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| CAS No.: | 2135-17-3 |
|---|---|
| Name: | Flumethasone |
| Molecular Structure: | |
|
|
|
| Formula: | C22H28F2O5 |
| Molecular Weight: | 410.458 |
| Synonyms: | U-10,974;Anaprime;Prestwick_229;Pregna-1,4-diene-3,20-dione, 6.alpha.,9-difluoro-11.beta.,17,21-trihydroxy-16.alpha.-methyl-;Flucorticin;6alpha,9alpha-Difluoro-16alpha-methylprednisolone;U-10974;Fluvet;Cortexillar;RS 2177;Flumethason;Flucort (Veterinary);6alpha-Fluorodexamethasone;Testosterone Undecanoate; |
| EINECS: | 218-370-9 |
| Density: | 1.36 g/cm3 |
| Melting Point: | 237-240oC |
| Boiling Point: | 569.8 °C at 760 mmHg |
| Flash Point: | 298.4 °C |
| Solubility: | 1mg/L(20 oC) |
| Appearance: | White crystalline powder |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 40 |
| Safety: | 22-36 |
| PSA: | 94.83000 |
| LogP: | 1.84370 |
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- 2135-17-3
flumetasone
| Conditions | Yield |
|---|---|
| With monoperoxyphthalic acid In dichloromethane; ethyl acetate at 27℃; | 93% |
| Conditions | Yield |
|---|---|
| With Curvularia lunata In water at 30℃; for 72h; Yield given; |
B
- 2135-17-3
flumetasone
| Conditions | Yield |
|---|---|
| With pyridine In propionic acid anhydride |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: potassium carbonate; water / methanol / 10 h 2: hydrogen fluoride / 5 h / -15 - -10 °C View Scheme |
- 2135-17-3
flumetasone
| Conditions | Yield |
|---|---|
| With hydrogen fluoride at -15 - -10℃; for 5h; |
- 2135-17-3
flumetasone
- 28416-82-2
6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid
| Conditions | Yield |
|---|---|
| With water; periodic acid In tetrahydrofuran at 20℃; for 1h; | 100% |
| With periodic acid In tetrahydrofuran; water at 0 - 20℃; for 2h; | 99.12% |
| With periodic acid In tetrahydrofuran; water at 0 - 20℃; for 5.75h; | 98% |
- 34914-36-8
2-(triphenylmethylthio)ethanoic acid
- 2135-17-3
flumetasone
| Conditions | Yield |
|---|---|
| With dmap In dichloromethane at 20℃; | 98% |
- 2135-17-3
flumetasone
| Conditions | Yield |
|---|---|
| With pyridine; N-Bromosuccinimide; sulfur dioxide at 20℃; for 1h; | 97.3% |
| Conditions | Yield |
|---|---|
| With trimethylsilyl iodide In acetonitrile at -20℃; for 2h; Inert atmosphere; | 93% |
- 2135-17-3
flumetasone
- 115-80-0
Triethyl orthopropionate
- 22593-09-5
6α,9α-difluoro-11β,17,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dione cyclic 17,21-(ethyl orthopropionate)
| Conditions | Yield |
|---|---|
| With toluene-4-sulfonic acid In N,N-dimethyl-formamide; toluene at 20℃; for 2h; | 90% |
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Specification
1. Introduction of Flumethasone
Flumethasone is an odorless, white to creamy white, crystalline powder. The IUPAC name is (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one.
2. Properties of Flumethasone
H bond acceptors: 5
H bond donors: 3
Freely Rotating Bonds: 5
Polar Surface Area: 61.83 Å2
Index of Refraction: 1.579
Molar Refractivity: 100.33 cm3
Molar Volume: 301.7 cm3
Surface Tension: 54.3 dyne/cm
Density: 1.36 g/cm3
Flash Point: 298.4 °C
Enthalpy of Vaporization: 98.19 kJ/mol
Boiling Point: 569.8 °C at 760 mmHg
Vapour Pressure: 2.33E-15 mmHg at 25°C
Storage temp.: 2-8°C
3. Structure Descriptors of Flumethasone
SMILES: O=C(CO)[C@]3(O)[C@]2(C[C@H](O)[C@]4(F)[C@@]/1(\C(=C/C(=O)\C=C\1)[C@@H](F)C[C@H]4[C@@H]2C[C@H]3C)C)C
InChI: InChI=1/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 Copy
InChIKey: WXURHACBFYSXBI-GQKYHHCABT
Std. 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
Std. InChIKey: WXURHACBFYSXBI-GQKYHHCASA-N
4. Safety Information of Flumethasone
Hazard Codes: 
Xn
Risk Statements: 40
40: Limited evidence of a carcinogenic effect
Safety Statements: 22-36
22: Do not breathe dust
36: Wear suitable protective clothing
WGK Germany: 3
RTECS: TU3832000
Experimental reproductive effects. When heated to decomposition it emits toxic fumes of F−.
5. Use of Flumethasone
Flumethasone is a glucocorticoid. It is an anti-inflammatory and a corticosteroid for topical use. Besides, flumethasone is also used for the treatment of otitis externa and otomycosis.