(1R,2S,8S,10S,11S,13S,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-13-(2H3)methyl-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one

• ChemBase ID: 169035
• Molecular Formular: C22H28F2O5
• Molecular Mass: 410.4515264
• Monoisotopic Mass: 410.19048044
• 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)CO)O)C)C)O)F)F)C
• Canonical SMILES: 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/C22H28F2O5/c1-11-6-13-14-8-16(23)15-7-12(26)4-5-19(15,2)21(14,24)17(27)9-20(13,3)22(11,29)18(28)10-25/h4-5,7,11,13-14,16-17,25,27,29H,6,8-10H2,1-3H3/t11-,13-,14-,16-,17-,19-,20-,21-,22-/m0/s1
• InChIKey: WXURHACBFYSXBI-XHIJKXOTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,8S,10S,11S,13S,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-13-(^2H₃)methyl-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• IUPAC Traditional name: (1R,2S,8S,10S,11S,13S,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-13-(^2H₃)methyl-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• Synonyms: (6α,11β,16α)-6,9-Difluoro-11,17,21-trihydroxy-16-(methyl-d3)pregna-1,4-diene-3,20-dione; 6α,9α-Difluoro-16α-(methyl-d3)prednisolone; 6α-Fluorodexamethasone-d3; 6α-Fluorodexamethazone-d3; Anaprime-d3; Aniprime-d3; Aniprome-d3; Cortexillar-d3; Flucort-d3; Flucorticin-d3; Flumetasone-d3; Flumethason-d3; Fluvet-d3; Methagon-d3; NSC 5402-d3; NSC 54702-d3; RS 2177-d3; U 10974-d3; Vecort; Flumethasone-d3

Database IDs

• PubChem SID: 162263167
• PubChem CID: 71316783

CALCULATED PROPERTIES

• Acid pKa: 12.418192
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.3418503
• LogD (pH = 7.4): 1.3418462
• Log P: 1.3418504
• Molar Refractivity: 102.3163 cm^3
• Polarizability: 39.40079 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 231-234°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - F455002

Labelled Flumethasone (F455000). A glucocorticoid. An anti-inflammatory.

REFERENCES

• Matuszewski, B, et al.: Anal. Chem., 75, 3019 (2003)
• Fekete, S., et al.: J. Pharm. Biomed. Anal., 49, 64 (2003)