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Dexamethasone

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Identification
Molecular formula
C22H29FO5
CAS number
50-02-2
IUPAC name
(1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one
State
State

At room temperature, dexamethasone is in a solid state. It is commonly found as a crystalline powder, which makes it easy to handle for various pharmaceutical applications, including formulation into tablets or injectables.

Melting point (Celsius)
262.00
Melting point (Kelvin)
535.15
Boiling point (Celsius)
570.00
Boiling point (Kelvin)
843.15
General information
Molecular weight
392.46g/mol
Molar mass
392.4610g/mol
Density
1.2600g/cm3
Appearence

Dexamethasone is typically found as a white to practically white, odorless crystalline powder. It may appear in small, fine granules or needle-like crystals, depending on its form and purification process. The powder is usually highly pure, with a consistent texture and look, which is ideal for pharmaceutical preparations.

Comment on solubility

Solubility Characteristics

The compound (1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one exhibits unique solubility properties primarily influenced by its complex chemical structure.

In general, the solubility of a compound can be characterized by several key factors:

  • Polarity: Due to the presence of various functional groups such as hydroxy (–OH) and fluorine (–F), this compound is likely to interact favorably with polar solvents like water.
  • Hydrogen Bonding: The hydroxy group is significant in promoting hydrogen bonding with solvent molecules, potentially enhancing solubility in polar solvents.
  • Hydrophobic Regions: The presence of bulky hydrocarbon portions (tetramethyl groups) may hinder solubility in aqueous environments by introducing hydrophobic characteristics.
  • Effect of Temperature: Solubility can also vary with temperature; higher temperatures may increase solubility for some compounds due to increased kinetic energy.

Overall, while the broad trends suggest some level of solubility in polar solvents, the exact solubility of this compound may not be straightforward and would require empirical testing for precise determination. As one eloquently summarized, "The solubility profile of a compound is a dance of molecular interactions, where each functional group plays its role."

In conclusion, expect a mixture of solubility behaviors that could vary dramatically based on environmental conditions and the presence of different solvents.

Interesting facts

Interesting Facts about 12-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one

This fascinating compound, known for its complex structure, is a member of the family of bioactive molecules that showcase a myriad of potentials in various scientific fields. Below are some intriguing insights regarding this unique chemical:

  • Stereochemistry: The compound contains multiple stereocenters, which contributes to its distinct 3D conformation. This stereochemical diversity is essential in determining the compound's biological activity, influencing how it interacts with biological targets.
  • Fluorine Substitution: The presence of a fluorine atom in its structure enhances molecular stability and alters the compound's lipophilicity, which can play a pivotal role in pharmacological applications. Fluorinated compounds are often designed to improve the pharmacokinetic properties of drugs.
  • Hydroxy Group: The hydroxy group in the molecule adds functional versatility, allowing for potential interactions in biological systems, such as hydrogen bonding with other molecules. This can be a critical factor in enhancing solubility and biological recognition.
  • Potential Applications: Compounds exhibiting such complex architectures are of growing interest in medicinal chemistry. They could serve as leads for developing new therapeutic agents, particularly in cancer treatment and other diseases where complex interactions matter.
  • Synthesis Challenges: The intricate arrangement of rings and functional groups poses significant challenges in synthetic chemistry. Creating such compounds often requires innovative methodologies, including multi-step synthesis and advanced reaction techniques.

In summary, the unique structural features and potential applications of this compound not only make it a subject of scientific curiosity but also highlight the wonders of synthetic organic chemistry and its implications in producing significant biomedical advancements.

Synonyms
TRIAMCINOLONE ACETONIDE
76-25-5
Azmacort
Nasacort
Vetalog
Aristoderm
Aristogel
Solodelf
Tramacin
Tricinolon
Zilretta
Oralone
Rineton
Triacet
Triderm
Kenacort-A
Nasacort AQ
Kenalog
Volon A
Flutone
Kenalone
Oracort
Triaceton
Triacort
Triatex
Triesence
Flutex
Trymex
AllerNaze
Aristocort A
Triam-Injekt
Adcortyl A
Kenalog-H
Omcilon A
Tri-Nasal
Nasacort HFA
Coupe-A
Kenalog in Orabase
Aristocort acetonide
Acetospan
Kenalog-10
Kenalog-40
Trivaris
Triamcinolone 16,17-acetonide
Volon A 40
Triamcincolone acetonide
Trianex
Triamsinolone acetonide
Triamcinolone (acetonide)
Nasacort Allergy 24 Hour
Triamcinolone Acetonide in Absorbase
CCRIS 5231
Extracort
Ftorocort
Volonimat
Ledercort cream
CHEBI:71418
EINECS 200-948-7
NSC 21916
NSC-21916
UNII-F446C597KA
9alpha-Fluoro-16alpha-17alpha-isopropyledenedioxyprednisolone
BRN 0060069
XIPERE
DTXSID6021371
Triamonide 40
F446C597KA
FX006
9alpha-Fluoro-16-hydroxyprednisolone acetonide
9-alpha-Fluoro-16-hydroxyprednisolone acetonide
MFCD00056834
9-alpha-Fluoro-16-alpha-17-alpha-isopropyledenedioxyprednisolone
Respicort
MLS000028538
DTXCID201371
CLS1001
TAC-3
Triamcinolone acetonide (Standard)
5-19-06-00568 (Beilstein Handbook Reference)
9-alpha-Fluoro-16-alpha-hydroxyprednisolone 16-alpha,17-alpha-acetonide
CLS-1001
NSC21916
9-alpha-Fluoro-16-alpha-17-alpha-isopropylidenedioxy-delta-1-hydrocortisone
9-Fluoro-11beta,16alpha,17,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with acetone
Kenalog 40
Tricort-40
SMR000058335
Asmacort [Common Misspelling of Azmacort]
9alpha-Fluoro-16alpha-hydroxyprednisolone 16alpha,17alpha-acetonide
Triamcinolone acetonide [USP:INN:BAN:JAN]
9alpha-fluoro-16alpha-17alpha-isopropylidenedioxy-Delta-1-hydrocortisone
MYCOLOG COMPONENT TRIAMCINOLONE ACETONIDE
MYKACET COMPONENT TRIAMCINOLONE ACETONIDE
MYTREX A COMPONENT TRIAMCINOLONE ACETONIDE
MYTREX F COMPONENT TRIAMCINOLONE ACETONIDE
(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS)-4b-fluoro-5-hydroxy-6b-(hydroxyacetyl)-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one
Vetalog (Veterinary)
(11beta,16alpha)-9-Fluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione
TRIAMCINOLONE ACETONIDE (MART.)
TRIAMCINOLONE ACETONIDE [MART.]
9-fluoro-11beta,16alpha,17,21-tetrahydroxypregna-1,4-diene-3,20-dione-16,17-acetonide
9alpha-Fluoro-11beta,21-dihydroxy-16alpha,17-isopropylidenedioxy-1,4-pregnadiene,3,20-dione
CAS-76-25-5
TRIAMCINOLONE ACETONIDE (USP-RS)
TRIAMCINOLONE ACETONIDE [USP-RS]
(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS)-4b-fluoro-6b-glycoloyl-5-hydroxy-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one
9alpha-fluoro-11beta,21-dihydroxy-16alpha,17alpha-isopropylidenedioxypregna-1,4-diene-3,20-dione
Asmacort (common misspelling of Azmacort)
Panolog Ointment (Veterinary)
Triamcinolone acetonide [JAN]
Triamcinolone acetonide (USP:INN:BAN:JAN)
TRIAMCINOLONE ACETONIDE (EP MONOGRAPH)
TRIAMCINOLONE ACETONIDE [EP MONOGRAPH]
TRIAMCINOLONE ACETONIDE (USP MONOGRAPH)
TRIAMCINOLONE ACETONIDE [USP MONOGRAPH]
Acetonide, Triamcinolone
MLS002638825
Nystadermal
Audicort
Aureocort
Protherix
Remiderm
Remotic
Silderm
Triasil
Medalone Cream
Nasal Allergy
Pediaderm Ta
Tri-Adcortyl
Trivix Lite
Gppe Ear Oint
Triloan SUIK
Vetalog Parenteral
Kenalone, Solodelf
NCGC00023193-04
Azmacort (TN)
Nasacort (TN)
Sila III
Triloan II SUIK
(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS)-4b-fluoro-6b-glycoloyl-5-hydroxy-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho(2',1':4,5)indeno(1,2-d)(1,3)dioxol-2-one
Gppe Ear Dps Cap
Adcortyl In Orabase
Kenalog (TN)
Pevaryl T.C.
Equate Nasal Allergy
Leader Nasal Allergy
ORAMEDY
TRITOCIN
Genesis Topical Spray
Topcare Nasal Allergy
Equaline nasal allergy
Pregna-1,4-diene-3,20-dione, 9-fluoro-11,21-dihydroxy-16,17-((1-methylethylidene)bis(oxy))-, (11beta,16alpha)-
Pro-C-Dure 5 Kit
Pro-C-Dure 6 Kit
Triamcinolone-Acetonide
Nasacort Allergy 24hr
Trianex 0.05%
ReadySharp Triamcinolone
Opera_ID_232
24 Hour Nasal Allergy
Nasal Allergy 24 Hour
DG Health Nasal Allergy
Basic Care Nasal Allergy
Good Sense Nasal Allergy
Up and Up Nasal Allergy
KENALOG-80
SCHEMBL4689
triamcinolone acetonide cream
9-alpha-Fluoro-11-beta,21-dihydroxy-16-alpha-isopropylidenedioxy-1,4-pregnadiene,3,20-dione
CHEMBL1504
kirkland signature aller cort
Signature Care Nasal Allergy
Triamcinolone Acetonide Nasal
9-alpha-Fluoro-11-beta,21-dihydroxy-16-alpha,17-alpha-isopropylidenedioxypregna-1,4-diene-3,20-dione
MLS001148264
MLS002207192
9.alpha.-Fluoro-16.alpha.-17.alpha.-isopropyledenedioxyprednisolone
GTPL2867
Triamcinolone Acetonide Ointment
0.015% triamcinolone acetonide
HY-B0636R
MSK2233
Triamcinolone Acetonide Suspension
9.alpha.-Fluoro-16.alpha.-hydroxyprednisolone 16.alpha.,17.alpha.-acetonide
HMS2232F22
HMS3259A20
Health Mart 24 hour nasal allergy
Triamcinolone Acetonide Cream .1%
HY-B0636
Tox21_110885
Tox21_201795
Tox21_303014
TRIAMCINOLONE ACETONIDE [MI]
BDBM50248362
Triamcinolone acetonide (JP18/USP)
AKOS015894871
Tox21_110885_1
AC-1239
CCG-269068
FT28384
KS-5330
NC00591
TRIAMCINOLONE ACETONIDE [VANDF]
FLUOCINOLONE ACETONIDE IMPURITY H
TRIAMCINOLONE ACETONIDE [WHO-DD]
foster and thrive 24 hour nasal allergy
NCGC00023193-05
NCGC00023193-06
NCGC00256560-01
NCGC00259344-01
Pregna-1,4-diene-3,20-dione, 9-fluoro-11-beta,16-alpha,17,21-tetrahydroxy-, cyclic 16,17-acetal with acetone
Pregna-1,4-diene-3,20-dione, 9-fluoro-11beta,16alpha,17,21-tetrahydroxy-, cyclic 16,17-acetal with acetone
TRIAMCINOLONE ACETONIDE [GREEN BOOK]
Triamcinolone acetonide, analytical standard
CS-0695000
NS00009342
S1628
TRIAMCINOLONE ACETONIDE [ORANGE BOOK]
Good Neighbor Pharmacy 24 Hour Nasal Allergy
Triamcinolone Acetonide Ointment USP, 0.05%
C08183
D00983
9.alpha.-Fluoro-16-hydroxyprednisolone acetonide
AB00383012-11
AB00383012_12
Triamcinolone acetonide 100 microg/mL in Methanol
TRIAMCINOLONE ACETONIDE COMPONENT OF MYCOLOG
TRIAMCINOLONE ACETONIDE COMPONENT OF MYKACET
Q2211240
TRIAMCINOLONE ACETONIDE COMPONENT OF MYTREX A
TRIAMCINOLONE ACETONIDE COMPONENT OF MYTREX F
9.alpha.-Fluoro-11.beta.,4-pregnadiene,3,20-dione
BRD-K53790871-001-08-6
TRIAMCINOLONE HEXACETONIDE IMPURITY A [EP IMPURITY]
Triamcinolone acetonide, European Pharmacopoeia (EP) Reference Standard
Triamcinolone acetonide, United States Pharmacopeia (USP) Reference Standard
TRIAMCINOLONE ACETONIDE; 76-25-5; Azmacort; Aristogel; Nasacort;
WLN: T F5 E5 B666 GO IO RV AHTTTT&J A1 BF CQ E1 FV1Q H1 H1
9.alpha.-Fluoro-16.alpha.-17.alpha.-isopropylidenedioxy-.delta.-1-hydrocortisone
Pregna-1,20-dione, 9-fluoro-11.beta.,21-dihydroxy-16.alpha.,17-(isopropylidenedioxy)-
Triamcinolone Acetonide, Pharmaceutical Secondary Standard; Certified Reference Material
(11?,16?)-9-Fluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]-pregna-1,4-diene-3,20-dione;Adcortyl;Azmacort
(1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one
(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS)-4b-fluoro-5-hydroxy-6b-(hydroxyacetyl)-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H,8H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one
1TA
200-948-7
Pregna-1,20-dione, 9-fluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]-, (11.beta.,16.alpha.)-
Pregna-1,20-dione, 9-fluoro-11.beta.,16.alpha.,17,21-tetrahydroxy-, cyclic 16,17-acetal with acetone
Pregna-1,20-dione, 9-fluoro-11.beta.,16.alpha.,17,21-tetrahydroxy-,cyclic 16,17-acetal with acetone
Triamcinolone acetonide for system suitability, European Pharmacopoeia (EP) Reference Standard