2-[(1R,2S,10S,11S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl]-2-oxoethyl acetate

• ChemBase ID: 171799
• Molecular Formular: C23H29FO6
• Molecular Mass: 420.4711632
• Monoisotopic Mass: 420.19481687
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@]2([C@H](C[C@]2([C@H]1CC[C@@]2(C(=O)COC(=O)C)O)C)O)F)C
• Canonical SMILES: CC(=O)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/C23H29FO6/c1-13(25)30-12-19(28)22(29)9-7-16-17-5-4-14-10-15(26)6-8-20(14,2)23(17,24)18(27)11-21(16,22)3/h6,8,10,16-18,27,29H,4-5,7,9,11-12H2,1-3H3/t16-,17-,18-,20-,21-,22-,23-/m0/s1
• InChIKey: ZOCUOMKMBMEYQV-GSLJADNHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1R,2S,10S,11S,14R,15S,17S)-1-fluoro-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-oxoethyl acetate
• IUPAC Traditional name: predef
• Synonyms: 21-Acetoxy-9-fluoro-11β,17-dihydroxypregna-1,4-diene-3,20-dione; 9-Fluoro-11β,17,21-trihydroxypregna-1,4-diene-3,20-dione 21-Acetate; 9α-Fluoroprednisolone 21-Acetate; 9α-Fluoroprednisolone Acetate; NSC 12600; NSC 37977; 9-Fluoroprednisolone Acetate; Predef; Predef R 2X; U 6013; 9α-Fluoro-11β,17α,21-trihydroxypregna-1,4-diene-3,20-dione 21-Acetate; Isoflupredone Acetate

Database IDs

• CAS Number: 338-98-7
• PubChem SID: 164227709
• PubChem CID: 224246

CALCULATED PROPERTIES

• Acid pKa: 12.57334
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.7577223
• LogD (pH = 7.4): 1.7577194
• Log P: 1.7577223
• Molar Refractivity: 107.1728 cm^3
• Polarizability: 41.642883 Å^3
• Polar Surface Area: 100.9 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - I816610

An anti-inflammatory drug used in veterinary medicine. It is a corticosteroid with both glucocorticoid and mineralocorticoid activity and has been shown to increase the frequency of severe hypokalemia in healthy cows.

REFERENCES

• Coffer, N.Y. et al.: Am. J. Vet. Res., 67, 1244 (2006)
• Seifi, H.A. et al.: J. Diary Sci., 90, 4181 (2006)