Compound: cortisone
SMILES: O=C1C=C2[C@]([C@H]3C(=O)C[C@@]4([C@@](O)(C(=O)CO)CC[C@H]4[C@@H]3CC2)C)(C)CC1
InChIKey: MFYSYFVPBJMHGN-ZPOLXVRWSA-N
Synonyms: cortisone, 53-06-5, Kendall's compound E, Reichstein's substance FA, Wintersteiner's compound F, 17-Hydroxy-11-dehydrocorticosterone, 11-Dehydro-17-hydroxycorticosterone, Pregn-4-ene-3,11,20-trione, 17,21-dihydroxy-, Cortisona, 17,21-Dihydroxypregn-4-ene-3,11,20-trione, Cortisonum, Kortison, 4-Pregnene-17alpha,21-diol-3,11,20-trione, 17alpha,21-Dihydroxypregn-4-ene-3,11,20-trione, Pregn-4-en-17alpha,21-diol-3,11,20-trione, 17alpha,21-Dihydroxy-4-pregnene-3,11,20-trione, NSC-9703, DTXSID5022857, V27W9254FZ, DTXCID102857, CHEBI:16962, (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^(2,7).0^(11,15))heptadec-6-ene-5,17-dione, Therapeutic Cortisone, RefChem:5705, Cortisonum 30 Special Order, H02AB10, S01BA03, 200-162-4, Cortivite, Adrenalex, Andreson, Cortisal, Cortistal, Reichstein Fa, Cortandren, Cortison, NSC 9703, Kendall's compound, [3H]-cortisone, MFCD00003610, Prestwick_132, 17alpha-Hydroxy-11-dehydrocorticosterone, delta(sup4)-pregnene-17alpha,21-diol-3,11,20-trione, MLS000028540, (8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,11-dione, [3H]cortisone, NSC9703, Cortisone (INN), SMR000058334, CORTISONE [INN], 17.alpha.-Hydroxy-11-dehydrocorticosterone, 17,21-Dihydroxy-pregn-4-ene-3,11,20-trione, Cortisone [INN:BAN], Cortisonum [INN-Latin], Cortisona [INN-Spanish], (8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-7,8,9,10,12,13,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,11(2H,6H)-dione, EINECS 200-162-4, Hydrocortisone EP Impurity B, UNII-V27W9254FZ, AI3-52938, CAS-53-06-5, NCGC00095935-01, Corlin (Salt/Mix), Cortisone (Standard), Cortelan (Salt/Mix), Ricortex (Salt/Mix), Cortadren (Salt/Mix), Scheroson (Salt/Mix), Kendall's compound E;, Cortisone, >=98%, Opera_ID_541, CORTISONE [MI], Prestwick0_000273, Prestwick1_000273, Prestwick2_000273, Prestwick3_000273, Spectrum5_002051, CORTISONE [VANDF], bmse000663, CORTISONE [USP-RS], CORTISONE [WHO-DD], Reichstein's Substance Fa;, SCHEMBL4888, CHEMBL1499, Lopac0_000240, BSPBio_000146, MLS001076142, MLS001424269, MLS002207137, Pregn-4-ene-3,11,20-trione, 17,21-dihydroxy, 17.alpha.,11,20-trione, SPBio_002365, Cortisone, 1mg/ml in Methanol, BPBio1_000162, GTPL5171, orb1699252, orb3139486, BDBM13739, MSK2228, Cortisone 0.1 mg/ml in Methanol, HMS1568H08, HMS2052A21, HMS2095H08, HMS2235P19, HMS3260P21, HMS3712H08, Tox21_111539, Tox21_301440, Tox21_500240, HY-17461R, LMST02030090, MSK2228-100A, s5869, 17-Hydroxy-11-dehydrocorticosterone;, AKOS015840096, AKOS015894868, MSK2228-1000A, Tox21_111539_1, CCG-101143, CS-5097, DB14681, FC20558, LP00240, NC00393, SDCCGSBI-0050228.P002, 4-Pregnene-17.alpha.,11,20-trione, NCGC00023939-03, NCGC00023939-04, NCGC00023939-05, NCGC00023939-06, NCGC00023939-07, NCGC00023939-08, NCGC00023939-09, NCGC00023939-11, NCGC00023939-15, NCGC00255108-01, NCGC00260925-01, Pregn-4-en-17.alpha.,11,20-trione, AC-33118, AS-11686, HY-17461, NCI60_042165, PREDNISONE IMPURITY A [EP IMPURITY], EU-0100240, NS00010356, Cortisone Solution in Acetonitrile, 100ug/mL, C 2755, C00762, Cortisone Solution in Acetonitrile, 1000ug/mL, D07749, D96089, HYDROCORTISONE IMPURITY B [EP IMPURITY], Pregn-4-ene-3,20-trione, 17,21-dihydroxy-, .delta.(sup4)-pregnene-17.alpha.,11,20-trione, 4-Pregnene-17.alpha.,21-diol-3,11,20-trione, Q423185, SR-01000000094, Pregn-4-en-17.alpha.,21-diol-3,11,20-trione, SR-01000000094-3, 17.alpha.,21-Dihydroxy-4-pregnene-3,11,20-trione, BRD-K43736954-001-03-3, Cortisone, certified reference material, TraceCERT(R), Delta(4)-pregnene-17alpha,21-diol-3,11,20-trione, WLN: L E5 B666 CV OV MUTJ A1 E1 FV1Q FQ, .DELTA.4-pregnene-17.alpha.,21-diol-3,11,20-trione, 17.alpha.,21.beta.-Dihydroxypregn-4-ene-3,11,20-trione, (10R,13S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,11-dione, Kendall's Compound E; 4-Pregnene-17alpha,21-diol-3,11,20-trione; Reichstein's Substance Fa, UQC
Theoretical properties:
molecular_formula: C21H28O5
molecular_weight: 360.4 g/mol
exact_mass: 360.19367399 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 2
heavy_atom_count: 26
topological_polar_surface_area: 91.7 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 222 °C
solubility: 0.28 mg/mL at 25 °C
Descriptions:
{"pubchem": "Cortisone is 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. It has a role as a mouse metabolite and a human metabolite. It is a primary alpha-hydroxy ketone, a tertiary alpha-hydroxy ketone, a glucocorticoid, a 17alpha-hydroxy steroid, a 21-hydroxy steroid, a 20-oxo steroid, an 11-oxo steroid, a 3-oxo-Delta(4) steroid and a C21-steroid. It derives from a hydride of a pregnane.", "chebi": "A C<small><sub>21</sub></small>-steroid that is pregn-4-ene substituted by hydroxy groups at positions 17 and 21 and oxo group at positions 3, 11 and 20.", "chembl": "CORTISONE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.", "wikipedia": "Cortisone is a naturally occurring, mostly inactive pregnene (21-carbon) steroid hormone. In the body, cortisone is produced as part of the Cortisol-Cortisone shunt, which protects vulnerable organs like the kidneys from cortisol. These organs produce the enzyme 11\u03b2-HSD2 which locally converts cortisol into inactive cortisone. Cortisone is later converted back into the active steroid cortisol by the enzyme 11\u03b2-HSD1, particularly in the liver, which maintains blood cortisol levels. Without the reaction converting cortisol into cortisone, cortisol binds with the mineralocorticoid receptors of the kidney, causing hypertension along with the other symptoms of apparent mineralocorticoid excess syndrome. Because it gets converted into cortisol by the body, it is sometimes used as a pharmaceutical prodrug as an alternative to directly taking cortisol.\nThe term \"cortisone\" is frequently misused to mean either any corticosteroid or hydrocortisone, which is in fact cortisol. Many who speak of receiving a \"cortisone shot\" or taking \"cortisone\" are more likely receiving hydrocortisone or one of many other, much more potent synthetic corticosteroids.\nCortisone can be administered as a prodrug, meaning it has to be converted by the body (specifically the liver, converting it into cortisol) after administration to be effective. It is used to treat a variety of ailments and can be administered intravenously, orally, intra-articularly (into a joint), or transcutaneously. Cortisone suppresses various elements of the immune system, thus reducing inflammation and attendant pain and swelling.  Risks exist, in particular in the long-term use of cortisone. However, using cortisone only results in very mild activity, and very often more potent steroids are used instead."}