Banner
Identification
Name Prednisone
Accession Number DB00635 (APRD00340)
Type small molecule
Groups approved
Description

A synthetic anti-inflammatory glucocorticoid derived from cortisone. It is biologically inert and converted to prednisolone in the liver. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Dehydrocortisone
Prednisona [INN-Spanish]
Prednisonum [INN-Latin]
Salts Not Available
Brand names
Name Company
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
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
First Prev Next Last
Brand mixtures
Brand Name Ingredients
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
Categories
  • Antineoplastic Agents
  • Anti-inflammatory Agents
  • Adrenergic Agents
  • Antineoplastic Agents, Hormonal
  • Glucocorticoids
CAS number 53-03-2
Weight Average: 358.4281
Monoisotopic: 358.178023942
Chemical Formula C21H26O5
InChI Key InChIKey=XOFYZVNMUHMLCC-ZPOLXVRWSA-N
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
Plain Text
IUPAC Name
(1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-diene-5,17-dione
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
Plain Text
Mass Spec show (12.5 KB)
Taxonomy
Kingdom Organic
Classes
  • Steroids and Steroid Derivatives
Substructures
  • Steroids and Steroid Derivatives
  • Hydroxy Compounds
  • Alkanes and Alkenes
  • Alcohols and Polyols
  • Ketones
Pharmacology
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.
Pharmacodynamics 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.
Mechanism of action 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.
Absorption Readily absorbed from the gastrointestinal tract.
Volume of distribution Not Available
Protein binding Extensively bound to plasma proteins.
Metabolism Hepatic.
Route of elimination Not Available
Half life 2 to 3 hours
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways
Pathway Name SMPDB ID
Smp00440 Prednisone Pathway SMP00440
Pharmacoeconomics
Manufacturers
  • Schering corp sub schering plough corp
  • Roxane laboratories inc
  • Wockhardt eu operations (swiss) ag
  • Muro pharmaceutical inc
  • Halsey drug co inc
  • Bayer pharmaceuticals corp
  • Pharmacia and upjohn co
  • Ferndale laboratories inc
  • Solvay pharmaceuticals
  • Parke davis div warner lambert co
  • Schwarz pharma inc
  • American therapeutics inc
  • Amneal pharmaceuticals ny llc
  • Cm bundy co
  • Cadista pharmaceuticals inc
  • Contract pharmacal corp
  • Duramed pharmaceuticals inc sub barr laboratories inc
  • Elkins sinn div ah robins co inc
  • Everylife
  • John j ferrante
  • Heather drug co inc
  • Impax laboratories inc
  • Inwood laboratories inc sub forest laboratories inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Kv pharmaceutical co
  • Lannett co inc
  • Lederle laboratories div american cyanamid co
  • Marshall pharmacal corp
  • Mutual pharmaceutical co inc
  • Nylos trading co inc
  • Panray corp sub ormont drug and chemical co inc
  • L perrigo co
  • Pharmavite pharmaceuticals
  • Phoenix laboratories inc
  • Purepac pharmaceutical co
  • Private formulations inc
  • Rexall drug co
  • Sandoz inc
  • Scherer laboratories inc
  • Sperti drug products inc
  • Superpharm corp
  • Teva pharmaceuticals usa inc
  • Udl laboratories inc
  • Upsher smith laboratories inc
  • Valeant pharmaceuticals international
  • Vangard laboratories inc div midway medical co
  • Vintage pharmaceuticals inc
  • Vitarine pharmaceuticals inc
  • Watson laboratories inc
  • West ward pharmaceutical corp
  • Whiteworth towne paulsen inc
Packagers
Dosage forms
Form Route Strength
Tablet Oral
Prices
Unit description Cost Unit
Sterapred DS 21 10 mg tablet Disp Pack 64.0 USD disp
Prednisone powder 3.36 USD g
Sterapred ds 10 mg tablet unipak 2.93 USD tablet
Prednisone 5 mg/ml solution 1.17 USD ml
PredniSONE 5 mg/5ml Solution 0.5 USD ml
Prednisone 50 mg tablet 0.47 USD tablet
Prednisone 20 mg tablet 0.29 USD tablet
Prednisone 10 mg tablet 0.27 USD tablet
Prednisone 2.5 mg tablet 0.25 USD tablet
Prednisone 1 mg tablet 0.23 USD tablet
Apo-Prednisone 50 mg Tablet 0.18 USD tablet
Winpred 1 mg Tablet 0.12 USD tablet
Apo-Prednisone 1 mg Tablet 0.11 USD tablet
Prednisone 5 mg tablet 0.08 USD tablet
Apo-Prednisone 5 mg Tablet 0.04 USD tablet
First Prev Next Last
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 234 dec °C PhysProp
water solubility 312 mg/L Not Available
logP 1.46 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
water solubility 1.11e-01 g/l ALOGPS
logP 2.07 ALOGPS
logP 1.66 ChemAxon
logS -3.5 ALOGPS
pKa (strongest acidic) 12.58 ChemAxon
pKa (strongest basic) -3.3 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 5 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 91.67 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 97.57 ChemAxon
polarizability 38.17 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C07370 Link_out
PubChem Compound 5865 Link_out
PubChem Substance 46508166 Link_out
ChemSpider 5656 Link_out
ChEBI 8382 Link_out
ChEMBL 8382 Link_out
Therapeutic Targets Database DAP001041 Link_out
PharmGKB PA451100 Link_out
Drug Product Database 868426 Link_out
RxList http://www.rxlist.com/cgi/generic/pred.htm Link_out
Drugs.com http://www.drugs.com/prednisone.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Prednisone Link_out
ATC Codes
  • A07EA03
  • H02AB07
  • H02AB15
AHFS Codes
  • 68:04.00
PDB Entries Not Available
FDA label Not Available
MSDS show (75.7 KB)
Interactions
Drug Interactions
Drug Interaction
Acenocoumarol The corticosteroid, prednisone, alters the anticoagulant effect, acenocoumarol.
Acetylsalicylic acid The corticosteroid, prednisone, may decrease the effect of the salicylate, acetylsalicylic acid.
Ambenonium The corticosteroid, prednisone, may decrease the effect of the anticholinesterase, ambenonium.
Amobarbital The barbiturate, amobarbital, may decrease the effect of the corticosteroid, prednisone.
Anisindione The corticosteroid, prednisone, alters the anticoagulant effect of anisindione.
Aprobarbital The barbiturate, aprobarbital, may decrease the effect of the corticosteroid, prednisone.
Bismuth Subsalicylate The corticosteroid, prednisone, may decrease the effect of the salicylate, bismuth subsalicylate.
Butabarbital The barbiturate, butabarbital, may decrease the effect of the corticosteroid, prednisone.
Butalbital The barbiturate, butalbital, may decrease the effect of the corticosteroid, prednisone.
Butethal The barbiturate, butethal, may decrease the effect of the corticosteroid, prednisone.
Chlorotrianisene The estrogenic agent, chlorotrianisene, may increase the effect of corticosteroid, prednisone.
Clomifene The estrogenic agent, clomifene, may increase the effect of corticosteroid, prednisone.
Conjugated Estrogens The estrogenic agent may increase the effect of corticosteroid, prednisone.
Dicumarol The corticosteroid, prednisone, alters the anticoagulant effect of dicumarol.
Diethylstilbestrol The estrogenic agent, diethylstilbestrol, may increase the effect of corticosteroid, prednisone.
Dihydroquinidine barbiturate The barbiturate, dihydroquinidine barbiturate, may decrease the effect of the corticosteroid, prednisone.
Edrophonium The corticosteroid, prednisone, may decrease the effect of the anticholinesterase, edrophonium.
Estradiol The estrogenic agent, estradiol, may increase the effect of corticosteroid, prednisone.
Estriol The estrogenic agent, estriol, may increase the effect of corticosteroid, prednisone.
Estrone The estrogenic agent, estrone, may increase the effect of corticosteroid, prednisone.
Estropipate The estrogenic agent, estropipate, may increase the effect of corticosteroid, prednisone.
Ethinyl Estradiol The estrogenic agent, ethinyl estradiol, may increase the effect of corticosteroid, prednisone.
Ethotoin The enzyme inducer, ethotoin, may decrease the effect of the corticosteroid, prednisone.
F decreases the effect of cortisone by metabolism alteration.
Fosphenytoin The enzyme inducer, fosphenytoin, may decrease the effect of the corticosteroid, prednisone.
Heptabarbital The barbiturate, heptabarbital, may decrease the effect of the corticosteroid, prednisone.
Hexobarbital The barbiturate, hexobarbital, may decrease the effect of the corticosteroid, prednisone.
Itraconazole The imidazole, itraconazole, may increase the effect and toxicity of the corticosteroid, prednisone.
Ketoconazole The imidazole, ketoconazole, may increase the effect and toxicity of the corticosteroid, prednisone.
Magnesium salicylate The corticosteroid, prednisolone, may decrease the effect of magnesium salicylate.
Mephenytoin The enzyme inducer, mephenytoin, may decrease the effect of the corticosteroid, prednisone.
Mestranol The estrogenic agent, mestranol, may increase the effect of corticosteroid, prednisone.
Methohexital The barbiturate, methohexital, may decrease the effect of the corticosteroid, prednisone.
Methylphenobarbital The barbiturate, methylphenobarbital, may decrease the effect of the corticosteroid, prednisone.
Midodrine Increased arterial pressure
Neostigmine The corticosteroid, prednisone, may decrease the effect of the anticholinesterase, neostigmine.
Pentobarbital The barbiturate, pentobarbital, may decrease the effect of the corticosteroid, prednisone.
Phenobarbital The barbiturate, phenobarbital, may decrease the effect of the corticosteroid, prednisone.
Phenytoin The enzyme inducer, phenytoin, may decrease the effect of the corticosteroid, prednisone.
Primidone The barbiturate, primidone, may decrease the effect of the corticosteroid, prednisone.
Pyridostigmine The corticosteroid, prednisone, may decrease the effect of the anticholinesterase, pyridostigmine.
Quinestrol The estrogenic agent, quinestrol, may increase the effect of corticosteroid, prednisone.
Quinidine barbiturate The barbiturate, quinidine barbiturate, may decrease the effect of the corticosteroid, prednisone.
Rifampin The enzyme inducer, rifampin, may decrease the effect of the corticosteroid, prednisone.
Salicylate-sodium The corticosteroid, prednisone, may decrease the effect of the salicylate, salicylate-sodium.
Salsalate The corticosteroid, prednisone, may decrease the effect of the salicylate, salsalate.
Secobarbital The barbiturate, secobarbital, may decrease the effect of the corticosteroid, prednisone.
Tacrine Tacrine and Prednisone may independently exacerbate muscle weakness in myasthenia gravis patients. Monitor for additive muscle weakness effects.
Talbutal The barbiturate, talbutal, may decrease the effect of the corticosteroid, prednisone.
Trastuzumab Trastuzumab may increase the risk of neutropenia and anemia. Monitor closely for signs and symptoms of adverse events.
Trisalicylate-choline The corticosteroid, prednisone, may decrease the effect of the salicylate, trisalicylate-choline.
Vecuronium Vecuronium may increase the adverse neuromuscular effects of systemic corticosteroids, such as Prednisone. Monitor for increased muscle weakness and signs of polyneuropathies and myopathy.
Warfarin The corticosteroid, prednisone, alters the anticoagulant effect of warfarin.
Food Interactions
  • Avoid alcohol.
  • Avoid taking with grapefruit juice.
  • Take with food to reduce irritation.
Targets

1. Glucocorticoid receptor

Pharmacological action: yes
Actions: agonist

Receptor for glucocorticoids (GC). Has a dual mode of action:as a transcription factor that binds to glucocorticoid response elements (GRE) and as a modulator of other transcription factors. Affects inflammatory responses, cellular proliferation and differentiation in target tissues. Could act as a coactivator for STAT5-dependent transcription upon growth hormone (GH) stimulation and could reveal an essential role of hepatic GR in the control of body growth

Organism class: human
UniProt ID: P04150 Link_out
Gene: NR3C1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Liu BG, Li ZY, Du M: [Effects of jingui shenqi pill combined prednisone on expression of glucocorticoid receptor and its clinical effect in treating bullous pemphigoid patients] Zhongguo Zhong Xi Yi Jie He Za Zhi. 2006 Oct;26(10):881-4. Pubmed
  2. Friel PN, Alexander T, Wright JV: Suppression of adrenal function by low-dose prednisone: assessment with 24-hour urinary steroid hormone profiles—a review of five cases. Altern Med Rev. 2006 Mar;11(1):40-6. Pubmed
  3. Diez JJ, Iglesias P: Pharmacological therapy of Cushing’s syndrome: drugs and indications. Mini Rev Med Chem. 2007 May;7(5):467-80. Pubmed
  4. Yano A, Fujii Y, Iwai A, Kawakami S, Kageyama Y, Kihara K: Glucocorticoids suppress tumor lymphangiogenesis of prostate cancer cells. Clin Cancer Res. 2006 Oct 15;12(20 Pt 1):6012-7. Pubmed
  5. Yano A, Fujii Y, Iwai A, Kageyama Y, Kihara K: Glucocorticoids suppress tumor angiogenesis and in vivo growth of prostate cancer cells. Clin Cancer Res. 2006 May 15;12(10):3003-9. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
Enzymes

1. Cytochrome P450 3A4

Actions: substrate, inhibitor, inducer

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. The enzyme also hydroxylates etoposide

UniProt ID: P08684 Link_out
Gene: CYP3A4
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 2C19

Actions: inducer

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

UniProt ID: P33261 Link_out
Gene: CYP2C19 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Epub 2009 Nov 24. Pubmed
Transporters

1. Multidrug resistance protein 1

Actions: substrate, inhibitor

Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells

UniProt ID: P08183 Link_out
Gene: ABCB1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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

2. Solute carrier organic anion transporter family member 1A2

Actions: inhibitor

Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity)

UniProt ID: P46721 Link_out
Gene: SLCO1A2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19