Identification

Name
Prednisone
Accession Number
DB00635
Description

A synthetic anti-inflammatory glucocorticoid derived from cortisone.1 It is biologically inert and converted to prednisolone in the liver.9

Prednisone was granted FDA approval on 21 February 1955.8

Type
Small Molecule
Groups
Approved, Vet approved
Structure
Thumb
Weight
Average: 358.4281
Monoisotopic: 358.178023942
Chemical Formula
C21H26O5
Synonyms
  • 1,2-Dehydrocortisone
  • 1,4-Pregnadiene-17α,21-diol-3,11,20-trione
  • 17,21-Dihydroxypregna-1,4-diene-3,11,20-trione
  • Dehydrocortisone
  • Prednisona
  • Prednisone
  • Prednisonum
External IDs
  • NSC-10023

Pharmacology

Indication

Prednisone is indicated as an anti-inflammatory or immunosuppressive drug for allergic, dermatologic, gastrointestinal, hematologic, ophthalmologic, nervous system, renal, respiratory, rheumatologic, infectious, endocrine, or neoplastic conditions as well as in organ transplant.9

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More
Pharmacodynamics

Corticosteroids bind to the glucocorticoid receptor, inhibiting pro-inflammatory signals, and promoting anti-inflammatory signals.1 Prednisone has a short duration of action as the half life is 2-3 hours.9 Corticosteroids have a wide therapeutic window as patients make require doses that are multiples of what the body naturally produces.1 Patients taking corticosteroids should be counselled regarding the risk of hypothalamic-pituitary-adrenal axis suppression and increased susceptibility to infections.1

Mechanism of action

Prednisone is first metabolized in the liver to its active form, prednisolone, a glucocorticoid agonist corticosteroid.9

The short term effects of corticosteroids are decreased vasodilation and permeability of capillaries, as well as decreased leukocyte migration to sites of inflammation.1 Corticosteroids binding to the glucocorticoid receptor mediates changes in gene expression that lead to multiple downstream effects over hours to days.1

Glucocorticoids inhibit neutrophil apoptosis and demargination; they inhibit phospholipase A2, which decreases the formation of arachidonic acid derivatives; they inhibit NF-Kappa B and other inflammatory transcription factors; they promote anti-inflammatory genes like interleukin-10.1

Lower doses of corticosteroids provide an anti-inflammatory effect, while higher doses are immunosuppressive.1 High doses of glucocorticoids for an extended period bind to the mineralocorticoid receptor, raising sodium levels and decreasing potassium levels.1

TargetActionsOrganism
AGlucocorticoid receptor
agonist
Humans
Absorption

Oral prednisone has a Tmax of 2 hours, while the delayed-release formulation has a Tmax of 6-6.5 hours.9 A 5mg dose of prednisone has an AUC of 572mL/min/1.73m2, a 20mg dose of prednisone has an AUC of 1034mL/min/1.73m2, and a 50mg dose of prednisone has an AUC of 2271mL/min/1.73m2.5 Data regarding the Cmax of prednisone is not readily available.9

Volume of distribution

Data regarding the volume of distribution for prednisone is not readily available.9 However, a 0.15mg/kg dose of prednisolone has a volume of distribution of 29.3L, while a 0.30mg/kg dose has a volume of distribution of 44.2L.6

Protein binding

Corticosteroids are generally bound to corticosteroid binding globulin7 and serum albumin2 in plasma. Prednisone is <50% bound to protein in plasma.3

Metabolism

Prednisone is metabolized to 17α,21-dihydroxy-pregnan-1,4,6-trien-3,11,30-trione (M-XVII), 20α-dihydro-prednisone (M-V), 6βhydroxy-prednisone (M-XII), 6α-hydroxy-prednisone (M-XIII), or 20β-dihydro-prednisone (M-IV).4 20β-dihydro-prednisone is metabolized to 17α,20ξ,21-trihydroxy-5ξ-pregn-1-en-3,11-dione(M-XVIII).4 Prednison is reversibly metabolized to prednisolone.4 Prednisolone is metabolized to Δ6-prednisolone (M-XI), 20α-dihydro-prednisolone (M-III), 20β-dihydro-prednisolone (M-II), 6αhydroxy-prednisolone (M-VII), or 6βhydroxy-prednisolone(M-VI).4 6αhydroxy-prednisolone is metabolized to 6α,11β,17α,20β,21-pentahydroxypregnan-1,4-diene-3-one (M-X).4 6βhydroxy-prednisolone is metabolized to 6β,11β,17α,20β,21-pentahydroxypregnan-1,4-diene-3-one (M-VIII), 6β,11β,17α,20α,21-pentahydroxypregnan-1,4-diene-3-one (M-IX), and 6β,11β,17α,21-tetrahydroxy-5ξ-pregn-1-en-3,20-dione (M-XIV).4 MVIII is metabolized to 6β,11β,17α,20β,21-pentahydroxy-5ξ-pregn-1-en-3-one (M-XV) and then to MXIV, while MIX is metabolized to 6β,11β,17α,20α,21-pentahydroxy-5ξ-pregn-1-en-3-one (M-XVI) and then to MXIV.4 These metabolites and their glucuronide conjugates are excreted predominantly in the urine.4

Hover over products below to view reaction partners

Route of elimination

Prednisone is excreted mainly in the urine as sulfate and glucuronide conjugates.9

Half-life

Prednisone and its active metabolite prednisolone have half lives of 2-3 hours from both immediate and delayed release preparations.9

Clearance

Data regarding the clearance of prednisone is not readily available.9

A 5.5µg/h/kg infusion of prednisolone has an average clearance of 0.066±0.12L/h/kg, while a 0.15±0.03L/h/kg infusion has an average clearance of 0.15L/h/kg.3

Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
Toxicity

Data regarding acute overdoses of prednisone are rare but prolonged high doses of prednisone can lead to a higher incidence and severity of adverse effects such as mental symptoms, moon face, abnormal fat deposits, fluid retention, excessive appetite, weight gain, hypertrichosis, acne, striae, ecchymosis, increased sweating, pigmentation, dry scaly skin, thinning scalp hair, increased blood pressure, tachycardia, thrombophlebitis, decreased resistance to infection, negative nitrogen balance with delayed bone and wound healing, headache, weakness, menstrual disorders, accentuated menopausal symptoms, neuropathy, fractures, osteoporosis, peptic ulcer, decreased glucose tolerance, hypokalemia, and adrenal insufficiency.9

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Prednisone Action PathwayDrug action
Prednisone Metabolism PathwayDrug metabolism
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirPrednisone may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbametapirThe serum concentration of Prednisone can be increased when it is combined with Abametapir.
AbataceptThe risk or severity of adverse effects can be increased when Prednisone is combined with Abatacept.
AcarboseThe risk or severity of hyperglycemia can be increased when Prednisone is combined with Acarbose.
AceclofenacThe risk or severity of gastrointestinal irritation can be increased when Aceclofenac is combined with Prednisone.
AcemetacinThe risk or severity of gastrointestinal irritation can be increased when Acemetacin is combined with Prednisone.
AcenocoumarolPrednisone may increase the anticoagulant activities of Acenocoumarol.
AcetazolamideAcetazolamide may increase the excretion rate of Prednisone which could result in a lower serum level and potentially a reduction in efficacy.
AcetohexamideThe risk or severity of hyperglycemia can be increased when Prednisone is combined with Acetohexamide.
AcetyldigitoxinThe risk or severity of adverse effects can be increased when Prednisone is combined with Acetyldigitoxin.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Avoid alcohol.
  • Take with food. Food reduces irritation.

Products

Active Moieties
NameKindUNIICASInChI Key
Prednisoloneprodrug9PHQ9Y1OLM50-24-8OIGNJSKKLXVSLS-VWUMJDOOSA-N
Product Images
International/Other Brands
Delta-Cortef (Upjohn) / Meticorten / Orasone
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
DeltasoneTablet50 mg/1OralPharmacia and Upjohn and Company2007-03-30Not applicableUs
DeltasoneTablet5 mg/1OralPharmacia and Upjohn and Company2007-03-30Not applicableUs
DeltasoneTablet2.5 mg/1OralPharmacia and Upjohn and Company2007-03-30Not applicableUs
DeltasoneTablet20 mg/1OralPharmacia and Upjohn and Company2007-03-30Not applicableUs
DeltasoneTablet10 mg/1OralPharmacia and Upjohn and Company2007-03-30Not applicableUs
DeltasoneTablet5 mg/1OralPhysicians Total Care, Inc.1992-12-012011-05-31Us
Deltasone 50mgTabletOralPharmacia & Upjohn Inc1972-12-312000-08-02Canada
Deltasone 5mgTabletOralPharmacia & Upjohn Inc1972-12-312000-08-02Canada
Jaa Prednisone Tab 1mg USPTabletOralJaapharm Canada Inc.1993-05-152002-04-02Canada
Jaa Prednisone Tab 50mg USPTabletOralJaapharm Canada Inc.1993-12-312002-04-02Canada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Alti-prednisone Tab 5mgTabletOralAltimed Pharma Inc.1984-12-311998-08-10Canada
Apo Prednisone Tab 1mg USPTabletOralApotex Corporation1984-12-31Not applicableCanada
Apo Prednisone Tab 50mgTabletOralApotex Corporation1982-12-31Not applicableCanada
Apo Prednisone Tab 5mgTabletOralApotex Corporation1982-12-31Not applicableCanada
DeltasoneTablet20 mg/1OralSonoma Pharmaceuticals, Inc.2003-02-13Not applicableUs
DeltasoneTablet20 mg/20mgOralOculus Innovative Scicences2009-08-03Not applicableUs
Perrigo PrednisoneTablet10 mg/1OralPerrigo International2006-05-192010-11-01Us
Perrigo PrednisoneTablet5 mg/1OralPerrigo International2006-05-192010-11-01Us
Perrigo PrednisoneTablet20 mg/1OralPerrigo International2006-10-112011-02-04Us
PrednisoneTablet5 mg/1OralWest-Ward Pharmaceuticals Corp2009-08-032022-06-30Us00143 9740 01 nlmimage10 e249716b
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Metreton TabPrednisone (2.5 mg) + Ascorbic acid (75 mg) + Chlorpheniramine maleate (2 mg)TabletOralSchering Plough1956-12-312007-08-03Canada
PrednisonePrednisone (5 mg/5mL) + Ethanol (5 mL/100mL)SolutionOralRoxane Laboratories2006-06-272006-09-01Us
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Contrast Allergy PreMed PackPrednisone (50 mg/50mg) + Diphenhydramine hydrochloride (50 mg/50mg)KitOralShertech Laboratories, Llc2016-09-13Not applicableUs

Categories

ATC Codes
A07EA03 — PrednisoneH02AB07 — Prednisone
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound 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.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Hydroxysteroids
Direct Parent
21-hydroxysteroids
Alternative Parents
Gluco/mineralocorticoids, progestogins and derivatives / 20-oxosteroids / 3-oxo delta-1,4-steroids / 17-hydroxysteroids / 11-oxosteroids / Delta-1,4-steroids / Tertiary alcohols / Alpha-hydroxy ketones / Cyclic ketones / Cyclic alcohols and derivatives
show 3 more
Substituents
11-oxosteroid / 17-hydroxysteroid / 20-oxosteroid / 21-hydroxysteroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid / Alcohol / Aliphatic homopolycyclic compound / Alpha-hydroxy ketone / Carbonyl group
show 13 more
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
17alpha-hydroxy steroid, glucocorticoid, 20-oxo steroid, 3-oxo-Delta(1),Delta(4)-steroid, 11-oxo steroid, 21-hydroxy steroid (CHEBI:8382) / Pregnane and derivatives [Fig] (C07370) / C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030180)

Chemical Identifiers

UNII
VB0R961HZT
CAS number
53-03-2
InChI Key
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
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
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

References

Synthesis Reference

Jean Buendia, Michel Vivat, "Process for the production of prednisone 17.21-diacylates." U.S. Patent US4601854, issued May, 1982.

US4601854
General References
  1. Yasir M, Sonthalia S: Corticosteroid Adverse Effects . [PubMed:30285357]
  2. Czock D, Keller F, Rasche FM, Haussler U: Pharmacokinetics and pharmacodynamics of systemically administered glucocorticoids. Clin Pharmacokinet. 2005;44(1):61-98. doi: 10.2165/00003088-200544010-00003. [PubMed:15634032]
  3. Frey BM, Frey FJ: Clinical pharmacokinetics of prednisone and prednisolone. Clin Pharmacokinet. 1990 Aug;19(2):126-46. doi: 10.2165/00003088-199019020-00003. [PubMed:2199128]
  4. Matabosch X, Pozo OJ, Perez-Mana C, Papaseit E, Segura J, Ventura R: Detection and characterization of prednisolone metabolites in human urine by LC-MS/MS. J Mass Spectrom. 2015 Mar;50(3):633-42. doi: 10.1002/jms.3571. [PubMed:25800201]
  5. Rose JQ, Yurchak AM, Jusko WJ: Dose dependent pharmacokinetics of prednisone and prednisolone in man. J Pharmacokinet Biopharm. 1981 Aug;9(4):389-417. doi: 10.1007/bf01060885. [PubMed:7310640]
  6. Pickup ME: Clinical pharmacokinetics of prednisone and prednisolone. Clin Pharmacokinet. 1979 Mar-Apr;4(2):111-28. doi: 10.2165/00003088-197904020-00004. [PubMed:378499]
  7. Gardill BR, Vogl MR, Lin HY, Hammond GL, Muller YA: Corticosteroid-binding globulin: structure-function implications from species differences. PLoS One. 2012;7(12):e52759. doi: 10.1371/journal.pone.0052759. Epub 2012 Dec 26. [PubMed:23300763]
  8. FDA Approved Drug Products: Meticorten Prednisone Oral Tablets (Discontinued) [Link]
  9. FDA Approved Drug Products: Rayos Prednisone Delayed-Release Oral Tablets [Link]
Human Metabolome Database
HMDB0014773
KEGG Drug
D00473
KEGG Compound
C07370
PubChem Compound
5865
PubChem Substance
46508166
ChemSpider
5656
RxNav
8640
ChEBI
8382
ChEMBL
CHEMBL635
ZINC
ZINC000003875357
Therapeutic Targets Database
DAP001041
PharmGKB
PA451100
PDBe Ligand
PDN
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Prednisone
AHFS Codes
  • 68:04.00 — Adrenals
MSDS
Download (132 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingBasic ScienceChronic Obstructive Pulmonary Disease (COPD)1
4Active Not RecruitingPreventionAsthma / Upper Respiratory Tract Infection1
4Active Not RecruitingTreatmentAdvanced Follicular Lymphoma1
4Active Not RecruitingTreatmentALK-negative Anaplastic Large Cell Lymphoma / Angioimmunoblastic T Cell Lymphoma / Angioimmunoblastic T-Cell Lymphoma / Enteropathy Associated T Cell Lymphoma / Enteropathy-Associated T-Cell Lymphoma / Hepatosplenic T Cell Lymphoma / Hepatosplenic T-Cell Lymphoma / Peripherial T Cell Lymphoma,Not Otherwise Specified / Subcutaneous Panniculitis Like T Cell Lymphoma1
4Active Not RecruitingTreatmentCytomegalovirus / Transplantation, Kidney1
4Active Not RecruitingTreatmentIgA Nephropathy1
4Active Not RecruitingTreatmentKidney Transplant Patients1
4Active Not RecruitingTreatmentKidney Transplant Rejection / Other Complications of Kidney Transplant1
4Active Not RecruitingTreatmentMetastatic Hormone Refractory Prostate Cancer1
4Active Not RecruitingTreatmentProstate Cancer1

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
  • Advanced Pharmaceutical Services Inc.
  • Amend
  • Amerisource Health Services Corp.
  • Apotheca Inc.
  • Apothecary Shop Wholesale
  • AQ Pharmaceuticals Inc.
  • A-S Medication Solutions LLC
  • Breckenridge Pharmaceuticals
  • Bryant Ranch Prepack
  • C.O. Truxton Inc.
  • Cadista Pharmaceuticals Inc.
  • Cardinal Health
  • Carlisle Laboratories Inc.
  • Comprehensive Consultant Services Inc.
  • Corepharma LLC
  • Darby Dental Supply Co. Inc.
  • Dept Health Central Pharmacy
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • H.J. Harkins Co. Inc.
  • Heartland Repack Services LLC
  • Innoviant Pharmacy Inc.
  • Kaiser Foundation Hospital
  • Keltman Pharmaceuticals Inc.
  • Lake Erie Medical and Surgical Supply
  • Liberty Pharmaceuticals
  • Major Pharmaceuticals
  • Mckesson Corp.
  • Merz Pharmaceuticals LLC
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mutual Pharmaceutical Co.
  • Neuman Distributors Inc.
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Perrigo Co.
  • Pharmacia Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Prescription Dispensing Service Inc.
  • Qualitest
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Roxane Labs
  • Sandhills Packaging Inc.
  • Southwood Pharmaceuticals
  • St Mary's Medical Park Pharmacy
  • Stat Rx Usa
  • Stat Scripts LLC
  • Tya Pharmaceuticals
  • UDL Laboratories
  • Vangard Labs Inc.
  • Vedco Inc.
  • Veratex Corp.
  • Vintage Pharmaceuticals Inc.
  • Wa Butler Co.
  • Watson Pharmaceuticals
  • West-Ward Pharmaceuticals
Dosage Forms
FormRouteStrength
KitOral
Tablet20 MG
Tablet50 MG
Tablet5 MG
TabletOral2.5 mg/1
TabletOral20 mg/20mg
TabletOral5 mg/1
TabletOral
Tablet10 MG
SolutionOral
SolutionOral5 mg/5mL
SolutionOral5 mg/1mL
TabletOral1 mg/1
TabletOral1.0 mg/1
TabletOral10 mg/1
TabletOral10 mg/201
TabletOral20 mg/1
TabletOral20 mg/201
TabletOral5.0 mg/1
TabletOral50 mg/1
Solution, concentrateOral5 mg/1mL
Tablet, delayed releaseOral1 mg/1
Tablet, delayed releaseOral2 mg/1
Tablet, delayed releaseOral5 mg/1
TabletOral
Prices
Unit descriptionCostUnit
Sterapred DS 21 10 mg tablet Disp Pack64.0USD disp
Prednisone powder3.36USD g
Sterapred ds 10 mg tablet unipak2.93USD tablet
Prednisone 5 mg/ml solution1.17USD ml
PredniSONE 5 mg/5ml Solution0.5USD ml
Prednisone 50 mg tablet0.47USD tablet
Prednisone 20 mg tablet0.29USD tablet
Prednisone 10 mg tablet0.27USD tablet
Prednisone 2.5 mg tablet0.25USD tablet
Prednisone 1 mg tablet0.23USD tablet
Apo-Prednisone 50 mg Tablet0.18USD tablet
Winpred 1 mg Tablet0.12USD tablet
Apo-Prednisone 1 mg Tablet0.11USD tablet
Prednisone 5 mg tablet0.08USD tablet
Apo-Prednisone 5 mg Tablet0.04USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US9186332No2015-11-172024-04-23Us
US8168218No2012-05-012028-01-07Us
US8309124No2012-11-132024-04-23Us
US8394407No2013-03-122024-04-23Us
US9040085No2015-05-262024-04-23Us
US6488960No2002-12-032020-03-14Us
US6677326No2004-01-132020-03-14Us
US9504699No2016-11-292027-08-03Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)230 - 235 °C (decomposes)MSDS
water solubilityVery slightly solubleMSDS
logP1.46MSDS
Predicted Properties
PropertyValueSource
Water Solubility0.111 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity97.57 m3·mol-1ChemAxon
Polarizability38.17 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9918
Blood Brain Barrier+0.9383
Caco-2 permeable-0.5096
P-glycoprotein substrateSubstrate0.7861
P-glycoprotein inhibitor INon-inhibitor0.7847
P-glycoprotein inhibitor IINon-inhibitor0.8383
Renal organic cation transporterNon-inhibitor0.7463
CYP450 2C9 substrateNon-substrate0.8496
CYP450 2D6 substrateNon-substrate0.9138
CYP450 3A4 substrateSubstrate0.7407
CYP450 1A2 substrateNon-inhibitor0.9406
CYP450 2C9 inhibitorNon-inhibitor0.9072
CYP450 2D6 inhibitorNon-inhibitor0.9418
CYP450 2C19 inhibitorNon-inhibitor0.9253
CYP450 3A4 inhibitorNon-inhibitor0.8902
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9095
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9597
BiodegradationNot ready biodegradable0.925
Rat acute toxicity1.8914 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.95
hERG inhibition (predictor II)Non-inhibitor0.584
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (12.5 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-05fs-2951000000-1a9b3a7e18f6088d28db
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00di-0900000000-1ea12664a8edc235b05c
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00di-1900000000-06d289c40615662ab14e
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00di-0900000000-f76738c3bedb48d0c7a3
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0019000000-d5b5ef89fce8ee6966ba
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00r5-0493000000-ae479d92cc77796a5177
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00ds-0690000000-f3df1438f8c0623811c1
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00dj-0970000000-b61d7f78a4036739cb07
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-05fs-0940000000-a9c08e5a06f9684fb000
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4l-0149000000-088a79de5c16e3384162
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-006w-2930000000-f901c87bc4fd3221d37e
MS/MS Spectrum - , positiveLC-MS/MSsplash10-05tg-0695000000-35841a4b47ea1535be95
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4m-0597000000-c12dc88504062b28c4be
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-2960000000-10bdddfba8bd2889acde

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modula...
Gene Name
NR3C1
Uniprot ID
P04150
Uniprot Name
Glucocorticoid receptor
Molecular Weight
85658.57 Da
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:17121036]
  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:16597193]
  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:17504182]
  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:17062674]
  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:16707595]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  7. Czock D, Keller F, Rasche FM, Haussler U: Pharmacokinetics and pharmacodynamics of systemically administered glucocorticoids. Clin Pharmacokinet. 2005;44(1):61-98. doi: 10.2165/00003088-200544010-00003. [PubMed:15634032]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
General Function
Vitamin d3 25-hydroxylase 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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Hardy KW, Crocker JF, McLellan H, Goralski KB, Renton KW, Acott PD: Paradoxical cyclosporine A requirements in pediatric renal transplants receiving high-dose steroids. J Clin Pharmacol. 2005 Feb;45(2):161-7. doi: 10.1177/0091270004271403. [PubMed:15647408]
  2. Pichard L, Fabre I, Daujat M, Domergue J, Joyeux H, Maurel P: Effect of corticosteroids on the expression of cytochromes P450 and on cyclosporin A oxidase activity in primary cultures of human hepatocytes. Mol Pharmacol. 1992 Jun;41(6):1047-55. [PubMed:1614409]
  3. Miura M, Inoue K, Kagaya H, Saito M, Habuchi T, Satoh S: Inter-individual difference determinant of prednisolone pharmacokinetics for Japanese renal transplant recipients in the maintenance stage. Xenobiotica. 2009 Dec;39(12):939-45. doi: 10.3109/00498250903294361. [PubMed:19795924]
  4. Usui T, Saitoh Y, Komada F: Induction of CYP3As in HepG2 cells by several drugs. Association between induction of CYP3A4 and expression of glucocorticoid receptor. Biol Pharm Bull. 2003 Apr;26(4):510-7. doi: 10.1248/bpb.26.510. [PubMed:12673034]
  5. Matoulkova P, Pavek P, Maly J, Vlcek J: Cytochrome P450 enzyme regulation by glucocorticoids and consequences in terms of drug interaction. Expert Opin Drug Metab Toxicol. 2014 Mar;10(3):425-35. doi: 10.1517/17425255.2014.878703. Epub 2014 Jan 23. [PubMed:24451000]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Steroid hydroxylase 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 im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Helsby NA, Hui CY, Goldthorpe MA, Coller JK, Soh MC, Gow PJ, De Zoysa JZ, Tingle MD: The combined impact of CYP2C19 and CYP2B6 pharmacogenetics on cyclophosphamide bioactivation. Br J Clin Pharmacol. 2010 Dec;70(6):844-53. doi: 10.1111/j.1365-2125.2010.03789.x. [PubMed:21175440]
  2. Matoulkova P, Pavek P, Maly J, Vlcek J: Cytochrome P450 enzyme regulation by glucocorticoids and consequences in terms of drug interaction. Expert Opin Drug Metab Toxicol. 2014 Mar;10(3):425-35. doi: 10.1517/17425255.2014.878703. Epub 2014 Jan 23. [PubMed:24451000]
  3. Cytochrome P450 drug interactions [File]
  4. Mayo medical laboratory document [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Oxygen binding
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 oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Dvorak Z, Pavek P: Regulation of drug-metabolizing cytochrome P450 enzymes by glucocorticoids. Drug Metab Rev. 2010 Nov;42(4):621-35. doi: 10.3109/03602532.2010.484462. [PubMed:20482443]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Vitamin d3 25-hydroxylase 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 react...

Components:
References
  1. Matoulkova P, Pavek P, Maly J, Vlcek J: Cytochrome P450 enzyme regulation by glucocorticoids and consequences in terms of drug interaction. Expert Opin Drug Metab Toxicol. 2014 Mar;10(3):425-35. doi: 10.1517/17425255.2014.878703. Epub 2014 Jan 23. [PubMed:24451000]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
References
  1. Matoulkova P, Pavek P, Maly J, Vlcek J: Cytochrome P450 enzyme regulation by glucocorticoids and consequences in terms of drug interaction. Expert Opin Drug Metab Toxicol. 2014 Mar;10(3):425-35. doi: 10.1517/17425255.2014.878703. Epub 2014 Jan 23. [PubMed:24451000]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Oxygen binding
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 oxidizes a variety of structurally un...
Gene Name
CYP1B1
Uniprot ID
Q16678
Uniprot Name
Cytochrome P450 1B1
Molecular Weight
60845.33 Da
References
  1. Matoulkova P, Pavek P, Maly J, Vlcek J: Cytochrome P450 enzyme regulation by glucocorticoids and consequences in terms of drug interaction. Expert Opin Drug Metab Toxicol. 2014 Mar;10(3):425-35. doi: 10.1517/17425255.2014.878703. Epub 2014 Jan 23. [PubMed:24451000]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Steroid hydroxylase 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 oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Matoulkova P, Pavek P, Maly J, Vlcek J: Cytochrome P450 enzyme regulation by glucocorticoids and consequences in terms of drug interaction. Expert Opin Drug Metab Toxicol. 2014 Mar;10(3):425-35. doi: 10.1517/17425255.2014.878703. Epub 2014 Jan 23. [PubMed:24451000]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Steroid hydroxylase 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 oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Matoulkova P, Pavek P, Maly J, Vlcek J: Cytochrome P450 enzyme regulation by glucocorticoids and consequences in terms of drug interaction. Expert Opin Drug Metab Toxicol. 2014 Mar;10(3):425-35. doi: 10.1517/17425255.2014.878703. Epub 2014 Jan 23. [PubMed:24451000]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Steroid hydroxylase 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 oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Matoulkova P, Pavek P, Maly J, Vlcek J: Cytochrome P450 enzyme regulation by glucocorticoids and consequences in terms of drug interaction. Expert Opin Drug Metab Toxicol. 2014 Mar;10(3):425-35. doi: 10.1517/17425255.2014.878703. Epub 2014 Jan 23. [PubMed:24451000]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
11-beta-hydroxysteroid dehydrogenase [nad(p)] activity
Specific Function
Catalyzes reversibly the conversion of cortisol to the inactive metabolite cortisone. Catalyzes reversibly the conversion of 7-ketocholesterol to 7-beta-hydroxycholesterol. In intact cells, the rea...
Gene Name
HSD11B1
Uniprot ID
P28845
Uniprot Name
Corticosteroid 11-beta-dehydrogenase isozyme 1
Molecular Weight
32400.665 Da
References
  1. Raza K, Hardy R, Cooper MS: The 11beta-hydroxysteroid dehydrogenase enzymes--arbiters of the effects of glucocorticoids in synovium and bone. Rheumatology (Oxford). 2010 Nov;49(11):2016-23. doi: 10.1093/rheumatology/keq212. Epub 2010 Jul 15. [PubMed:20634231]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Ferry JJ, Wagner JG: The nonlinear pharmacokinetics of prednisone and prednisolone. II. Plasma protein binding of prednisone and prednisolone in rabbit and human plasma. Biopharm Drug Dispos. 1987 May-Jun;8(3):261-72. [PubMed:3593903]
  2. Czock D, Keller F, Rasche FM, Haussler U: Pharmacokinetics and pharmacodynamics of systemically administered glucocorticoids. Clin Pharmacokinet. 2005;44(1):61-98. doi: 10.2165/00003088-200544010-00003. [PubMed:15634032]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Steroid binding
Specific Function
Major transport protein for glucocorticoids and progestins in the blood of almost all vertebrate species.
Gene Name
SERPINA6
Uniprot ID
P08185
Uniprot Name
Corticosteroid-binding globulin
Molecular Weight
45140.49 Da
References
  1. Gardill BR, Vogl MR, Lin HY, Hammond GL, Muller YA: Corticosteroid-binding globulin: structure-function implications from species differences. PLoS One. 2012;7(12):e52759. doi: 10.1371/journal.pone.0052759. Epub 2012 Dec 26. [PubMed:23300763]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
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]
  3. Dilger K, Schwab M, Fromm MF: Identification of budesonide and prednisone as substrates of the intestinal drug efflux pump P-glycoprotein. Inflamm Bowel Dis. 2004 Sep;10(5):578-83. [PubMed:15472518]
  4. Matoulkova P, Pavek P, Maly J, Vlcek J: Cytochrome P450 enzyme regulation by glucocorticoids and consequences in terms of drug interaction. Expert Opin Drug Metab Toxicol. 2014 Mar;10(3):425-35. doi: 10.1517/17425255.2014.878703. Epub 2014 Jan 23. [PubMed:24451000]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
Gene Name
SLCO1A2
Uniprot ID
P46721
Uniprot Name
Solute carrier organic anion transporter family member 1A2
Molecular Weight
74144.105 Da
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]

Drug created on June 13, 2005 07:24 / Updated on August 04, 2020 17:13

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