(1R,2S,8S,10S,11S,14R,15S,17S)-1,8-difluoro-17-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl butanoate

• ChemBase ID: 167422
• Molecular Formular: C25H32F2O6
• Molecular Mass: 466.5147864
• Monoisotopic Mass: 466.21669518
• SMILES: C1=C[C@]2(C(=CC1=O)[C@H](C[C@@H]1[C@@]2([C@H](C[C@]2([C@H]1CC[C@@]2(C(=O)CO)OC(=O)CCC)C)O)F)F)C
• Canonical SMILES: CCCC(=O)O[C@@]1(CC[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2C[C@@H](C2=CC(=O)C=C[C@]12C)F)F)C(=O)CO
• InChI: InChI=1S/C25H32F2O6/c1-4-5-21(32)33-24(20(31)13-28)9-7-15-16-11-18(26)17-10-14(29)6-8-22(17,2)25(16,27)19(30)12-23(15,24)3/h6,8,10,15-16,18-19,28,30H,4-5,7,9,11-13H2,1-3H3/t15-,16-,18-,19-,22-,23-,24-,25-/m0/s1
• InChIKey: BQEJAAIPKDQEPV-MXHGPKCJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,8S,10S,11S,14R,15S,17S)-1,8-difluoro-17-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl butanoate
• IUPAC Traditional name: (1R,2S,8S,10S,11S,14R,15S,17S)-1,8-difluoro-17-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl butanoate
• Synonyms: (6α,11β)-6,9-Difluoro-11,21-dihydroxy-17-(1-oxobutoxy)pregna-1,4-diene-3,20-dione; 6α,9-Difluoro Prednisolone 17-Butyrate; 21-Desacetyl Difluprednate; 21-Desacetyl Difluprednate

Database IDs

• CAS Number: 23640-96-2
• PubChem SID: 162261555
• PubChem CID: 12986413

CALCULATED PROPERTIES

• Acid pKa: 13.353764
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.5631075
• LogD (pH = 7.4): 2.563107
• Log P: 2.5631075
• Molar Refractivity: 116.2241 cm^3
• Polarizability: 45.08009 Å^3
• Polar Surface Area: 100.9 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D445825

21-Desacetyl Difluprednate is an anti-inflammatory steroid.

REFERENCES

• Gardi, R., et al.: J. Med. Chem., 15, 556 (1972)
• Yagi, M., et al.: Chem. Pharm. Bull., 38, 2513 (1972)
• He, J., et al.: J. Pharm. Biomed Anal., 10, 289 (1972)