Drug/Small Molecule:
prednisone

2D structure

Overview

Generic Names: Dehydrocortisone; PRD; Prednisona [INN-Spanish]; Prednisonum [INN-Latin]
IUPAC Name: (8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,12,14,15,16-octahydrocyclopenta[a]phenanthrene-3,11-dione
Trade Names: Adasone; Ancortone; Apo-prednisone; Betapar; Bicortone; Cartancyl; Colisone; Cortan; Cortancyl; Cortidelt; Cotone; Dacorten; Dacortin; Decortancyl; Decortin; Decortisyl; Dekortin; Delcortin; Dellacort; Dellacort A; Delta Cortelan; Delta E; Delta-cortelan; Delta-cortisone; Delta-cortone; Delta-dome; Deltacortene; Deltacortisone; Deltacortone; Deltasone; Deltison; Deltisona; Deltisone; Deltra; Di-Adreson; Diadreson; Econosone; Encorton; Encortone; Enkorton; Fernisone; Fiasone; Hostacortin; In-Sone; Incocortyl; Juvason; Lisacort; Me-Korti; Metacortandracin; Meticorten; Nisona; Nizon; Novoprednisone; Nurison; Orasone; Origen Prednisone; Panafcort; Panasol; Paracort; Parmenison; Pehacort; Precort; Predeltin; Prednicen-M; Prednicorm; Prednicort; Prednicot; Prednidib; Prednilonga; Prednison; Prednisone Intensol; Prednitone; Prednizon; Prednovister; Presone; Pronison; Rectodelt; Retrocortine; Servisone; Sone; Sterapred; Supercortil; Ultracorten; Ultracortene; Winpred; Wojtab; Zenadrid
Brand Mixtures: Cortab (Biotin + Chlorpheniramine Maleate + D-Pantothenic Acid + Inositol + Nicotinic Acid + Prednisone + Pyridoxine Hydrochloride + Thiamine Mononitrate + Vitamin a + Vitamin B2 + Vitamin D + Vitamin E (Dl-Alpha Tocopheryl Acetate)); Metreton Tab (Chlorpheniramine Maleate + Prednisone + Vitamin C); Predniderm Tab (Inositol + Pheniramine Maleate + Phosphatidyl Choline + Prednisone + Vitamin a + Vitamin D2 + Vitamin E); Sterolin Liq (Biotin + Fatty Acids Unsaturated + Inositol + Nicotinic Acid + Pheniramine Maleate + Phosphatidyl Choline + Prednisone + Vitamin a Palmitate + Vitamin B2 + Vitamin D2 + Vitamin E)
PharmGKB Accession Id: PA451100

Description

A synthetic anti-inflammatory glucocorticoid derived from cortisone. It is biologically inert and converted to prednisolone in the liver. [PubChem]

Indication

For the treatment of drug-induced allergic reactions, perennial or seasonal allergic rhinitis, serum sickness, giant cell arteritis acute rheumatic or nonrheumatic carditis, systemic dermatomyositis, systemic lupus erythematosus, atopic dermatitis, contact dermatitis, exfoliative dermatitis, bullous dermatitis herpetiformis, severe seborrheic dermatitis, severe (Stevens-Johnson syndrome) erythema multiforme, mycosis fungoides, pemphigus, severe psoriasis, acute adrenocortical insufficiency, Addison's disease, secondary adrenocortical insufficiency, congenital adrenal hyperplasia, hypercalcemia associated with neoplasms, nonsuppurative thyroiditis, ulceratice colitis, Crohn's disease, acquired hemolytic anemia, congenital hypoplastic anemia, erythroblastopenia, adult secondary thrombocytopenia, adult idiopathic thrombocytopenia purpura, acute or subacute bursitis, epicondylitis, acute nonspecific tenosynovitis, acute or chronic lymphocytic leukemia, Hodgkin's or non-Hodgkin's lynphomas, Waldenstrom's macroglobulinemia, primary brain tumors (adjunct), nephrotic syndrome, tuberculous meningitis, multiple sclerosis, myasthenia gravis. cerebral edema, chorioretinitis, diffuse posterior choroiditis, aleergic conjunctivitis, Herpes zoster ophthalmicus, anterior segment inflammation, iridocyclitis, iritis, keratitis, optoc neuritis, sympathetic ophthalmia, corneal marginal allergic ulcers, symptomatic sarcoidosis, Loeffler's syndrome not manageable by other means, berylliosis, fulminating or disseminated pulmonary tuberculosis when used concurrently with appropriate antituberculous chemotherapy and aspiration pneumonitis.

ATC Therapeutic Categories

  • A07EA:Corticosteroids acting locally
  • H02AB:Glucocorticoids

Pharmacology and Interactions

Mechanism Of Action

Prednisone is a glucocorticoid 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.

Pharmacology

Prednisone, the most commonly-prescribed corticosteroid, is used to treat allograft rejection, asthma, systemic lupus erythematosus, and many other inflammatory states. Prednisone has very little mineralocorticoid activity.

Food Interactions

Avoid alcohol. Avoid taking with grapefruit juice. Take with food to reduce irritation.

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Hepatic.

Protein Binding

Extensively bound to plasma proteins.

Absorption

Readily absorbed from the gastrointestinal tract.

Half Life

2 to 3 hours

Chemical Properties

Chemical Formula:

C21H26O5

SMILES Code:

C[C@]12CC(=O)[C@H]3[C@H]([C@@H]1CC[C@@]2(C(=O)CO)O)CCC4=CC(=O)C=C[C@]34C

(Format: OpenEye Isomeric)

Molecular Weight ( average / monoisotopic )

358.4281 / 358.178

Curated Information

The following genes are in curated knowledge about this drug.

  Gene Relationship Evidence
Phenotype data available Genotype Data Available Literature annotations available Has annotations
ABCB1
  • CO
  • PD
  • PK
  •   
  • GN
Publications
No phenotype data No genotype data Literature annotations available Not annotated
CREBBP
  •   
  • PD
  •   
  •   
  •   
Pathways
Phenotype data available Genotype Data Available Literature annotations available Has annotations
CYP3A4
  • CO
  • PD
  • PK
  •   
  • GN
Publications
Phenotype data available Genotype Data Available Literature annotations available Has annotations
CYP3A5
  • CO
  • PD
  • PK
  •   
  • GN
Publications
No phenotype data No genotype data No literature annotations Not annotated
FKBP4
  •   
  • PD
  •   
  •   
  •   
Pathways
Phenotype data available Genotype Data Available Literature annotations available Not annotated
GSTM1
  • CO
  • PD
  • PK
  •   
  • GN
Publications
Phenotype data available Genotype Data Available Literature annotations available Has annotations
GSTP1
  • CO
  • PD
  • PK
  •   
  • GN
Publications
Phenotype data available Genotype Data Available Literature annotations available Not annotated
GSTT1
  • CO
  • PD
  • PK
  •   
  • GN
Publications
No phenotype data No genotype data Literature annotations available Not annotated
HSP90AA1
  •   
  • PD
  •   
  •   
  •   
Pathways
No phenotype data No genotype data Literature annotations available Not annotated
HSPA4
  •   
  • PD
  •   
  •   
  •   
Pathways
No phenotype data Genotype Data Available Literature annotations available Not annotated
IL10
  •   
  • PD
  •   
  •   
  • GN
Publications
Phenotype data available No genotype data Literature annotations available Not annotated
MSH6
  • CO
  •   
  •   
  •   
  • GN
Publications
Phenotype data available Genotype Data Available Literature annotations available Has annotations
MTHFR
  • CO
  • PD
  • PK
  •   
  • GN
Publications
No phenotype data No genotype data Literature annotations available Not annotated
NCOA3
  •   
  • PD
  •   
  •   
  •   
Pathways
Phenotype data available Genotype Data Available Literature annotations available Not annotated
NR3C1
  • CO
  • PD
  • PK
  •   
  • GN
Publications, Pathways
No phenotype data No genotype data Literature annotations available Not annotated
SAA1
  •   
  • PD
  •   
  •   
  •   
Publications
No phenotype data No genotype data Literature annotations available Not annotated
SERPINA6
  •   
  • PD
  •   
  •   
  •   
Pathways
Phenotype data available Genotype Data Available Literature annotations available Has annotations
SLC19A1
  • CO
  • PD
  • PK
  •   
  • GN
Publications
No phenotype data No genotype data No literature annotations Not annotated
ST13
  •   
  • PD
  •   
  •   
  •   
Pathways
No phenotype data Genotype Data Available No literature annotations Not annotated
TBP
  •   
  • PD
  •   
  •   
  •   
Pathways
Phenotype data available Genotype Data Available Literature annotations available Has annotations
TPMT
  • CO
  • PD
  • PK
  •   
  • GN
Publications
Phenotype data available Genotype Data Available Literature annotations available Has annotations
TYMS
  • CO
  • PD
  • PK
  •   
  • GN
Publications
Phenotype data available Genotype Data Available Literature annotations available Has annotations
UGT1A1
  • CO
  • PD
  • PK
  •   
  • GN
Publications
Phenotype data available Genotype Data Available Literature annotations available Has annotations
VDR
  • CO
  • PD
  • PK
  •   
  • GN
Publications

Non-Curated Information

A list of non-curated publications that mention this drug along with other genes is available.

Metabolizing Enzymes

Drug Targets

Non-Curated Information

A list of non-curated publications that mention this drug along with other drugs is available.

Drug Interactions

acenocoumarol The corticosteroid alters the anticoagulant effect
ambenonium The corticosteroid decreases the effect of anticholinesterases
amobarbital The barbiturate decreases the effect of the corticosteroid
anisindione The corticosteroid alters the anticoagulant effect
aprobarbital The barbiturate decreases the effect of the corticosteroid
aspirin The corticosteroid decreases the effect of salicylates
bismuth subsalicylate The corticosteroid decreases the effect of salicylates
butabarbital The barbiturate decreases the effect of the corticosteroid
butalbital The barbiturate decreases the effect of the corticosteroid
butethal The barbiturate decreases the effect of the corticosteroid
chlorotrianisene The estrogenic agent increases the effect of corticosteroid
clomifene The estrogenic agent increases the effect of corticosteroid
conjugated estrogens The estrogenic agent increases the effect of corticosteroid
dicumarol The corticosteroid alters the anticoagulant effect
diethylstilbestrol The estrogenic agent increases the effect of corticosteroid
dihydroquinidine barbiturate The barbiturate decreases the effect of the corticosteroid
edrophonium The corticosteroid decreases the effect of anticholinesterases
estradiol The estrogenic agent increases the effect of corticosteroid
estriol The estrogenic agent increases the effect of corticosteroid
estrone The estrogenic agent increases the effect of corticosteroid
estropipate The estrogenic agent increases the effect of corticosteroid
ethinyl estradiol The estrogenic agent increases the effect of corticosteroid
ethotoin The enzyme inducer decreases the effect of the corticosteroid
fosphenytoin The enzyme inducer decreases the effect of the corticosteroid
heptabarbital The barbiturate decreases the effect of the corticosteroid
hexobarbital The barbiturate decreases the effect of the corticosteroid
itraconazole The imidazole increases the effect and toxicity of the corticosteroid
ketoconazole The imidazole increases the effect and toxicity of the corticosteroid
mephenytoin The enzyme inducer decreases the effect of the corticosteroid
mestranol The estrogenic agent increases the effect of corticosteroid
methohexital The barbiturate decreases the effect of the corticosteroid
methylphenobarbital The barbiturate decreases the effect of the corticosteroid
midodrine Increased arterial pressure
neostigmine The corticosteroid decreases the effect of anticholinesterases
pentobarbital The barbiturate decreases the effect of the corticosteroid
phenobarbital The barbiturate decreases the effect of the corticosteroid
phenytoin The enzyme inducer decreases the effect of the corticosteroid
primidone The barbiturate decreases the effect of the corticosteroid
pyridostigmine The corticosteroid decreases the effect of anticholinesterases
quinestrol The estrogenic agent increases the effect of corticosteroid
quinidine barbiturate The barbiturate decreases the effect of the corticosteroid
rifampin The enzyme inducer decreases the effect of the corticosteroid
salicylate-magnesium The corticosteroid decreases the effect of salicylates
salicylate-sodium The corticosteroid decreases the effect of salicylates
salsalate The corticosteroid decreases the effect of salicylates
secobarbital The barbiturate decreases the effect of the corticosteroid
talbutal The barbiturate decreases the effect of the corticosteroid
trisalicylate-choline The corticosteroid decreases the effect of salicylates
warfarin The corticosteroid alters the anticoagulant effect

Curated Information

The following diseases are in curated knowledge about this drug.

  Disease Relationship Evidence
No phenotype data No genotype data Literature annotations available Not annotated
Arthritis, Rheumatoid
  •   
  • PD
  •   
  •   
  •   
Publications
Phenotype data available Genotype Data Available Literature annotations available Not annotated
Precursor Cell Lymphoblastic Leukemia-Lymphoma
  • CO
  • PD
  • PK
  •   
  • GN
Publications

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

Curated Phenotype Datasets

These datasets are sorted alphabetically by title.

Additional Datasets

These datasets are minimally curated and are sorted alphabetically by title.

  1. Genetic predictors of glucocorticoid-induced hypertension in children with acute lymphoblastic leukemia
  2. Genome-wide copy number profiling reveals molecular evolution from diagnosis to relapse in childhood acute lymphoblastic leukemia
  3. Osteonecrosis in Children with Acute Lymphoblastic Leukemia: A Report from the Children's Oncology Group
  4. Pharmacogenetics of Minimal Residual Disease Response in Children with B-Precursor Acute Lymphoblastic Leukemia (ALL): A Report from the Children's Oncology Group
  5. Physicochemical determinants of human renal clearance
  6. The Connectivity Map: using gene-expression signatures to connect small molecules, genes, and disease

Downloads

You must sign in before you can download data.

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB00635
KEGG Compound ID:
C07370
PubChem Compound ID:
5865
PubChem Substance ID:
148670

Common Searches

Search PubMed
Search Medline Plus
Search PubChem
Search CTD

Non-Curated Publications

A list of non-curated publications that mention this drug is available.

PharmGKB integrates drug information from different sources: DrugBank, Open Eye Scientific Software.
The PharmGKB is financially supported by the NIH/ NIGMS and is managed at Stanford University (U01GM61374).
©2001-2010 PharmGKB.