2-[(1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl]-2-oxoethyl acetate

• ChemBase ID: 169036
• Molecular Formular: C24H30F2O6
• Molecular Mass: 452.4882064
• Monoisotopic Mass: 452.20104512
• SMILES: C1=C[C@]2(C(=CC1=O)[C@H](C[C@@H]1[C@@]2([C@H](C[C@]2([C@H]1C[C@H]([C@@]2(C(=O)COC(=O)C)O)C)C)O)F)F)C
• Canonical SMILES: CC(=O)OCC(=O)[C@@]1(O)[C@H](C)C[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
• InChI: InChI=1S/C24H30F2O6/c1-12-7-15-16-9-18(25)17-8-14(28)5-6-21(17,3)23(16,26)19(29)10-22(15,4)24(12,31)20(30)11-32-13(2)27/h5-6,8,12,15-16,18-19,29,31H,7,9-11H2,1-4H3/t12-,15+,16+,18+,19+,21+,22+,23+,24+/m1/s1
• InChIKey: ISSQQUKLQJHHOR-OSNGSNEUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-2,13,15-trimethyl-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: 2-[(1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]-2-oxoethyl acetate
• Synonyms: Flumethasone 21-Acetate; 6α-Fluorodexamethasone 21-Acetate; 6α,9-Difluoro-11β,17,21-trihydroxy-16α-methyl-pregna-1,4-diene-3,20-dione 21-Acetate; Flumethasone Acetate

Database IDs

• CAS Number: 2823-42-9
• PubChem SID: 162263168
• PubChem CID: 11155198

CALCULATED PROPERTIES

• Acid pKa: 12.43502
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.7829758
• LogD (pH = 7.4): 1.7829717
• Log P: 1.7829758
• Molar Refractivity: 111.4678 cm^3
• Polarizability: 43.257286 Å^3
• Polar Surface Area: 100.9 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F455005

An anti-inflammatory corticosteroid.

REFERENCES

• Weber, D., et al.: J. Pharm. Sci., 61, 689 (1972)
• Biagi, G., et al.: J. Med. Chem., 18, 873 (1972)