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

• ChemBase ID: 179849
• Molecular Formular: C21H27FO5
• Molecular Mass: 378.4344832
• Monoisotopic Mass: 378.18425218
• SMILES: [C@]12([C@@](C(=O)CO)(CC[C@H]1[C@H]1[C@@]([C@@]3(C(=CC(=O)C=C3)CC1)C)([C@H](C2)O)F)O)C
• Canonical SMILES: OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2CCC2=CC(=O)C=C[C@]12C)F
• InChI: InChI=1S/C21H27FO5/c1-18-7-5-13(24)9-12(18)3-4-15-14-6-8-20(27,17(26)11-23)19(14,2)10-16(25)21(15,18)22/h5,7,9,14-16,23,25,27H,3-4,6,8,10-11H2,1-2H3/t14-,15-,16-,18-,19-,20-,21-/m0/s1
• InChIKey: WAIJIHDWAKJCBX-BULBTXNYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,10S,11S,14R,15S,17S)-1-fluoro-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
• IUPAC Traditional name: (1R,2S,10S,11S,14R,15S,17S)-1-fluoro-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
• Synonyms: 9-Fluoroprednisolone; Deltafludrocortisone; Isoflupredone

Database IDs

• CAS Number: 338-95-4
• PubChem SID: 164235759
• PubChem CID: 127516

CALCULATED PROPERTIES

• Acid pKa: 12.549859
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.3165969
• LogD (pH = 7.4): 1.3165938
• Log P: 1.3165969
• Molar Refractivity: 98.0213 cm^3
• Polarizability: 37.78934 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

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

Product Information

• Application(s): Antiinflammatory agent; Immunosuppressive

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