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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H32O6
Molecular Weight 416.5073
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHYLPREDNISOLONE ACETATE

SMILES

[H][C@@]12CC[C@](O)(C(=O)COC(C)=O)[C@@]1(C)C[C@H](O)[C@@]3([H])[C@@]2([H])C[C@H](C)C4=CC(=O)C=C[C@]34C

InChI

InChIKey=PLBHSZGDDKCEHR-LFYFAGGJSA-N
InChI=1S/C24H32O6/c1-13-9-16-17-6-8-24(29,20(28)12-30-14(2)25)23(17,4)11-19(27)21(16)22(3)7-5-15(26)10-18(13)22/h5,7,10,13,16-17,19,21,27,29H,6,8-9,11-12H2,1-4H3/t13-,16-,17-,19-,21+,22-,23-,24-/m0/s1

HIDE SMILES / InChI

Molecular Formula C24H32O6
Molecular Weight 416.5073
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/pro/medrol.html

Methylprednisolone is a prednisolone derivative with similar anti-inflammatory and immunosuppressive action. It is adjunctive therapy for short-term administration in rheumatoid arthritis. It is indicated in the following conditions: endocrine disorders, rheumatic disorders, collagen diseases, allergic states etc. Methylprednisolone is marketed in the USA and Canada under the brand names Medrol and Solu-Medrol. Methylprednisolone is a GR receptor agonist.

Originator

Curator's Comment: # Pfizer

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
2.4 nM [EC50]
1.07 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MEDROL

Approved Use

INDICATIONS AND USAGE MEDROL Tablets are indicated in the following conditions: 1. Endocrine Disorders Primary or secondary adrenocortical insufficiency (hydrocortisone or cortisone is the first choice; synthetic analogs may be used in conjunction with mineralocorticoids where applicable; in infancy mineralocorticoid supplementation is of particular importance). Congenital adrenal hyperplasia Nonsuppurative thyroiditis Hypercalcemia associated with cancer 2. Rheumatic Disorders As adjunctive therapy for short-term administration (to tide the patient over an acute episode or exacerbation) in: Rheumatoid arthritis, including juvenile rheumatoid arthritis (selected cases may require low-dose maintenance therapy) Ankylosing spondylitis Acute and subacute bursitis Synovitis of osteoarthritis Acute nonspecific tenosynovitis Post-traumatic osteoarthritis Psoriatic arthritis Epicondylitis Acute gouty arthritis 3. Collagen Diseases During an exacerbation or as maintenance therapy in selected cases of: Systemic lupus erythematosus Systemic dermatomyositis (polymyositis) Acute rheumatic carditis 4. Dermatologic Diseases Bullous dermatitis herpetiformis Severe erythema multiforme (Stevens-Johnson syndrome) Severe seborrheic dermatitis Exfoliative dermatitis Mycosis fungoides Pemphigus Severe psoriasis 5. Allergic States Control of severe or incapacitating allergic conditions intractable to adequate trials of conventional treatment: Seasonal or perennial allergic rhinitis Drug hypersensitivity reactions Serum sickness Contact dermatitis Bronchial asthma Atopic dermatitis 6. Ophthalmic Diseases Severe acute and chronic allergic and inflammatory processes involving the eye and its adnexa such as: Allergic corneal marginal ulcers Herpes zoster ophthalmicus Anterior segment inflammation Diffuse posterior uveitis and choroiditis Sympathetic ophthalmia Keratitis Optic neuritis Allergic conjunctivitis Chorioretinitis Iritis and iridocyclitis 7. Respiratory Diseases Symptomatic sarcoidosis Berylliosis Loeffler's syndrome not manageable by other means Fulminating or disseminated pulmonary tuberculosis when used concurrently with appropriate antituberculous chemotherapy Aspiration pneumonitis 8. Hematologic Disorders Idiopathic thrombocytopenic purpura in adults Secondary thrombocytopenia in adults Acquired (autoimmune) hemolytic anemia Erythroblastopenia (RBC anemia) Congenital (erythroid) hypoplastic anemia 9. Neoplastic Diseases For palliative management of: Leukemias and lymphomas in adults Acute leukemia of childhood 10. Edematous States To induce a diuresis or remission of proteinuria in the nephrotic syndrome, without uremia, of the idiopathic type or that due to lupus erythematosus. 11. Gastrointestinal Diseases To tide the patient over a critical period of the disease in: Ulcerative colitis Regional enteritis 12. Nervous System Acute exacerbations of multiple sclerosis 13. Miscellaneous Tuberculous meningitis with subarachnoid block or impending block when used concurrently with appropriate antituberculous chemotherapy. Trichinosis with neurologic or myocardial involvement.

Launch Date

1957
Primary
MEDROL

Approved Use

INDICATIONS AND USAGE MEDROL Tablets are indicated in the following conditions: 1. Endocrine Disorders Primary or secondary adrenocortical insufficiency (hydrocortisone or cortisone is the first choice; synthetic analogs may be used in conjunction with mineralocorticoids where applicable; in infancy mineralocorticoid supplementation is of particular importance). Congenital adrenal hyperplasia Nonsuppurative thyroiditis Hypercalcemia associated with cancer 2. Rheumatic Disorders As adjunctive therapy for short-term administration (to tide the patient over an acute episode or exacerbation) in: Rheumatoid arthritis, including juvenile rheumatoid arthritis (selected cases may require low-dose maintenance therapy) Ankylosing spondylitis Acute and subacute bursitis Synovitis of osteoarthritis Acute nonspecific tenosynovitis Post-traumatic osteoarthritis Psoriatic arthritis Epicondylitis Acute gouty arthritis 3. Collagen Diseases During an exacerbation or as maintenance therapy in selected cases of: Systemic lupus erythematosus Systemic dermatomyositis (polymyositis) Acute rheumatic carditis 4. Dermatologic Diseases Bullous dermatitis herpetiformis Severe erythema multiforme (Stevens-Johnson syndrome) Severe seborrheic dermatitis Exfoliative dermatitis Mycosis fungoides Pemphigus Severe psoriasis 5. Allergic States Control of severe or incapacitating allergic conditions intractable to adequate trials of conventional treatment: Seasonal or perennial allergic rhinitis Drug hypersensitivity reactions Serum sickness Contact dermatitis Bronchial asthma Atopic dermatitis 6. Ophthalmic Diseases Severe acute and chronic allergic and inflammatory processes involving the eye and its adnexa such as: Allergic corneal marginal ulcers Herpes zoster ophthalmicus Anterior segment inflammation Diffuse posterior uveitis and choroiditis Sympathetic ophthalmia Keratitis Optic neuritis Allergic conjunctivitis Chorioretinitis Iritis and iridocyclitis 7. Respiratory Diseases Symptomatic sarcoidosis Berylliosis Loeffler's syndrome not manageable by other means Fulminating or disseminated pulmonary tuberculosis when used concurrently with appropriate antituberculous chemotherapy Aspiration pneumonitis 8. Hematologic Disorders Idiopathic thrombocytopenic purpura in adults Secondary thrombocytopenia in adults Acquired (autoimmune) hemolytic anemia Erythroblastopenia (RBC anemia) Congenital (erythroid) hypoplastic anemia 9. Neoplastic Diseases For palliative management of: Leukemias and lymphomas in adults Acute leukemia of childhood 10. Edematous States To induce a diuresis or remission of proteinuria in the nephrotic syndrome, without uremia, of the idiopathic type or that due to lupus erythematosus. 11. Gastrointestinal Diseases To tide the patient over a critical period of the disease in: Ulcerative colitis Regional enteritis 12. Nervous System Acute exacerbations of multiple sclerosis 13. Miscellaneous Tuberculous meningitis with subarachnoid block or impending block when used concurrently with appropriate antituberculous chemotherapy. Trichinosis with neurologic or myocardial involvement.

Launch Date

1957
Primary
MEDROL

Approved Use

INDICATIONS AND USAGE MEDROL Tablets are indicated in the following conditions: 1. Endocrine Disorders Primary or secondary adrenocortical insufficiency (hydrocortisone or cortisone is the first choice; synthetic analogs may be used in conjunction with mineralocorticoids where applicable; in infancy mineralocorticoid supplementation is of particular importance). Congenital adrenal hyperplasia Nonsuppurative thyroiditis Hypercalcemia associated with cancer 2. Rheumatic Disorders As adjunctive therapy for short-term administration (to tide the patient over an acute episode or exacerbation) in: Rheumatoid arthritis, including juvenile rheumatoid arthritis (selected cases may require low-dose maintenance therapy) Ankylosing spondylitis Acute and subacute bursitis Synovitis of osteoarthritis Acute nonspecific tenosynovitis Post-traumatic osteoarthritis Psoriatic arthritis Epicondylitis Acute gouty arthritis 3. Collagen Diseases During an exacerbation or as maintenance therapy in selected cases of: Systemic lupus erythematosus Systemic dermatomyositis (polymyositis) Acute rheumatic carditis 4. Dermatologic Diseases Bullous dermatitis herpetiformis Severe erythema multiforme (Stevens-Johnson syndrome) Severe seborrheic dermatitis Exfoliative dermatitis Mycosis fungoides Pemphigus Severe psoriasis 5. Allergic States Control of severe or incapacitating allergic conditions intractable to adequate trials of conventional treatment: Seasonal or perennial allergic rhinitis Drug hypersensitivity reactions Serum sickness Contact dermatitis Bronchial asthma Atopic dermatitis 6. Ophthalmic Diseases Severe acute and chronic allergic and inflammatory processes involving the eye and its adnexa such as: Allergic corneal marginal ulcers Herpes zoster ophthalmicus Anterior segment inflammation Diffuse posterior uveitis and choroiditis Sympathetic ophthalmia Keratitis Optic neuritis Allergic conjunctivitis Chorioretinitis Iritis and iridocyclitis 7. Respiratory Diseases Symptomatic sarcoidosis Berylliosis Loeffler's syndrome not manageable by other means Fulminating or disseminated pulmonary tuberculosis when used concurrently with appropriate antituberculous chemotherapy Aspiration pneumonitis 8. Hematologic Disorders Idiopathic thrombocytopenic purpura in adults Secondary thrombocytopenia in adults Acquired (autoimmune) hemolytic anemia Erythroblastopenia (RBC anemia) Congenital (erythroid) hypoplastic anemia 9. Neoplastic Diseases For palliative management of: Leukemias and lymphomas in adults Acute leukemia of childhood 10. Edematous States To induce a diuresis or remission of proteinuria in the nephrotic syndrome, without uremia, of the idiopathic type or that due to lupus erythematosus. 11. Gastrointestinal Diseases To tide the patient over a critical period of the disease in: Ulcerative colitis Regional enteritis 12. Nervous System Acute exacerbations of multiple sclerosis 13. Miscellaneous Tuberculous meningitis with subarachnoid block or impending block when used concurrently with appropriate antituberculous chemotherapy. Trichinosis with neurologic or myocardial involvement.

Launch Date

1957
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
213 ng/mL
32 mg single, intravenous
dose: 32 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
METHYLPREDNISOLONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
931 ng × h/mL
32 mg single, intravenous
dose: 32 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
METHYLPREDNISOLONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.3 h
32 mg single, intravenous
dose: 32 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
METHYLPREDNISOLONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
23%
METHYLPREDNISOLONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1000 mg/kg single, intravenous
Highest studied dose
Dose: 1000 mg/kg
Route: intravenous
Route: single
Dose: 1000 mg/kg
Sources:
unhealthy, 0-15 years
n = 26
Health Status: unhealthy
Condition: sickle cell disease
Age Group: 0-15 years
Sex: M+F
Population Size: 26
Sources:
1250 mg 1 times / day multiple, oral
Highest studied dose
Dose: 1250 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1250 mg, 1 times / day
Sources:
unhealthy, 18–59 years
n = 24
Health Status: unhealthy
Condition: multiple sclerosis relapse
Age Group: 18–59 years
Sex: M+F
Population Size: 24
Sources:
120 mg 1 times / week multiple, intramuscular
Highest studied dose
Dose: 120 mg, 1 times / week
Route: intramuscular
Route: multiple
Dose: 120 mg, 1 times / week
Sources:
unhealthy, adult
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Hypotension, bradycardia, and asystole after high-dose intravenous methylprednisolone in a monitored patient.
1998 Jul
Pulse methylprednisolone therapy for arthritis causing muscle weakness.
1999 Sep
[Lactic acidosis: a complication of spinal cord injury in multiple trauma].
2000 Jun
A case of normotensive scleroderma renal crisis after high-dose methylprednisolone treatment.
2000 Jun
[A senile case of acute necrotizing myopathy presenting prolonged severe muscle paralysis due to high dose glucocorticoid and muscle relaxant].
2000 Mar
Corticosteroids for acute severe asthma in hospitalised patients.
2001
Stress-induced osteolysis of distal clavicle: imaging patterns and treatment using CT-guided injection.
2001
Lupus nephritis in a child with AIDS.
2001 Apr
Glucocorticosteroid dependent decrease in the activity of calcineurin in the peripheral blood mononuclear cells of patients with systemic lupus erythematosus.
2001 Apr
Three cases of C-ANCA-positive vasculitis treated with immunoadsorption: possible benefit in early treatment.
2001 Feb
Selective involvement of the choroid plexus on cerebral magnetic resonance images: a new radiological sign in patients with systemic lupus erythematosus with neurological symptoms.
2001 Feb
[Contact allergy caused by poison ivy (Toxicodendron spp].
2001 Feb
Multiple corticosteroid allergies.
2001 Feb
Monocyte-derived dendritic cells: a potential target for therapy in multiple sclerosis (MS).
2001 Feb
[Is it useful to perform a (67)gallium scintigraphy in the follow-up of patients with gastric lymphoma?].
2001 Feb
Early complications of high-dose methylprednisolone sodium succinate treatment in the follow-up of acute cervical spinal cord injury.
2001 Feb 15
Standard cyclosporine A-based versus completely steroid-free FK506-based immunosuppression after liver transplantation.
2001 Feb-Mar
Daclizumab induction therapy in combination with tacrolimus.
2001 Feb-Mar
Conversion at first rejection: a prospective trial comparing cyclosporine microemulsion with tacrolimus in renal transplant recipients.
2001 Feb-Mar
Daclizumab induction for primary kidney transplant recipients using tacrolimus, mycophenolate mofetil, and steroids as maintenance immunosuppression.
2001 Feb-Mar
[Severe chronic actinic dermatitis treated with cyclosporine: 2 cases].
2001 Jan
Enhancement of goblet cell hyperplasia and airway hyperresponsiveness by salbutamol in a rat model of atopic asthma.
2001 Jan
Glucocorticoid receptor-mediated suppression of activator protein-1 activation and matrix metalloproteinase expression after spinal cord injury.
2001 Jan 1
[Intramural hematoma of the large intestine caused by cytomegalovirus vasculitis in a patient with SLE].
2001 Mar
Lymph draining from foot joints in rheumatoid arthritis provides insight into local cytokine and chemokine production and transport to lymph nodes.
2001 Mar
Effects of preoperative steroid administration on surgical stress in hepatic resection: prospective randomized trial.
2001 Mar
Spinal taurine levels are increased 7 and 30 days following methylprednisolone treatment of spinal cord injury in rats.
2001 Mar 2
Intrathecal methylprednisolone for postherpetic neuralgia.
2001 Mar 29
Intrathecal methylprednisolone for postherpetic neuralgia.
2001 Mar 29
Patents

Sample Use Guides

In Vivo Use Guide
Each Medrol Tablet (methylprednisolone) for oral administration contains 2 mg, 4 mg, 8 mg, 16 mg or 32 mg of methylprednisolone. The initial dosage of Medrol Tablets may vary from 4 mg to 48 mg of methylprednisolone per day depending on the specific disease entity being treated.
Route of Administration: Other
Treatment with methylprednisolone concentrations above 50 uM could ignificantly reduce the proliferation activity of human CLL cell line MEC-1 by 23.34%, 30.73%, 30.57% after 24 h, and 28.48%, 42.35%, 44.56% after 48 h respectively
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:07:28 GMT 2023
Edited
by admin
on Fri Dec 15 15:07:28 GMT 2023
Record UNII
43502P7F0P
Record Status Validated (UNII)
Record Version
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Name Type Language
METHYLPREDNISOLONE ACETATE
EP   GREEN BOOK   JAN   MART.   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
Common Name English
METHYLPREDNISOLONE ACETATE [USP MONOGRAPH]
Common Name English
M-PREDROL
Brand Name English
METHYLPREDNISOLONE ACETATE [EP MONOGRAPH]
Common Name English
DEPO-MEDROL
Brand Name English
METHYLPREDNISOLONE ACETATE [VANDF]
Common Name English
METHYLPREDNISOLONE ACETATE [ORANGE BOOK]
Common Name English
METHYLPREDNISOLONE HYDROGEN SUCCINATE IMPURITY C [EP IMPURITY]
Common Name English
METHYLPREDNISOLONE ACETATE COMPONENT OF NEO-MEDROL ACETATE
Common Name English
METHYLPREDNISOLONE ACETATE [USP-RS]
Common Name English
NSC-48985
Code English
METHYLPREDNISOLONE ACETATE [MART.]
Common Name English
METHYLPREDNISOLONE 21-ACETATE
MI  
Common Name English
METHYLPREDNISOLONE ACETATE [GREEN BOOK]
Common Name English
NEO-MEDROL ACETATE COMPONENT METHYLPREDNISOLONE ACETATE
Common Name English
METHYLPREDNISOLONE ACETATE [USP IMPURITY]
Common Name English
MEDROL ACETATE
Brand Name English
PREGNA-1,4-DIENE-3,20-DIONE, 21-(ACETYLOXY)-11,17-DIHYDROXY-6-METHYL-, (6.ALPHA.,11.BETA.)-
Systematic Name English
Methylprednisolone acetate [WHO-DD]
Common Name English
11β,17,21-Trihydroxy-6α-methylpregna-1,4-diene-3,20-dione 21-acetate
Systematic Name English
METHYLPREDNISOLONE IMPURITY J [EP IMPURITY]
Common Name English
METHYLPREDNISOLONE ACETATE [JAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C521
Created by admin on Fri Dec 15 15:07:28 GMT 2023 , Edited by admin on Fri Dec 15 15:07:28 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID7023302
Created by admin on Fri Dec 15 15:07:28 GMT 2023 , Edited by admin on Fri Dec 15 15:07:28 GMT 2023
PRIMARY
PUBCHEM
5877
Created by admin on Fri Dec 15 15:07:28 GMT 2023 , Edited by admin on Fri Dec 15 15:07:28 GMT 2023
PRIMARY
RXCUI
155323
Created by admin on Fri Dec 15 15:07:28 GMT 2023 , Edited by admin on Fri Dec 15 15:07:28 GMT 2023
PRIMARY RxNorm
CAS
53-36-1
Created by admin on Fri Dec 15 15:07:28 GMT 2023 , Edited by admin on Fri Dec 15 15:07:28 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-171-3
Created by admin on Fri Dec 15 15:07:28 GMT 2023 , Edited by admin on Fri Dec 15 15:07:28 GMT 2023
PRIMARY
EVMPD
SUB03255MIG
Created by admin on Fri Dec 15 15:07:28 GMT 2023 , Edited by admin on Fri Dec 15 15:07:28 GMT 2023
PRIMARY
DRUG CENTRAL
1770
Created by admin on Fri Dec 15 15:07:28 GMT 2023 , Edited by admin on Fri Dec 15 15:07:28 GMT 2023
PRIMARY
WIKIPEDIA
Methylprednisolone acetate
Created by admin on Fri Dec 15 15:07:28 GMT 2023 , Edited by admin on Fri Dec 15 15:07:28 GMT 2023
PRIMARY
NSC
48985
Created by admin on Fri Dec 15 15:07:28 GMT 2023 , Edited by admin on Fri Dec 15 15:07:28 GMT 2023
PRIMARY
DRUG BANK
DBSALT001157
Created by admin on Fri Dec 15 15:07:28 GMT 2023 , Edited by admin on Fri Dec 15 15:07:28 GMT 2023
PRIMARY
RS_ITEM_NUM
1436006
Created by admin on Fri Dec 15 15:07:28 GMT 2023 , Edited by admin on Fri Dec 15 15:07:28 GMT 2023
PRIMARY
CHEBI
6889
Created by admin on Fri Dec 15 15:07:28 GMT 2023 , Edited by admin on Fri Dec 15 15:07:28 GMT 2023
PRIMARY
NCI_THESAURUS
C48003
Created by admin on Fri Dec 15 15:07:28 GMT 2023 , Edited by admin on Fri Dec 15 15:07:28 GMT 2023
PRIMARY
DAILYMED
43502P7F0P
Created by admin on Fri Dec 15 15:07:28 GMT 2023 , Edited by admin on Fri Dec 15 15:07:28 GMT 2023
PRIMARY
MESH
C000873
Created by admin on Fri Dec 15 15:07:28 GMT 2023 , Edited by admin on Fri Dec 15 15:07:28 GMT 2023
PRIMARY
MERCK INDEX
m7454
Created by admin on Fri Dec 15 15:07:28 GMT 2023 , Edited by admin on Fri Dec 15 15:07:28 GMT 2023
PRIMARY Merck Index
SMS_ID
100000091568
Created by admin on Fri Dec 15 15:07:28 GMT 2023 , Edited by admin on Fri Dec 15 15:07:28 GMT 2023
PRIMARY
FDA UNII
43502P7F0P
Created by admin on Fri Dec 15 15:07:28 GMT 2023 , Edited by admin on Fri Dec 15 15:07:28 GMT 2023
PRIMARY
ChEMBL
CHEMBL650
Created by admin on Fri Dec 15 15:07:28 GMT 2023 , Edited by admin on Fri Dec 15 15:07:28 GMT 2023
PRIMARY
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