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Fluocinolone acetonide

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Identification
Molecular formula
C24H30FNO6
CAS number
67-73-2
IUPAC name
[2-[(8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxo-ethyl] pyridine-4-carboxylate
State
State

At room temperature, Fluocinolone acetonide is found in a solid state. Being a crystalline powder, it is handled with care in laboratories and pharmaceutical settings to avoid airborne dispersion and ensure accurate measurement in formulations.

Melting point (Celsius)
273.00
Melting point (Kelvin)
546.00
Boiling point (Celsius)
400.00
Boiling point (Kelvin)
673.00
General information
Molecular weight
452.50g/mol
Molar mass
452.4960g/mol
Density
1.3960g/cm3
Appearence

Fluocinolone acetonide appears as a white to off-white crystalline powder. It is odorless and is typically finely milled for use in pharmaceutical formulations. The texture is fine and it has a distinctly crystalline structure that scatters light evenly.

Comment on solubility

Solubility of 2-[(8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxo-ethyl] pyridine-4-carboxylate

The solubility of complex organic compounds such as 2-[(8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxo-ethyl] pyridine-4-carboxylate can vary significantly depending on a variety of factors.

Key considerations include:

  • Polarity: The presence of hydrophilic groups (such as hydroxyl (-OH) and carboxylate (-COO-)) can enhance solubility in polar solvents, while non-polar regions may hinder this.
  • Solvent Type: Solubility is largely dependent on the solvent used; for instance, organic solvents (like ethanol or acetone) may dissolve this compound better than water.
  • Temperature: Increasing temperature often increases solubility, although this can vary for different chemicals.
  • Interactions: Potential hydrogen bonding and van der Waals forces could significantly affect how well this compound dissolves.

In general, compounds with complex structures like this one may exhibit moderate solubility in organic solvents, but low solubility in water due to their intricate molecular configuration.

As a rule of thumb, if you are testing for solubility, always conduct a series of experiments using multiple solvents and concentrations to gauge the most effective conditions for dissolution. Understanding the solubility profile is crucial for applications in pharmaceuticals and materials science.

Interesting facts

Interesting Facts about 2-[(8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxo-ethyl] pyridine-4-carboxylate

This complex compound features several intriguing characteristics that make it a subject of interest in the field of organic chemistry and medicinal research.

  • Stereochemistry: The compound displays a rich stereochemical landscape, with multiple chiral centers. This complexity can lead to varied biological activities, making stereoisomerism a crucial aspect in the study of its pharmacological properties.
  • Original Use: This compound is synthesized for its potential therapeutic applications, particularly in the fields of oncology and hormone modulation. Its structure suggests it might interact with steroid receptors, which could be beneficial in hormone-related disorders.
  • Fluorine Substitution: The inclusion of a fluorine atom enhances metabolic stability and alters lipophilicity. This makes the compound more appealing for development as a drug, as fluorinated compounds often exhibit improved bioavailability.
  • Framework: The presence of multiple cyclic structures, including an octahydrocyclopenta[a]phenanthrene moiety, indicates a complex molecular backbone that could influence its interaction with biological targets, leading to unique mechanisms of action.

As scientists continue to explore the therapeutic potential of compounds with intricate frameworks like this one, we are reminded of the importance of structure-activity relationships in drug design. It is a dance of atoms and forces that promises exciting discoveries in the quest for innovative treatments.

The study of such compounds reveals the *artistry of chemistry*, where nature's building blocks can lead to transformative medicinal advances.

Synonyms
DEXAMETHASONE ISONICOTINATE
Dexamethasone 21-isonicotinate
Auxilson
Auxilsone
Voren
dexamethasone-21-isonicotinate
UNII-8LGC0BOA71
EINECS 218-866-5
8LGC0BOA71
AUXISONE
Dexamethasone 21-(4-Pyridinecarboxylate)
DTXSID3057690
Voren [veterinary] (TN)
Pyridine-4-carboxylic acid-(dexamethasone-21') ester
Pyridin-4-carbonsaeure-(dexamethason-21')-ester [German]
DTXCID0031479
Pyridin-4-carbonsaeure-(dexamethason-21')-ester
DEXAMETHASONE ISONICOTINATE [MART.]
DEXAMETHASONE 21-ISONICOTINATE [MI]
DEXAMETHASONE ISONICOTINATE [WHO-DD]
DEXAMETHASONE ISONICOTINATE [EP IMPURITY]
DEXAMETHASONE ISONICOTINATE [EP MONOGRAPH]
Pregna-1,4-diene-3,20-dione, 9-fluoro-11,17-dihydroxy-16-methyl-21-((4-pyridinylcarbonyl)oxy)-, (11beta,16alpha)-
Pregna-1,4-diene-3,20-dione, 9-fluoro-11-beta,17,21-trihydroxy-16-alpha-methyl-, 21-isonicotinate
PREGNA-1,4-DIENE-3,20-DIONE, 9-FLUORO-11,17-DIHYDROXY-16-METHYL-21-((4-PYRIDINYLCARBONYL)OXY)-,(11.BETA.,16.ALPHA.)-
DEXAMETHASONE ISONICOTINATE (MART.)
DEXAMETHASONE ISONICOTINATE (EP IMPURITY)
DEXAMETHASONE ISONICOTINATE (EP MONOGRAPH)
2-((1R,2S,10S,11S,13R,14R,15S,17S)-1-fluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo(8.7.0.02,?.011,1?)heptadeca-3,6-dien-14-yl)-2-oxoethyl pyridine-4-carboxylate
2-[(1R,2S,10S,11S,13R,14R,15S,17S)-1-fluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.02,?.011,1?]heptadeca-3,6-dien-14-yl]-2-oxoethyl pyridine-4-carboxylate
Voren (veterinary)
Isonicotinate, Dexamethasone
Pregna-1,4-diene-3,20-dione, 9-fluoro-11,17-dihydroxy-16-methyl-21-[(4-pyridinylcarbonyl)oxy]-, (11.beta.,16.alpha.)-
PREGNA-1,4-DIENE-3,20-DIONE, 9-FLUORO-11,17-DIHYDROXY-16-METHYL-21-((4-PYRIDINYLCARBONYL)OXY)-,(11BETA,16ALPHA)-
2265-64-7
[2-[(8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] pyridine-4-carboxylate
Auxison
HE 111
SCHEMBL7811
CHEMBL3186453
BQTXJHAJMDGOFI-NJLPOHDGSA-N
CHEBI:177639
Tox21_113679
DB11487
NCGC00249903-01
CAS-2265-64-7
NS00008313
D07797
Q5268313
[2-[(8S,9R,10S,11S,13S,14S,16R,17R)-9-luoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] pyridine-4-carboxylate