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Structure Database (LMSD)

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Common Name

prednisone

Systematic Name

17,21-dihydroxypregna-1,4-diene-3,11,20-trione

Synonyms

1,2-Dehydrocortisone
1,4-Pregnadiene-17alpha,21-diol-3,11,20-trione
17,21-Dihydroxypregna-1,4-diene-3,11,20-trione
Prednisone

LM ID

LMST02030180

Formula

C₂₁H₂₆O₅

Exact Mass

Calculate m/z

358.178025

Sum Composition

ST 21:5;O5

Status

Curated

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Classification

Biological Context

Prednisone is a synthetic glucocorticoid with anti-inflammatory and immunosuppressant activities.¹ It inhibits paw swelling induced by sodium urate in mice by 86% when administered at a dose of 12 mg/kg.² Prednisone reduces release of IL-6, monocyte chemoattractant protein-2 (MCP-2), MCP-3, RANTES, and TNF-α in stented arteries in a rabbit model of atherosclerosis.³ Formulations containing prednisone have been used in the treatment of non-Hodgkin lymphoma as part of CHOP chemotherapy and as anti-inflammatory or immunosuppressive agents.

This information has been provided by Cayman Chemical

References

1. Brownie, A.C. The metabolism of adrenal cortical steroids. The Adrenal Gland 2, 209-225 (1992).

2. Fitzgerald, T.J., Williams, B., and Uyeki, E.M. Effects of antimitotic and anti-inflammatory agents on sodium urate-induced paw swelling in mice. Pharmacology 6(5), 265-273 (1971).

3. Ribichini, F., Joner, M., Ferrero, V., et al. Effects of oral prednisone after stenting in a rabbit model of established atherosclerosis. J. Am. Coll. Cardiol. 50(2), 176-185 (2007).

String Representations

InChiKey (Click to copy)

XOFYZVNMUHMLCC-ZPOLXVRWSA-N

InChi (Click to copy)

InChI=1S/C21H26O5/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/h5,7,9,14-15,18,22,26H,3-4,6,8,10-11H2,1-2H3/t14-,15-,18+,19-,20-,21-/m0/s1

SMILES (Click to copy)

C1C[C@@](C(=O)CO)(O)[C@@]2(C)CC(=O)[C@]3([H])[C@@]4(C)C=CC(=O)C=C4CC[C@@]3([H])[C@@]21[H]