methylprednisolone

Also known as 6alpha-methyl-11beta,17alpha,21-triol-1,4-pregnadiene-3,20-dione, 1-dehydro-6alpha-methylhydrocortisone, (6alpha,11beta)-11,17,21-trihydroxy-6-methylpregna-1,4-diene-3,20-dione, 1-dehydro-6α-methylhydrocortisone, (6α,11β)-11,17,21-trihydroxy-6-methylpregna-1,4-diene-3,20-dione, delta(1)-6alpha-methylhydrocortisone

Methylprednisolone, sold under the brand name Medrol among others, is a synthetic glucocorticoid, primarily prescribed for its anti-inflammatory and immunosuppressive effects. It is either used at low doses for chronic illnesses or used at high doses during acute flares. Methylprednisolone and its derivatives can be administered orally or parenterally.

Key facts

Drug.pregnancy_AU: A
Drug.verifiedrevid: 4771699945
Drug.image: Methylprednisolone.svg
Drug.image_class: skin-invert-image
Drug.width: 250
Drug.image2: Methylprednisolone.png
Drug.image_class2: bg-transparent
Drug.width2: 215
Drug.tradename: Medrol, others
Drug.MedlinePlus: a682795
Drug.DailyMedID: Methylprednisolone
Drug.routes_of_administration: By mouth, intramuscular, intra-articular, intravenous
Drug.class: Corticosteroid
Drug.ATC_prefix: D07
Drug.ATC_suffix: AA01
Drug.ATC_supplemental: , , , , , ,
Drug.legal_CA: Rx-only
Drug.legal_UK: POM

via Wikipedia infobox

Chemical data

Formula: C22H30O5
Molecular weight: 374.5 g/mol
IUPAC name: (6S,8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-hydroxyacetyl)-6,10,13-trimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one
SMILES: C[C@H]1C[C@H]2[C@@H]3CC[C@@]([C@]3(C[C@@H]([C@@H]2[C@@]4(C1=CC(=O)C=C4)C)O)C)(C(=O)CO)O
InChIKey: VHRSUDSXCMQTMA-PJHHCJLFSA-N
XLogP: 1.9
Polar surface area: 94.8 Å²
H-bond donors: 3
H-bond acceptors: 5
Formal charge: 0

via PubChem

Research

33,874 papers

Methylprednisolone anaphylaxis.The American journal of emergency medicine · 1999
Methylprednisolone suleptanate Pharmacia Corp.Current opinion in investigational drugs (London, England : 2000) · 2000
Methylprednisolone.The Veterinary record · 1984
Methylprednisolone treatment in multiple sclerosis: effect of treatment, pharmacokinetics, future.Multiple sclerosis (Houndmills, Basingstoke, England) · 1996
Dangers from methylprednisolone acetate therapy by intraspinal injection.Archives of neurology · 1988

via PubMed

Wikidata facts

Mass: 374.209

Show 7 more facts

chemical formula: C₂₂H₃₀O₅
isomeric SMILES: C[C@H]1C[C@H]2[C@@H]3CC[C@@]([C@]3(C[C@@H]([C@@H]2[C@@]4(C1=CC(=O)C=C4)C)O)C)(C(=O)CO)O
canonical SMILES: CC1CC2C3CCC(C3(CC(C2C4(C1=CC(=O)C=C4)C)O)C)(C(=O)CO)O
World Health Organisation international non-proprietary name: methylprednisolone
Commons category: Methylprednisolone
stylized name: methylPREDNISolone
defined daily dose: 20

Sources (9)

via Wikidata · CC0

~33 min read

Article

38 sections

Contents

Medical uses
Asthma
Rheumatic diseases
Primary or secondary adrenocortical insufficiency
Labeled indications
Oral methylprednisolone
Parenteral methylprednisolone
Off-label indications
Available forms
Contraindications
Adverse effects
Central nervous system
Metabolic and endocrine
Infections
Musculoskeletal
Exhaustive list
Withdrawal
Drug interactions
Enzyme inducers
Cytochrome P450 (CYP) 3A4 inhibitors
Oral contraceptives
P-glycoprotein inhibitors
Ciclosporin, tacrolimus, sirolimus (Rapamycin)
Cox1 inhibitors
Anticoagulants
Pharmacology
Signal transduction
Genomic signaling
Post-transcriptional modifications
Non-genomic signaling
The HPA
Pharmacokinetics
Physical properties
Chemistry
Synthesis
History
Research
References

Regardless of the route of administration, methylprednisolone integrates systemically as exhibited by its effectiveness to quickly reduce inflammation during acute flares. It is associated with many adverse reactions that require tapering off the drug as soon as the disease is under control. Serious side effects include iatrogenic Cushing's syndrome, hypertension, osteoporosis, diabetes, infection, psychosis, and skin atrophy.