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


Classification

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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Updated at
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