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

Solid: At room temperature, dexamethasone exists as a crystalline solid.

Melting point (Celsius)
262.00
Melting point (Kelvin)
535.00
Boiling point (Celsius)
524.00
Boiling point (Kelvin)
797.00
General information
Molecular weight
392.46g/mol
Molar mass
392.4700g/mol
Density
1.3100g/cm3
Appearence

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

Comment on solubility

Solubility Overview

The compound (8S,9R,10S,11S,13S,14S,17R)-9-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one demonstrates unique solubility characteristics due to its complex structure. Understanding its solubility is crucial for applications in pharmaceuticals and organic chemistry.

Factors Influencing Solubility

The solubility of this compound can be affected by a variety of factors, including:

  • Polarity: The presence of hydroxyl groups increases polarity, which may enhance solubility in polar solvents.
  • Hydrogen Bonding: The dihydroxy functional groups could form hydrogen bonds, facilitating interactions with solvents like water and alcohols.
  • Structural Complexity: Its multi-ring structure and additional substituents may hinder solubility by creating steric hindrance.

Solubility Characteristics

While specific solubility data for this compound may not be readily available, it is often expected that:

  • Higher Solubility: It is likely to have higher solubility in organic solvents such as ethanol and methanol.
  • Low Water Solubility: Due to its bulky structure, it may exhibit low solubility in water.

In conclusion, the solubility of (8S,9R,10S,11S,13S,14S,17R)-9-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one is intricately linked to its molecular properties, which makes it an intriguing subject of study for scientists seeking to enhance its utility in practical applications.

Interesting facts

Interesting Facts about (8S,9R,10S,11S,13S,14S,17R)-9-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one

This complex chemical compound belongs to a class of steroid-like molecules that exhibit numerous intriguing characteristics, primarily due to its unique stereochemistry and functional groups. Here are some compelling points to consider:

  • Stereochemistry: The specific configuration denoted by the S and R notations emphasizes the molecule's chirality, which plays a crucial role in its biological activity.
  • Fluorine Substitution: The presence of a fluorine atom introduces significant biological and physical effects, such as increased metabolic stability and altered pharmacokinetics, which can enhance the compound's therapeutic potential.
  • Hydroxyl Groups: The dual hydroxyl functional groups are essential for forming hydrogen bonds, which can improve solubility and affinity for biological targets, potentially making this compound an interesting candidate for drug development.
  • Dimethyl Groups: The dimethyl substitutions provide additional steric hindrance, influencing the arrangement and interactions of the compound within biological systems.

Researchers are captivated by such compounds due to their potential applications in medicinal chemistry. The biochemical pathways they may influence, especially in hormonal regulation and as potential therapeutic agents, are a rich field for investigation.

As one researcher aptly stated, "Complexity in molecular structure often leads to a greater understanding of biological intricacies." This compound exemplifies that philosophy, representing a promising avenue for future studies and developments in pharmaceutical sciences.

Synonyms
fludrocortisone
127-31-1
Astonin-H
Alflorone
Fluohydrisone
Fluorocortisol
Fluorocortisone
Fluohydrocortisone
Fludrocortone
Fludronef
Fludrone
9alpha-Fluorocortisol
F-Cortef
F-COL
9-Fluorocortisol
Fludrocortisona
Fludrocortisonum
9-Fluorohydrocortisone
9alpha-Fludrocortisone
U 5963
9alpha-Fluoro-17-hydroxycorticosterone
DTXSID7023061
NSC-11318
9-Fluoro-11beta,17,21-trihydroxypregn-4-ene-3,20-dione
(8S,9R,10S,11S,13S,14S,17R)-9-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one
CHEBI:50885
U0476M545B
Pregn-4-ene-3,20-dione, 9-fluoro-11,17,21-trihydroxy-, (11beta)-
DTXCID503061
Pregn-4-ene-3,20-dione, 9-fluoro-11beta,17,21-trihydroxy-
9alpha-fluoro-11beta,17alpha,21-trihydroxy-pregn-4-ene-3,20-dione
NSC11318
Astonin Merck
9 Fluorocortisol
Astonin H
Merck, Astonin
9 alpha Fludrohydrocortisone
9 alpha-Fluorohydrocortisone
9 Fluorohydrocortisone
9-Fluoro-17-Hydroxycortisone
9 alpha Fluorohydrocortisone
9 Fluoro 17 Hydroxycortisone
9 alpha-Fluoro-17-Hydroxycorticosterone
9 alpha Fluoro 17 Hydroxycorticosterone
(8S,9R,10S,11S,13S,14S,17R)-9-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta(a)phenanthren-3-one
RefChem:56418
204-833-2
Fluodrocortisone
Cortisol, 9-fluoro-
StC 1400
9-AFH
9 .alpha. FF
9.alpha.-Fluorocortisol
9-AF
9.alpha.-Fluorohydrocortisone
Corticosterone, 9-fluoro-17-hydroxy-
NSC 11318
Fludrocortisone (INN)
9.alpha.-Fluoro-17-hydroxycorticosterone
C21H29FO5
127-31-1 (free)
9 alpha FF
LMST02030103
NCGC00181081-01
9-Fluoro-11.beta.,17,21-trihydroxypregn-4-ene-3,20-dione
9-alpha-Fluorocortisol
9-alpha-Fludrocortisone
Fludrocortisonum [INN-Latin]
Fludrocortisona [INN-Spanish]
FLUDROCORTISONE [INN]
Fludrocortisone [INN:BAN]
9-alpha-Fluorohydrocortisone
9alpha-Fluoro-hydrocortisone
Hydrocortisone-9alpha-fluoro
(8S,9R,10S,11S,13S,14S,17R)-9-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one
CAS-127-31-1
9-alpha-Fluoro-17-hydroxycorticosterone
Astonin-H (TN)
HSDB 3332
EINECS 204-833-2
BRN 3014278
MFCD00083333
9-Fluoro-11-beta,17,21-trihydroxypregn-4-ene-3,20-dione
UNII-U0476M545B
Pregn-4-ene-3,20-dione, 9-fluoro-11,17,21-trihydroxy-, (11.beta.)-
9alpha-Fluoro-11beta,17alpha,21-trihydroxy-4-pregnene-3,20-dione
Prestwick_648
9alpha-Flourocortisol
ZK5
9.alpha.-Fluorcortisol
(11beta)-9-Fluoro-11,17,21-trihydroxypregn-4-ene-3,20-dione
bmse000987
bmse001009
SCHEMBL4545
FLUDROCORTISONE [MI]
4-08-00-03427 (Beilstein Handbook Reference)
FLUDROCORTISONE [HSDB]
FLUDROCORTISONE [VANDF]
GTPL2873
CHEMBL1201388
FLUDROCORTISONE [WHO-DD]
MSK8566
9-Fludrocortisone;9-Fluorcortisol
HY-B1203
Pregn-4-ene-3,20-dione, 9-fluoro-11-beta,17,21-trihydroxy-
Tox21_112700
Tox21_113344
9.alpha.-Fluoro-11.beta.,17.alpha.,21-trihydroxy-4-pregnene-3,20-dione
AKOS040742512
Tox21_113344_1
CS-4832
DB00687
FF23321
NCGC00274078-01
DA-63474
NS00010380
C07004
D07967
G60915
EN300-19737599
Q2697578
Pregn-4-ene-3, 9-fluoro-11.beta.,17,21-trihydroxy-
WLN: L E5 B666 OV MUTJ A1 BF CQ E1 FV1Q FQ
9-Fluoro-11.beta.,21-trihydroxypregn-4-ene-3,20-dione
(11.beta.)-9-Fluoro-11,17,21-trihydroxypregn-4-ene-3,20-dione
(11alpha)-9-fluoro-11,17,21-trihydroxypregn-4-ene-3,20-dione
9.alpha.-Fluoro-11.beta.,21-trihydroxy-4-pregnene-3,20-dione
Pregn-4-ene-3, 9-fluoro-11,17,21-trihydroxy-, (11.beta.)-
Pregn-4-ene-3,20-dione, 9-fluoro-11.beta.,17,21-trihydroxy-
9-Fluoro-11,17,21-trihydroxypregn-4-ene-3,20-dione, (11.beta.)- #
(1R,3aS,3bS,9aS,9bR,10S,11aS)-9b-fluoro-1,10-dihydroxy-1-(2-hydroxyacetyl)-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one