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Fluocinolone acetonide

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Identification
Molecular formula
C24H30FO6
CAS number
67-73-2
IUPAC name
(6S,8S,9S,10R,11S,13S,14S,16R,17S)-6-fluoro-11-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
State
State

At room temperature, fluocinolone acetonide is in a solid state.

Melting point (Celsius)
265.00
Melting point (Kelvin)
538.00
Boiling point (Celsius)
487.00
Boiling point (Kelvin)
760.00
General information
Molecular weight
452.50g/mol
Molar mass
452.4960g/mol
Density
1.4000g/cm3
Appearence

Fluocinolone acetonide is typically presented as a white to off-white crystalline powder. It is practically insoluble in water but very soluble in acetone and ethanol. The compound has a faint, characteristic odor.

Comment on solubility

Solubility Profile

The solubility of the compound (6S, 8S, 9S, 10R, 11S, 13S, 14S, 16R, 17S)-6-fluoro-11-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one can be complex due to its extensive structural features. Here are some key points to consider regarding its solubility:

  • Polarity: The presence of hydroxy groups often increases the polarity of the molecule, potentially enhancing its solubility in polar solvents like water.
  • Hydrophobic regions: The large hydrophobic portions of the structure, due to multiple methyl groups, may lead to decreased solubility in polar solvents.
  • Interactions: H-bonding ability from the hydroxy groups can promote solubility in certain organic solvents, particularly those that can accept H-bonds.
  • Solvent choice: This compound may show variable solubility in different solvents such as:
    • High solubility in alcohols and ethers
    • Limited solubility in n-hexane and other nonpolar solvents

Overall, the solubility of this compound likely varies significantly with the solvent used, and testing in different environments is critical for determining its practical applications in both laboratory and industrial settings.

Interesting facts

Interesting Facts About (6S,8S,9S,10R,11S,13S,14S,16R,17S)-6-fluoro-11-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one

This compound, characterized by its complex structure and numerous chiral centers, is a fascinating example in the realm of synthetic organic chemistry. Its intricate configuration allows for unique interactions with biological systems, making it of interest in pharmacology and medicinal chemistry.

Key Features:

  • Fluorine Substitution: The presence of a fluoro group can significantly enhance the metabolic stability of the compound, potentially improving its efficacy as a therapeutic agent.
  • Hydroxy and Acetyl Groups: The hydroxy and 2-hydroxyacetyl functionalities could contribute to the compound's solubility and reactivity, which are critical factors for biological activity.
  • Tetrahydrocyclopenta Phenanthrene Core: This unique structural backbone is known for its rigid structure, often leading to high selectivity in biological systems.
  • Chirality: The multiple stereocenters indicate that this compound could have different enantiomers, each potentially exhibiting different biological activities.

In the field of drug design, compounds like this one are meticulously studied for their potential to interact with specific biological targets, providing insights into their mechanism of action. Research efforts continue to explore how modifications to this structure can lead to enhanced therapeutic profiles.

As a summary, the exploration of such complex compounds not only reveals the marvels of organic synthesis but also the vast potential they hold in advancing pharmaceutical sciences. One can often find scientists quoting, "In complexity lies beauty and potential," reflecting the aspirations in the ongoing quest for innovative therapies.

Synonyms
FLUOCORTOLONE
152-97-6
Fluocortolon
Fluorcortolone
Fluocortolona
Fluorocortolone
Ultralan oral
Fluocortolonum
SH 742
Fluocortolonum [INN-Latin]
Fluocortolona [INN-Spanish]
Fluocortolone [USAN:INN:BAN]
EINECS 205-811-5
65VXC1MH0J
BRN 3122594
SH-742
FLUOCORTOLONE [MI]
FLUOCORTOLONE [INN]
FLUOCORTOLONE [JAN]
FLUOCORTOLONE [USAN]
6alpha-Fluoro-11beta,21-dihydroxy-16alpha-methylpregna-1,4-diene-3,20-dione
FLUOCORTOLONE [MART.]
6-alpha-Fluoro-16-alpha-methyl-1-dehydrocorticosterone
FLUOCORTOLONE [WHO-DD]
Pregna-1,4-diene-3,20-dione, 6-fluoro-11,21-dihydroxy-16-methyl-, (6alpha,11beta,16alpha)-
DTXSID00861835
EC 205-811-5
6-alpha-Fluoro-11-beta,21-dihydroxy-16-alpha-methylpregna-1,4-diene-3,20-dione
6-alpha-Fluoro-16-alpha-methylpregna-1,4-diene-11-beta,21-diol-3,20-dione
6-alpha-Fluoro-16-alpha-methyl-delta(sup 1,4)-pregnadiene-11-beta-diol-3,20-dione
(6S,8S,9S,10R,11S,13S,14S,16R,17S)-6-fluoro-11-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
Fluocortolonum (INN-Latin)
Fluocortolona (INN-Spanish)
FLUOCORTOLONE (MART.)
PREGNA-1,4-DIENE-3,20-DIONE, 6-FLUORO-11,21-DIHYDROXY-16-METHYL-, (6.ALPHA.,11.BETA.,16.ALPHA.)-
UNII-65VXC1MH0J
Ultraproct
Ficoid 2-plus
Ficoid 2
6-Fluoro-11-hydroxy-17-(2-hydroxy-acetyl)-10,13,16-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-cyclopenta(a)phenanthren-3-one
6-Fluoro-11-hydroxy-17-(2-hydroxy-acetyl)-10,13,16-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one
Fluocortolone (USAN/INN)
SCHEMBL4644
CHEMBL251634
C05AA08
D07AC05
D07XC05
DTXCID80820884
H02AB03
CHEBI:135581
BCP9000698
DB08971
FF23336
BCP0726000096
HY-142123
CS-0377811
NS00004826
D04218
EN300-19767700
Q5462793
(6alpha,11beta,16alpha)-6-fluoro-11,21-dihydroxy-16-methylpregna-1,4-diene-3,20-dione
16alpha-Methyl-6alpha-fluoro-Delta1,4-pregnadien-11beta,21-diol-3,20-dione
6.ALPHA.-FLUORO-11.BETA.,21-DIHYDROXY-16.ALPHA.-METHYLPREGNA-1,4-DIENE-3,20-DIONE
6alpha-fluoro-11beta,21 -dihydroxy-16alpha-methyl-1,4-pregnadiene-3,20-dione
(1S,2R,3aS,3bS,5S,9aR,9bS,10S,11aS)-5-fluoro-10-hydroxy-1-(2-hydroxyacetyl)-2,9a,11a-trimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one
(6a,11b,16a)-6-Fluoro-11,21-dihydroxy-16-methylpregna-1,4-diene-3 ,20-dione;16a-Methyl-6a-fluoro-d1,4-pregnadien-11b,21-diol-3,20-dione
205-811-5