CHEBI:8382 - prednisone

ChEBI IDCHEBI:8382
ChEBI Nameprednisone
Stars
DefinitionA synthetic glucocorticoid drug that is particularly effective as an immunosuppressant, and affects virtually all of the immune system. Prednisone is a prodrug that is converted by the liver into prednisolone (a β-hydroxy group instead of the oxo group at position 11), which is the active drug and also a steroid.
Last Modified21 October 2021
DownloadsMolfile
FormulaC21H26O5
Net Charge0
Average Mass358.434
Monoisotopic Mass358.17802
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@@]21C
InChIInChI=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
InChIKeyXOFYZVNMUHMLCC-ZPOLXVRWSA-N
Wikipedia
Roles Classification
Biological Roles:
adrenergic agent  Any agent that acts on an adrenergic receptor or affects the life cycle of an adrenergic transmitter.
immunosuppressive agent  An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
hormone  Originally referring to an endogenous compound that is formed in specialized organ or group of cells and carried to another organ or group of cells, in the same organism, upon which it has a specific regulatory function, the term is now commonly used to include non-endogenous, semi-synthetic and fully synthetic analogues of such compounds.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
adrenergic agent  Any agent that acts on an adrenergic receptor or affects the life cycle of an adrenergic transmitter.
anti-inflammatory drug  A substance that reduces or suppresses inflammation.
prodrug  A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
immunosuppressive agent  An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
ChEBI Ontology
Outgoing Relation(s)
prednisone (CHEBI:8382) has role adrenergic agent (CHEBI:37962)
prednisone (CHEBI:8382) has role anti-inflammatory drug (CHEBI:35472)
prednisone (CHEBI:8382) has role antineoplastic agent (CHEBI:35610)
prednisone (CHEBI:8382) has role immunosuppressive agent (CHEBI:35705)
prednisone (CHEBI:8382) has role prodrug (CHEBI:50266)
prednisone (CHEBI:8382) is a 11-oxo steroid (CHEBI:47787)
prednisone (CHEBI:8382) is a 17α-hydroxy steroid (CHEBI:35342)
prednisone (CHEBI:8382) is a 20-oxo steroid (CHEBI:36885)
prednisone (CHEBI:8382) is a 21-hydroxy steroid (CHEBI:35344)
prednisone (CHEBI:8382) is a 3-oxo-Δ14-steroid (CHEBI:77166)
prednisone (CHEBI:8382) is a C21-steroid (CHEBI:61313)
prednisone (CHEBI:8382) is a glucocorticoid (CHEBI:24261)
prednisone (CHEBI:8382) is a primary α-hydroxy ketone (CHEBI:139590)
prednisone (CHEBI:8382) is a tertiary α-hydroxy ketone (CHEBI:139592)
Incoming Relation(s)
20α-dihydroprednisone (CHEBI:182969) has functional parent prednisone (CHEBI:8382)
20β-dihydroprednisone (CHEBI:182970) has functional parent prednisone (CHEBI:8382)
6α-hydroxyprednisone (CHEBI:180929) has functional parent prednisone (CHEBI:8382)
6β-hydroxyprednisone (CHEBI:180930) has functional parent prednisone (CHEBI:8382)
cortancyl (CHEBI:34655) has functional parent prednisone (CHEBI:8382)
Δ6-prednisone (CHEBI:180928) has functional parent prednisone (CHEBI:8382)
IUPAC Name 
17,21-dihydroxypregna-1,4-diene-3,11,20-trione
INNs  Source
prednisoneChEBI
prednisonaChemIDplus
prednisonumChemIDplus
prednisoneChemIDplus
Synonyms  Source
1,2-DehydrocortisoneChemIDplus
1,4-Pregnadiene-17α,21-diol-3,11,20-trioneChemIDplus
17,21-Dihydroxypregna-1,4-diene-3,11,20-trioneChemIDplus
DehydrocortisoneChEBI
prednisonChEBI
Manual XrefsDatabases
C07370KEGG COMPOUND
DB00635DrugBank
US2897216Patent
US2837464Patent
US3134718Patent
US2579479Patent
PrednisoneWikipedia
2253DrugCentral
Registry NumbersSources
Reaxys:2065301Reaxys
CAS:53-03-2ChemIDplus
Citations