Structure Database (LMSD)
Common Name
prednisolone
Systematic Name
11β,17,21-trihydroxypregna-1,4-diene-3,20-dione
Synonyms
- (11beta)-11,17,21-trihydroxypregna-1,4-diene-3,20-dione
- 1,4-pregnadiene-11beta,17alpha,21-triol-3,20-dione
- 1,4-pregnadiene-3,20-dione-11beta,17alpha,21-triol
- 3,20-dioxo-11beta,17alpha,21-trihydroxy-1,4-pregnadiene
- Delta(1)-dehydrocortisol
- Delta(1)-dehydrohydrocortisone
- Delta(1)-hydrocortisone
- Prednisolone
- hydroretrocortine
- metacortandralone
LM ID
LMST02030179
Formula
Exact Mass
Calculate m/z
360.193675
Sum Composition
Status
Curated
3D model of prednisolone
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
Prednisolone is a glucocorticoid and mineralocorticoid receptor agonist and an active metabolite of the prodrugs and synthetic glucocorticoids prednisolone phosphate and prednisone .1,2,3 It selectively binds to the glucocorticoid and mineralocorticoid receptors over the progesterone, androgen, and estrogen receptors (Kis = 2.4, 37, >5,000, 2,762, and >1,000 nM, respectively) and induces transactivation in reporter assays using CV-1 cells expressing the human glucocorticoid receptor or human mineralocorticoid receptor (EC50s = 6.9 and 3.78 nM, respectively).2,3 Prednisolone reduces pulmonary eosinophil infiltration in a rat model of sephadex-induced asthma (ED50 = 1.2 mg/kg).2 Formulations containing prednisolone have been used as anti-inflammatory or immunosuppressive agents.
This information has been provided by Cayman Chemical
References
1. Grossmann, C., Scholz, T., Rochel, M., et al. Transactivation via the human glucocorticoid and mineralocorticoid receptor by therapeutically used steroids in CV-1 cells: A comparison of their glucocorticoid and mineralocorticoid properties. Eur. J. Endocrinol. 151(3), 397-406 (2004).
2. Frey, B.M., Seeberger, M., and Frey, F.J. Pharmacokinetics of 3 prednisolone prodrugs. Evidence of therapeutic inequivalence in renal transplant patients with rejection. Transplantation 39(3), 270-274 (1985).
String Representations
InChiKey (Click to copy)
OIGNJSKKLXVSLS-VWUMJDOOSA-N
InChi (Click to copy)
InChI=1S/C21H28O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h5,7,9,14-16,18,22,24,26H,3-4,6,8,10-11H2,1-2H3/t14-,15-,16-,18+,19-,20-,21-/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)CCC1=CC(=O)C=C2)C
Other Databases
Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID
PDB ID
GuidePharm ID
Calculated Physicochemical Properties
Heavy Atoms
26
Rings
4
Aromatic Rings
0
Rotatable Bonds
2
Van der Waals Molecular Volume
355.81
Topological Polar Surface Area
94.83
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
5
logP
2.42
Molar Refractivity
96.56
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