C2755

Cortisone

Name: Cortisone
Brand: SIGMA

synthetic, ≥95%, anti-inflammatory, powder

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

NACRES:

NA.77

PubChem Substance ID:

24278304

UNSPSC Code:

51111800

EC Number:

200-162-4

MDL number:

MFCD00003610

Beilstein/REAXYS Number:

1356062

Product Name

Cortisone, ≥95%

InChI key

MFYSYFVPBJMHGN-ZPOLXVRWSA-N

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

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

biological source

synthetic

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

Quality Level

200

Gene Information

human ... SERPINA6(866)

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Bioactive Small Molecules

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

GHS08

signalword

Warning

hcodes

H361d

pcodes

P201 - P202 - P280 - P308 + P313 - P405 - P501

Hazard Classifications

Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Alterations in placental 11 beta-hydroxysteroid dehydrogenase (11 betaHSD) activities and fetal cortisol:cortisone ratios induced by nutritional restriction prior to conception and at defined stages of gestation in ewes.

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

Detection of physiological concentrations of cortisol and cortisone in human hair.

Jean-Sébastien Raul et al.

Clinical biochemistry, 37(12), 1105-1111 (2004-12-14)

Since the 1960s, glucocorticoids are used by athletes to improve their performances. Their use is restricted in sports. Hair can document chronic abuse and can be therefore a complementary matrix for doping control. We have developed a new extraction, purification

Anti-angiogenic effect of a Palladium(II)-Saccharinate Complex of Terpyridine in vitro and in vivo.

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

Effects of cortisone and vitamin A on wound healing.

H P Ehrlich et al.

Annals of surgery, 167(3), 324-328 (1968-03-01)

Endogenous glucocorticoids in inflammation: contributions of systemic and local responses.

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

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