CHEBI:8382 - prednisone

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ChEBI Name prednisone
ChEBI ID CHEBI:8382
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C21H26O5
Net Charge 0
Average Mass 358.42810
Monoisotopic Mass 358.17802
InChI 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
InChIKey XOFYZVNMUHMLCC-ZPOLXVRWSA-N
SMILES [H][C@@]12CCC3=CC(=O)C=C[C@]3(C)[C@@]1([H])C(=O)C[C@@]1(C)[C@@]2([H])CC[C@]1(O)C(=O)CO
Roles Classification
Biological Role(s): 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.
(via steroid hormone )
Application(s): 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.
anti-inflammatory drug
A substance that reduces or suppresses inflammation.
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.
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.
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ChEBI Ontology
Outgoing 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-Δ1,Δ4-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 Δ6-prednisone (CHEBI:180928) has functional parent prednisone (CHEBI:8382)
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)
IUPAC Name
17,21-dihydroxypregna-1,4-diene-3,11,20-trione
INNs Sources
prednisona ChemIDplus
prednisone ChEBI
prednisone ChemIDplus
prednisonum ChemIDplus
Synonyms Sources
1,2-Dehydrocortisone ChemIDplus
1,4-Pregnadiene-17α,21-diol-3,11,20-trione ChemIDplus
17,21-Dihydroxypregna-1,4-diene-3,11,20-trione ChemIDplus
Dehydrocortisone ChEBI
prednison ChEBI
Manual Xrefs Databases
2253 DrugCentral
C07370 KEGG COMPOUND
DB00635 DrugBank
Prednisone Wikipedia
US2579479 Patent
US2837464 Patent
US2897216 Patent
US3134718 Patent
View more database links
Registry Numbers Types Sources
2065301 Reaxys Registry Number Reaxys
53-03-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10438974 PubMed citation Europe PMC
15859934 PubMed citation Europe PMC
18971570 PubMed citation Europe PMC
23093541 PubMed citation Europe PMC
23395281 PubMed citation Europe PMC
Last Modified
21 October 2021