ContaminantDB: Prednisone

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (4)XML

Record Information

Version

1.0

Creation Date

2014-09-11 02:05:57 UTC

Update Date

2026-05-14 16:44:43 UTC

Accession Number

CHEM003668

Identification

Common Name

Prednisone

Class

Small Molecule

Description

Prednisone is only found in individuals that have used or taken this drug. It is a synthetic anti-inflammatory glucocorticoid derived from cortisone. It is biologically inert and converted to prednisolone in the liver. Prednisone is a glucocorticoid receptor agonist. It is first metabolized in the liver to its active form, prednisolone. Prednisolone crosses cell membranes and binds with high affinity to specific cytoplasmic receptors. The result includes inhibition of leukocyte infiltration at the site of inflammation, interference in the function of mediators of inflammatory response, suppression of humoral immune responses, and reduction in edema or scar tissue. The antiinflammatory actions of corticosteroids are thought to involve phospholipase A2 inhibitory proteins, lipocortins, which control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes.

Contaminant Sources

HMDB Contaminants - Urine
IARC Carcinogens Group 3
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Anti-Inflammatory Agent
Antineoplastic Agent, Hormonal
Drug
Ester
Glucocorticoid
Human Neurotoxin
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,2-Dehydrocortisone	ChEBI
1,4-Pregnadiene-17alpha,21-diol-3,11,20-trione	ChEBI
17,21-Dihydroxypregna-1,4-diene-3,11,20-trione	ChEBI
Dehydrocortisone	ChEBI
Prednison	ChEBI
Prednisona	ChEBI
Prednisonum	ChEBI
1,4-Pregnadiene-17a,21-diol-3,11,20-trione	Generator
1,4-Pregnadiene-17α,21-diol-3,11,20-trione	Generator
Aventis brand OF prednisone	HMDB
Diba brand OF prednisone	HMDB
Fawns and mcallan brand OF prednisone	HMDB
Halsey drug brand OF prednisone	HMDB
Kortancyl	HMDB
Lichtenstein brand OF prednisone	HMDB
Merck brand OF prednisone	HMDB
Orasone	HMDB
Prednison galen	HMDB
Pronisone	HMDB
Sterapred	HMDB
Winpred	HMDB
Mibe brand OF prednisone	HMDB
Dacortin	HMDB
Decortisyl	HMDB
Deltasone	HMDB
Encorton	HMDB
Hoechst brand OF prednisone	HMDB
Panafcort	HMDB
Panasol	HMDB
Prednison acsis	HMDB
Schering-plough brand OF prednisone	HMDB
Solvay brand OF prednisone	HMDB
Apo-prednisone	HMDB
Cortan	HMDB
Cutason	HMDB
Decortin	HMDB
Enkortolon	HMDB
GALENpharma brand OF prednisone	HMDB
ICN brand OF prednisone	HMDB
Merz brand OF prednisone	HMDB
Meticorten	HMDB
Predniment	HMDB
Seatrace brand OF prednisone	HMDB
Sone	HMDB
Trommsdorff brand OF prednisone	HMDB
Ultracorten	HMDB
Apotex brand OF prednisone	HMDB
Cortancyl	HMDB
Encortone	HMDB
Ferring brand OF prednisone	HMDB
Hexal brand OF prednisone	HMDB
Liquid pred	HMDB
Pharmacia brand OF prednisone	HMDB
Predni tablinen	HMDB
Prednidib	HMDB
Prednison hexal	HMDB
Rectodelt	HMDB
Acis brand OF prednisone	HMDB
delta-Cortisone	HMDB
Acsis, prednison	HMDB

Chemical Formula

C₂₁H₂₆O₅

Average Molecular Mass

358.428 g/mol

Monoisotopic Mass

358.178 g/mol

CAS Registry Number

53-03-2

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

Traditional Name

prednisone

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

InChI Identifier

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

InChI Key

XOFYZVNMUHMLCC-ZPOLXVRWSA-N

Chemical Taxonomy

Description

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

Substituents

21-hydroxysteroid
Progestogin-skeleton
Pregnane-skeleton
20-oxosteroid
3-oxo-delta-1,4-steroid
3-oxosteroid
17-hydroxysteroid
Oxosteroid
11-oxosteroid
Delta-1,4-steroid
Alpha-hydroxy ketone
Tertiary alcohol
Cyclic alcohol
Cyclic ketone
Ketone
Organic oxygen compound
Organooxygen compound
Primary alcohol
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

17alpha-hydroxy steroid (CHEBI:8382 )
glucocorticoid (CHEBI:8382 )
20-oxo steroid (CHEBI:8382 )
3-oxo-Delta(1),Delta(4)-steroid (CHEBI:8382 )
11-oxo steroid (CHEBI:8382 )
21-hydroxy steroid (CHEBI:8382 )
Pregnane and derivatives [Fig] (C07370 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030180 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Prednisone Pathway	Not Available	Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	233 - 235°C
Boiling Point	Not Available
Solubility	1.11e-01 g/L

Predicted Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	2.07	ALOGPS
logP	1.66	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	12.58	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	97.57 m³·mol⁻¹	ChemAxon
Polarizability	38.17 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

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-4976000000-e89b93e4bd7a96264eff	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0079-5612900000-e8fe74535be00b772cad	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-05tg-0695000000-35841a4b47ea1535be95	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0a4m-0597000000-c12dc88504062b28c4be	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0002-2960000000-10bdddfba8bd2889acde	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-00di-0900000000-1ea12664a8edc235b05c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-00di-1900000000-06d289c40615662ab14e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-00di-0900000000-f76738c3bedb48d0c7a3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4i-0019000000-d5b5ef89fce8ee6966ba	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00r5-0493000000-ae479d92cc77796a5177	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00ds-0690000000-f3df1438f8c0623811c1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00dj-0970000000-b61d7f78a4036739cb07	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-05fs-0940000000-a9c08e5a06f9684fb000	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0a4l-0149000000-088a79de5c16e3384162	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-006w-2930000000-f901c87bc4fd3221d37e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-05tg-0695000000-35841a4b47ea1535be95	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0a4m-0597000000-c12dc88504062b28c4be	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0002-2960000000-10bdddfba8bd2889acde	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-00dj-0970000000-b61d7f78a4036739cb07	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-0a4l-0149000000-e36403a2dae0a4f97002	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-05fs-0940000000-7721562715b13df56087	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4l-0019000000-be6ec5707cb4a10cdd52	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0596-0269000000-63f648937479bcaf1b1c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00lr-3491000000-bbe8b03c42791ca28e7e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0019000000-70601e80fb30c3ac38c4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052b-3089000000-4a4f905a7eb26d17adcc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-6092000000-d6e3f920b0cd1bc32f08	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-05fs-2951000000-1a9b3a7e18f6088d28db	Spectrum

Toxicity Profile

Route of Exposure

Readily absorbed from the gastrointestinal tract. Rayos, the delayed-release formulation, has a 4-hour release time. To compare, the delayed-release formulation has a Tmax of 6.0 - 6.5 hours in healthy male subjects, whereas the immediate-release formulation has a Tmax of 2.0 hours. The rate of absorption, Cmax, and exposure is comparable between formulations.

Mechanism of Toxicity

Prednisone is a glucocorticoid receptor agonist. It is first metabolized in the liver to its active form, prednisolone. Prednisolone crosses cell membranes and binds with high affinity to specific cytoplasmic receptors. The result includes inhibition of leukocyte infiltration at the site of inflammation, interference in the function of mediators of inflammatory response, suppression of humoral immune responses, and reduction in edema or scar tissue. The antiinflammatory actions of corticosteroids are thought to involve phospholipase A2 inhibitory proteins, lipocortins, which control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes. Prednisone can stimulate secretion of various components of gastric juice. Suppression of the production of corticotropin may lead to suppression of endogenous corticosteroids. Prednisone has slight mineralocorticoid activity, whereby entry of sodium into cells and loss of intracellular potassium is stimulated. This is particularly evident in the kidney, where rapid ion exchange leads to sodium retention and hypertension.

Metabolism

Prednisone is completely converted to the active metabolite prednisolone by 11‘_-hydroxysteroid dehydrogenases. It is then further metabolized mainly in the liver. The exposure of prednisolone is 4-6 fold higher than that of prednisone. Route of Elimination: Excreted in the urine as sulfate and glucuronide conjugates. Half Life: Half life of both the immediate- and delayed- release formulation is 2 to 3 hours.

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Prednisone is not classifiable as to its carcinogenicity to humans (Group 3). Prednisone is part of MOPP, a combination chemotherapy regimen that is carcinogenic to humans (Group 1). (1)

Uses/Sources

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

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID