CAS 53-06-5|CAS 50-04-4|Kendall's Compound E.|Δ<sup>4</sup>-Pregnene-17, 21-diol-3, 11, 20-trione|CORTISONE|(1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7....

General Information

Structure

Molecular Formula

C₂₁H₂₈O₅

Molecular Mass

360.44402

Exact Mass

360.193674

Charge

InChI

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

InChIKey

MFYSYFVPBJMHGN-ZPOLXVRWSA-N

Canonic Smiles

OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)CC(=O)[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C

Isomeric Smiles

O=C(CO)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3C(=O)C[C@]12C

Calculated Properties

JChem

LogD (pH = 7.4)

1.66

LogD (pH = 5.5)

1.66

Log P

1.66

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

12.58

Polar Surface Area

91.67

Polarizability

38.90

Molar Refractivity

96.47

LOG S

-2.87

Data Source

Names and Identifiers

Synonyms

Kendall's Compound E.CORTISONEΔ⁴-Pregnene-17, 21-diol-3, 11, 20-trioneCYANODIHYDROPHENARSAZINE17α-Hydroxy-11-dehydrocorticosterone17α,21-Dihydroxy-4-pregnene-3,11,20-trioneKendall’s Compound ECortisone4-Pregnene-17α,21-diol-3,11,20-trioneReichstein’s Substance FaCortogenAdrenalex17,21-Dihydroxy-pregn-4-ene-3,11,20-trioneCortoneCompound ENSC 9703Cortivite11-Dehydro-17-hydroxycorticosteroneCortisate17-Hydroxy-11-dehydrocorticosteroneWintersteiner's compound FReichstein's Substance FaKendall's compound E17alpha,21-Dihydroxy-4-pregnene-3,11,20-trioneKendall's compound Epregn-4-en-17alpha,21-diol-3,11,20-trioneCortisoneReichstein's substance FaDelta(4)-pregnene-17alpha,21-diol-3,11,20-trione11-dehydro-17-hydroxycorticosterone17alpha,21-dihydroxy-4-pregnene-3,11,20-trioneCortison4-pregnene-17alpha,21-diol-3,11,20-trionecortisone17-hydroxy-11-dehydrocorticosteroneKortisoncortisoneWintersteiner's compound F

IUPAC name

(1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,17-dione (1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0?,?.0??,??]heptadec-6-ene-5,17-dione (1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,17-dione (1R,3aS,3bS,9aR,9bS,11aS)-1-hydroxy-1-(2-hydroxyacetyl)-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthrene-7,10-dione

IUPAC Traditional name

cortisone (1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,17-dione

Names and Identifiers

Registration numbers

CAS Number

EC Number

KEGG ID

Chemspider ID

CHEBI ID

Registration numbers

Properties

Product Information

Certificate of Analysis

Download link

Empirical Formula (Hill Notation)

C21H28O5

Purity

≥98%

Biological Source

Adrenal cortical hormone

Application(s)

Used in rheumatoid arthritis and rheumatic fever therapy

Immunosuppressive

Antiinflammatory agent

Pharmacology Properties

Gene Information

human ... SERPINA6(866)

Mechanism of Action

Properties

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

MP Biomedicals

05203904

MP Biomedicals Rare Chemical collection

Crystalline

C2755

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.
Packaging
1, 5 g in glass bottle
250 mg in glass bottle

TRC

C696500

Glucocorticoid, anti-inflammatory agent.

ChEBI

CHEBI:16962

A C21-steroid that is pregn-4-ene substituted by hydroxy groups at positions 17 and 21 and oxo group at positions 3, 11 and 20.

Molecule Details

References

PubChem Literature

From Data Sources

• Honda, A., et al.: J. Biol. Chem., 268, 7759 (1993)

• Narko, K., et al.: J. Clin. Endocrinol. Metab., 86, 1765 (1993)

• Michael, A., et al.: Reproduction, 126, 425 (1993)

• Reichstein, T., Helv. Chim. Acta, 1936, 19, 1107; 1937, 20, 978, (isol, Cortisone)

• Sarett, L.H., J.A.C.S., 1948, 70, 1454, (synth)

• Sarett, L.H. et al., J.A.C.S., 1952, 74, 4974, (synth)

• Genard, P. et al., Steroids, 1968, 12, 763, (ms, Cortisone)

• Hazen, G.G., J. Chem. Educ., 1980, 57, 291, (synth)

• drich Library of 13C and 1H FT NMR Spectra, 1992, 3, 587A; 602B, (nmr)

• Horiguchi, Y. et al., J.O.C., 1986, 51, 4323, (synth)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6296; 6940, (synonyms)

• Green, G.F.H. et al., J.C.S., 1965, 7328, (pmr, Cortisone)

• Weeks, C.M. et al., J.A.C.S., 1973, 95, 2865, (struct)

• Kirk, D.N. et al., J.C.S. Perkin 2, 1990, 1567, (pmr)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CNS800; CNS825

• Rosenkranz, G. et al., J.A.C.S., 1951, 73, 4055, (synth)

• Hayden, A.L., Anal. Chem., 1955, 27, 1486, (ir, Cortisone)

• Muhtadi, F.J., Anal. Profiles Drug Subst., 1999, 26, 167-246, (rev)

• Smit, A. et al., Rec. Trav. Chim. (J. R. Neth. Chem. Soc.), 1966, 85, 731

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 727

• Woodward, R.B. et al., J.A.C.S., 1951, 73, 4057, (synth)

• Saucy, G. et al., Helv. Chim. Acta, 1967, 50, 1394, (synth, uv, ir, pmr, 10-form)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC name

IUPAC Traditional name

cortisone (1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,17-dione

Molecule Details

MP Biomedicals

05203904

MP Biomedicals Rare Chemical collection

Crystalline

C2755

C696500

Glucocorticoid, anti-inflammatory agent.

ChEBI

CHEBI:16962

A C21-steroid that is pregn-4-ene substituted by hydroxy groups at positions 17 and 21 and oxo group at positions 3, 11 and 20.

References

PubChem Literature

From Data Sources

• Honda, A., et al.: J. Biol. Chem., 268, 7759 (1993)

• Narko, K., et al.: J. Clin. Endocrinol. Metab., 86, 1765 (1993)

• Michael, A., et al.: Reproduction, 126, 425 (1993)

• Reichstein, T., Helv. Chim. Acta, 1936, 19, 1107; 1937, 20, 978, (isol, Cortisone)

• Sarett, L.H., J.A.C.S., 1948, 70, 1454, (synth)

• Sarett, L.H. et al., J.A.C.S., 1952, 74, 4974, (synth)

• Genard, P. et al., Steroids, 1968, 12, 763, (ms, Cortisone)

• Hazen, G.G., J. Chem. Educ., 1980, 57, 291, (synth)

• drich Library of 13C and 1H FT NMR Spectra, 1992, 3, 587A; 602B, (nmr)

• Horiguchi, Y. et al., J.O.C., 1986, 51, 4323, (synth)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6296; 6940, (synonyms)

• Green, G.F.H. et al., J.C.S., 1965, 7328, (pmr, Cortisone)

• Weeks, C.M. et al., J.A.C.S., 1973, 95, 2865, (struct)

• Kirk, D.N. et al., J.C.S. Perkin 2, 1990, 1567, (pmr)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CNS800; CNS825

• Rosenkranz, G. et al., J.A.C.S., 1951, 73, 4055, (synth)

• Hayden, A.L., Anal. Chem., 1955, 27, 1486, (ir, Cortisone)

• Muhtadi, F.J., Anal. Profiles Drug Subst., 1999, 26, 167-246, (rev)

• Smit, A. et al., Rec. Trav. Chim. (J. R. Neth. Chem. Soc.), 1966, 85, 731

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 727

• Woodward, R.B. et al., J.A.C.S., 1951, 73, 4057, (synth)

• Saucy, G. et al., Helv. Chim. Acta, 1967, 50, 1394, (synth, uv, ir, pmr, 10-form)

Bioactivity

PubChem BioAssay

Registration numbers

CAS Number

EC Number

KEGG ID

Chemspider ID

CHEBI ID

Properties

Product Information

Certificate of Analysis

Download link

Empirical Formula (Hill Notation)

C21H28O5

Purity

≥98%

Biological Source

Adrenal cortical hormone

Application(s)

Used in rheumatoid arthritis and rheumatic fever therapy

Immunosuppressive

Antiinflammatory agent

Pharmacology Properties

Gene Information

human ... SERPINA6(866)

Mechanism of Action

Molecule

ID:105422