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Fluticasone propionate
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  • Name Fluticasone propionate
  • EINECS617-082-4
  • CAS No. 80474-14-2
  • Density1.32 g/cm3
  • PSA105.97000
  • LogP4.43000
  • SolubilityDMSO: ≥10 mg/mL
  • Melting Point275 °C
  • FormulaC25H31F3O5S
  • Boiling Point568.3 °C at 760 mmHg
  • Molecular Weight500.579
  • Flash Point297.5 °C
  • Transport InformationN/A
  • AppearanceCrystalline solid
  • Safety22-24/25
  • Risk CodesN/A
  • Molecular Structure
    Molecular Structure of 80474-14-2 (Fluticasone propionate)
  • Hazard SymbolsN/A
  • SynonymsN/A
  • Article Data22

Fluticasone propionate Synthetic route

709002-83-5

S-hydroxymethyl 6α,9α-difluoro-16α-methyl-3-oxo-11β-hydroxy-17α-propionyloxyandrosta-1,4-diene-17β-carbothioate

80474-14-2

flixotide

Conditions
ConditionsYield
With diethylamino-sulfur trifluoride In tetrahydrofuran at -20℃; for 0.333333h;68%
With (bis-(2-methoxyethyl)amino)sulfur trufluoride In dichloromethane at -60℃; for 0.166667h;35%

6α,9α-difluoro-11β-hydroxy-17α-propionyloxy-16α-methylpregna-3-oxo-1,4-diene-17β-thiocarboxylic acid diisopropylethylamine salt

593-70-4

R32

80474-14-2

flixotide

Conditions
ConditionsYield
In acetonitrile at 5 - 50℃; under 975.098 Torr; for 22.5h;60%
In acetonitrile at 5 - 50℃; under 760.051 - 975.098 Torr; for 22.5h;60%
373-52-4

bromofluoromethane

80474-45-9

17-propionate carbothioic acid

80474-14-2

flixotide

Conditions
ConditionsYield
With potassium hydrogencarbonate In N,N-dimethyl-formamide at -10 - 20℃; for 2h;91.7%
With potassium carbonate In acetone at -5 - 0℃; for 2 - 5h; Product distribution / selectivity;84.51%
Stage #1: 17-propionate carbothioic acid With potassium carbonate In acetone at 20℃; for 0.5h;
Stage #2: bromofluoromethane In acetone at 0 - 5℃;		80%
80474-67-5

S-iodomethyl-6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-oxo-androsta-1,4-diene-17β-carbothioate

80474-14-2

flixotide

Conditions
ConditionsYield
With calcium fluoride; silver fluoride In acetonitrile at -15 - -10℃; for 48h;75%
With silver fluoride In acetonitrile for 4h; Ambient temperature;74%
With calcium fluoride; silver fluoride In acetonitrile at -15 - -10℃; for 48h; Product distribution / selectivity;60%
With silver fluoride In acetonitrile at 0 - 5℃; for 75h; Product distribution / selectivity;40%
Multi-step reaction with 2 steps
1: 74.2 percent / acetonitrile / 1.17 h / 20 °C
2: 43 percent Spectr. / KF, KI, aminopolyether 2.2.2 / acetonitrile / 0.58 h / 100 °C / 1050.08 Torr
View Scheme
373-53-5

fluoroiodomethane

80474-45-9

17-propionate carbothioic acid

80474-14-2

flixotide

Conditions
ConditionsYield
With caesium carbonate In acetonitrile at 20℃; for 6h; chemoselective reaction;82%
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 22 - 25℃; for 0.25h;67.1%
With potassium carbonate; sodium hydrogensulfite In acetone at -10℃;
1414857-56-9

C27H30F6O6S

80474-14-2

flixotide

Conditions
ConditionsYield
With methanol; ammonia at 0℃; for 0.0833333h;
With ammonia In methanol at 0℃; for 0.0833333h;0.041 g
192191-49-4

S-fluoromethyl 6α-fluoro-9β,11β-epoxy-16α-methyl-17α-propionyloxy-3-oxoandrosta-1,4-diene-17β-carbothioate

80474-14-2

flixotide

Conditions
ConditionsYield
With hydrogen fluoride In water at -20℃; for 7h;

6α,9α-difluoro-11β-hydroxy-17α-propionyloxy-16α-methyl-pregna-3-oxo-1,4-diene-17β-thiocarboxylic acid triethylamine salt

593-70-4

R32

80474-14-2

flixotide

Conditions
ConditionsYield
In acetonitrile at 5 - 50℃; under 975.098 Torr; for 22.5h;

6α,9α-difluoro-11β-hydroxy-17α-propionyloxy-16α-methyl-pregna-3-oxo-1,4-diene-17β-thiocarboxylic acid N-methylpiperidine salt

593-70-4

R32

80474-14-2

flixotide

Conditions
ConditionsYield
In acetonitrile at 5 - 50℃; under 975.098 Torr; for 22.5h;

diethylammonium 6α,9α-difluoro-16α-methyl-3-oxo-11β-hydroxy;-17α-propionyloxyandrosta-1,4-diene-17β-thiocarboxylate

593-70-4

R32

80474-14-2

flixotide

Conditions
ConditionsYield
In acetonitrile at 5 - 50℃; under 975.098 Torr; for 22.5h;

Fluticasone propionate Specification

1. Introduction of Fluticasone propionate

Fluticasone propionate, with the IUPAC Name of [(6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-Difluoro-17-(fluoromethylsulfanylcarbonyl)-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate, is one kind of white crystalline powder. And this chemical belongs to the Product Categories which include Biochemistry; Hydroxyketosteroids; Steroids; Intermediates & Fine Chemicals; Pharmaceuticals; Fluticasone. What's more, Fluticasone propionate is used as antiallergic and anti inflammatory.

2. Properties of Fluticasone propionate

Fluticasone propionate has the following property datas: (1)Index of Refraction: 1.555; (2)Molar Refractivity: 121.14 cm3; (3)Molar Volume: 377 cm3; (4)Index of Refraction: 1.555; (5)Surface Tension: 48 dyne/cm; (6)Density: 1.32 g/cm3; (7)Flash Point: 297.5 °C; (8)Melting Point: 275 °C; (9)Enthalpy of Vaporization: 97.97 kJ/mol; (10)Boiling Point: 568.3 °C at 760 mmHg; (11)Vapour Pressure: 2.79E-15 mmHg at 25°C; (12)Solubility: DMSO: ≥10 mg/mL.

3. Structure Descriptors of Fluticasone propionate

You could convert the following datas into the molecular structure:
(1).SMILES: O=C(SCF)[C@]3(OC(=O)CC)[C@]2(C[C@H](O)[C@]4(F)[C@@]/1(\C(=C/C(=O)\C=C\1)[C@@H](F)CC4[C@@H]2C[C@H]3C)C)C
(2).InChI: InChI=1/C25H31F3O5S/c1-5-20(31)33-25(21(32)34-12-26)13(2)8-15-16-10-18(27)17-9-14(29)6-7-22(17,3)24(16,28)19(30)11-23(15,25)4/h6-7,9,13,15-16,18-19,30H,5,8,10-12H2,1-4H3/t13-,15+,16?,18+,19+,22+,23+,24+,25+/m1/s1
(3).InChIKey: WMWTYOKRWGGJOA-ZHLGSTKJBY
(4).Std. InChI: InChI=1S/C25H31F3O5S/c1-5-20(31)33-25(21(32)34-12-26)13(2)8-15-16-10-18(27)17-9-14(29)6-7-22(17,3)24(16,28)19(30)11-23(15,25)4/h6-7,9,13,15-16,18-19,30H,5,8,10-12H2,1-4H3/t13-,15+,16?,18+,19+,22+,23+,24+,25+/m1/s1
(5).Std. InChIKey: WMWTYOKRWGGJOA-ZHLGSTKJSA-N

4. Toxicity of Fluticasone propionate

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LC inhalation > 40770ug/m3/1 (40.77mg/m3) CARDIAC: CHANGES IN HEART WEIGHT Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 20, Pg. 1501, 1992.
rat LD50 oral > 2gm/kg (2000mg/kg)   Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 20, Pg. 1493, 1992.
rat LD50 subcutaneous > 1gm/kg (1000mg/kg) ENDOCRINE: OTHER CHANGES

BLOOD: "CHANGES IN SERUM COMPOSITION (E.G., TP, BILIRUBIN, CHOLESTEROL)"		 Yakuri to Chiryo. Pharmacology and Therapeutics. Vol.

5. Safety Information of Fluticasone propionate

Safety Statements: 22-24/25
S22: Do not breathe dust. 
S24/25: Avoid contact with skin and eyes.
WGK Germany: 2
RTECS: BV7980000

6. Preparation of Fluticasone propionate

Compounds (Ⅰ) first react with N, N-Dimethyl formamide thio chloride, and then hydrolysis ,obtaining thio-carboxylic acid (Ⅱ), and then, esterification with Bromo - fluoro-methane,  Fluticasone propionate is derived.

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