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Fluticasone Propionate

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Identification
Molecular formula
C25H31F3O5S
CAS number
80474-14-2
IUPAC name
disodium;[2-[(1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-6,6,9,13-tetramethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-8-yl]-2-oxo-ethyl] phosphate
State
State

Solid

At room temperature, fluticasone propionate exists in a solid state as a crystalline powder.

Melting point (Celsius)
273.00
Melting point (Kelvin)
546.15
Boiling point (Celsius)
310.00
Boiling point (Kelvin)
583.15
General information
Molecular weight
500.57g/mol
Molar mass
500.5700g/mol
Density
1.4000g/cm3
Appearence

Fluticasone propionate appears as a white to off-white powder. It is practically insoluble in water but is soluble in dimethyl sulfoxide and dimethylformamide. The compound is frequently formulated as a fine, micronic powder for use in inhalers.

Comment on solubility

Solubility of Disodium [2-[(1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-6,6,9,13-tetramethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-8-yl]-2-oxo-ethyl] phosphate

The solubility of disodium [2-[(1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-6,6,9,13-tetramethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-8-yl]-2-oxo-ethyl] phosphate can be examined through various factors:

  • Presence of Sodium Ions: The affinity of sodium ions for water can enhance solubility, particularly for phosphate compounds.
  • Complex Molecular Structure: The intricate structure involving multiple cyclic components may hinder solubility in aqueous solutions.
  • Solvent Interaction: Compatibility with polar solvents will influence the extent of solubility.

In general, phosphate esters, such as this compound, can exhibit variable solubility based on their specific structural configurations. They often demonstrate better solubility in:

  • Aqueous buffers
  • Organic solvents

Moreover, it is essential to note that specific conditions like pH and temperature can impact the solubility profile significantly. As with most compounds, solubility must be evaluated on a case-by-case basis, keeping in mind the surrounding chemical environment and interactions.

Interesting facts

Interesting Facts about Disodium Salt of the Compound

The disodium salt of this complex compound is a fascinating example of a phosphoric acid derivative, with various intriguing features and applications in the field of chemistry. Here are some key aspects to consider:

  • Structural Complexity: This compound boasts a unique pentacyclic structure that presents significant challenges and opportunities for synthesis and analysis. The intricate arrangement of rings and functional groups makes it a subject of interest for organic chemists.
  • Biological Relevance: Compounds with similar structures have been investigated for potential pharmaceutical applications. The presence of a fluorine atom and hydroxy group may influence its interaction with biological systems.
  • Phosphate Group: The inclusion of a phosphate moiety is significant, as these groups are essential in various biochemical processes, including energy transfer through adenosine triphosphate (ATP) in cellular metabolism.
  • Stereochemistry: The specification of stereochemistry (1S, 2S, 4R, 8S, 9S, 11S, 12R, 13S) indicates that this compound can exhibit different physical and chemical properties based on its 3D arrangement. This is crucial in understanding its biological activity and reaction mechanisms.

As chemists continue to explore the applications of such compounds, understanding their detailed characteristics can lead to advancements in synthetic chemistry and potential medicinal uses. Overall, this compound exemplifies the beauty of molecular design in chemistry.

Synonyms
TRIAMCINOLONE ACETONIDE SODIUM PHOSPHATE
1997-15-5
Aristosol
CL 61965
CL 106359
UNII-R2MZ7K74S8
CL-1965
R2MZ7K74S8
EINECS 217-878-8
Triamcinolone acetonide sodium Phosphate [USAN]
CL-61965
CL-106359
SODIUM PHOSPHATE TRIAMCINOLONE ACETONIDE
Triamcinolone acetonide sodium phosphate (USAN)
Pregna-1,4-diene-3,20-dione, 9-fluoro-11-hydroxy-16,17-[(1-methylethylidene)bis(oxy)]-21-(phosphonooxy)-, disodium salt, (11beta,16alpha)-
Pregna-1,4-diene-3,20-dione, 9-fluoro-11.beta.,16.alpha.,17,21-tetrahydroxy-, cyclic 16,17-acetal with acetone, 21-(dihydrogen phosphate), disodium salt
Triamcinolone acetonide 21-disodium phosphate
TRIAMCINOLONE ACETONIDE SODIUM PHOSPHATE [WHO-DD]
TRIAMCINOLONE ACETONIDE 21-DISODIUM PHOSPHATE [MI]
9-FLUORO-11.BETA.,16.ALPHA.,17,21-TETRAHYDROXYPREGNA-1,4-DIENE-3,20-DIONE CYCLIC 16,17-ACETAL WITH ACETONE 21-(DISODIUM PHOSPHATE)
9.ALPHA.-FLUORO-11.BETA.,21-DIHYDROXY-16.ALPHA.,17.ALPHA.-(ISOPROPYLIDENEDIOXY)-1,4-PREGNADIENE-3,20-DIONE 21-(DISODIUM PHOSPHATE)
9.ALPHA.-FLUORO-16.ALPHA.-HYDROXYPREDNISOLONE 16.ALPHA.,17.ALPHA.-ACETONIDE 21-DISODIUM PHOSPHATE
PREGNA-1,4-DIENE-3,20-DIONE, 9-FLUORO-11-HYDROXY-16,17-((1-METHYLETHYLIDENE)BIS(OXY))-21-(PHOSPHONOOXY)-, DISODIUM SALT, (11.BETA.,16.ALPHA.)-
Pregna-1,4-diene-3,20-dione, 9-fluoro-11-hydroxy-16,17-((1-methylethylidene)bis(oxy))-21-(phosphonooxy)-, disodium salt, (11beta,16alpha)-
217-878-8
9-FLUORO-11BETA,16ALPHA,17,21-TETRAHYDROXYPREGNA-1,4-DIENE-3,20-DIONE CYCLIC 16,17-ACETAL WITH ACETONE 21-(DISODIUM PHOSPHATE)
9ALPHA-FLUORO-11BETA,21-DIHYDROXY-16ALPHA,17ALPHA-(ISOPROPYLIDENEDIOXY)-1,4-PREGNADIENE-3,20-DIONE 21-(DISODIUM PHOSPHATE)
9ALPHA-FLUORO-16ALPHA-HYDROXYPREDNISOLONE 16ALPHA,17ALPHA-ACETONIDE 21-DISODIUM PHOSPHATE
PREGNA-1,4-DIENE-3,20-DIONE, 9-FLUORO-11BETA,16ALPHA,17,21-TETRAHYDROXY-, CYCLIC 16,17-ACETAL WITH ACETONE, 21-(DIHYDROGEN PHOSPHATE), DISODIUM SALT
disodium;[2-[(1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-6,6,9,13-tetramethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-8-yl]-2-oxoethyl] phosphate
CHEMBL3989672
DTXSID30941876
9-Fluoro-11beta,16alpha,17,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with acetone 21-(dihydrogen phosphate) disodium salt
D06216
Q27287706
Disodium 2-(4b-fluoro-5-hydroxy-4a,6a,8,8-tetramethyl-2-oxo-2,4a,4b,5,6,6a,9a,10,10a,10b,11,12-dodecahydro-6bH,8H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-6b-yl)-2-oxoethyl phosphate
PREGNA-1,4-DIENE-3,20-DIONE, 9-FLUORO-11-HYDROXY-16,17-((1-METHYLETHYLIDENE)BIS(OXY))-21-(PHOSPHONOOXY)-, SODIUM SALT (1:2), (11.BETA.,16.ALPHA.)-