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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H31O8P
Molecular Weight 454.4505
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHYLPREDNISOLONE DIHYDROGEN PHOSPHATE

SMILES

[H][C@@]12CC[C@](O)(C(=O)COP(O)(O)=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=PWTIEVRZANUUHG-PJHHCJLFSA-N
InChI=1S/C22H31O8P/c1-12-8-14-15-5-7-22(26,18(25)11-30-31(27,28)29)21(15,3)10-17(24)19(14)20(2)6-4-13(23)9-16(12)20/h4,6,9,12,14-15,17,19,24,26H,5,7-8,10-11H2,1-3H3,(H2,27,28,29)/t12-,14-,15-,17-,19+,20-,21-,22-/m0/s1

HIDE SMILES / InChI

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
Use of epidural steroids after discectomy may predispose to infection.
2000 Feb 15
[A senile case of acute necrotizing myopathy presenting prolonged severe muscle paralysis due to high dose glucocorticoid and muscle relaxant].
2000 Mar
The development of clinical signs of rheumatoid synovial inflammation is associated with increased synthesis of the chemokine CXCL8 (interleukin-8).
2001
Three cases of C-ANCA-positive vasculitis treated with immunoadsorption: possible benefit in early treatment.
2001 Feb
Steroid-resistant kidney transplant rejection: diagnosis and treatment.
2001 Feb
[Is it useful to perform a (67)gallium scintigraphy in the follow-up of patients with gastric lymphoma?].
2001 Feb
Glucocorticoid inhibition of neuropathic hyperalgesia and spinal Fos expression.
2001 Feb
Postnatal glucocorticoids in very preterm infants: "the good, the bad, and the ugly"?
2001 Feb
Cytokine characteristics of jaundice in mouse liver.
2001 Feb 7
Pharmacoeconomic study of tacrolimus-based versus cyclosporine-based immunosuppressive therapy following liver transplantation.
2001 Feb-Mar
Prospective randomized trial of tacrolimus and prednisone versus tacrolimus, prednisone, and mycophenolate mofetil: complete report on 350 primary adult liver transplantations.
2001 Feb-Mar
Graft failure in a patient with systemic lupus erythematosus (SLE) treated with high-dose immunosuppression and autologous stem cell rescue.
2001 Jan
[Anesthetic management for mitral valve replacement in a patient with idiopathic hypereosinophilic syndrome].
2001 Jan
Two cases of severe bronchopneumonia due to influenza A (H3N2) virus: detection of influenza virus gene using reverse transcription polymerase chain reaction.
2001 Jan
New treatment for postherpetic neuralgia.
2001 Jan
High-dose methylprednisolone therapy in multiple sclerosis induces apoptosis in peripheral blood leukocytes.
2001 Jan
Conservative management of Gradenigo syndrome in a child.
2001 Jan
High-dose methylprednisolone treatment in experimental focal cerebral ischemia.
2001 Jan
Osteonecrosis of the femoral head after allogeneic bone marrow transplantation.
2001 Jan
The contribution of indocyanine green angiography to the appraisal and management of Vogt-Koyanagi-Harada disease.
2001 Jan
Spinal cord injury.
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
Recurrent orbital inflammation from metastatic orbital carcinoid tumor.
2001 Mar
[Intramural hematoma of the large intestine caused by cytomegalovirus vasculitis in a patient with SLE].
2001 Mar
The impact of attaining a minimal disease state after high-dose melphalan and autologous transplantation for multiple myeloma.
2001 Mar
Use of daclizumab as initial immunosuppression in liver transplant recipients with impaired renal function.
2001 Mar
Intrathecal methylprednisolone for postherpetic neuralgia.
2001 Mar 29
[Comparison of two different treatments of lateral humeral epicondylitis--"tennis elbow". A randomized controlled trial].
2001 Mar 5
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
Name Type Language
METHYLPREDNISOLONE DIHYDROGEN PHOSPHATE
Common Name English
PREGNA-1,4-DIENE-3,20-DIONE, 11,17-DIHYDROXY-6-METHYL-21-(PHOSPHONOOXY)-, (6.ALPHA.,11.BETA.)-
Systematic Name English
METHYLPREDNISOLONE 21-PHOSPHATE
Common Name English
METHYLPREDNISOLONE 21-(DIHYDROGEN PHOSPHATE)
Common Name English
PREGNA-1,4-DIENE-3,20-DIONE, 11.BETA.,17,21-TRIHYDROXY-6.ALPHA.-METHYL-, 21-(DIHYDROGEN PHOSPHATE)
Common Name English
Code System Code Type Description
ECHA (EC/EINECS)
244-869-6
Created by admin on Fri Dec 15 18:08:41 GMT 2023 , Edited by admin on Fri Dec 15 18:08:41 GMT 2023
PRIMARY
FDA UNII
1D9M23IY4Y
Created by admin on Fri Dec 15 18:08:41 GMT 2023 , Edited by admin on Fri Dec 15 18:08:41 GMT 2023
PRIMARY
PUBCHEM
63018
Created by admin on Fri Dec 15 18:08:41 GMT 2023 , Edited by admin on Fri Dec 15 18:08:41 GMT 2023
PRIMARY
EPA CompTox
DTXSID30944908
Created by admin on Fri Dec 15 18:08:41 GMT 2023 , Edited by admin on Fri Dec 15 18:08:41 GMT 2023
PRIMARY
CAS
22252-38-6
Created by admin on Fri Dec 15 18:08:41 GMT 2023 , Edited by admin on Fri Dec 15 18:08:41 GMT 2023
PRIMARY