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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H28O5
Molecular Weight 372.4556
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MEPREDNISONE

SMILES

C[C@@]1([H])C[C@@]2([H])[C@]3([H])CCC4=CC(=O)C=C[C@]4(C)[C@@]3([H])C(=O)C[C@]2(C)[C@]1(C(=O)CO)O

InChI

InChIKey=PIDANAQULIKBQS-RNUIGHNZSA-N
InChI=1S/C22H28O5/c1-12-8-16-15-5-4-13-9-14(24)6-7-20(13,2)19(15)17(25)10-21(16,3)22(12,27)18(26)11-23/h6-7,9,12,15-16,19,23,27H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,19+,20-,21-,22-/m0/s1

HIDE SMILES / InChI
Meprednisone, also known as NSC-63278 and Betapar, is a glucocorticoid receptor agonist.It has anti-inflammatory and immunosuppressive activity. It was approved since 1978, but its marketing in USA was discontinied since. Meprednisone is marketed in Argentina under trade name Copytren for treatment of rheumatic diseases, diseases of collagen, dermatological, gastrointestinal, respiratory and ophtalmological diseases.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
BETAPAR

Approved Use

Meprednisone (16-β-methylprednisone) is a steroid anti-inflammatory with poor mineralocorticoid action due to the methylation of prednisone at the carbon 16 level. Corticosteroids have anti-inflammatory and immunosuppressive activity. The mechanism of anti-inflammatory action is due to the decrease of the tissue response to the inflammatory processes, without modifying the underlying causes. Steroids diffuse through the cell membrane and bind to specific cytoplasmic receptors. Then, this complex enters the nucleus, where it binds to other transcriptional factors and to DNA producing induction and repression of genes that lead to its anti-inflammatory, immunosuppressive and mild mineralocorticoid effect. Other effects are: suppression of pituitary corticotropin production leading to secondary adrenal insufficiency, decreased absorption and increased calcium excretion, increased surfactant factor production in type 2 pneumocytes, protein catabolism in lymphoid, muscle, Connective tissue and skin, hepatic gluconeogenesis with decreased peripheral glucose utilization, decreased formation and increased bone resorption. The mechanism by which corticosteroids decrease immunity involves inhibition of cell-mediated immune reactions, reduction of T lymphocyte, monocyte and eosinophil concentration, decreased binding of immunoglobulins to cell-surface receptors, and release and / or synthesis of interleukins.

Launch Date

2.54534402E11
Palliative
BETAPAR

Approved Use

Meprednisone (16-β-methylprednisone) is a steroid anti-inflammatory with poor mineralocorticoid action due to the methylation of prednisone at the carbon 16 level. Corticosteroids have anti-inflammatory and immunosuppressive activity. The mechanism of anti-inflammatory action is due to the decrease of the tissue response to the inflammatory processes, without modifying the underlying causes. Steroids diffuse through the cell membrane and bind to specific cytoplasmic receptors. Then, this complex enters the nucleus, where it binds to other transcriptional factors and to DNA producing induction and repression of genes that lead to its anti-inflammatory, immunosuppressive and mild mineralocorticoid effect. Other effects are: suppression of pituitary corticotropin production leading to secondary adrenal insufficiency, decreased absorption and increased calcium excretion, increased surfactant factor production in type 2 pneumocytes, protein catabolism in lymphoid, muscle, Connective tissue and skin, hepatic gluconeogenesis with decreased peripheral glucose utilization, decreased formation and increased bone resorption. The mechanism by which corticosteroids decrease immunity involves inhibition of cell-mediated immune reactions, reduction of T lymphocyte, monocyte and eosinophil concentration, decreased binding of immunoglobulins to cell-surface receptors, and release and / or synthesis of interleukins.

Launch Date

2.54534402E11
Primary
BETAPAR

Approved Use

Meprednisone (16-β-methylprednisone) is a steroid anti-inflammatory with poor mineralocorticoid action due to the methylation of prednisone at the carbon 16 level. Corticosteroids have anti-inflammatory and immunosuppressive activity. The mechanism of anti-inflammatory action is due to the decrease of the tissue response to the inflammatory processes, without modifying the underlying causes. Steroids diffuse through the cell membrane and bind to specific cytoplasmic receptors. Then, this complex enters the nucleus, where it binds to other transcriptional factors and to DNA producing induction and repression of genes that lead to its anti-inflammatory, immunosuppressive and mild mineralocorticoid effect. Other effects are: suppression of pituitary corticotropin production leading to secondary adrenal insufficiency, decreased absorption and increased calcium excretion, increased surfactant factor production in type 2 pneumocytes, protein catabolism in lymphoid, muscle, Connective tissue and skin, hepatic gluconeogenesis with decreased peripheral glucose utilization, decreased formation and increased bone resorption. The mechanism by which corticosteroids decrease immunity involves inhibition of cell-mediated immune reactions, reduction of T lymphocyte, monocyte and eosinophil concentration, decreased binding of immunoglobulins to cell-surface receptors, and release and / or synthesis of interleukins.

Launch Date

2.54534402E11
Palliative
BETAPAR

Approved Use

Meprednisone (16-β-methylprednisone) is a steroid anti-inflammatory with poor mineralocorticoid action due to the methylation of prednisone at the carbon 16 level. Corticosteroids have anti-inflammatory and immunosuppressive activity. The mechanism of anti-inflammatory action is due to the decrease of the tissue response to the inflammatory processes, without modifying the underlying causes. Steroids diffuse through the cell membrane and bind to specific cytoplasmic receptors. Then, this complex enters the nucleus, where it binds to other transcriptional factors and to DNA producing induction and repression of genes that lead to its anti-inflammatory, immunosuppressive and mild mineralocorticoid effect. Other effects are: suppression of pituitary corticotropin production leading to secondary adrenal insufficiency, decreased absorption and increased calcium excretion, increased surfactant factor production in type 2 pneumocytes, protein catabolism in lymphoid, muscle, Connective tissue and skin, hepatic gluconeogenesis with decreased peripheral glucose utilization, decreased formation and increased bone resorption. The mechanism by which corticosteroids decrease immunity involves inhibition of cell-mediated immune reactions, reduction of T lymphocyte, monocyte and eosinophil concentration, decreased binding of immunoglobulins to cell-surface receptors, and release and / or synthesis of interleukins.

Launch Date

2.54534402E11
Palliative
BETAPAR

Approved Use

Meprednisone (16-β-methylprednisone) is a steroid anti-inflammatory with poor mineralocorticoid action due to the methylation of prednisone at the carbon 16 level. Corticosteroids have anti-inflammatory and immunosuppressive activity. The mechanism of anti-inflammatory action is due to the decrease of the tissue response to the inflammatory processes, without modifying the underlying causes. Steroids diffuse through the cell membrane and bind to specific cytoplasmic receptors. Then, this complex enters the nucleus, where it binds to other transcriptional factors and to DNA producing induction and repression of genes that lead to its anti-inflammatory, immunosuppressive and mild mineralocorticoid effect. Other effects are: suppression of pituitary corticotropin production leading to secondary adrenal insufficiency, decreased absorption and increased calcium excretion, increased surfactant factor production in type 2 pneumocytes, protein catabolism in lymphoid, muscle, Connective tissue and skin, hepatic gluconeogenesis with decreased peripheral glucose utilization, decreased formation and increased bone resorption. The mechanism by which corticosteroids decrease immunity involves inhibition of cell-mediated immune reactions, reduction of T lymphocyte, monocyte and eosinophil concentration, decreased binding of immunoglobulins to cell-surface receptors, and release and / or synthesis of interleukins.

Launch Date

2.54534402E11
Doses

Doses

DosePopulationAdverse events​
5 mg 1 times / day multiple, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5 mg, 1 times / day
Sources: Page: p.142
unhealthy, 16-31
n = 12
Health Status: unhealthy
Condition: Hyperandrogenism
Age Group: 16-31
Sex: F
Population Size: 12
Sources: Page: p.142
40 mg 2 times / day multiple, oral
Studied dose
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Sources: Page: p.2
unhealthy, 71
n = 1
Health Status: unhealthy
Condition: Lupus nephropathy
Age Group: 71
Sex: F
Population Size: 1
Sources: Page: p.2
Other AEs: Osteoporosis...
Other AEs:
Osteoporosis
Sources: Page: p.2
AEs

AEs

AESignificanceDosePopulation
Osteoporosis
40 mg 2 times / day multiple, oral
Studied dose
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Sources: Page: p.2
unhealthy, 71
n = 1
Health Status: unhealthy
Condition: Lupus nephropathy
Age Group: 71
Sex: F
Population Size: 1
Sources: Page: p.2
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes
yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
[Drug-induced lichenoid eruptions].
2006 Apr
Henoch-Schönlein Purpura in adults.
2008 Apr
Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism.
2008 Apr
[Fulminating sclerosant peritonitis. Spectacular response to treatment with steroids].
2010
Patents

Sample Use Guides

Meprednisone is administered orally, maintenance daily dose is 4-8 mg in adults.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
MEPREDNISONE
INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   WHO-DD  
INN   USAN  
Official Name English
MEPREDNISONE [USAN]
Common Name English
MEPREDNISONE [ORANGE BOOK]
Common Name English
MEPREDNISONE [USP]
Common Name English
MEPREDNISONE [MI]
Common Name English
BETAPAR
Brand Name English
SCH-4358
Code English
NSC-527579
Code English
MEPREDNISONE [MART.]
Common Name English
MEPREDNISONE [INN]
Common Name English
MEPREDNISONE [USP-RS]
Common Name English
PREGNA-1,4-DIENE-3,11,20-TRIONE, 17,21-DIHYDROXY-16-METHYL-, (16.BETA.)-
Systematic Name English
17,21-DIHYDROXY-16.BETA.-METHYLPREGNA-1,4-DIENE-3,11,20-TRIONE
Systematic Name English
SCH 4358
Code English
MEPREDNISONE [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-VATC QH02AB15
Created by admin on Sat Jun 26 05:52:52 UTC 2021 , Edited by admin on Sat Jun 26 05:52:52 UTC 2021
WHO-ATC H02AB15
Created by admin on Sat Jun 26 05:52:52 UTC 2021 , Edited by admin on Sat Jun 26 05:52:52 UTC 2021
NCI_THESAURUS C521
Created by admin on Sat Jun 26 05:52:52 UTC 2021 , Edited by admin on Sat Jun 26 05:52:52 UTC 2021
Code System Code Type Description
EVMPD
SUB08756MIG
Created by admin on Sat Jun 26 05:52:52 UTC 2021 , Edited by admin on Sat Jun 26 05:52:52 UTC 2021
PRIMARY
RXCUI
29523
Created by admin on Sat Jun 26 05:52:52 UTC 2021 , Edited by admin on Sat Jun 26 05:52:52 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB09383
Created by admin on Sat Jun 26 05:52:52 UTC 2021 , Edited by admin on Sat Jun 26 05:52:52 UTC 2021
PRIMARY
ChEMBL
CHEMBL1201148
Created by admin on Sat Jun 26 05:52:52 UTC 2021 , Edited by admin on Sat Jun 26 05:52:52 UTC 2021
PRIMARY
MESH
C008352
Created by admin on Sat Jun 26 05:52:52 UTC 2021 , Edited by admin on Sat Jun 26 05:52:52 UTC 2021
PRIMARY
WIKIPEDIA
MEPREDNISONE
Created by admin on Sat Jun 26 05:52:52 UTC 2021 , Edited by admin on Sat Jun 26 05:52:52 UTC 2021
PRIMARY
MERCK INDEX
M7198
Created by admin on Sat Jun 26 05:52:52 UTC 2021 , Edited by admin on Sat Jun 26 05:52:52 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C66096
Created by admin on Sat Jun 26 05:52:52 UTC 2021 , Edited by admin on Sat Jun 26 05:52:52 UTC 2021
PRIMARY
EPA CompTox
1247-42-3
Created by admin on Sat Jun 26 05:52:52 UTC 2021 , Edited by admin on Sat Jun 26 05:52:52 UTC 2021
PRIMARY
FDA UNII
67U96J8P35
Created by admin on Sat Jun 26 05:52:52 UTC 2021 , Edited by admin on Sat Jun 26 05:52:52 UTC 2021
PRIMARY
PUBCHEM
5284587
Created by admin on Sat Jun 26 05:52:52 UTC 2021 , Edited by admin on Sat Jun 26 05:52:52 UTC 2021
PRIMARY
DRUG CENTRAL
1702
Created by admin on Sat Jun 26 05:52:52 UTC 2021 , Edited by admin on Sat Jun 26 05:52:52 UTC 2021
PRIMARY
CAS
1247-42-3
Created by admin on Sat Jun 26 05:52:52 UTC 2021 , Edited by admin on Sat Jun 26 05:52:52 UTC 2021
PRIMARY
INN
1967
Created by admin on Sat Jun 26 05:52:52 UTC 2021 , Edited by admin on Sat Jun 26 05:52:52 UTC 2021
PRIMARY
USP_CATALOG
1388005
Created by admin on Sat Jun 26 05:52:52 UTC 2021 , Edited by admin on Sat Jun 26 05:52:52 UTC 2021
PRIMARY USP-RS
ECHA (EC/EINECS)
214-996-1
Created by admin on Sat Jun 26 05:52:52 UTC 2021 , Edited by admin on Sat Jun 26 05:52:52 UTC 2021
PRIMARY