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

• ChemBase ID: 134258
• Molecular Formular: C22H28F2O5
• Molecular Mass: 410.4515264
• Monoisotopic Mass: 410.19048044
• SMILES: C[C@@H]1C[C@H]2[C@@H]3C[C@@H](C4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@]1(C(=O)CO)O)C)O)F)C)F
• 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+/m1/s1
• InChIKey: WXURHACBFYSXBI-GQKYHHCASA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 2135-17-3
• EC Number: 218-370-9
• MDL Number: MFCD00056464
• PubChem SID: 162228535; 24894998
• PubChem CID: 16490

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: White Solid
• Melting Point: 237-240°C

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: TU3832000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 40
• Safety Statements: 22-36
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H351
• GHS Precautionary statements: P281
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: 2-8°C

DETAILS

Sigma Aldrich - F9507

Application
Flumethasone pivalate is a topical corticosteroid. Prompt decrease in inflammation, exudation and itching is experienced after application. It is a difluorinated corticosteroid ester with anti-inflammatory, antipruritic and vasoconstrictive properties. Flumethasone is a corticosteroid commonly used in veterinary practice1 and has been used in cortisol assays to study early porcine conceptus development2.
Biochem/physiol Actions
Flumethasone is a glucocorticoid receptor agonist used in studies on plasma transcortin binding.
Flumethasone is a glucocorticoid receptor agonist. It binds to the nucleus causing a variety of genetic activation and repressions. The anti-inflammatory actions of flumethasone is thought to involve lipocortins and phospholipase A2 inhibitory proteins, which results in the inhibition of arachidonic acid and the control of prostaglandin and leukotriene biosynthesis. Flumethasone suppresses the immune system due to a decrease in the function of the lymphatic system, a reduction in immunoglobulin and complement concentrations, the precipitation of lymphocytopenia, and interference with antigen-antibody binding .

Toronto Research Chemicals - 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)