4-{2-[(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0?,?.0??,??]heptadeca-3,6-dien-14-yl]-2-oxoethoxy}-4-oxobutanoic acid

• ChemBase ID: 104544
• Molecular Formular: C25H32O8
• Molecular Mass: 460.51678
• Monoisotopic Mass: 460.20971798
• SMILES: O=C(O)CCC(=O)OCC(=O)[C@@]1(O)CC[C@H]2[C@H]3[C@H]([C@@H](O)C[C@]12C)[C@]1(C=CC(=O)C=C1CC3)C
• Canonical SMILES: OC(=O)CCC(=O)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/C25H32O8/c1-23-9-7-15(26)11-14(23)3-4-16-17-8-10-25(32,24(17,2)12-18(27)22(16)23)19(28)13-33-21(31)6-5-20(29)30/h7,9,11,16-18,22,27,32H,3-6,8,10,12-13H2,1-2H3,(H,29,30)/t16-,17-,18-,22+,23-,24-,25-/m0/s1
• InChIKey: APGDTXUMTIZLCJ-CGVGKPPMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{2-[(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0?,?.0??,??]heptadeca-3,6-dien-14-yl]-2-oxoethoxy}-4-oxobutanoic acid; 4-{2-[(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]-2-oxoethoxy}-4-oxobutanoic acid
• IUPAC Traditional name: solu-delta-cortef; 4-{2-[(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]-2-oxoethoxy}-4-oxobutanoic acid
• Synonyms: Δ^1-Hydrocortisone 21-hemisuccinate; 1,4-Pregnadiene-11β,17,21-triol-3,20-dione 21-hemisuccinate; 11β,17α,21-Trihydroxy-1,4-pregnadiene-3,20-dione 21-hemisuccinate; PREDNISOLONE 21-HEMISUCCINATE FREE ACID; PREDNISOLONE 21-HEMISUCCINATE; Prednisolone hemisuccinate

Database IDs

• CAS Number: 2920-86-7; 1715-33-9
• EC Number: 220-861-8
• PubChem SID: 162091884
• PubChem CID: 656804

CALCULATED PROPERTIES

• Acid pKa: 3.6580515
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -0.30034757
• LogD (pH = 7.4): -1.7829142
• Log P: 1.5389781
• Molar Refractivity: 118.5381 cm^3
• Polarizability: 46.148277 Å^3
• Polar Surface Area: 138.2 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 206°C (decomposes)

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: TU4153400

Pharmacology Properties

• Mechanism of Action: ACTH antagonist; ACTH secretion inhibitor; Calcium mobilizer; Glucocorticoid; Gluconeogenesis promoter; Glycogen deposition inhibitor; Phosphorus mobilizer

Product Information

• Application(s): Antiallergic agent; Antiinflammatory,; Immunosuppressive

DETAILS

MP Biomedicals - 02156347

Free Acid
Crystalline

MP Biomedicals - 02156348

(Δ^1-Hydrocortisone 21-hemisuccinate; 1,4-Pregnadiene-11β,17,21-triol-3,20-dione 21-hemisuccinate; 11β,17α,21-Trihydroxy-1,4-pregnadiene-3,20-dione 21-hemisuccinate)
Sodium Salt
White powder.

REFERENCES

• McAleer, W.J. et al., J.O.C., 1958, 23, 508, (synth)
• Smith, L.L. et al., J.O.C., 1958, 23, 960, (spectra)
• Pechet, M.M. et al., J. Colloid Sci., 1959, 38, 681, (pharmacol)
• Herzog, H.L. et al., Tetrahedron, 1962, 18, 581, (synth, ir, pmr, uv)
• Gladiali, S. et al., Chem. Ind. (London), 1977, 982, (synth)
• Martindale, The Extra Pharmacopoeia, 28th/29th edn., Pharmaceutical Press, 1982, 12869