Compound: prednisone
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)C=C1
InChIKey: XOFYZVNMUHMLCC-ZPOLXVRWSA-N
Synonyms: prednisone, 53-03-2, Dehydrocortisone, Deltasone, Decortin, Meticorten, Metacortandracin, Supercortil, Orasone, Paracort, 1,2-Dehydrocortisone, Deltacortisone, Colisone, Decortisyl, Prednison, Di-Adreson, Ancortone, Bicortone, Decortancyl, Deltacortone, Hostacortin, Prednilonga, Servisone, Sterapred, Dacortin, Deltison, Encorton, Lodotra, Cortan, Delta-Cortelan, Liquid Pred, Prednicen-M, Delta-Dome, Ultracortene, Cortidelt, Dekortin, Delta E, Enkorton, Lisacort, Prednizon, Pronison, Adasone, Deltra, Juvason, Nurison, Prednisone Intensol, Deltacortene, Econosone, Panafcort, Predeltin, Prednicort, Prednidib, Prednisona, Prednisonum, Prednitone, delta-Cortisone, SK-Prednisone, Pregna-1,4-diene-3,11,20-trione, 17,21-dihydroxy-, Prednisone tablets, delta-1-Cortisone, prednisone anhydrous, Rayos, 1,4-Pregnadiene-17alpha,21-diol-3,11,20-trione, Fernisone, 3en3hg4wsw, delta(sup 1)-Cortisone, delta-1-Dehydrocortisone, NSC-10023, delta(sup 1)-Dehydrocortisone, NCI-C04897, NSC 10023, CHEBI:8382, VB0R961HZT, Deltadehydrocortisone, DTXSID4021185, 1,4-Pregnadiene-17-alpha,21-diol-3,11,20-trione, (8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,12,14,15,16-octahydrocyclopenta[a]phenanthrene-3,11-dione, DTXCID701185, NSC10023, Pregna-1,4-diene-3,11,20-trione monohydrate, 17,21-dihydroxy-, delta1-Cortisone, Predicorten, Predniment, Ofisolona, Predicor, Promifen, Meprosona-F, Panasol-S, Acsis, Prednison, Perrigo Prednisone, Delta 1-Cortisone, Dr Adam Au, (8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,12,14,15,16-octahydrocyclopenta(a)phenanthrene-3,11-dione, RefChem:6162, 1, 2-Dehydrocortisone, A07EA03, H02AB07, PredniSONE Tablets, USP, 5 mg, PredniSONE Tablets, USP, 10 mg, PredniSONE Tablets, USP, 20 mg, P-PACK PREDNISONE 20MG, 7-DAY TAPERING DOSE PACK, (1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo(8.7.0.02,7.011,15)heptadeca-3,6-diene-5,17-dione, 200-160-3, Rectodelt, Ultracorten, Diadreson, Encortone, Zenadrid, Cotone, Wojtab, In-Sone, Cartancyl, Deltisona, Winpred, Deltisone, Prednisonum [INN-Latin], Prednisona [INN-Spanish], Zenadrid (veterinary), 1-Dehydrocortisone, MFCD00003608, Prednisone(Adasone), U 6020, Zenadrid [veterinary], Novoprednisone, Dellacort, Incocortyl, Parmenison, Prednicorm, Prednicot, Prednovister, Retrocortine, Dacorten, Fiasone, Panasol, Pehacort, Presone, delta cortelan, Nisona, Nizon, Sone, Apo-Prednisone, Dellacort A, Me-Korti, Origen Prednisone, (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-3H-cyclopenta[a]phenanthrene-3,11(6H)-dione, .delta.-Cortisone, .delta.1-Cortisone, NCGC00090766-01, Precort, .delta.1-Dehydrocortisone, 1-Cortisone, Meticorten (Veterinary), Lodtra, SMR000718760, SMR001227202, Delta E., CCRIS 2646, HSDB 3168, MLS002638114, EINECS 200-160-3, UNII-VB0R961HZT, Prednisone [USP:INN:BAN], AI3-52939, .delta.sone, Prednisone CRS, .delta.-Cortone, .delta.-Cortelan, CAS-53-03-2, Prestwick_405, .delta. E, .delta.-E, Prednisone (Adasone), Prednisone (Standard), Prednisone, >=98%, PREDNISONE [MI], PREDNISONE [INN], Prestwick0_000077, Prestwick1_000077, Prestwick2_000077, Prestwick3_000077, PREDNISONE [HSDB], PREDNISONE [IARC], .delta.(sup1)-Cortisone, P1276, PREDNISONE [VANDF], CHEMBL635, Epitope ID:923993, PREDNISONE [MART.], SCHEMBL3288, PREDNISONE [USP-RS], PREDNISONE [WHO-DD], BSPBio_000293, MLS001061265, MLS001304073, MLS001335907, MLS001335908, MLS002154191, MLS002207083, MLS002548880, SPBio_002214, BPBio1_000323, GTPL7096, MEGxm0_000443, orb1710534, orb3140036, PREDNISONE [GREEN BOOK], 17alpha,21-dihydroxypregna-1,4-diene-3,11,20-trione, PREDNISONE [ORANGE BOOK], ACon0_000082, ACon1_000297, HY-B0214R, MSK2227, PREDNISONE [EP MONOGRAPH], GLXC-07880, HMS1568O15, HMS2090J13, HMS2095O15, HMS2231I24, HMS3039K07, HMS3259I09, HMS3712O15, HMS3884C04, PREDNISONE [USP MONOGRAPH], 1,21-diol-3,11,20-trione, HY-B0214, PREDNISONE TABLETS [USP-RS], Tox21_111014, Tox21_201564, Tox21_300196, BDBM50550126, EBC-26720, LMST02030180, MSK2227-100A, s1622, AKOS005267096, AKOS007930684, MSK2227-1000A, MSK2227-1000M, Tox21_111014_1, CCG-220077, DB00635, FP27134, NC00475, NCGC00090766-02, NCGC00090766-03, NCGC00090766-04, NCGC00090766-05, NCGC00090766-07, NCGC00254096-01, NCGC00259113-01, (1R,3aS,3bS,9aR,9bS,11aS)-1-hydroxy-1-(2-hydroxyacetyl)-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthrene-7,10-dione, AC-11112, AS-11685, NCI60_000008, NS00007844, PREDNISOLONE IMPURITY B [EP IMPURITY], Prednisone Solution in Methanol, 1000ug/mL, Pregna-1,11,20-trione, 17,21-hydroxy-, T1018, EN300-52605, Pregna-1,11,20-trione, 17,21-dihydroxy-, C07370, Prednisone Solution in Acetonitrile, 100ug/mL, Prednisone Solution in Acetonitrile, 1000ug/mL, 1,4-Pregnadiene-17a,21-diol-3,11,20-trione, Q424972, SR-01000837536, SR-01000837536-3, BRD-K85883481-001-04-2, BRD-K85883481-001-08-3, BRD-K85883481-001-22-4, BRD-K85883481-001-25-7, WLN: L E5 B666 CV OV AHTTT&J A1 E1 FV1Q FQ, Z756390288, Prednisone, British Pharmacopoeia (BP) Reference Standard, Prednisone, European Pharmacopoeia (EP) Reference Standard, Prednisone, United States Pharmacopeia (USP) Reference Standard, Prednisone, Pharmaceutical Secondary Standard; Certified Reference Material, Prednisone for peak identification, European Pharmacopoeia (EP) Reference Standard, Prednisone, pharmaceutical secondary standard; traceable to USP, PhEur and BP, (8S,10R,13S,17R)-17-Hydroxy-17-(2-hydroxy-acetyl)-10,13-dimethyl-7,8,9,10,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,11-dione
Theoretical properties:
molecular_formula: C21H26O5
molecular_weight: 358.4 g/mol
exact_mass: 358.17802393 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:
physical_state: Crystals
color: Crystals
odor: Odorless
melting_point: 451 to 455 °F (DEC) (NTP, 1992)
solubility: Very slightly soluble (NTP, 1992)
Descriptions:
{"pubchem": "Prednisone is a synthetic glucocorticoid drug that is particularly effective as an immunosuppressant, and affects virtually all of the immune system. Prednisone is a prodrug that is converted by the liver into prednisolone (a beta-hydroxy group instead of the oxo group at position 11), which is the active drug and also a steroid. It has a role as an anti-inflammatory drug, an antineoplastic agent, an immunosuppressive agent, an adrenergic agent and a prodrug. 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 C21-steroid and a 3-oxo-Delta(1),Delta(4)-steroid.", "chebi": "A synthetic glucocorticoid drug that is particularly effective as an immunosuppressant, and affects virtually all of the immune system. Prednisone is a prodrug that is converted by the liver into prednisolone (a \u03b2-hydroxy group instead of the oxo group at position 11), which is the active drug and also a steroid.", "chembl": "PREDNISONE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Prednisone is a glucocorticoid medication mostly used to suppress the immune system and decrease inflammation in conditions such as asthma, COPD, and rheumatologic diseases. It is also used to treat high blood calcium due to cancer and adrenal insufficiency along with other corticosteroids. It is taken by mouth.\nCommon side effects may include cataracts, bone loss, easy bruising, muscle weakness, and thrush. Other side effects include weight gain, swelling, high blood sugar, increased risk of infection, and psychosis. It is generally considered safe in pregnancy and low doses appear to be safe while the user is breastfeeding. After prolonged use, prednisone must be stopped gradually.\nPrednisone is a prodrug and must be converted to prednisolone by the liver before it becomes active. Prednisolone then binds to glucocorticoid receptors, activating them and triggering changes in gene expression. These changes inhibit function and decrease the number of key leukocytes in the bloodstream.\nPrednisone was patented in 1954 and approved for medical use in the United States in 1955. Prednisone is a therapeutic alternative on the World Health Organization's List of Essential Medicines. It is available as a generic medication. In 2023, it was the 38th most commonly prescribed medication in the United States, with more than 15 million prescriptions."}