Structure Database (LMSD)

Common Name
6alpha-methylprednisolone
Systematic Name
11β,17,21-trihydroxy-6α-methylpregna-1,4-diene-3,20-dione
Synonyms
  • (6alpha,11beta)-11,17,21-trihydroxy-6-methylpregna-1,4-diene-3,20-dione
  • 1-dehydro-6alpha-methylhydrocortisone
  • 6alpha-methyl-11beta,17alpha,21-triol-1,4-pregnadiene-3,20-dione
  • Delta(1)-6alpha-methylhydrocortisone
  • Methylprednisolone
LM ID
LMST02030178
Formula
Exact Mass
Calculate m/z
374.209326
Sum Composition
Status
Curated

Classification

Biological Context

Methylprednisolone is a synthetic glucocorticoid, an agonist of glucocorticoid and mineralocorticoid receptors, and an active metabolite of the prodrug 6α-methylprednisolone 21-hemisuccinate (MPS).1 It transactivates glucocorticoid and mineralocorticoid receptors in a reporter assay using CV-1 cells (EC50s = 2.92 and 2.31 nM for the human receptors, respectively). Methylprednisolone (40 mg/kg) reduces endotoxin-induced complement activation in rabbits.2 It induces T cell apoptosis and reduces the number of T cell spinal cord infiltrates in a rat model of experimental autoimmune encephalomyelitis (EAE) when administered at a dose of 50 mg/kg.3 It decreases the number of reactive spinal astrocytes, improves proprioceptive limb placing and coordination, and reduces spinal edema and the number of spinal necrotic cells in a rat model of spinal crush injury.4 Formulations containing methylprednisolone have been used in the treatment of immune and autoimmune disorders, such as rheumatoid arthritis, systemic lupus erythematosus, psoriasis, corneal ulcers, ulcerative colitis, and allergies, among others.

This information has been provided by Cayman Chemical

References

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Synthetic steroid

String Representations

InChiKey (Click to copy)
VHRSUDSXCMQTMA-PJHHCJLFSA-N
InChi (Click to copy)
InChI=1S/C22H30O5/c1-12-8-14-15-5-7-22(27,18(26)11-23)21(15,3)10-17(25)19(14)20(2)6-4-13(24)9-16(12)20/h4,6,9,12,14-15,17,19,23,25,27H,5,7-8,10-11H2,1-3H3/t12-,14-,15-,17-,19+,20-,21-,22-/m0/s1
SMILES (Click to copy)
[C@]12([C@]3([H])[C@]([H])([C@@]4([H])[C@](C)(C[C@@H]3O)[C@@](O)(C(=O)CO)CC4)C[C@H](C)C1=CC(=O)C=C2)C

Other Databases

HMDB ID
CHEBI ID
PubChem CID
Cayman ID
GuidePharm ID

Calculated Physicochemical Properties

Heavy Atoms 27
Rings 4
Aromatic Rings 0
Rotatable Bonds 2
Van der Waals Molecular Volume 373.11
Topological Polar Surface Area 94.83
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 5
logP 2.66
Molar Refractivity 101.11

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Created at
-
Updated at
2nd Apr 2025