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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,16S,17R)-9-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
State
State
Dexamethasone is solid at room temperature and is generally supplied as a crystalline powder. It is stable under normal conditions if stored properly, away from light and moisture.
Melting point (Celsius)
262.00
Melting point (Kelvin)
535.15
Boiling point (Celsius)
224.00
Boiling point (Kelvin)
497.15
General information
Molecular weight
392.47g/mol
Molar mass
392.4700g/mol
Density
1.3297g/cm3
Appearence

Dexamethasone is a white to almost white, crystalline powder. It is practically odorless and possesses a slightly bitter taste. The crystalline form may appear as a fine, white, odorless powder.

Comment on solubility

Solubility Characteristics

The compound (8S,9R,10S,11S,13S,14S,16S,17R)-9-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one exhibits complex solubility behavior influenced by its unique chemical structure.

  • Polarity: The presence of hydroxyl groups enhances its polarity, potentially increasing solubility in polar solvents.
  • Hydroxyl Groups: These functional groups typically facilitate hydrogen bonding, which could contribute to better solubility in water and other hydrophilic environments.
  • Fluorine Substitution: The fluorine atom may also affect solubility, as fluorinated compounds often display different solubility traits compared to their non-fluorinated counterparts.
  • Hydroxyacetyl Moiety: The introduction of a 2-hydroxyacetyl group further adds to the potential for hydrogen bonding and possibly enhances interactions with polar solvents.

Overall, based on the intricate balance between hydrophobic regions stemming from its hydrocarbon backbone and hydrophilic parts due to the functional groups, the solubility of this compound can be described as:

  • Potentially soluble in polar solvents such as water and alcohols.
  • Less soluble in non-polar solvents due to its structural composition.

In conclusion, the solubility of this compound is likely to be moderate, showing dependency on the solvent's polarity and condition. Collectively, these factors underscore the importance of considering both the chemical structure and the nature of the surrounding medium when predicting solubility.

Interesting facts

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

This complex compound, with its intricate chiral centers, showcases the fascinating world of stereochemistry. Here are some intriguing aspects about it:

  • Stereochemical Configuration: The designation of chiral centers as S or R signifies the specific arrangement of atoms and can dramatically influence the compound's biological activity and interaction with receptors. The complexity of its structure may pose challenges in synthesis but presents remarkable opportunities for drug design.
  • Fluorine in Chemistry: The incorporation of fluorine is noteworthy; compounds containing fluorine often exhibit enhanced metabolic stability and improved pharmacological properties. The introduction of a fluorine atom can alter the affinity of the compound for biological targets, making it a valuable addition in medicinal chemistry.
  • Hydroxyl Groups: With two hydroxyl (-OH) groups, this compound may exhibit interesting hydrogen bonding capabilities, affecting solubility and reactivity. Hydroxyl groups are known to enhance the polarity of a molecule, which can influence its behavior in biological systems.
  • Potential Biological Activity: The structural features suggest the possibility of this compound having therapeutic implications. Exploring its interaction with biological macromolecules could reveal its potential as an anti-inflammatory or anticancer agent.
  • Natural Product Inspiration: Many complex compounds like this one are derived from natural products or inspired by nature. Researching natural sources or synthesis pathways of such compounds often leads to discoveries beneficial in pharmaceuticals.

Furthermore, as a chemist or a student in the field, understanding such compounds challenges one to think critically about their properties and potential uses. It is not just the molecular structure that excites, but the myriad of possibilities for innovation and discovery that compounds like these represent.

Synonyms
betamethasone
378-44-9
Betadexamethasone
Flubenisolone
Celestene
Rinderon
Visubeta
Betamethazone
Becort
Desacort-Beta
Betamamallet
Betametasone
Betacorlan
Betacortril
Betapredol
Betasolon
Betnelan
Betsolan
Methazon
Bebate
Bedifos
Cidoten
beta-Methasone
Betametasona
beta-Methasone alcohol
Celestone
Rinderon A
Betamethasone cream
Betamethasonum
Betamethasone alcohol
SCH 4831
NSC-39470
9alpha-Fluoro-16beta-methylprednisolone
9-Fluoro-16beta-methylprednisolone
SCH-4831
Betametasona [INN-Spanish]
Betamethasonum [INN-Latin]
HSDB 3015
Betamethasone (Celestone)
9-alpha-Fluoro-16-beta-methylprednisolone
EINECS 206-825-4
MFCD00062969
NSC 39470
Prednisolone, 9-fluoro-16beta-methyl-
BRN 3176546
FLOSTERON
CHEBI:3077
MLS000859943
Betamethasone, topical
DTXSID3022667
UNII-9842X06Q6M
9842X06Q6M
9a-Fluoro-11b,17a,21-trihydroxy-16b-methylpregna-1,4-diene-3,20-dione
9-Fluoro-11beta,17,21-trihydroxy-16beta-methylpregna-1,4-diene-3,20-dione
Pregna-1,4-diene-3,20-dione, 9-fluoro-11,17,21-trihydroxy-16-methyl-, (11.beta.,16.beta.)-
DTXCID002667
Corticosterone, 1-dehydro-9-fluoro-17-hydroxy-16beta-methyl-
EC 206-825-4
Betametasone [DCIT]
4-08-00-03501 (Beilstein Handbook Reference)
NSC39470
NCS-39470
(8S,9R,10S,11S,13S,14S,16S,17R)-9-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
NCGC00164401-01
Betamethasone [USAN:USP:INN:BAN:JAN]
SMR000058601
Betametasona (INN-Spanish)
Betamethasonum (INN-Latin)
16beta-Methyl-1,4-pregnadiene-9alpha-fluoro-11beta,17alpha,21-triol-3,20-dione
BETAMETHASONE (MART.)
BETAMETHASONE [MART.]
BETAMETHASONE (USP-RS)
BETAMETHASONE [USP-RS]
.beta.-Methasone
BETAMETHASONE (EP IMPURITY)
BETAMETHASONE [EP IMPURITY]
BETAMETHASONE (EP MONOGRAPH)
BETAMETHASONE [EP MONOGRAPH]
BETAMETHASONE (USP MONOGRAPH)
BETAMETHASONE [USP MONOGRAPH]
9-Fluoro-16.beta.-methylprednisolone
Rinderon (TN)
Betamethasone (USAN:USP:INN:BAN:JAN)
.beta.-Methasone alcohol
9.alpha.-Fluoro-16.beta.-methylprednisolone
DEXAMETHASONE IMPURITY B (EP IMPURITY)
DEXAMETHASONE IMPURITY B [EP IMPURITY]
Desacort-.beta.
(11beta,16beta)-9-Fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione
.beta.-Corlan
9alpha-Fluoro-11beta,17alpha,21-trihydroxy-16beta-methyl-1,4-pregnadiene-3,20-dione
NCGC00091019-08
CAS-378-44-9
Prestwick_703
Prednisolone, 9-fluoro-16.beta.-methyl-
9-Fluoro-11-beta,17,21-trihydroxy-16-beta-methylpregna-1,4-diene-3,20-dione
Pregna-1,4-diene-3,20-dione, 9-fluoro-11,17,21-trihydroxy-16-methyl-, (11beta,16beta)-
Celestone; Flubenisolone
Betamethasone (Standard)
Betamethasone, >=98%
Prestwick0_000362
Prestwick1_000362
Prestwick2_000362
Prestwick3_000362
BETAMETHASONE [MI]
CHEMBL632
BETAMETHASONE [INN]
BETAMETHASONE [JAN]
cid_9782
SCHEMBL4565
16-beta-Methyl-1,4-pregnadiene-9-alpha-fluoro-11-beta,17-alpha,21-triol-3,20-dione
9-alpha-Fluoro-16-beta-methyl-1,4-pregnadiene-11-beta,17-alpha,21-triol-3,20-dione
BETAMETHASONE [USAN]
Pregna-1,4-diene-3,20-dione, 9-fluoro-11beta,17,21-trihydroxy-16beta-methyl-
BIDD:PXR0047
BETAMETHASONE [VANDF]
BSPBio_000483
MLS001066413
MLS001332616
MLS002153244
SPBio_002404
BETAMETHASONE [WHO-DD]
BETAMETHASONE [WHO-IP]
Corticosterone, 1-dehydro-9-fluoro-17-hydroxy-16.beta.-methyl-
BPBio1_000533
GTPL7061
BDBM73823
A07EA04
Betamethasone (JP17/USP/INN)
C05AA05
D07AC01
D07XC01
H02AB01
R03BA04
S01BA06
S01CB04
S02BA07
S03BA03
Betamethasone - Bio-X trade mark
BCPP000345
HMS1569I05
HMS2096I05
HMS2233I08
HMS3713I05
BETAMETHASONE [ORANGE BOOK]
BCP02020
Tox21_112115
Tox21_301455
HY-13570R
MFCD00062929
s1500
BETAMETHASONUM [WHO-IP LATIN]
AKOS008901360
AKOS015894863
Tox21_112115_1
BCP9000393
CCG-220362
CS-1897
DB00443
FB18562
KS-5302
9-Fluoro-11.beta.,17,21-trihydroxy-16.beta.-methylpregna-1,4-diene-3,20-dione
SMP1_000043
NCGC00164401-02
NCGC00164401-03
NCGC00255195-01
(8S,9R,10S,11S,13S,14S,16S,17R)-9-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
BB300033
HY-13570
BETAMETHASONE DIPROPIONATE IMPURITY A
B1837
Betamethasone 100 microg/mL in Acetonitrile
D1961
NS00073847
Betamethasone, meets USP testing specifications
C06848
D00244
D88866
EN300-119511
Betamethasone, VETRANAL(TM), analytical standard
Q416132
SR-01000780582
SR-01000780582-2
BETAMETHASONE ACETATE IMPURITY A [EP IMPURITY]
BETAMETHASONE VALERATE IMPURITY A [EP IMPURITY]
BRD-K39188321-001-03-9
Z1521553714
Betamethasone, British Pharmacopoeia (BP) Reference Standard
Betamethasone, European Pharmacopoeia (EP) Reference Standard
Betamethasone, pharmaceutical impurity standard, >=95.0% (HPLC)
Betamethasone, United States Pharmacopeia (USP) Reference Standard
(11.beta.,16.beta.)-9-Fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione
9-.alpha.-Fluoro-11-.beta.,17,21-trihydroxy-16-.beta.-methylpregna-1,4-diene-3,20-dione
9-FLUORO-11.BETA.,17,21-TRIHYDROXY-16.BETA.-METHYLPREGNA-1,4-DIENE-3,20-DIONE.
9-fluoro-16beta-methyl-11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione
9alpha-Fluoro-11beta,17alpha,21-trihydroxy-16beta-methylpregna-1,4-diene-3,20-dione
9alpha-Fluoro-16beta-methyl-11beta,17alpha,21-trihydroxy-1,4-pregnadiene-3,20-dione
Betamethasone, Pharmaceutical Secondary Standard; Certified Reference Material
Pregna-1,4-diene-3,20-dione, 9-fluoro-11.beta.,17,21-trihydroxy-16.beta.-methyl-
Pregna-1,4-diene-3,20-dione, 9alpha-fluoro-11beta,17alpha,21-trihydroxy-16beta-methyl-
(11b,16b)-9-Fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione;9a-Fluoro-16b-methylprednisolone;Betadexamethasone
(1R,2S,10S,11S,13S,14R,15S,17S)-1-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
(1R,2S,3aS,3bS,9aS,9bR,10S,11aS)-9b-fluoro-1,10-dihydroxy-1-(2-hydroxyacetyl)-2,9a,11a-trimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one
16-.beta.-Methyl-1,4-pregnadiene-9-.alpha.-fluoro-11-.beta.,17-.alpha.,21-triol-3,20-dione
206-825-4
9-.alpha.-Fluoro-11-.beta.,17-.alpha.,21-trihydroxy-16-.beta.-methylpregna-1,4-diene-3,20-dione
9-.alpha.-Fluoro-16-.beta.-methyl-1,4-pregnadiene-11-.beta.,17-.alpha.,21-triol-3,20-dione
9-Fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione, (11.beta.,16.beta.) #