4-Pregnadiene-17alpha,21-diol-3,11,20-trioneChEBI
17,21-Dihydroxypregna-1,4-diene-3,11,20-trioneChEBI
DehydrocortisoneChEBI
PrednisonChEBI
PrednisonaChEBI
PrednisonumChEBI
1,4-Pregnadiene-17a,21-diol-3,11,20-trioneGenerator
1,4-Pregnadiene-17α,21-diol-3,11,20-trioneGenerator
Aventis brand OF prednisoneHMDB
Diba brand OF prednisoneHMDB
Fawns and mcallan brand OF prednisoneHMDB
Halsey drug brand OF prednisoneHMDB
KortancylHMDB
Lichtenstein brand OF prednisoneHMDB
Merck brand OF prednisoneHMDB
OrasoneHMDB
Prednison galenHMDB
PronisoneHMDB
SterapredHMDB
WinpredHMDB
Mibe brand OF prednisoneHMDB
DacortinHMDB
DecortisylHMDB
DeltasoneHMDB
EncortonHMDB
Hoechst brand OF prednisoneHMDB
PanafcortHMDB
PanasolHMDB
Prednison acsisHMDB
Schering-plough brand OF prednisoneHMDB
Solvay brand OF prednisoneHMDB
Apo-prednisoneHMDB
CortanHMDB
CutasonHMDB
DecortinHMDB
EnkortolonHMDB
GALENpharma brand OF prednisoneHMDB
ICN brand OF prednisoneHMDB
Merz brand OF prednisoneHMDB
MeticortenHMDB
PrednimentHMDB
Seatrace brand OF prednisoneHMDB
SoneHMDB
Trommsdorff brand OF prednisoneHMDB
UltracortenHMDB
Apotex brand OF prednisoneHMDB
CortancylHMDB
EncortoneHMDB
Ferring brand OF prednisoneHMDB
Hexal brand OF prednisoneHMDB
Liquid predHMDB
Pharmacia brand OF prednisoneHMDB
Predni tablinenHMDB
PrednidibHMDB
Prednison hexalHMDB
RectodeltHMDB
Acis brand OF prednisoneHMDB
delta-CortisoneHMDB
Acsis, prednisonMeSH
Chemical FormulaC21H26O5
Average Molecular Weight358.4281
Monoisotopic Molecular Weight358.178023942
IUPAC Name(1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-diene-5,17-dione
Traditional Nameprednisone
CAS Registry Number53-03-2
SMILES
[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C=C[C@]12C
InChI Identifier
InChI=1S/C21H26O5/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/h5,7,9,14-15,18,22,26H,3-4,6,8,10-11H2,1-2H3/t14-,15-,18+,19-,20-,21-/m0/s1
InChI KeyXOFYZVNMUHMLCC-ZPOLXVRWSA-N
Chemical Taxonomy
Description 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
  • 3-oxo-delta-1,4-steroid
  • 3-oxosteroid
  • 17-hydroxysteroid
  • Oxosteroid
  • 11-oxosteroid
  • Delta-1,4-steroid
  • Alpha-hydroxy ketone
  • Tertiary alcohol
  • Cyclic alcohol
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Primary alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Route of exposure:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point233 - 235 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.11 g/LNot Available
LogP0.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
logP2.07ALOGPS
logP1.66ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)12.58ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity97.57 m³·mol⁻¹ChemAxon
Polarizability38.17 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-4976000000-e89b93e4bd7a96264effSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0079-5612900000-e8fe74535be00b772cadSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-05tg-0695000000-35841a4b47ea1535be95Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0a4m-0597000000-c12dc88504062b28c4beSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0002-2960000000-10bdddfba8bd2889acdeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-0900000000-1ea12664a8edc235b05cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-1900000000-06d289c40615662ab14eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-0900000000-f76738c3bedb48d0c7a3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0019000000-d5b5ef89fce8ee6966baSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00r5-0493000000-ae479d92cc77796a5177Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00ds-0690000000-f3df1438f8c0623811c1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00dj-0970000000-b61d7f78a4036739cb07Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-05fs-0940000000-a9c08e5a06f9684fb000Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4l-0149000000-088a79de5c16e3384162Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-006w-2930000000-f901c87bc4fd3221d37eSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-05tg-0695000000-35841a4b47ea1535be95Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4m-0597000000-c12dc88504062b28c4beSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-2960000000-10bdddfba8bd2889acdeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-0019000000-be6ec5707cb4a10cdd52Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0596-0269000000-63f648937479bcaf1b1cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lr-3491000000-bbe8b03c42791ca28e7eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0019000000-70601e80fb30c3ac38c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052b-3089000000-4a4f905a7eb26d17adccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6092000000-d6e3f920b0cd1bc32f08Spectrum
MSMass Spectrum (Electron Ionization)splash10-05fs-2951000000-1a9b3a7e18f6088d28dbSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00635 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00635 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00635
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5656
KEGG Compound IDC07370
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPrednisone
METLIN IDNot Available
PubChem Compound5865
PDB IDNot Available
ChEBI ID8382
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). FDA label . .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in monooxygenase 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 xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
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 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
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 ]

Transporters

General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
References
  1. Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. [PubMed:14985103 ]
  2. Yates CR, Chang C, Kearbey JD, Yasuda K, Schuetz EG, Miller DD, Dalton JT, Swaan PW: Structural determinants of P-glycoprotein-mediated transport of glucocorticoids. Pharm Res. 2003 Nov;20(11):1794-803. [PubMed:14661924 ]
General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids
Gene Name:
SLCO1A2
Uniprot ID:
P46721
Molecular weight:
74144.1
References
  1. Bossuyt X, Muller M, Hagenbuch B, Meier PJ: Polyspecific drug and steroid clearance by an organic anion transporter of mammalian liver. J Pharmacol Exp Ther. 1996 Mar;276(3):891-6. [PubMed:8786566 ]