(1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-diene-5,17-dione

• ChemBase ID: 517
• Molecular Formular: C21H26O5
• Molecular Mass: 358.42814
• Monoisotopic Mass: 358.17802393
• SMILES: O[C@]1([C@@]2([C@H]([C@H]3[C@@H]([C@@]4(C(=CC(=O)C=C4)CC3)C)C(=O)C2)CC1)C)C(=O)CO
• Canonical SMILES: OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)CC(=O)[C@H]1[C@H]2CCC2=CC(=O)C=C[C@]12C
• InChI: InChI=1S/C21H26O5/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/h5,7,9,14-15,18,22,26H,3-4,6,8,10-11H2,1-2H3/t14-,15-,18+,19-,20-,21-/m0/s1
• InChIKey: XOFYZVNMUHMLCC-ZPOLXVRWSA-N

NAMES AND DATABASE IDS

Names

• 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}]heptadeca-3,6-diene-5,17-dione; (1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-5,17-dione
• IUPAC Traditional name: prednisone; (1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-5,17-dione
• Brand Name: Delta-cortelan; Delta-cortisone; Delta-cortone; Delta-dome; Adasone; Ancortone; Apo-prednisone; Betapar; Bicortone; Cartancyl; Colisone; Cortan; Cortancyl; Cortidelt; Cotone; Dacorten; Dacortin; Decortancyl; Decortin; Decortisyl; Dekortin; Delcortin; Dellacort; Dellacort A; Delta Cortelan; Delta E; Deltacortene; Deltacortisone; Deltacortone; Deltasone; Deltison; Deltisona; Deltisone; Deltra; Di-Adreson; Diadreson; Econosone; Encorton; Encortone; Enkorton; Fernisone; Fiasone; Hostacortin; In-Sone; Incocortyl; Juvason; Lisacort; Me-Korti; Metacortandracin; Meticorten; Nisona; Nizon; Novoprednisone; Nurison; Orasone; Origen Prednisone; Panafcort; Panasol; Paracort; Parmenison; Pehacort; Precort; Predeltin; Prednicen-M; Prednicorm; Prednicort; Prednicot; Prednidib; Prednilonga; Prednison; Prednisone Intensol; Prednitone; Prednizon; Prednovister; Presone; Pronison; Rectodelt; Retrocortine; Servisone; Sone; Sterapred; Supercortil; Ultracorten; Ultracortene; Winpred; Wojtab; Zenadrid
• Synonyms: 1,4-Pregnadiene-17α,21-diol-3,11,20-trione; 17α,21-Dihydroxy-1,4-pregnadiene-3,11,20-trione; Prednisone; Liquid Pree; Deltacortisone; Prednisonum; Prednisona [INN-Spanish]; Prednisonum [INN-Latin]; PRD; Dehydrocortisone; Prednisone; Deltasone; Liquid Pred; Orasone; Adasone; (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; 1-Cortisone; 17α, 21-Dihydroxypregna-1,4-dien-3,11,20-trione; 1,4-Pregnadiene-17α,21-diol-3,11,20-trione; 17,21-Dihydroxypregna-1,4-diene-3,11,20-trione; 1,2-Dehydrocortisone; Ancortone; Apo-Prednisone; Bicortone; Prednicorm; Prednicort; Retrocortine; Sone; Ultracorten; Δ1-Dehydrocortisone; (1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-diene-5,17-dione; 1-可的松; 17Α,21-二羟基-1,4-孕甾二烯-3,11,20-三酮; 去氢可的松; 强的松; 泼尼松; 泼尼松

Database IDs

• CAS Number: 53-03-2
• EC Number: 200-160-3
• MDL Number: MFCD00003608
• Beilstein Number: 2065301
• PubChem SID: 160963980; 24898748; 46508166; 24887849
• PubChem CID: 5865
• CHEBI ID: 8382
• ATC CODE: H02AB07; A07EA03
• CHEMBL: 635
• Chemspider ID: 5656
• DrugBank ID: DB00635
• KEGG ID: C07370
• Unique Ingredient Identifier: 3EN3HG4WSW
• Wikipedia Title: Prednisone
• Medline Plus: a601102

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.576199
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.6585041
• LogD (pH = 7.4): 1.6585013
• Log P: 1.6585041
• Molar Refractivity: 97.5681 cm^3
• Polarizability: 37.495747 Å^3
• Polar Surface Area: 91.67 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.07
• LOG S: -3.51
• Solubility (Water): 1.11e-01 g/l

PROPERTIES

Physical Property

• Solubility: 312 mg/L; Dioxane; DMSO; Ethanol; Pyridine
• Apperance: White Solid
• Melting Point: 220-225°C; 236-238 °C(lit.); 253 - 255°C; decomposes 233-235 °C
• Optical Rotation: [α]25/D +169°, c = 0.5 in dioxane
• Hydrophobicity(logP): 0.6; 1.661

Safety Information

• Storage Condition: -20°C; Refrigerator; Room Temperature (15-30°C)
• RTECS: TU4154100
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 63
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H361
• GHS Precautionary statements: P281
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Pharmacology Properties

• Admin Routes: Oral, Nasal, Rectal, Injection, IV
• Bioavailability: 70%
• Excretion: Renal
• Half Life: 1 hour
• Metabolism: prednisolone (liver)
• Legal Status: Rx Only (US)
• Pregnancy Category: C
• Mechanism of Action: ACTH antagonist; ACTH secretion inhibitor; Calcium mobilizer; Corticosteroid; Gluconeogenesis promoter; Glycogen deposition inhibitor; Phosphorus mobilizer

Product Information

• Purity: ≥98%; 95%; 98%
• Grade: Ph Eur
• Salt Data: Free Base
• Application(s): Antiinflammatory; Immunosuppressive
• Pharmacopeia: testing & handling conforms to Pharmacopeia
• Pharmacopeia Traceability: traceable to BP 553; traceable to PhEur P2900000; traceable to USP 1559006
• Empirical Formula (Hill Notation): C21H26O5

DETAILS

MP Biomedicals - 05218172

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02102718

Crystalline

DrugBank - DB00635

• Drug Groups: approved
• Description: A synthetic anti-inflammatory glucocorticoid derived from cortisone. It is biologically inert and converted to prednisolone in the liver. [PubChem]
• Indication: For the treatment of drug-induced allergic reactions, perennial or seasonal allergic rhinitis, serum sickness, giant cell arteritis acute rheumatic or nonrheumatic carditis, systemic dermatomyositis, systemic lupus erythematosus, atopic dermatitis, contact dermatitis, exfoliative dermatitis, bullous dermatitis herpetiformis, severe seborrheic dermatitis, severe (Stevens-Johnson syndrome) erythema multiforme, mycosis fungoides, pemphigus, severe psoriasis, acute adrenocortical insufficiency, Addison's disease, secondary adrenocortical insufficiency, congenital adrenal hyperplasia, hypercalcemia associated with neoplasms, nonsuppurative thyroiditis, ulceratice colitis, Crohn's disease, acquired hemolytic anemia, congenital hypoplastic anemia, erythroblastopenia, adult secondary thrombocytopenia, adult idiopathic thrombocytopenia purpura, acute or subacute bursitis, epicondylitis, acute nonspecific tenosynovitis, acute or chronic lymphocytic leukemia, Hodgkin's or non-Hodgkin's lynphomas, Waldenstrom's macroglobulinemia, primary brain tumors (adjunct), nephrotic syndrome, tuberculous meningitis, multiple sclerosis, myasthenia gravis. cerebral edema, chorioretinitis, diffuse posterior choroiditis, aleergic conjunctivitis, Herpes zoster ophthalmicus, anterior segment inflammation, iridocyclitis, iritis, keratitis, optoc neuritis, sympathetic ophthalmia, corneal marginal allergic ulcers, symptomatic sarcoidosis, Loeffler's syndrome not manageable by other means, berylliosis, fulminating or disseminated pulmonary tuberculosis when used concurrently with appropriate antituberculous chemotherapy and aspiration pneumonitis.
• Pharmacology: Prednisone, the most commonly-prescribed corticosteroid, is used to treat allograft rejection, asthma, systemic lupus erythematosus, and many other inflammatory states. Prednisone has very little mineralocorticoid activity.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: Readily absorbed from the gastrointestinal tract.
• Half Life: 2 to 3 hours
• Protein Binding: Extensively bound to plasma proteins.
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1622

Research Area: Immunology
Biological Activity:
Prednisone(Adasone) is a synthetic corticosteroid agent that is particularly effective as an immunosuppressant compound. Prednisone(Adasone) is used to treat certain inflammatory diseases and (at higher doses) some types of cancer, but has significant adverse effects. Because prednisone (Adasone) suppresses the immune system, prednisone (Adasone) leaves patients more susceptible to infections. Prednisone(Adasone) is usually taken orally but can be delivered by intramuscular injection or intravenous injection. Prednisone(Adasone) has a mainly glucocorticoid effect. Prednisone (Adasone) is converted by the liver into prednisolone, which is the active compound and also a steroid. [1]

Sigma Aldrich - P6254

Biochem/physiol Actions
Prednisone is a synthetic glucocorticoid with anti-inflammatory and immunosuppressive activity.
包装
1 g in poly tube
5, 10, 25 g in poly bottle

Sigma Aldrich - 286990

Packaging
5 g in glass bottle

Toronto Research Chemicals - P703780

Adrenocortical steroid. Glucocorticoid, antiinflammatory.

REFERENCES

• http://en.wikipedia.org/wiki/Prednisone
• Lennon, V., et al.: Lancet, 364, 2106 (2004)
• Wingerchuk, D., et al.: Neurology, 66, 1485 (2004)
• Fliri, A.F., et al.: J. Med. Chem., 52, 8038 ((2004)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 587B, (nmr)
• Nobile, A. et al., J.A.C.S., 1955, 77, 4184, (synth)
• Herzog, H.L. et al., Science (Washington, D.C.), 1955, 121, 176, (struct)
• Ger. Pat., 1960, 1 089 755; CA, 55, 20008, (succinate)
• Ger. Pat., 1960, 1 090 208; CA, 55, 26044b, (sulfate)
• Herzog, H.L. et al., Tetrahedron, 1962, 18, 581, (synth)
• Gardi, R. et al., Gazz. Chim. Ital., 1963, 93, 431, (ir, uv)
• Pickup, M.E., Clin. Pharmacokinet., 1979, 4, 111, (rev)
• Hickey, J.P. et al., J. Magn. Reson., 1980, 38, 501, (cmr)
• Gambertoglio, J.G. et al., J. Pharmacokinet. Biopharm., 1980, 8, 1, (rev)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6213
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 738
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, PLZ000; PLZ100