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Dexamethasone

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Identification
Molecular formula
C22H29FO5
CAS number
50-02-2
IUPAC name
(8S,9R,10S,11S,13S,14S,17S)-9-fluoro-11,17-dihydroxy-10,13,17-trimethyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one
State
State
At room temperature, dexamethasone exists in a solid crystalline form.
Melting point (Celsius)
262.00
Melting point (Kelvin)
535.15
Boiling point (Celsius)
287.00
Boiling point (Kelvin)
560.15
General information
Molecular weight
392.47g/mol
Molar mass
392.4680g/mol
Density
1.4203g/cm3
Appearence

Dexamethasone is a white to practically white, odorless, crystalline powder. It is often found in solid form when used in the laboratory or pharmaceutical products.

Comment on solubility

Solubility of (8S,9R,10S,11S,13S,14S,17S)-9-fluoro-11,17-dihydroxy-10,13,17-trimethyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one

The solubility of (8S,9R,10S,11S,13S,14S,17S)-9-fluoro-11,17-dihydroxy-10,13,17-trimethyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one can be quite complex due to its unique structure and functional groups. Here are some key points regarding its solubility characteristics:

  • Polarity: The presence of hydroxy groups (–OH) typically enhances solubility in polar solvents like water.
  • Hydrophobic Regions: Conversely, the hydrophobic nature of the cyclopenta[a]phenanthren core can reduce solubility in polar environments, suggesting a more favorable solubility in non-polar organic solvents.
  • Solvent Effects: The choice of solvent can significantly affect solubility, and this compound may exhibit differential solubility in ethanol, dimethyl sulfoxide (DMSO), and chloroform.
  • Temperature Influence: Increased temperature may enhance solubility in many cases, allowing for better dissolution of the compound in various solvents.

In summary, while the solubility of this compound may show some degree of general trends, it is heavily influenced by factors such as polarity, solvent type, and temperature. Understanding these aspects is essential for practical applications and further studies.

Interesting facts

Interesting Facts About the Compound

This compound is a fascinating example of the complexity and beauty found in organic chemistry, particularly within the class of steroids. Its elaborate structure showcases the rich stereochemistry that plays a pivotal role in the biological activity of similar compounds. Here are some noteworthy aspects:

  • Chiral Centers: This compound features multiple chiral centers, specifically at positions 8, 9, 10, 11, 13, 14, and 17. The configuration at these points is crucial, as even minor changes can significantly impact the compound's biological function.
  • Biological Relevance: Compounds similar to this one are often investigated for their hormonal activities. They might mimic or inhibit steroid hormones, which could have implications in therapeutic applications.
  • Fluorination: The presence of a fluorine atom can enhance the compound's metabolic stability and lipophilicity, influencing the pharmacokinetic properties of drug candidates derived from similar structures.
  • Stereochemical Complexity: The precise arrangement of functional groups dramatically affects interactions with biological targets, leading to varied physiological responses. Understanding this stereochemical complexity is essential for medicinal chemistry.

As a synthesis challenge, the intricate structure demands skilled methodologies such as asymmetric synthesis and modern techniques to achieve high yields. Scientists often express the sentiment: "The beauty of chemistry lies not just in the compounds themselves but in the paths we take to create them." This particular compound serves as a reminder of the delicate interplay between structure and function in the realm of organic chemistry.

Synonyms
fluoxymesterone
76-43-7
Fluoximesterone
Halotestin
Androfluorene
Androfluorone
Fluoxymestrone
Fluotestin
Ora-Testryl
Androsterolo
Fluosterone
Flusteron
Flutestos
Oralsterone
Oratestin
Testoral
Ultandren
Ultandrene
Fluoximesteronum
Android-f
Neo-Ormonal
Ora Testryl
Fluoximesterona
Fluoxymesteronum
Fluossimesterone [DCIT]
Fluossimesterone
Fluoxymesteronum [INN-Latin]
Fluoximesterona [INN-Spanish]
NSC-12165
Androxy
Halodrin
Fluoxymesterone ciii
9alpha-Fluoro-11beta-hydroxy-17-methyltestosterone
9-Fluoro-11beta,17beta-dihydroxy-17-methylandrost-4-en-3-one
CCRIS 9036
U 6040
HSDB 3333
UNII-9JU12S4YFY
(8S,9R,10S,11S,13S,14S,17S)-9-fluoro-11,17-dihydroxy-10,13,17-trimethyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one
EINECS 200-961-8
9JU12S4YFY
NSC 10704
NSC-10704
BRN 2008796
CHEBI:5120
Testosterone, 9-fluoro-11beta-hydroxy-17-methyl-
9-alpha-Fluoro-11-beta-hydroxy-17-methyltestosterone
AI3-52940
17-alpha-Methyl-9-alpha-fluoro-11-beta-hydroxytesterone
FXM
9-Fluoro-11-beta,17-beta-dihydroxy-17-methylandrost-4-en-3-one
9alpha-Fluoro-17alpha-methyl-11beta,17-dihydroxy-4-androsten-3-one
17alpha-Methyl-9alpha-fluoro-11beta-hydroxytesterone
11beta,17beta-Dihydroxy-9alpha-fluoro-17alpha-methyl-4-androsten-3-one
9-alpha-Fluoro-17-alpha-methyl-11-beta,17-dihydroxy-4-androsten-3-one
9alpha-Fluoro-11beta,17beta-dihydroxy-17alpha-methyl-4-androstene-3-one
11-beta,17-beta-Dihydroxy-9-alpha-fluoro-17-alpha-methyl-4-androster-3-one
9-alpha-Fluoro-11-beta,17-beta-dihydroxy-17-alpha-methyl-4-androstene-3-one
Androst-4-en-3-one, 9-fluoro-11,17-dihydroxy-17-methyl-, (11beta,17beta)-
Fluoximesteron
DTXSID8033512
Androst-4-en-3-one, 9-fluoro-11beta,17beta-dihydroxy-17-methyl-
Anadroid-F
11beta,17beta-Dihydroxy-9alpha-fluoro-17alpha-methyl-4-androster-3-one
4-08-00-02057 (Beilstein Handbook Reference)
NSC12165
Fluoro-9-alpha dihydroxy-11-beta,17-beta methyl-17-alpha androstene-4 one-3
Fluoxymesterone [USP:INN:BAN:JAN]
component of Halodrin
9-fluoro-11beta,17beta-dihydroxy-17alpha-methylandrost-4-en-3-one
(11beta,17beta)-9-fluoro-11,17-dihydroxy-17-methylandrost-4-en-3-one
Fluoxymesteron
Fluoxymesteronum (INN-Latin)
Fluoximesterona (INN-Spanish)
FLUOXYMESTERONE (MART.)
FLUOXYMESTERONE [MART.]
9.alpha.-Fluoro-11.beta.-hydroxy-17-methyltestosterone
DTXCID6013512
9alpha-Fluoro-11beta,17beta-dihydroxy-17-methylandrost-4-en-3-one
Fluoxymesterone (USP:INN:BAN:JAN)
FLUOXYMESTERONE CIII (USP-RS)
FLUOXYMESTERONE CIII [USP-RS]
FLUOXYMESTERONE (USP MONOGRAPH)
FLUOXYMESTERONE [USP MONOGRAPH]
9.alpha.-Fluoro-11.beta.,17.beta.-dihydroxy-17.alpha.-methyl-4-androstene-3-one
CAS-76-43-7
Halotestin (TN)
(8S,9R,10S,11S,13S,14S,17S)-9-fluoro-11,17-dihydroxy-10,13,17-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one
Fluoxymesterone (1.0 mg/ml in Methanol)
Fluoxymesterone (1mg/ml in Acetonitrile)
Fluoxymesterone (1mg/ml in 1,2-Dimethoxyethane)
Testosterone, 9-fluoro-11.beta.-hydroxy-17-methyl-
Androst-4-en-3-one, 9-fluoro-11,17-dihydroxy-17-methyl-, (11.beta.,17.beta.)-
NCGC00182970-01
Androxy (TN)
Fluoro-9-alpha dihydroxy-11-beta,17-beta methyl-17-alpha androstene-4 one-3 [French]
SCHEMBL5096
CHEMBL1445
FLUOXYMESTERONE [MI]
FLUOXYMESTERONE [INN]
FLUOXYMESTERONE [JAN]
MLS001055414
FLUOXYMESTERONE [HSDB]
FLUOXYMESTERONE [VANDF]
GTPL2861
9alpha-Fluoro-11beta-hydroxy-17alpha-methyltestosterone
FLUOXYMESTERONE [WHO-DD]
BDBM18189
Fluoxymesterone (JAN/USP/INN)
G03BA01
YLRFCQOZQXIBAB-RBZZARIASA-N
HMS2272B06
BCP10776
NSC10704
Tox21_113158
Tox21_200854
FLUOXYMESTERONE [ORANGE BOOK]
LMST02020025
AKOS015895109
Androst-4-en-3-one, 9-fluoro-11beta,17beta-dihydroxy-17-methyl- (VAN)
Androst-4-en-3-one, 9-fluoro-11beta,17beta-dihydroxy-17-methyl-(VAN)
DB01185
Fluoxymesterone, solid (photosensitive)
Fluoxymesterone, 1mg/ml in Acetonitrile
NCGC00091037-01
NCGC00091037-02
NCGC00258408-01
AC-29744
SMR000686158
Fluoxymesterone 1.0 mg/ml in Acetonitrile
D00327
A838701
Q410663
BRD-K24255045-001-05-3
(1R,2S,10S,11S,14S,15S,17S)-1-fluoro-14,17-dihydroxy-2,14,15-trimethyltetracyclo[8.7.0.0;{2,7}.0;{11,15}]heptadec-6-en-5-one
(8S,9R,10S,11S,13S,14S,17S)-9-fluoranyl-10,13,17-trimethyl-11,17-bis(oxidanyl)-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one
200-961-8