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

• ChemBase ID: 169060
• Molecular Formular: C26H35FO5
• Molecular Mass: 446.5515032
• Monoisotopic Mass: 446.24685244
• SMILES: C1=C[C@]2(C(=CC1=O)[C@H](C[C@@H]1[C@@H]2[C@H](C[C@]2([C@H]1C[C@H]([C@@H]2C(=O)C(=O)OCCCC)C)C)O)F)C
• Canonical SMILES: CCCCOC(=O)C(=O)[C@H]1[C@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2C[C@@H](C2=CC(=O)C=C[C@]12C)F
• InChI: InChI=1S/C26H35FO5/c1-5-6-9-32-24(31)23(30)21-14(2)10-17-16-12-19(27)18-11-15(28)7-8-25(18,3)22(16)20(29)13-26(17,21)4/h7-8,11,14,16-17,19-22,29H,5-6,9-10,12-13H2,1-4H3/t14-,16+,17+,19+,20+,21-,22-,25+,26+/m1/s1
• InChIKey: XWTIDFOGTCVGQB-FHIVUSPVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: butyl 2-[(1S,2R,8S,10S,11S,13R,14S,15S,17S)-8-fluoro-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-oxoacetate
• IUPAC Traditional name: fluocortin butyl
• Synonyms: (6α,11β,16α)-6-Fluoro-11-hydroxy-16-methyl-3,20-dioxopregna-1,4-dien-21-oic Acid Butyl Ester; Fluocortin butyl; SH K 203; Varlane; Vaspit; Butyl 6α-Fluoro-11β-hydroxy-16α-methyl-3,20-dioxopregna-1,4-dien-21-oate; Butyl 6α-Fluoro-11β-hydroxy-3,20-dioxo-16α-methyl-1,4-pregnadien-21-oate; Fluocortin Butyl Ester

Database IDs

• CAS Number: 41767-29-7
• PubChem SID: 162263192
• PubChem CID: 15942715

CALCULATED PROPERTIES

• Acid pKa: 15.161767
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 4.4476852
• LogD (pH = 7.4): 4.4476833
• Log P: 4.4476833
• Molar Refractivity: 120.2007 cm^3
• Polarizability: 46.475674 Å^3
• Polar Surface Area: 80.67 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F500495

A glucocorticoid with antiinflammatory activity with little or no side effects.

REFERENCES

• Heite, H.J. et al.: Arzneim.-Forsch., 27, 2234 (1977)
• Andersson, K.V. et al.: Svensk Farm. Tids., 80, 256 (1977)
• Kapp, J.F. et al.: ARzneim.-Forsch., 27, 2191 (1977)