(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one

• ChemBase ID: 738
• Molecular Formular: C21H28O5
• Molecular Mass: 360.44402
• Monoisotopic Mass: 360.193674
• SMILES: O[C@]1([C@@]2([C@H]([C@H]3[C@H]([C@@H](O)C2)[C@@]2(C(=CC(=O)C=C2)CC3)C)CC1)C)C(=O)CO
• Canonical SMILES: OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2CCC2=CC(=O)C=C[C@]12C
• 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/h5,7,9,14-16,18,22,24,26H,3-4,6,8,10-11H2,1-2H3/t14-,15-,16-,18+,19-,20-,21-/m0/s1
• InChIKey: OIGNJSKKLXVSLS-VWUMJDOOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one; (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one
• IUPAC Traditional name: prednisolone; (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• Brand Name: Ak-Pred; Ak-Tate; Alphadrol; Articulose-50; Co-Hydeltra; Codelcortone; Cordrol; Cortalone; Cotogesic; Cotolone; Decaprednil; Decortin H; Delcortol; Delta F; Delta-Cortef; Delta-Stab; Deltacortenol; Deltacortril; Deltacortril Enteric; Deltasolone; Deltisilone; Depo-Medrol; Derpo Pd; Dexa-Cortidelt Hostacortin H; Di-Adreson F; Dicortol; Donisolone; Dydeltrone; Eazolin D; Econopred; Econopred Plus; Erbacort; Erbasona; Estilsona; Fernisolone; Fernisolone P; Fernisolone-P; Flamasone; Hostacortin H; Hydeltra; Hydeltra-Tba; Hydeltrasol; Hydeltrone; Hydrodeltalone; Hydrodeltisone; Hydroretrocortin; Hydroretrocortine; I-Pred; Inflamase Forte; Inflamase Mild; Key-Pred; Klismacort; Lentosone; Lite Pred; M-Predrol; Medrol; Medrol Acetate; Metacortandralone; Meti-Derm; Meticortelone; Metreton; Nisolone; Nor-Pred T.B.A.; Ocu-Pred; Ocu-Pred Forte; Ophtho-Tate; Orapred; Panafcortelone; Paracortol; Paracotol; Pediapred; Precortalon; Precortancyl; Precortilon; Precortisyl; Pred Forte; Pred Mild; Predair; Predair A; Predair Forte; Predalone 50; Predalone T.B.A.; Predate Tba; Predate-50; Predcor-25; Predcor-50; Predcor-Tba; Predne-Dome; Prednelan; Predni-Dome; Prednicen; Predniliderm; Predniretard; Prednis; Predonin; Predonine; Prelone; Prenolone; Rolisone; Scherisolon; Solone; Steran; Sterane; Sterolone; Supercortisol; Ulacort; Ultra Pred; Ultracorten H; Ultracortene H; Ultracortene-H; Ultracortene-Hydrogen
• Synonyms: 11β, 17α, 21-Trihydroxypregna-1,4-diene-3,20-dione; 1-Dehydrocortisol; 1-Dehydrohydrocortisone; 1,4-Pregnadiene-11β,17α,21-triol-3,20-dione; Prednisolone; (8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one; 1,4-Pregnadiene-11β,17α,21-triol-3,20-dione; 11β,17α,21-Trihydroxy-1,4-pregnadiene-3,20-dione; PRDL; Deltahydrocortisone; Methylprednisolone Acetate; Predisolone Sodium Phosphate; Prednisolona [INN-Spanish]; Prednisolone Acetate; Prednisolone Sodium Phosphate; Prednisolone Tebutate; Prednisolonum [INN-Latin]; Prednisolone; Hydroretrocortine; Decaprednil; Predonine; Delta-Cortef; Hydeltra; (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one; 1,4-孕甾二烯-11β,17α,21-三醇-3,20-二酮; 1-去氢氢化可的松; 1-去氢皮质醇; 11β,17α,21-三羟基-1,4-孕甾二烯-3,20-二酮; 泼尼松龙

Database IDs

• CAS Number: 50-24-8
• EC Number: 200-021-7
• MDL Number: MFCD00003649
• Beilstein Number: 1354103
• PubChem SID: 46504847; 160964201; 24898079; 24870351; 24898725
• PubChem CID: 5755

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.584675
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.2729899
• LogD (pH = 7.4): 1.2729871
• Log P: 1.2729899
• Molar Refractivity: 98.4933 cm^3
• Polarizability: 38.038647 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.66
• LOG S: -3.18
• Solubility (Water): 2.39e-01 g/l

PROPERTIES

Physical Property

• Solubility: 223 mg/L
• Melting Point: 236 - 238°C; 240 °C (dec.)(lit.); decomposes 237-239 °C
• Hydrophobicity(logP): 1; 1.423

Safety Information

• Storage Condition: -20°C; Room Temperature (15-30°C)
• RTECS: TU4152000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Gene Information: human ... AR(367), ESR1(2099), NR3C1(2908), NR3C2(4306), PGR(5241), SERPINA6(866)mouse ... Nr3c1(14815)rat ... Ar(24208)
• Mechanism of Action: Glucocorticoid receptor agonist.; On binding, the corticoreceptor-ligand complex translocates itself into the cell nucleus, where it binds to many glucocorticoid response elements (GRE) in the promoter region of the target genes.; The DNA bound receptor then interacts with basic transcription factors, causing an increase or decrease in expression of specific target genes, including suppression of IL2 (interleukin 2) expression.

Product Information

• Purity: ≥99%; 95%
• Grade: analytical standard; VETRANAL™, analytical standard
• Salt Data: Free Base
• Packaging: vial of 250 mg
• Impurities: ≤1.5 mol/mol water
• Application(s): Adrenergic agent; Antiinflammatory agent; Antineoplastic agent
• Pharmacopeia Traceability: traceable to BP 464; traceable to PhEur P2700000; traceable to USP 1555005
• Empirical Formula (Hill Notation): C21H28O5

DETAILS

MP Biomedicals - 02102717

Crystalline

DrugBank - DB00860

• Drug Groups: approved
• Description: A glucocorticoid with the general properties of the corticosteroids. It is the drug of choice for all conditions in which routine systemic corticosteroid therapy is indicated, except adrenal deficiency states. [PubChem]
• Indication: For the treatment of primary or secondary adrenocortical insufficiency, such as congenital adrenal hyperplasia, thyroiditis. Also used to treat psoriatic arthritis, rheumatoid arthritis, ankylosing spondylitis, bursitis, acute gouty arthritis and epicondylitis. Also indicated for treatment of systemic lupus erythematosus, pemphigus and acute rhematic carditis. Can be used in the treatment of leukemias, lymphomas, thrombocytopenia purpura and autoimmune hemolytic anemia. Can be used to treat celiac disease, insulin resistance, ulcerative colitis and liver disorders.
• Pharmacology: Prednisolone is a synthetic glucocorticoid used as antiinflammatory or immunosuppressive agent. Prednisolone is indicated in the treatment of various conditions, including congenital adrenal hyperplasia, psoriatic arthritis, systemic lupus erythematosus, bullous dermatitis herpetiformis, seasonal or perennial allergic rhinitis, allergic corneal marginal ulcers, symptomatic sarcoidosis, idiopathic thrombocytopenic purpura in adults, leukemias and lymphomas in adults, and ulcerative colitis. Glucocorticoids are adrenocortical steroids and cause profound and varied metabolic effects. In addition, they modify the body's immune responses to diverse stimuli.
• Toxicity: LD₅₀=500 mg/kg (oral, rat), short-term side effects include high blood glucose levels and fluid retention. Long term side effects include Cushing's syndrome, weight gain, osteoporosis, glaucoma, type II diabetes and adrenal suppression.
• Affected Organisms: Humans and other mammals
• Biotransformation: Excreted in the urine as either free or glucoconjugate.
• Absorption: Readily absorbed by gastrointestinal tract, peak plasma concentration is reached 1-2 hours after administration.
• Half Life: 2-3 hours
• Protein Binding: Very high (>90%)
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1737

Research Area: Inflammation
Biological Activity:
Prednisolone(Hydroretrocortine) is a synthetic glucocorticoid with anti-inflammatory and immunomodulating properties. After cell surface receptor attachment and cell entry, prednisolone enters the nucleus where it binds to and activates specific nuclear receptors, resulting in an altered gene expression and inhibition of proinflammatory cytokine production. This agent also decreases the number of circulating lymphocytes, induces cell differentiation, and stimulates apoptosis in sensitive tumor cells populations. [1,2]

Sigma Aldrich - P0152

包装
Supplied in amber screw-cap vials

Sigma Aldrich - P6004

Analysis Note
Actual content given on label
Biochem/physiol Actions
Prednisolone is a glucocorticoid with anti-inflammatory and immunosuppressive activity.
包装
1, 5, 10, 25 g in poly bottle
100 mg in poly bottle

Sigma Aldrich - 46656

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

REFERENCES

• http://en.wikipedia.org/wiki/Prednisolone
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 585B, (nmr)
• Nobile, A. et al., J.A.C.S., 1955, 77, 4184, (biosynth)
• Herzog, H.L. et al., Science (Washington, D.C.), 1955, 121, 176, (struct)
• Zicha, L. et al., Arzneim.-Forsch., 1960, 10, 728; 831, (pharmacol, derivs)
• Herzog, H.L. et al., Tetrahedron, 1962, 18, 581, (synth)
• Hirschmann, R. et al., J.A.C.S., 1964, 86, 3903, (synth)
• Toft, P. et al., Can. J. Spectrosc., 1970, 15, 137, (ms)
• Gambertoglis, J.G. et al., J. Pharmacokinet. Biopharm., 1980, 8, 1, (rev, pharmacol)
• Jusko, W.J. et al., Ther. Drug Monit., 1980, 2, 169, (rev, pharmacol)
• Gonzalez, M.D. et al., Org. Magn. Reson., 1984, 22, 586, (cmr)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6297; 6321; 6941
• Kirk, D.N. et al., J.C.S. Perkin 2, 1990, 1567, (pmr)
• Ali, S.L., Anal. Profiles Drug Subst., 1992, 21, 415, (rev)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 737
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, AAF625; PMA000; PMA100; SOV100; PLY300