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Name	Flumethasone	EINECS	218-370-9
CAS No.	2135-17-3	Density	1.36 g/cm³
PSA	94.83000	LogP	1.84370
Solubility	1mg/L(20 oC)	Melting Point	237-240oC
Formula	C₂₂H₂₈F₂O₅	Boiling Point	569.8 °C at 760 mmHg
Molecular Weight	410.458	Flash Point	298.4 °C
Transport Information	N/A	Appearance	White crystalline powder
Safety	22-36	Risk Codes	40
Molecular Structure		Hazard Symbols	Xn
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;

Flumethasone Synthetic route

: C24H30F2O5

: 2135-17-3
flumetasone

Conditions

Conditions	Yield
With monoperoxyphthalic acid In dichloromethane; ethyl acetate at 27℃;	93%

: 2002-29-1
flumethasone pivalate

: 2135-17-3
flumetasone

Conditions

Conditions	Yield
With Curvularia lunata In water at 30℃; for 72h; Yield given;

: 4,6 alpha,9 alpha-trifluoro-11 beta,17 alpha-dihydroxy-16 alpha-methyl-3-oxoandrosta-1,4-diene

A: 4,6 alpha,9 alpha-trifluoro-11 beta-hydroxy-16 alpha-methyl-3-oxo-17 alpha-propionyloxyandrosta-1,4-diene

B: 2135-17-3
flumetasone

Conditions

Conditions	Yield
With pyridine In propionic acid anhydride

Conditions

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

epoxyparamethasone: epoxyparamethasone

: 2135-17-3
flumetasone

Conditions

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

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

: flumethasone 2-(tritylmercapto)acetate

Conditions

Conditions	Yield
With dmap In dichloromethane at 20℃;	98%

: 2135-17-3
flumetasone

: C22H27BrF2O4

Conditions

Conditions	Yield
With pyridine; N-Bromosuccinimide; sulfur dioxide at 20℃; for 1h;	97.3%

: 2135-17-3
flumetasone

: 2607-06-9
6α,9-difluoro-11β,21-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione

Conditions

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

Conditions	Yield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide; toluene at 20℃; for 2h;	90%

Flumethasone 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: Harmful 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.

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