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

• ChemBase ID: 167390
• Molecular Formular: C27H36F2O5
• Molecular Mass: 478.5685464
• Monoisotopic Mass: 478.25308069
• 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@@H]2C(=O)COC(=O)CCCC)C)C)O)F)F)C
• Canonical SMILES: CCCCC(=O)OCC(=O)[C@H]1[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/C27H36F2O5/c1-5-6-7-23(33)34-14-21(31)24-15(2)10-17-18-12-20(28)19-11-16(30)8-9-26(19,4)27(18,29)22(32)13-25(17,24)3/h8-9,11,15,17-18,20,22,24,32H,5-7,10,12-14H2,1-4H3/t15-,17+,18+,20+,22+,24-,25+,26+,27+/m1/s1
• InChIKey: HHJIUUAMYGBVSD-YTFFSALGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1R,2S,8S,10S,11S,13R,14S,15S,17S)-1,8-difluoro-17-hydroxy-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 pentanoate
• IUPAC Traditional name: diflucortolone valerate
• Synonyms: (6α,11β,16α)-6,9-Difluoro-11-hydroxy-16-methyl-21-[(1-oxopentyl)oxy]pregna-1,4-diene-3,20-dione; Diflucortolone Valerate; Neriforte; Nerisona; Nerisone; Nerisone Forte; Temetex; Texmeten; Travazol; Diflucortolone 21-Valerate

Database IDs

• CAS Number: 59198-70-8
• PubChem SID: 162261523
• PubChem CID: 91670

CALCULATED PROPERTIES

• Acid pKa: 13.561301
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 4.0421205
• LogD (pH = 7.4): 4.04212
• Log P: 4.0421205
• Molar Refractivity: 123.9737 cm^3
• Polarizability: 48.062042 Å^3
• Polar Surface Area: 80.67 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D445620

The 9α-fluoro derivative of Fluocortolone (F500500). Anti-inflammmatory.

REFERENCES

• Kieslich, et al.: Arzneim.-Forsch., 26, 1462 (1976)