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C2755

Sigma-Aldrich

Cortisone

≥95%

Synonym(s):

17α,21-Dihydroxy-4-pregnene-3,11,20-trione, 17α-Hydroxy-11-dehydrocorticosterone, 4-Pregnene-17α,21-diol-3,11,20-trione, Kendall’s Compound E, Reichstein’s Substance Fa

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About This Item

Empirical Formula (Hill Notation):
C21H28O5
CAS Number:
53-06-5
Molecular Weight:
360.44
Beilstein:
1356062
EC Number:
200-162-4
MDL number:
MFCD00003610
UNSPSC Code:
51111800
PubChem Substance ID:
24278304
NACRES:
NA.77

biological source

synthetic

Quality Level

200

sterility

non-sterile

Assay

≥95%

form

powder

technique(s)

inhibition assay: suitable

mp

223-228 °C (dec.) (lit.)

solubility

chloroform: methanol (1:1): 50 mg/mL, clear to very slightly hazy, colorless to faintly yellow

shipped in

ambient

storage temp.

room temp

SMILES string

C[C@]12CCC(=O)C=C1CC[C@H]3[C@@H]4CC[C@](O)(C(=O)CO)[C@@]4(C)CC(=O)[C@H]23

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/h9,14-15,18,22,26H,3-8,10-11H2,1-2H3/t14-,15-,18+,19-,20-,21-/m0/s1

InChI key

MFYSYFVPBJMHGN-ZPOLXVRWSA-N

Gene Information

human ... SERPINA6(866)

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Application

Cortisone has been used:
  • to validate a 1β-HSD1 (11β-hydroxysteroid dehydrogenase type 1) inhibitor
  • to study the sensitivity of erythropoietic and granulopoietic progenitor cells to cortisone
  • in the determination of rates of cortisol oxidation by 11βHSD

Biochem/physiol Actions

Cortisone (11 dehydro 17 hydroxycortico-sterone) is an anti-inflammatory glucocorticoid that delays wound healing after surgeries. It postpones the healing process by affecting the appearance of inflammatory cells, ground substance, fibroblasts, collagen, regenerating capillaries, and epithelial migration. Glucocorticoids have anti-inflammatory, anti-allergic and immunosuppressive properties and are extensively used in treatment and therapy.
Cortisone is a glucocorticoid; a corticosterone analog that has approximately twice the anti-inflammatory potency as corticosterone but much lower Na2+ retention potency.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H361d

Hazard Classifications

Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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S McMullen et al.
Reproduction (Cambridge, England), 127(6), 717-725 (2004-06-04)
In the placenta, cortisol is inactivated by NADP(+)- and NAD(+)-dependent isoforms of 11beta-hydroxysteroid dehydrogenase (11betaHSD). Decreased placental 11betaHSD activities have been implicated in intrauterine growth restriction (IUGR) and fetal programming of adult diseases. The objective of this study was to
H G Boman
Immunological reviews, 173, 5-16 (2000-03-17)
This paper discusses the following ten subtitles with the contents indicated. 1. To meet a microbe: discusses the four alternatives in host-microbe interactions. 2. Receptors and signal transduction giving gene activation: discusses the lipopolysaccharide receptor and the limitations of cell
Elif I Ikitimur-Armutak et al.
Microvascular research, 109, 26-33 (2016-10-30)
Anti-angiogenic activity of palladium (Pd)(II)-based complexes is unknown despite their quite powerful anticancer activity. This study was therefore carried out to evaluate both in vivo anti-angiogenic effect and in vitro cytotoxic activity of a Pd(II)-based complex. ([Pd(sac)(terpy)](sac)·4H2O(sac=saccharinate and terpy=2,2':6',2″-terpyridine)) on
Rowan S Hardy et al.
Swiss medical weekly, 142, w13650-w13650 (2012-08-08)
The anti-inflammatory actions of therapeutic glucocorticoids are well established and these drugs are widely used to treat a variety of inflammatory conditions. It is also clear that endogenously synthesised glucocorticoids have an important role in regulating inflammatory responses. Traditionally, our
Hengmiao Cheng et al.
Bioorganic & medicinal chemistry letters, 20(9), 2897-2902 (2010-04-07)
The design and development of a series of highly selective pyrrolidine carboxamide 11beta-HSD1 inhibitors are described. These compounds including PF-877423 demonstrated potent in vitro activity against both human and mouse 11beta-HSD1 enzymes. In an in vivo assay, PF-877423 inhibited the
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