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Fluocinolone acetonide

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Identification
Molecular formula
C24H30F2O6
CAS number
67-73-2
IUPAC name
(6S,8S,9R,10S,11S,13S,14S,17R)-17-acetyl-9-fluoro-11,17-dihydroxy-6,10,13-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
State
State

At room temperature, fluocinolone acetonide is a solid compound.

Melting point (Celsius)
274.00
Melting point (Kelvin)
547.15
Boiling point (Celsius)
327.15
Boiling point (Kelvin)
600.15
General information
Molecular weight
452.50g/mol
Molar mass
452.4980g/mol
Density
1.2940g/cm3
Appearence

Fluocinolone acetonide typically appears as a white to creamy white crystalline powder. It is poorly soluble in water, readily soluble in acetone, and slightly soluble in chloroform and ethanol.

Comment on solubility

Solubility of (6S,8S,9R,10S,11S,13S,14S,17R)-17-acetyl-9-fluoro-11,17-dihydroxy-6,10,13-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one

The solubility of this complex organic compound is influenced by several factors, including its structural composition and molecular interactions. Understanding the solubility characteristics can greatly aid in its application and formulation in various environments. Here are some key points to consider:

  • Polarity: The presence of multiple hydroxyl (-OH) groups suggests that the compound may exhibit increased solubility in polar solvents. Hydroxyl groups are known to create hydrogen bonds, which enhance interactions with water.
  • Hydrophobic Regions: Despite its polar functional groups, the molecule contains a substantial hydrophobic region due to the bulky hydrocarbon structure. This can reduce solubility in water, leading to a preference for organic solvents.
  • Solvent Effects: The choice of solvent is critical. For instance, it may dissolve better in dimethyl sulfoxide (DMSO) or ethanol compared to water, owing to its complex molecular architecture.
  • Temperature Influence: Solubility can also be temperature-dependent. As temperature increases, solubility in many solvents may improve due to enhanced molecular motion.
  • Chemical Form: The specific polymorphic form of the compound can also determine its solubility; different crystalline forms can exhibit varying degrees of solubility.

In summary, the solubility of this compound is a multifaceted area that requires careful consideration of its structural attributes and environmental conditions. As quoted, "The right solvent can unlock the potential of a compound, while the wrong choice can render it practically useless."

Interesting facts

Exploring the Compound: (6S,8S,9R,10S,11S,13S,14S,17R)-17-acetyl-9-fluoro-11,17-dihydroxy-6,10,13-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one

This compound is a fascinating example of a complex organic molecule with significant biological importance. Below are some interesting facts that highlight its unique characteristics and relevance:

  • Structural Complexity: This compound features a unique octahydrocyclopenta[a]phenanthrene skeleton, which allows for a variety of stereoisomers. The specific configuration of its many chiral centers contributes to its biological activity.
  • Functional Groups: The presence of multiple functional groups, such as ketones (acetyl), alcohols (hydroxyls), and a fluorine atom, enhances its reactivity and influences its interactions with biological systems.
  • Biological Significance: Compounds structured similarly are often researched for their roles in pharmacology, particularly in hormone regulation and potential anti-inflammatory activities.
  • Synthesis Challenges: The synthesis of this compound can be quite challenging due to its intricate stereochemistry and the need for selective reactions to create the desired configuration without unwanted by-products.
  • Research Applications: Due to its unique properties, it may serve as a model compound in medicinal chemistry, offering insights into the design of new therapies and drugs.

As a compound rich with organic functionality and a layered structure, this molecule represents the intricate beauty of chemistry. Its ongoing study not only deepens our understanding of molecular interactions but also opens doors to potential therapeutic applications that could significantly impact healthcare.

Synonyms
fluorometholone
426-13-1
Oxylone
Fluormetholone
Flumetholon
Fluor-Op
Cortilet
Delmeson
Trilcin
Fluoromethalone
FML Liquifilm
Fluorometolona
FML Forte
Fluormetholonum
Fluorometholonum
Fluorometolone
NSC 33001
Fluormetholon
FML
Fluorometholonum [INN-Latin]
Fluorometolona [INN-Spanish]
Fluorometholon
U 8614
CHEBI:31625
component of Neo-Oxylone
9-Fluoro-11beta,17-dihydroxy-6alpha-methylpregna-1,4-diene-3,20-dione
UNII-SV0CSG527L
EINECS 207-041-5
SV0CSG527L
NSC-33001
(6S,8S,9R,10S,11S,13S,14S,17R)-17-acetyl-9-fluoro-11,17-dihydroxy-6,10,13-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
DTXSID7047435
AI3-52813
NSC33001
MFCD00056461
Fluorometholone (Standard)
9-Fluoro-11-beta,17-dihydroxy-6-alpha-methylpregna-1,4-diene-3,20-dione
MLS000069537
MLS001076157
DTXCID5027435
Pregna-1,4-diene-3,20-dione, 9-fluoro-11-beta,17-dihydroxy-6-alpha-methyl-
Fluorometholone [USP:INN:BAN:JAN]
FML-S COMPONENT FLUOROMETHOLONE
Pregna-1,4-diene-3,20-dione, 9-fluoro-11,17-dihydroxy-6-methyl-, (6alpha,11beta)-
SMR000058598
9-Fluoro-11,17-dihydroxy-6-methylpregna-1,4-diene-3,20-dione
Fluorometolone [DCIT]
Neo-Oxylone
11beta,17alpha-Dihydroxy-9-fluoro-6-methyl-1,4-pregnadiene-3,20-dione
Pregna-1,4-diene-3,20-dione, 9-fluoro-11beta,17-dihydroxy-6alpha-methyl-
FML-S Liquifilm
FML S.O.P.
Fluorometholonum (INN-Latin)
Fluorometolona (INN-Spanish)
FLUOROMETHOLONE (MART.)
FLUOROMETHOLONE [MART.]
FLUOROMETHOLONE (USP-RS)
FLUOROMETHOLONE [USP-RS]
Fluorometholone (USP:INN:BAN:JAN)
FLUOROMETHOLONE (USP MONOGRAPH)
FLUOROMETHOLONE [USP MONOGRAPH]
(6alpha,11beta)-9-Fluoro-11,17-dihydroxy-6-methylpregna-1,4-diene-3,20-dione
Pregna-1,4-diene-3,20-dione, 9-fluoro-11,17-dihydroxy-6-methyl-, (6.alpha.,11.beta.)-
Oxylone (TN)
Fluor-op (TN)
Fml (TN)
NCGC00016442-01
(1R,2S,8S,10S,11S,14R,15S,17S)-14-acetyl-1-fluoro-14,17-dihydroxy-2,8,15-trimethyltetracyclo(8.7.0.02,7.011,15)heptadeca-3,6-dien-5-one
(1R,2S,8S,10S,11S,14R,15S,17S)-14-acetyl-1-fluoro-14,17-dihydroxy-2,8,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one
CAS-426-13-1
Prestwick_227
Opera_ID_341
Prestwick0_000718
Prestwick1_000718
Prestwick2_000718
Prestwick3_000718
F0414
Fluorometholone, >=98%
SCHEMBL5051
FLUOROMETHOLONE [MI]
BSPBio_000935
FLUOROMETHOLONE [INN]
FLUOROMETHOLONE [JAN]
SPBio_002856
FLUOROMETHOLONE [VANDF]
BPBio1_001029
GTPL7079
CHEMBL1200600
FLUOROMETHOLONE [WHO-DD]
HY-B1893R
C05AA06
D07AB06
D07XB04
D10AA01
S01BA07
S01CB05
FAOZLTXFLGPHNG-KNAQIMQKSA-N
Pregna-1,4-diene-3,20-dione, 9-fluoro-11.beta.,17-dihydroxy-6.alpha.-methyl-
Fluorometholone (JP17/USP/INN)
GLXC-15335
HMS1570O17
HMS2097O17
HMS2234F16
HMS3714O17
HY-B1893
Tox21_110440
Tox21_302593
BDBM50103631
FLUOROMETHOLONE [ORANGE BOOK]
s5486
AKOS015895108
Tox21_110440_1
AC-3520
CCG-220718
DB00324
FF23440
NCGC00021575-03
NCGC00021575-05
NCGC00256631-01
AS-12363
FLUOROMETHOLONE COMPONENT OF FML-S
NCI60_002886
CS-0013955
CS-0694990
NS00007682
Progesterone, 17-dihydroxy-6.alpha.-methyl-
D01367
EN300-24430753
Q607349
SR-01000003019
SR-01000003019-2
BRD-K64862097-001-03-9
BRD-K64862097-001-12-0
Fluorometholone, British Pharmacopoeia (BP) Reference Standard
Fluorometholone, United States Pharmacopeia (USP) Reference Standard
Pregna-1,20-dione, 9-fluoro-11.beta.,17-dihydroxy-6.alpha.-methyl-
Progesterone, 1-dehydro-9-fluoro-11.beta., 17-dihydroxy-6.alpha.-methyl-
Pregna-1,20-dione, 9-fluoro-11,17-dihydroxy-6-methyl-, (6.alpha.,11.beta.)-
Pregna-1,4-diene-3,20-dione, 9-fluoro-11,17-dihydroxy-6-methyl-, (6I+/-,11I(2))-
(1R,2S,8S,10S,11S,14R,15S,17S)-14-acetyl-1-fluoro-14,17-dihydroxy-2,8,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one
(1R,3aS,3bS,5S,9aS,9bR,10S,11aS)-1-acetyl-9b-fluoro-1,10-dihydroxy-5,9a,11a-trimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one
(6a,11b)-9-Fluoro-11,17-dihydroxy-6-methylpregna-1,4-diene-3,20-dione;21-Desoxy-9a-fluoro-6-methylprednisolone;6a-Methyl-9a-fluoro-1 1b,17a-dihydroxypregna-1,4-diene-3,20-dione11b,17a-dihydroxypregna-1,4-diene-3,20-dione
207-041-5
Pregna-1, 4-diene-3,20-dione, 9-fluoro-11,17-dihydroxy-6-methyl-, (6.alpha., 11.beta.)-