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Dexamethasone

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Identification
Molecular formula
C22H29FO5
CAS number
50-02-2
IUPAC name
(6S,8S,9S,10R,11S,13S,14S,16R,17R)-6-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one
State
State

Solid

Melting point (Celsius)
262.00
Melting point (Kelvin)
535.00
Boiling point (Celsius)
585.70
Boiling point (Kelvin)
858.90
General information
Molecular weight
392.46g/mol
Molar mass
392.4640g/mol
Density
1.3000g/cm3
Appearence

Dexamethasone is a white to practically white, odorless, crystalline powder.

Comment on solubility

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

The solubility of the compound C22H29FO5 can be characterized by its structural functional groups and the overall hydrophobic nature of its complex polycyclic architecture. Several factors contribute to the solubility behavior of this compound:

  • Hydrophilic Functional Groups: The presence of hydroxyl groups (-OH) suggests that the compound may exhibit some degree of solubility in polar solvents like water. Such functional groups typically enhance solubility due to their ability to form hydrogen bonds.
  • Hydrophobic Regions: The extensive hydrocarbon framework can hinder overall solubility in water, as nonpolar segments resist interaction with polar solvents.
  • Fluorine Atom: The presence of a fluorine atom may influence solubility, potentially enhancing interaction with polar solvents, but it also adds to the compound's overall complexity.
  • Organic Solvent Compatibility: The compound is likely to be more soluble in organic solvents such as ethanol, methanol, or dimethyl sulfoxide (DMSO), where its hydrophobic regions can better interact.

In conclusion, while ((6S,8S,9S,10R,11S,13S,14S,16R,17R)-6-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one) exhibits potential solubility in both polar and nonpolar solvents, the balance between its hydrophilic and hydrophobic characteristics complicates a straightforward solubility profile. As such, empirical testing in various solvents would be essential to ascertain its solubility accurately.

Interesting facts

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

This compound, a complex steroid-like structure, showcases the fascinating interplay of synthetic and natural chemistry. Its intricate design suggests significant biological activity, making it a subject of interest in medicinal chemistry and pharmacology. Here are some engaging facts about this compound:

  • Fluorine Incorporation: The introduction of fluorine in pharmaceuticals can enhance metabolic stability and lipophilicity, potentially leading to improved bioactivity.
  • Hydroxyl Groups: Exhibiting dihydroxy functional groups, this compound may interact with biological systems via hydrogen bonding or enzyme inhibition.
  • Stereoisomerism: The multiple stereocenters highlight the significance of chirality in drug design, as different isomers can exhibit profoundly different pharmacological effects.
  • Cyclopenta[a]phenanthrene Framework: This unique ring system is related to a class of compounds that are often biologically active and can mimic steroid hormones.
  • Applications: Due to its structure, the compound may have potential applications in treating hormonal disorders or certain types of cancers, warranting further investigation.

In summary, this compound not only offers a glimpse into the complexity of chemical design but also serves as an excellent example of the potential advancements in therapeutic applications that can arise from detailed structural modifications. In the words of a famous chemist, "The only difference between science and art is the question of what is to be considered a successful outcome." This compound holds promise, reflecting the artistry involved in creating useful compounds in the realm of chemistry.

Synonyms
paramethasone
53-33-8
Dillar
Flumethone
Paramezone
Cassenne
Cortiden
Metilar
Parametasona
Parametasone
Paramethasonum
Parametasone [DCIT]
Paramethasone [INN:BAN]
Parametasona [INN-Spanish]
Paramethasonum [INN-Latin]
Dillar (TN)
Paramethasone (INN)
CS 1483
16alpha-Methyl-6alpha-fluoroprednisolone
6alpha-Fluoro-16alpha-methylprednisolone
HSDB 3376
EINECS 200-169-2
UNII-VFC6ZX3584
CHEBI:7922
VFC6ZX3584
Pregna-1,4-diene-3,20-dione, 6-fluoro-11,17,21-trihydroxy-16-methyl-, (6alpha,11beta,16alpha)-
PARAMETHASONE [MI]
PARAMETHASONE [INN]
PARAMETHASONE [HSDB]
PARAMETHASONE [VANDF]
PARAMETHASONE [WHO-DD]
(6S,8S,9S,10R,11S,13S,14S,16R,17R)-6-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one
DTXSID3023421
Pregna-1,4-diene-3,20-dione, 6alpha-fluoro-11beta,17,21-trihydroxy-16alpha-methyl-
Parametasona (INN-Spanish)
Paramethasonum (INN-Latin)
(6alpha,11beta,16alpha)-6-fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione
(1S,2R,8S,10S,11S,13R,14R,15S,17S)-8-fluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one
(6.ALPHA.,11.BETA.,16.ALPHA.)-6-FLUORO-11,17,21-TRIHYDROXY-16-METHYLPREGNA-1,4-DIENE-3,20-DIONE
PREGNA-1,4-DIENE-3,20-DIONE, 6-FLUORO-11,17,21-TRIHYDROXY-16-METHYL-, (6.ALPHA.,11.BETA.,16.ALPHA.)-
Paramethason
(1S,2R,8S,10S,11S,13R,14R,15S,17S)-8-fluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo(8.7.0.0^(2,7).0^(11,15))heptadeca-3,6-dien-5-one
SCHEMBL4355
CHEMBL1579
DTXCID103421
H02AB05
MKPDWECBUAZOHP-AFYJWTTESA-N
HY-A0179
AKOS040753431
DB01384
(6alpha,11beta,16alpha)-6-Fluoro-11,17,21-trihydroxy-16-methyl-pregna-1,4-diene-3,20-dione
Cortiden; 6-Fluoro-16-methylprednisolone
DA-76594
FP100930
CS-0017521
NS00041037
C07413
D07464
Q7135218
6alpha-Fluoro-11beta,17,21-trihydroxy-16-methyl-pregna-1,4-diene-3,20-dione
(6S,8S,9S,10R,11S,13S,14S,16R,17R)-6-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one
200-169-2