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
3D model of 6alpha-methylprednisolone
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
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
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
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
Admin
Created at
-
Updated at
2nd Apr 2025