PREDNISONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H26O5
Molecular Weight	358.4281
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=XOFYZVNMUHMLCC-ZPOLXVRWSA-N

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

HIDE SMILES / InChI

Molecular Formula	C21H26O5
Molecular Weight	358.4281
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/202020s003lbl.pdf
Curator's Comment: description was created based on several sources, including

Prednisone is a synthetic anti-inflammatory glucocorticoid derived from cortisone. Prednisone is a corticosteroid indicated as an anti-inflammatory or immunosuppressive agent allergic, dermatologic, gastrointestinal, hematologic, ophthalmologic, nervous system, renal, respiratory, rheumatologic, specific infectious diseases or conditions and organ transplantation; for the treatment of certain endocrine conditions; for palliation of certain neoplastic conditions. The pharmacological effects of prednisone which are due to its corticosteroid properties include: promotion of gluconeogenesis; increased deposition of glycogen in the liver; inhibition of the utilization of glucose; anti-insulin activity; increased catabolism of protein; increased lipolysis; stimulation of fat synthesis and storage; increased glomerular filtration rate and resulting increase in urinary excretion of urate (creatinine excretion remains unchanged); and increased calcium excretion. Depressed production of eosinophils and lymphocytes occurs, but erythropoiesis and production of polymorphonuclear leukocytes are stimulated. Inflammatory processes (edema, fibrin deposition, capillary dilatation, migration of leukocytes and phagocytosis) and the later stages of wound healing (capillary proliferation, deposition of collagen, cicatrization) are inhibited. 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. Prednisone is completely converted to the active metabolite prednisolone, which is further metabolized mainly in the liver and excreted in the urine as sulfate and glucuronide conjugates. The exposure of prednisolone is 4-6 fold higher than that of prednisone.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glucocorticoid receptor 172 Target ID: CHEMBL2034 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/202020s003lbl.pdf	Agonist 2678

Conditions

Condition	Modality	Highest Phase	Product
Atopic dermatitis 43 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/202020s003lbl.pdf	Palliative	Approved 8429	RAYOS Approved Use RAYOS is a corticosteroid indicated as an anti-inflammatory or immunosuppressive agent for certain allergic, dermatologic, gastrointestinal, hematologic, ophthalmologic, nervous system, renal, respiratory, rheumatologic, specific infectious diseases or conditions and organ transplantation; for the treatment of certain endocrine conditions; for palliation of certain neoplastic conditions Launch Date 2012
Severe erythema multiforme (Stevens-Johnson syndrome) 1 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/202020s003lbl.pdf	Palliative	Approved 8429	RAYOS Approved Use RAYOS is a corticosteroid indicated as an anti-inflammatory or immunosuppressive agent for certain allergic, dermatologic, gastrointestinal, hematologic, ophthalmologic, nervous system, renal, respiratory, rheumatologic, specific infectious diseases or conditions and organ transplantation; for the treatment of certain endocrine conditions; for palliation of certain neoplastic conditions Launch Date 2012
Congenital adrenal hyperplasia 41 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/202020s003lbl.pdf	Palliative	Approved 8429	RAYOS Approved Use RAYOS is a corticosteroid indicated as an anti-inflammatory or immunosuppressive agent for certain allergic, dermatologic, gastrointestinal, hematologic, ophthalmologic, nervous system, renal, respiratory, rheumatologic, specific infectious diseases or conditions and organ transplantation; for the treatment of certain endocrine conditions; for palliation of certain neoplastic conditions Launch Date 2012
Crohn's disease 42 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/202020s003lbl.pdf	Palliative	Approved 8429	RAYOS Approved Use RAYOS is a corticosteroid indicated as an anti-inflammatory or immunosuppressive agent for certain allergic, dermatologic, gastrointestinal, hematologic, ophthalmologic, nervous system, renal, respiratory, rheumatologic, specific infectious diseases or conditions and organ transplantation; for the treatment of certain endocrine conditions; for palliation of certain neoplastic conditions Launch Date 2012
Diamond-Blackfan anemia 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/202020s003lbl.pdf	Palliative	Approved 8429	RAYOS Approved Use RAYOS is a corticosteroid indicated as an anti-inflammatory or immunosuppressive agent for certain allergic, dermatologic, gastrointestinal, hematologic, ophthalmologic, nervous system, renal, respiratory, rheumatologic, specific infectious diseases or conditions and organ transplantation; for the treatment of certain endocrine conditions; for palliation of certain neoplastic conditions Launch Date 2012
Aggressive lymphoma 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/202020s003lbl.pdf	Palliative	Approved 8429	RAYOS Approved Use RAYOS is a corticosteroid indicated as an anti-inflammatory or immunosuppressive agent for certain allergic, dermatologic, gastrointestinal, hematologic, ophthalmologic, nervous system, renal, respiratory, rheumatologic, specific infectious diseases or conditions and organ transplantation; for the treatment of certain endocrine conditions; for palliation of certain neoplastic conditions Launch Date 2012

C_max

Value	Dose	Co-administered	Analyte	Population
15.4 μg/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/17925494	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:		PREDNISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

AUC

Value	Dose	Co-administered	Analyte	Population
97 μg × h/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/17925494	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:		PREDNISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

T_1/2

Value	Dose	Co-administered	Analyte	Population
3.85 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/17925494	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:		PREDNISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

F_unbound

Value	Dose	Co-administered	Analyte	Population
50% EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2199128			PREDNISONE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
100 mg 1 times / day multiple, oral Highest studied dose Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: https://doi.org/10.1016/B978-0-12-385157-4.00633-3 https://pubmed.ncbi.nlm.nih.gov/33663183	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://doi.org/10.1016/B978-0-12-385157-4.00633-3 https://pubmed.ncbi.nlm.nih.gov/33663183	Sources: https://doi.org/10.1016/B978-0-12-385157-4.00633-3 https://pubmed.ncbi.nlm.nih.gov/33663183
5 mg 1 times / day steady, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: steady Dose: 5 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202020Orig1s000MedR.pdf Page: p. 92	unhealthy, adult n = 144 Health Status: unhealthy Age Group: adult Population Size: 144 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202020Orig1s000MedR.pdf Page: p. 92	Disc. AE: Vertigo, Abdominal pain upper... AEs leading to discontinuation/dose reduction: Vertigo (1%) Abdominal pain upper (1%) Gastroesophageal reflux disease (1%) Intestinal functional disorder (1%) Nausea (1%) Dizziness (1%) Aphasia (1%) Headache (1%) Renal pain (1%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202020Orig1s000MedR.pdf Page: p. 92

AEs

AE	Significance	Dose	Population
Abdominal pain upper	1% Disc. AE	5 mg 1 times / day steady, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: steady Dose: 5 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202020Orig1s000MedR.pdf Page: p. 92	unhealthy, adult n = 144 Health Status: unhealthy Age Group: adult Population Size: 144 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202020Orig1s000MedR.pdf Page: p. 92
Aphasia	1% Disc. AE	5 mg 1 times / day steady, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: steady Dose: 5 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202020Orig1s000MedR.pdf Page: p. 92	unhealthy, adult n = 144 Health Status: unhealthy Age Group: adult Population Size: 144 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202020Orig1s000MedR.pdf Page: p. 92
Dizziness	1% Disc. AE	5 mg 1 times / day steady, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: steady Dose: 5 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202020Orig1s000MedR.pdf Page: p. 92	unhealthy, adult n = 144 Health Status: unhealthy Age Group: adult Population Size: 144 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202020Orig1s000MedR.pdf Page: p. 92
Gastroesophageal reflux disease	1% Disc. AE	5 mg 1 times / day steady, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: steady Dose: 5 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202020Orig1s000MedR.pdf Page: p. 92	unhealthy, adult n = 144 Health Status: unhealthy Age Group: adult Population Size: 144 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202020Orig1s000MedR.pdf Page: p. 92
Headache	1% Disc. AE	5 mg 1 times / day steady, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: steady Dose: 5 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202020Orig1s000MedR.pdf Page: p. 92	unhealthy, adult n = 144 Health Status: unhealthy Age Group: adult Population Size: 144 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202020Orig1s000MedR.pdf Page: p. 92
Intestinal functional disorder	1% Disc. AE	5 mg 1 times / day steady, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: steady Dose: 5 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202020Orig1s000MedR.pdf Page: p. 92	unhealthy, adult n = 144 Health Status: unhealthy Age Group: adult Population Size: 144 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202020Orig1s000MedR.pdf Page: p. 92
Nausea	1% Disc. AE	5 mg 1 times / day steady, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: steady Dose: 5 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202020Orig1s000MedR.pdf Page: p. 92	unhealthy, adult n = 144 Health Status: unhealthy Age Group: adult Population Size: 144 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202020Orig1s000MedR.pdf Page: p. 92
Renal pain	1% Disc. AE	5 mg 1 times / day steady, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: steady Dose: 5 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202020Orig1s000MedR.pdf Page: p. 92	unhealthy, adult n = 144 Health Status: unhealthy Age Group: adult Population Size: 144 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202020Orig1s000MedR.pdf Page: p. 92
Vertigo	1% Disc. AE	5 mg 1 times / day steady, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: steady Dose: 5 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202020Orig1s000MedR.pdf Page: p. 92	unhealthy, adult n = 144 Health Status: unhealthy Age Group: adult Population Size: 144 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202020Orig1s000MedR.pdf Page: p. 92

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	11-beta-HSD2 27 11-beta-HSD1 12 P-gp 1537	P-gp 257 BCRP 75 MRP1 48 MRP4 32 MRP5 22 ABCC12 22 MRP2 111 MRP3 53

Drug as perpetrator

Target	Modality	Activity
ABCC12 22	inducer 1573 Sources: https://www.sciencedirect.com/science/article/pii/S0143400412002895 Page: -	no
BCRP 773	inducer 1573 Sources: https://www.sciencedirect.com/science/article/pii/S0143400412002895 Page: -	no
MRP1 172	inducer 1573 Sources: https://www.sciencedirect.com/science/article/pii/S0143400412002895 Page: -	no
MRP3 207	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/15979871/ Page: -	no
MRP4 238	inducer 1573 Sources: https://www.sciencedirect.com/science/article/pii/S0143400412002895 Page: -	no
MRP5 48	inducer 1573 Sources: https://www.sciencedirect.com/science/article/pii/S0143400412002895 Page: -	no
P-gp 1650	inducer 1573 Sources: https://www.sciencedirect.com/science/article/pii/S0143400412002895 Page: -	no
MRP2 475	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/15979871/ Page: -	yes

Drug as victim

Target	Modality	Activity
11-beta-HSD2 27	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6349812/ Page: -	major
11-beta-HSD1 12	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6349812/ Page: -	minor
P-gp 1537	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6349812/ Page: -	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:8382	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8382
ChemicalBook	CB44844383	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB44844383
ChemicalBook	CB6716222	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6716222
MolPort	MolPort-001-740-041	https://www.molport.com/shop/molecule-link/MolPort-001-740-041
Selleck Chemicals	Prednisone	http://www.selleckchem.com/products/Prednisone.html
ZINC	ZINC000003875357	http://zinc15.docking.org/substances/ZINC000003875357
eMolecules	29549912	https://www.emolecules.com/cgi-bin/more?vid=29549912
eMolecules	29703823	https://www.emolecules.com/cgi-bin/more?vid=29703823
eMolecules	31411020	https://www.emolecules.com/cgi-bin/more?vid=31411020
eMolecules	494851	https://www.emolecules.com/cgi-bin/more?vid=494851

PubMed

Title	Date	PubMed
An unusual adverse reaction to self-medication with prednisone: an irrational crime during a fugue-state.	1976-1977	1052090
Relation between long-term steroid treatment after heart transplantation, hypofibrinolysis and myocardial microthrombi generation.	1999 Jul	10452346
Nephrotic syndrome and acute interstitial nephritis associated with the use of diclofenac.	1999 Jul 9	10444806
Pseudotumor cerebri secondary to intermediate-dose cytarabine HCl.	1999 May	10369621
Lamotrigine as prophylaxis against steroid-induced mania.	1999 Oct	10549692
Behavioral effects of corticosteroids in steroid-sensitive nephrotic syndrome.	1999 Oct	10506276
Delayed generalized allergic reactions to corticosteroids.	2000	10894975
Influence of cyclosporin A on radiological progression in early rheumatoid arthritis patients: a 42-month prospective study.	2000	10776690
Interstitial nephritis in children with Crohn's disease.	2000 Apr	10791141
Mesalamine-induced chest pain: a case report.	2000 May	10833545
Cognitive sequelae in children treated for acute lymphoblastic leukemia with dexamethasone or prednisone.	2000 May-Jun	10864051
Acute neurotoxicity in children with B-lineage acute lymphoblastic leukemia (B-ALL) treated with intermediate risk protocols.	2000 Nov	11070476
Choroidal granulomas in systemic sarcoidosis.	2001	11217928
Hodgkin's disease: clinical presentation and treatment.	2001	11191130
The risk of upper gastrointestinal complications associated with nonsteroidal anti-inflammatory drugs, glucocorticoids, acetaminophen, and combinations of these agents.	2001	11178116
Cyclophosphamide-based, seven-drug hybrid and low-dose involved field radiation for the treatment of childhood and adolescent Hodgkin disease.	2001 Feb	11216711
The usefulness of quantitative orbital magnetic resonance imaging in Graves' ophthalmopathy.	2001 Feb	11207635
Mycophenolic acid plasma concentrations: influence of comedication.	2001 Feb	11206040
Interstitial nephritis in patients with inflammatory bowel disease treated with mesalamine.	2001 Feb	11205659
Can we induce tolerance in rheumatoid arthritis?	2001 Feb	11177772
Perinuclear antineutrophilic cytoplasmic antibody-positive cutaneous polyarteritis nodosa associated with minocycline therapy for acne vulgaris.	2001 Feb	11174376
Fistulation of the auditory tube diverticulum (guttural pouch) with a neodymium:yttrium-aluminum-garnet laser for treatment of chronic empyema in two horses.	2001 Feb 1	11201568
Remission of precapillary pulmonary hypertension in systemic lupus erythematosus.	2001 Jan	11220068
Pyodera gangrenosum after aortic valve replacement.	2001 Jan	11216779
Gingival overgrowth as the initial paraneoplastic manifestation of Hodgkin's lymphoma in a child. A case report.	2001 Jan	11210066
Lupus-like syndrome with submassive hepatic necrosis associated with hepatitis A.	2001 Jan	11206308
Longitudinal assessment of everolimus in de novo renal transplant recipients over the first post-transplant year: pharmacokinetics, exposure-response relationships, and influence on cyclosporine.	2001 Jan	11180038
Phase II study of rituximab in combination with chop chemotherapy in patients with previously untreated, aggressive non-Hodgkin's lymphoma.	2001 Jan 15	11208830
High-dose therapy and autologous bone marrow transplantation for follicular lymphoma in first complete or partial remission: results of a phase II clinical trial.	2001 Jan 15	11154216
Autologous bone marrow transplantation for aggressive non-Hodgkin's lymphoma: lessons learned and challenges remaining.	2001 Jan 3	11136829
Improved outcome for children with acute lymphoblastic leukemia: results of Dana-Farber Consortium Protocol 91-01.	2001 Mar 1	11222362

Patents

Sample Use Guides

In Vivo Use Guide

The initial dosage of RAYOS (prednisone) may vary from 5 to 60 mg per day depending on the specific disease entity being treated based on relative potency.

Route of Administration: Oral

In Vitro Use Guide

Peripheral blood lymphocytes (PBL) or peripheral CD4(+) and CD8(+) T cell subsets were cultured in the presence of prednisone (PDN) at 10(-3)-10(-12)M concentrations for 72, 96 and 120h. Apoptosis is clearly increased by PDN and the apoptotic effect of PDN is stronger on CD8(+) than on CD4(+) T lymphocytes.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:51:36 GMT 2023` Edited by `admin` on `Fri Dec 15 15:51:36 GMT 2023`
Record UNII	VB0R961HZT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PREDNISONE

Official Name

English

17,21-Dihydroxypregna-1,4-diene-3,11,20-trione

Systematic Name

English

PREGNA-1,4-DIENE-3,11,20-TRIONE, 17,21-DIHYDROXY-

Systematic Name

English

PREDNISONE TABLETS [USP-RS]

Common Name

English

PREDNISONE INTENSOL

Brand Name

English

Prednisone [WHO-DD]

Common Name

English

SUPERCORTIL

Common Name

English

METACORTANDRACIN

Common Name

English

PREDNISONE [USP MONOGRAPH]

Common Name

English

PREDNISONE ANHYDROUS

Common Name

English

3EN3HG4WSW

Common Name

English

PREDNISONE [GREEN BOOK]

Common Name

English

NSC-10023

Code

English

prednisone [INN]

Common Name

English

DELTASONE

Brand Name

English

DEHYDROCORTISONE

Common Name

English

PREDNISONE [USP-RS]

Common Name

English

PREDNISONE [ORANGE BOOK]

Common Name

English

PREDNISONE [EP MONOGRAPH]

Common Name

English

PREDNISONE TABLETS

Common Name

English

PREDNISONE [IARC]

Common Name

English

PREDNISONE [VANDF]

Common Name

English

PREDNISONE [HSDB]

Common Name

English

PREDNISONE [MART.]

Common Name

English

PREDNISONE [MI]

Common Name

English

DECORTIN

Brand Name

English

PREDNISOLONE IMPURITY B [EP IMPURITY]

Common Name

English

Classification Tree Code System Code

WHO-ATC

H02AB07