2-[(1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-6,6,9,13-tetramethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-8-yl]-2-oxoethyl cyclopropanecarboxylate

• ChemBase ID: 164778
• Molecular Formular: C28H34F2O7
• Molecular Mass: 520.5621664
• Monoisotopic Mass: 520.22725987
• 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]1[C@]2(OC(O1)(C)C)C(=O)COC(=O)C1CC1)C)O)F)F)C
• Canonical SMILES: O=C1C=C[C@]2(C(=C1)[C@@H](F)C[C@@H]1[C@]2(F)[C@@H](O)C[C@]2([C@H]1C[C@@H]1[C@]2(OC(O1)(C)C)C(=O)COC(=O)C1CC1)C)C
• InChI: InChI=1S/C28H34F2O7/c1-24(2)36-22-11-16-17-10-19(29)18-9-15(31)7-8-25(18,3)27(17,30)20(32)12-26(16,4)28(22,37-24)21(33)13-35-23(34)14-5-6-14/h7-9,14,16-17,19-20,22,32H,5-6,10-13H2,1-4H3/t16-,17-,19-,20-,22+,25-,26-,27-,28+/m0/s1
• InChIKey: TZBDXWBBMOEVPI-XBQQDWOSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-6,6,9,13-tetramethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-14,17-dien-8-yl]-2-oxoethyl cyclopropanecarboxylate
• IUPAC Traditional name: ciprocinonide
• Synonyms: (6α,11β,16α)-21-[(Cyclopropylcarbonyl)oxy]-6,9-difluoro-11-hydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione; RS 2386; Fluocinolone Acetonide 21-Cyclopropylcarboxylate; Ciprocinonide

Database IDs

• CAS Number: 58524-83-7
• PubChem SID: 162258913
• PubChem CID: 11954352

CALCULATED PROPERTIES

• Acid pKa: 13.551555
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 2.8253202
• LogD (pH = 7.4): 2.82532
• Log P: 2.8253202
• Molar Refractivity: 127.9639 cm^3
• Polarizability: 49.950184 Å^3
• Polar Surface Area: 99.13 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C482450

A corticosteroid with anti-inflammatory activity.

REFERENCES

• Shek, E. et al.: Int. J. Pharmac., 11, 257 (1982)