C2755

Sigma-Aldrich

Cortisone

≥98%

Synonym(s):
Kendall’s Compound E, 4-Pregnene-17α,21-diol-3,11,20-trione, 17α,21-Dihydroxy-4-pregnene-3,11,20-trione, 17α-Hydroxy-11-dehydrocorticosterone, Reichstein’s Substance Fa
Empirical Formula (Hill Notation):
C21H28O5
CAS Number:
Molecular Weight:
360.44
Beilstein/REAXYS Number:
1356062
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

biological source

synthetic

sterility

non-sterile

assay

≥98%

form

powder

application(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

Packaging

250 mg in glass bottle
1, 5 g in glass bottle
Bottomless glass bottle. Contents are inside inserted fused cone.

Biochem/physiol Actions

Cortisone is a glucocorticoid; a corticosterone analog that has approximately twice the anti-inflammatory potency as corticosterone but much lower Na2+ retention potency.
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.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Pictograms

Health hazard

Signal Word

Warning

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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...
Peter J Mark et al.
Endocrinology, 147(11), 5147-5152 (2006-07-29)
Exposure of the fetus and placenta to maternal glucocorticoids is normally limited by the placental glucocorticoid barrier, which consists primarily of placental 11beta-hydroxy-steroid dehydrogenase type 2-mediated conversion of cortisol to the biologically inactive cortisone. Studies in the rodent brain show...
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...
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...
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...

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