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Fluticasone

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Identification
Molecular formula
C22H27F1O8
CAS number
80474-14-2
IUPAC name
(6S,8S,9S,10R,11S,13S,14S,17R)-6-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one
State
State

At room temperature, Fluticasone is usually in a solid state. It is stable under normal conditions, but characteristics might vary slightly with different formulations such as propionate or furoate used in medical aerosols and ointments.

Melting point (Celsius)
273.40
Melting point (Kelvin)
546.60
Boiling point (Celsius)
398.60
Boiling point (Kelvin)
671.80
General information
Molecular weight
444.52g/mol
Molar mass
444.5180g/mol
Density
1.4900g/cm3
Appearence

Fluticasone is a white to off-white solid crystalline powder. It appears opaque or translucent and can have a waxy texture. The substance is typically used in pharmaceuticals and may vary slightly in form depending on the specific formulation or salt type.

Comment on solubility

Solubility of (6S,8S,9S,10R,11S,13S,14S,17R)-6-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one (C22H27F1O8)

The solubility of this complex organic compound is influenced by several factors due to its intricate structure, which comprises multiple functional groups. Here are some important considerations:

  • Polarity: The presence of hydroxyl (-OH) groups adds polarity to the molecule, likely enhancing its solubility in polar solvents such as water.
  • Hydrogen Bonding: The hydroxyl groups enable hydrogen bonding, which can significantly increase solubility in solvents that can engage in such interactions.
  • Hydrophobic Character: The cyclic structure and the presence of a fluorine atom may contribute to hydrophobic characteristics, potentially lowering solubility in highly polar environments.
  • Solvent Type: Selective solubility is expected; hence, it may dissolve better in organic solvents such as ethanol or acetone compared to water.

As quoted, "Like dissolves like," meaning that the solubility largely depends on the solvent's chemical nature. Thus, this compound's unique composition will require specific conditions to facilitate its full solubility.

In summary, while the compound displays potential solubility due to its polar functional groups, the overall solubility characteristics will vary depending on the chosen solvent and the environmental factors in play.

Interesting facts

Interesting Facts About (6S,8S,9S,10R,11S,13S,14S,17R)-6-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one

This compound is an intriguing member of the class of steroids, particularly notable for its complex structure and biological implications. Here are some engaging insights about this fascinating chemical:

  • Fluorinated Compounds: The presence of a fluorine atom introduces unique properties, such as increased stability and altered biological activity. Fluorination often enhances pharmacological profiles, making compounds more effective as therapeutic agents.
  • Hydroxyl Groups: The dual hydroxyl (-OH) groups contribute to the compound's polarity and potential hydrogen bonding capabilities. This functionality can influence solubility and reactivity, enabling interactions with biological targets.
  • Structure Complexity: Its intricate cyclopenta[a]phenanthrene core structure exemplifies the chemical elegance found in steroid compounds. The stereochemistry—highlighted by specific chiral centers—suggests that even slight variations can lead to significant changes in biological activity.
  • Potential Biological Activity: Compounds with similar structures are often investigated for their roles as hormones or therapeutic agents. Studies may focus on their impact on cell signaling pathways, particularly regarding inflammation and endocrine functions.
  • Applications in Medicine: Research into such compounds is crucial for drug discovery, especially in developing new treatments for various diseases, including hormonal disorders and cancer.
  • Ecological Aspect: Understanding the environmental behavior of synthetic steroids can also be vital, as they may affect ecosystems, particularly through their breakdown products.

As we delve deeper into the properties and potential applications of this compound, it serves as a reminder of the remarkable interplay between chemistry and biology. Ongoing research could unveil new therapeutic targets, enhancing our capacity to combat diseases effectively.

Synonyms
fluprednisolone
53-34-9
Alphadrol
Etadrol
Isopredon
Vladicort
6alpha-Fluoroprednisolone
Fluprednisolonum
Prednisolone, 6alpha-fluoro-
fluprednisolona
F. I. 6150
HSDB 3335
EINECS 200-170-8
6alpha-Fluoro-1-dehydrohydrocortisone
NSC 47439
NSC-47439
Fluprednisolonum [INN-Latin]
U 7800
U-7800
FI 6150
Pregna-1,4-diene-3,20-dione, 6-fluoro-11,17,21-trihydroxy-, (6alpha,11beta)-
Corticosterone, 1-dehydro-6alpha-fluoro-
DTXSID5046067
UNII-9H05937G3X
6|A-Fluoroprednisolone
9H05937G3X
6alpha-Fluoro-11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione
(6S,8S,9S,10R,11S,13S,14S,17R)-6-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one
DTXCID3026067
CHEBI:34474
6a-Fluprednisolone
6alpha-Fluoro-1,4-pregnadiene-11beta,17alpha,21-triol-3,20-dione
NSC47439
Pregna-1,4-diene-3,20-dione, 6alpha-fluoro-11beta,17,21-trihydroxy-
NCGC00182067-02
B 673
Fluprednisolonum (INN-Latin)
FLUPREDNISOLONE (MART.)
FLUPREDNISOLONE [MART.]
6alpha-Fluprednisolone
6-Fluoroprednisolone
6alpha-Fluoro-11beta,17alpha,21-trihydroxypregna-1,4-diene-3,20-dione
CAS-53-34-9
6.alpha.-Fluoroprednisolone
6-|A-Fluoroprednisolone
6-alpha-Fluoroprednisolone
Prednisolone, 6.alpha.-fluoro-
Pregna-1,4-diene-3,20-dione, 6-fluoro-11,17,21-trihydroxy-, (6.alpha.,11.beta.)-
Alphadrol (TN)
NCGC00159474-02
Fluprednisolone [USAN:INN:BAN:NF]
Corticosterone, 1-dehydro-6.alpha.-fluoro-
FLUPREDNISOLONE [MI]
Fluprednisolone (USAN/INN)
SCHEMBL24232
6- alpha -Fluoroprednisolone
FLUPREDNISOLONE [INN]
FLUPREDNISOLONE [HSDB]
FLUPREDNISOLONE [USAN]
CHEMBL1200774
FLUPREDNISOLONE [WHO-DD]
6-alpha-Fluoroprednisolone 100 microg/mL in Acetonitrile
MYYIMZRZXIQBGI-HVIRSNARSA-N
Tox21_111698
Tox21_113143
FLUPREDNISOLONE [ORANGE BOOK]
AKOS040759634
Tox21_111698_1
DB09378
FF36696
NCGC00159474-03
DA-73407
TS-09934
HY-107935
CS-0030934
D04227
EN300-19651649
Q732234
6-alpha-Fluoroprednisolone, VETRANAL(TM), analytical standard
Pregna-1,20-dione, 6.alpha.-fluoro-11.beta.,17,21-trihydroxy-
6.alpha.-Fluoro-11.beta.,21-trihydroxypregna-1,4-diene-3,20-dione
Pregna-1,20-dione, 6-fluoro-11,17,21-trihydroxy-, (6.alpha.,11.beta.)-
(1R,3aS,3bS,5S,9aR,9bS,10S,11aS)-5-fluoro-1,10-dihydroxy-1-(2-hydroxyacetyl)-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one
200-170-8