Prednisone
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Identification
- Summary
Prednisone is a corticosteroid used to treat inflammation or immune-mediated reactions and to treat endocrine or neoplastic diseases.
- Brand Names
- Deltasone, Rayos, Winpred
- Generic Name
- Prednisone
- DrugBank Accession Number
- DB00635
- Background
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
- 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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Acne vulgaris ••• ••••• Treatment of Acquired hemolytic anemia •••••••••••• ••••••••• ••••••••• •••••••••••• ••••••• ••••••• ••••••• ••••••• Treatment of Acute exacerbation of chronic obstructive pulmonary disease •••••••••••• ••••••• ••••••• ••••••• Management of Acute gouty arthritis •••••••••••• ••••••••• ••••••••• •••••••••••• ••••••• ••••••• ••••••• ••••••• Treatment of Acute leukemia •••••••••••• •••••••• ••••••••• ••••••••• •••••••••••• •••••• - Associated Therapies
- Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- 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
Target Actions Organism AGlucocorticoid receptor agonistHumans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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
- Pathways
Pathway Category Prednisone Action Pathway Drug action Prednisone Metabolism Pathway Drug 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Prednisone may decrease the excretion rate of Abacavir which could result in a higher serum level. Abametapir The serum concentration of Prednisone can be increased when it is combined with Abametapir. Abatacept The risk or severity of adverse effects can be increased when Prednisone is combined with Abatacept. Acarbose The risk or severity of hyperglycemia can be increased when Prednisone is combined with Acarbose. Aceclofenac The risk or severity of gastrointestinal irritation can be increased when Prednisone is combined with Aceclofenac. - Food Interactions
- Avoid alcohol.
- Take with food. Food reduces irritation.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Active Moieties
Name Kind UNII CAS InChI Key Prednisolone prodrug 9PHQ9Y1OLM 50-24-8 OIGNJSKKLXVSLS-VWUMJDOOSA-N - Product Images
- International/Other Brands
- Delta-Cortef (Upjohn) / Meticorten / Orasone
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Deltasone Tablet 50 mg/1 Oral Pharmacia and Upjohn and Company 2007-03-30 Not applicable US Deltasone Tablet 5 mg/1 Oral Pharmacia and Upjohn and Company 2007-03-30 Not applicable US Deltasone Tablet 20 mg/1 Oral Pharmacia and Upjohn and Company 2007-03-30 Not applicable US Deltasone Tablet 2.5 mg/1 Oral Pharmacia and Upjohn and Company 2007-03-30 Not applicable US Deltasone Tablet 5 mg/1 Oral Physicians Total Care, Inc. 1992-12-01 2011-05-31 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Alti-prednisone Tab 5mg Tablet 5 mg / tab Oral Altimed Pharma Inc. 1984-12-31 1998-08-10 Canada Apo Prednisone Tab 1mg USP Tablet 1 mg Oral Apotex Corporation 1984-12-31 Not applicable Canada Apo Prednisone Tab 50mg Tablet 50 mg Oral Apotex Corporation 1982-12-31 Not applicable Canada Apo Prednisone Tab 5mg Tablet 5 mg Oral Apotex Corporation 1982-12-31 Not applicable Canada Deltasone Tablet 20 mg/20mg Oral Oculus Innovative Scicences 2009-08-03 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Metreton Tab Prednisone (2.5 mg) + Ascorbic acid (75 mg) + Chlorpheniramine maleate (2 mg) Tablet Oral Schering Plough 1956-12-31 2007-08-03 Canada Prednisone Prednisone (5 mg/5mL) + Ethanol (5 mL/100mL) Solution Oral Roxane Laboratories 2006-06-27 2006-09-01 US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Contrast Allergy PreMed Pack Prednisone (50 mg/50mg) + Diphenhydramine hydrochloride (50 mg/50mg) Kit Oral Shertech Laboratories, Llc 2016-09-13 Not applicable US
Categories
- ATC Codes
- A07EA03 — Prednisone
- A07EA — Corticosteroids acting locally
- A07E — INTESTINAL ANTIINFLAMMATORY AGENTS
- A07 — ANTIDIARRHEALS, INTESTINAL ANTIINFLAMMATORY/ANTIINFECTIVE AGENTS
- A — ALIMENTARY TRACT AND METABOLISM
- Drug Categories
- Adrenal Cortex Hormones
- Adrenals
- Alimentary Tract and Metabolism
- Anti-Inflammatory Agents
- Antidiarrheals, Intestinal Antiinflammatory/antiinfective Agents
- Antineoplastic Agents
- Antineoplastic Agents, Hormonal
- Corticosteroid Hormone Receptor Agonists
- Corticosteroids
- Corticosteroids Acting Locally
- Corticosteroids for Systemic Use
- Corticosteroids for Systemic Use, Plain
- Cytochrome P-450 CYP2A6 Inducers
- Cytochrome P-450 CYP2B6 Inducers
- Cytochrome P-450 CYP2B6 Inducers (strength unknown)
- Cytochrome P-450 CYP2C19 Inducers
- Cytochrome P-450 CYP2C19 Inducers (strength unknown)
- Cytochrome P-450 CYP2C8 Inducers
- Cytochrome P-450 CYP2C8 Inducers (strength unknown)
- Cytochrome P-450 CYP2C9 Inducers
- Cytochrome P-450 CYP2C9 Inducers (strength unknown)
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strength unknown)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Inducers
- Cytochrome P-450 CYP3A5 Inducers (strength unknown)
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Substrates
- Drugs that are Mainly Renally Excreted
- Fused-Ring Compounds
- Glucocorticoids
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Hyperglycemia-Associated Agents
- Immunosuppressive Agents
- Intestinal Antiinflammatory Agents
- P-glycoprotein inducers
- P-glycoprotein inhibitors
- P-glycoprotein substrates
- Prednisolone and Prodrugs
- Pregnadienediols
- Pregnadienes
- Pregnanes
- Steroids
- Systemic Hormonal Preparations, Excl. Sex Hormones and Insulins
- Thyroxine-binding globulin inhibitors
- 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)
- Affected organisms
- Humans and other mammals
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
- (1R,3aS,3bS,9aR,9bS,11aS)-1-hydroxy-1-(2-hydroxyacetyl)-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthrene-7,10-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
- Yasir M, Sonthalia S: Corticosteroid Adverse Effects . [Article]
- 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. [Article]
- Frey BM, Frey FJ: Clinical pharmacokinetics of prednisone and prednisolone. Clin Pharmacokinet. 1990 Aug;19(2):126-46. doi: 10.2165/00003088-199019020-00003. [Article]
- 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. [Article]
- 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. [Article]
- Pickup ME: Clinical pharmacokinetics of prednisone and prednisolone. Clin Pharmacokinet. 1979 Mar-Apr;4(2):111-28. doi: 10.2165/00003088-197904020-00004. [Article]
- 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. [Article]
- FDA Approved Drug Products: Meticorten Prednisone Oral Tablets (Discontinued) [Link]
- FDA Approved Drug Products: Rayos Prednisone Delayed-Release Oral Tablets [Link]
- EMA Approved Drug Products: Lynparza (olaparib) Oral Tablets (March 2023) [Link]
- External Links
- Human Metabolome Database
- HMDB0014773
- KEGG Drug
- D00473
- KEGG Compound
- C07370
- PubChem Compound
- 5865
- PubChem Substance
- 46508166
- ChemSpider
- 5656
- 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
- MSDS
- Download (132 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Active Not Recruiting Not Available Large B-Cell / Large B-Cell, Diffuse / Lymphoma 1 somestatus stop reason just information to hide Not Available Active Not Recruiting Treatment Diffuse Large B-Cell Lymphoma (DLBCL) / Non-Hodgkin's Lymphoma (NHL) 1 somestatus stop reason just information to hide Not Available Active Not Recruiting Treatment End Stage Renal Disease (ESRD) 1 somestatus stop reason just information to hide Not Available Active Not Recruiting Treatment Prostate Cancer 1 somestatus stop reason just information to hide Not Available Approved for Marketing Not Available Genital Diseases, Male / Genital Neoplasms, Male / Genitourinary tract neoplasm / Neoplasms of the Prostate 1 somestatus stop reason just information to hide
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
Form Route Strength Tablet Oral 5 mg Tablet Oral 5.000 mg Kit Oral Tablet Oral 20 MG Tablet Oral 2.5 mg/1 Tablet Oral 20 mg/20mg Tablet Oral 5 mg/1 Tablet Oral 50 mg / tab Tablet Oral 5 mg / tab Tablet Oral 50.0000 mg Tablet Oral 1.0 mg Tablet Oral 2 MG Tablet, delayed release Oral 1 mg Tablet, delayed release Oral 2 mg Tablet, delayed release Oral 5 mg Tablet, delayed release Oral 1.00 mg/tablet Tablet, delayed release Oral 2.00 mg/tablet Tablet, delayed release Oral 5.00 mg/tablet Tablet Oral 5.00 mg Tablet Oral 50.000 mg Tablet Oral Tablet Oral 10 MG Tablet Oral 50 mg Solution Oral Solution Oral 5 mg/5mL Solution Oral 5 mg/1mL Tablet Oral Tablet Oral 1 mg/1 Tablet Oral 1.0 mg/1 Tablet Oral 10 mg/1 Tablet Oral 20 mg/1 Tablet Oral 20 mg/201 Tablet Oral 5.0 mg/1 Tablet Oral 50 mg/1 Solution, concentrate Oral 5 mg/1mL Tablet Oral 2.5 MG Tablet Oral 30 MG Tablet Oral 25 MG Tablet, delayed release Oral 1 mg/1 Tablet, delayed release Oral 2 mg/1 Tablet, delayed release Oral 5 mg/1 Suppository 100 MG Suppository Tablet Oral 1 mg - Prices
Unit description Cost Unit Sterapred DS 21 10 mg tablet Disp Pack 64.0USD disp Prednisone powder 3.36USD g Sterapred ds 10 mg tablet unipak 2.93USD tablet Prednisone 5 mg/ml solution 1.17USD ml PredniSONE 5 mg/5ml Solution 0.5USD ml Prednisone 50 mg tablet 0.47USD tablet Prednisone 20 mg tablet 0.29USD tablet Prednisone 10 mg tablet 0.27USD tablet Prednisone 2.5 mg tablet 0.25USD tablet Prednisone 1 mg tablet 0.23USD tablet Apo-Prednisone 50 mg Tablet 0.18USD tablet Winpred 1 mg Tablet 0.12USD tablet Apo-Prednisone 1 mg Tablet 0.11USD tablet Prednisone 5 mg tablet 0.08USD tablet Apo-Prednisone 5 mg Tablet 0.04USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US9186332 No 2015-11-17 2024-04-23 US US8168218 No 2012-05-01 2028-01-07 US US8309124 No 2012-11-13 2024-04-23 US US8394407 No 2013-03-12 2024-04-23 US US9040085 No 2015-05-26 2024-04-23 US US6488960 No 2002-12-03 2020-03-14 US US6677326 No 2004-01-13 2020-03-14 US US9504699 No 2016-11-29 2027-08-03 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 230 - 235 °C (decomposes) MSDS water solubility Very slightly soluble MSDS logP 1.46 MSDS - Predicted Properties
Property Value Source logP 1.66 Chemaxon 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 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 97.57 m3·mol-1 Chemaxon Polarizability 38.2 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9918 Blood Brain Barrier + 0.9383 Caco-2 permeable - 0.5096 P-glycoprotein substrate Substrate 0.7861 P-glycoprotein inhibitor I Non-inhibitor 0.7847 P-glycoprotein inhibitor II Non-inhibitor 0.8383 Renal organic cation transporter Non-inhibitor 0.7463 CYP450 2C9 substrate Non-substrate 0.8496 CYP450 2D6 substrate Non-substrate 0.9138 CYP450 3A4 substrate Substrate 0.7407 CYP450 1A2 substrate Non-inhibitor 0.9406 CYP450 2C9 inhibitor Non-inhibitor 0.9072 CYP450 2D6 inhibitor Non-inhibitor 0.9418 CYP450 2C19 inhibitor Non-inhibitor 0.9253 CYP450 3A4 inhibitor Non-inhibitor 0.8902 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9095 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.9597 Biodegradation Not ready biodegradable 0.925 Rat acute toxicity 1.8914 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.95 hERG inhibition (predictor II) Non-inhibitor 0.584
Spectra
- Mass Spec (NIST)
- Download (12.5 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 192.9933462 predictedDarkChem Lite v0.1.0 [M-H]- 174.7123494 predictedDarkChem Lite v0.1.0 [M-H]- 193.8716462 predictedDarkChem Lite v0.1.0 [M-H]- 182.98608 predictedDeepCCS 1.0 (2019) [M+H]+ 194.6862462 predictedDarkChem Lite v0.1.0 [M+H]+ 177.2265669 predictedDarkChem Lite v0.1.0 [M+H]+ 194.2374462 predictedDarkChem Lite v0.1.0 [M+H]+ 184.88148 predictedDeepCCS 1.0 (2019) [M+Na]+ 193.7847462 predictedDarkChem Lite v0.1.0 [M+Na]+ 191.0416805 predictedDarkChem Lite v0.1.0 [M+Na]+ 193.3606462 predictedDarkChem Lite v0.1.0 [M+Na]+ 191.55984 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Receptor for glucocorticoids (GC) (PubMed:27120390, PubMed:37478846). 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 modulator of other transcription factors (PubMed:28139699). Affects inflammatory responses, cellular proliferation and differentiation in target tissues. Involved in chromatin remodeling (PubMed:9590696). Plays a role in rapid mRNA degradation by binding to the 5' UTR of target mRNAs and interacting with PNRC2 in a ligand-dependent manner which recruits the RNA helicase UPF1 and the mRNA-decapping enzyme DCP1A, leading to RNA decay (PubMed:25775514). 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 (By similarity)
- Specific Function
- core promoter sequence-specific DNA binding
- Gene Name
- NR3C1
- Uniprot ID
- P04150
- Uniprot Name
- Glucocorticoid receptor
- Molecular Weight
- 85658.57 Da
References
- 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. [Article]
- 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. [Article]
- Diez JJ, Iglesias P: Pharmacological therapy of Cushing's syndrome: drugs and indications. Mini Rev Med Chem. 2007 May;7(5):467-80. [Article]
- 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. [Article]
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- 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. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of polyunsaturated fatty acids (PUFA) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates PUFA specifically at the omega-1 position (PubMed:18577768). Catalyzes the epoxidation of double bonds of PUFA (PubMed:19965576, PubMed:20972997). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). 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. Hydroxylates fenbendazole at the 4' position (PubMed:23959307)
- Specific Function
- (R)-limonene 6-monooxygenase activity
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55944.565 Da
References
- 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. [Article]
- 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. [Article]
- Cytochrome P450 drug interactions [File]
- Mayo medical laboratory document [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of steroid hormones and vitamins (PubMed:10681376, PubMed:11093772, PubMed:12865317, PubMed:2732228). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:10681376, PubMed:11093772, PubMed:12865317, PubMed:2732228). Exhibits high catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes 6beta-hydroxylation of the steroid hormones testosterone, progesterone, and androstenedione (PubMed:2732228). Catalyzes the oxidative conversion of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes all trans-retinoic acid (atRA) to 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Also involved in the oxidative metabolism of xenobiotics, including calcium channel blocking drug nifedipine and immunosuppressive drug cyclosporine (PubMed:2732228)
- Specific Function
- aromatase activity
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- 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. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
Components:
Name | UniProt ID |
---|---|
Cytochrome P450 3A4 | P08684 |
Cytochrome P450 3A43 | Q9HB55 |
Cytochrome P450 3A5 | P20815 |
Cytochrome P450 3A7 | P24462 |
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General 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. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity
- Specific Function
- arachidonic acid epoxygenase activity
- Gene Name
- CYP2A6
- Uniprot ID
- P11509
- Uniprot Name
- Cytochrome P450 2A6
- Molecular Weight
- 56517.005 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:15258110, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:15258110, PubMed:20972997). Exhibits catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2- and 4-hydroxy E1 and E2. Displays a predominant hydroxylase activity toward E2 at the C-4 position (PubMed:11555828, PubMed:12865317). Metabolizes testosterone and progesterone to B or D ring hydroxylated metabolites (PubMed:10426814). May act as a major enzyme for all-trans retinoic acid biosynthesis in extrahepatic tissues. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376, PubMed:15258110). Catalyzes the epoxidation of double bonds of certain PUFA. Converts arachidonic acid toward epoxyeicosatrienoic acid (EpETrE) regioisomers, 8,9-, 11,12-, and 14,15- EpETrE, that function as lipid mediators in the vascular system (PubMed:20972997). Additionally, displays dehydratase activity toward oxygenated eicosanoids hydroperoxyeicosatetraenoates (HpETEs). This activity is independent of cytochrome P450 reductase, NADPH, and O2 (PubMed:21068195). Also involved in the oxidative metabolism of xenobiotics, particularly converting polycyclic aromatic hydrocarbons and heterocyclic aryl amines procarcinogens to DNA-damaging products (PubMed:10426814). Plays an important role in retinal vascular development. Under hyperoxic O2 conditions, promotes retinal angiogenesis and capillary morphogenesis, likely by metabolizing the oxygenated products generated during the oxidative stress. Also, contributes to oxidative homeostasis and ultrastructural organization and function of trabecular meshwork tissue through modulation of POSTN expression (By similarity)
- Specific Function
- aromatase activity
- Gene Name
- CYP1B1
- Uniprot ID
- Q16678
- Uniprot Name
- Cytochrome P450 1B1
- Molecular Weight
- 60845.33 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of endocannabinoids and steroids (PubMed:12865317, PubMed:21289075). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the epoxidation of double bonds of arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:21289075). Hydroxylates steroid hormones, including testosterone at C-16 and estrogens at C-2 (PubMed:12865317, PubMed:21289075). Plays a role in the oxidative metabolism of xenobiotics, including plant lipids and drugs (PubMed:11695850, PubMed:22909231). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850)
- Specific Function
- anandamide 11,12 epoxidase activity
- Gene Name
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Primarily catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) with a preference for the last double bond (PubMed:15766564, PubMed:19965576, PubMed:7574697). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes all trans-retinoic acid toward its 4-hydroxylated form (PubMed:11093772). Displays 16-alpha hydroxylase activity toward estrogen steroid hormones, 17beta-estradiol (E2) and estrone (E1) (PubMed:14559847). Plays a role in the oxidative metabolism of xenobiotics. It is the principal enzyme responsible for the metabolism of the anti-cancer drug paclitaxel (taxol) (PubMed:26427316)
- Specific Function
- arachidonic acid epoxygenase activity
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031)
- Specific Function
- (R)-limonene 6-monooxygenase activity
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Controls the reversible conversion of biologically active glucocorticoids such as cortisone to cortisol, and 11-dehydrocorticosterone to corticosterone in the presence of NADP(H) (PubMed:10497248, PubMed:12460758, PubMed:14973125, PubMed:15152005, PubMed:15280030, PubMed:17593962, PubMed:21453287, PubMed:27927697, PubMed:30902677). Participates in the corticosteroid receptor-mediated anti-inflammatory response, as well as metabolic and homeostatic processes (PubMed:10497248, PubMed:12414862, PubMed:15152005, PubMed:21453287). Plays a role in the secretion of aqueous humor in the eye, maintaining a normotensive, intraocular environment (PubMed:11481269). Bidirectional in vitro, predominantly functions as a reductase in vivo, thereby increasing the concentration of active glucocorticoids (PubMed:10497248, PubMed:11481269, PubMed:12414862, PubMed:12460758). It has broad substrate specificity, besides glucocorticoids, it accepts other steroid and sterol substrates (PubMed:15095019, PubMed:15152005, PubMed:17593962, PubMed:21453287). Interconverts 7-oxo- and 7-hydroxy-neurosteroids such as 7-oxopregnenolone and 7beta-hydroxypregnenolone, 7-oxodehydroepiandrosterone (3beta-hydroxy-5-androstene-7,17-dione) and 7beta-hydroxydehydroepiandrosterone (3beta,7beta-dihydroxyandrost-5-en-17-one), among others (PubMed:17593962). Catalyzes the stereo-specific conversion of the major dietary oxysterol, 7-ketocholesterol (7-oxocholesterol), into the more polar 7-beta-hydroxycholesterol metabolite (PubMed:15095019, PubMed:15152005). 7-oxocholesterol is one of the most important oxysterols, it participates in several events such as induction of apoptosis, accumulation in atherosclerotic lesions, lipid peroxidation, and induction of foam cell formation (PubMed:15095019). Mediates the 7-oxo reduction of 7-oxolithocholate mainly to chenodeoxycholate, and to a lesser extent to ursodeoxycholate, both in its free form and when conjugated to glycine or taurine, providing a link between glucocorticoid activation and bile acid metabolism (PubMed:21453287). Catalyzes the synthesis of 7-beta-25-dihydroxycholesterol from 7-oxo-25-hydroxycholesterol in vitro, which acts as a ligand for the G-protein-coupled receptor (GPCR) Epstein-Barr virus-induced gene 2 (EBI2) and may thereby regulate immune cell migration (PubMed:30902677)
- Specific Function
- 11-beta-hydroxysteroid dehydrogenase (NADP+) activity
- Gene Name
- HSD11B1
- Uniprot ID
- P28845
- Uniprot Name
- 11-beta-hydroxysteroid dehydrogenase 1
- Molecular Weight
- 32400.665 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInducer
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
- Specific Function
- antioxidant activity
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Albumin
- Molecular Weight
- 69365.94 Da
References
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Major transport protein for glucocorticoids and progestins in the blood of almost all vertebrate species
- Specific Function
- serine-type endopeptidase inhibitor activity
- Gene Name
- SERPINA6
- Uniprot ID
- P08185
- Uniprot Name
- Corticosteroid-binding globulin
- Molecular Weight
- 45140.49 Da
References
- 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. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInducer
- General Function
- Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218)
- Specific Function
- ABC-type xenobiotic transporter activity
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- ATP-dependent translocase ABCB1
- Molecular Weight
- 141477.255 Da
References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Na(+)-independent transporter that mediates the cellular uptake of a broad range of organic anions such as the endogenous bile salts cholate and deoxycholate, either in their unconjugated or conjugated forms (taurocholate and glycocholate), at the plasmam membrane (PubMed:19129463, PubMed:7557095). Responsible for intestinal absorption of bile acids (By similarity). Transports dehydroepiandrosterone 3-sulfate (DHEAS), a major circulating steroid secreted by the adrenal cortex, as well as estrone 3-sulfate and 17beta-estradiol 17-O-(beta-D-glucuronate) (PubMed:11159893, PubMed:12568656, PubMed:19129463, PubMed:23918469, PubMed:25560245, PubMed:9539145). Mediates apical uptake of all-trans-retinol (atROL) across human retinal pigment epithelium, which is essential to maintaining the integrity of the visual cycle and thus vision (PubMed:25560245). Involved in the uptake of clinically used drugs (PubMed:17301733, PubMed:20686826, PubMed:27777271). Capable of thyroid hormone transport (both T3 or 3,3',5'-triiodo-L-thyronine, and T4 or L-tyroxine) (PubMed:19129463, PubMed:20358049). Also transports prostaglandin E2 (PubMed:19129463). Plays roles in blood-brain and -cerebrospinal fluid barrier transport of organic anions and signal mediators, and in hormone uptake by neural cells (By similarity). May also play a role in the reuptake of neuropeptides such as substance P/TAC1 and vasoactive intestinal peptide/VIP released from retinal neurons (PubMed:25132355). May play an important role in plasma and tissue distribution of the structurally diverse chemotherapeutic drugs methotrexate and paclitaxel (PubMed:23243220). Shows a pH-sensitive substrate specificity which may be ascribed to the protonation state of the binding site and leads to a stimulation of substrate transport in an acidic microenvironment (PubMed:19129463). Hydrogencarbonate/HCO3(-) acts as the probable counteranion that exchanges for organic anions (PubMed:19129463). May contribute to regulate the transport of organic compounds in testis across the blood-testis-barrier (Probable)
- Specific Function
- bile acid transmembrane transporter activity
- Gene Name
- SLCO1A2
- Uniprot ID
- P46721
- Uniprot Name
- Solute carrier organic anion transporter family member 1A2
- Molecular Weight
- 74144.105 Da
References
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 21, 2024 12:37