ChemSpider 2D Image | Dexamethasone | C22H29FO5


  • Molecular FormulaC22H29FO5
  • Average mass392.461 Da
  • Monoisotopic mass392.199890 Da
  • ChemSpider ID5541
  • defined stereocentres - 8 of 8 defined stereocentres

More details:

Featured data source

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

Dexamethasone [BAN] [INN] [JAN] [JP15] [USP] [Wiki]
(11β,16α)-9-Fluor-11,17,21-trihydroxy-16-methylpregna-1,4-dien-3,20-dion [German] [ACD/IUPAC Name]
(11β,16α)-9-Fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione [ACD/IUPAC Name]
(11β,16α)-9-Fluoro-11,17,21-trihydroxy-16-méthylprégna-1,4-diène-3,20-dione [French] [ACD/IUPAC Name]
(8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-17-(hydroxyacétyl)-10,13,16-triméthyl-6,7,8,9,10,11,12,13,14,15,16,17-dodécahydro-3H-cyclopenta[a]phénanthrén-3-one [French]

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

31375_FLUKA [DBID]
AI3-50934 [DBID]
C15643 [DBID]
D00292 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Toxicity:

      Drug; Anti-Inflammatory Agent; Antiemetic; Antineoplastic Agent, Hormonal; Metabolite; Synthetic Compound; Glucocorticoid Toxin, Toxin-Target Database T3D4982
    • Safety:

      36/37 Alfa Aesar A17590
      63 Alfa Aesar A17590
      A01AC02 Wikidata Q422252
      C05AA09 Wikidata Q422252
      D07AB19 Wikidata Q422252
      D07XB05 Wikidata Q422252
      D10AA03 Wikidata Q422252
      H02AB02 Wikidata Q422252
      H361d Alfa Aesar A17590
      P280h Alfa Aesar A17590
      R01AD03 Wikidata Q422252
      S01BA01 Wikidata Q422252
      S01CB01 Wikidata Q422252
      S02BA06 Wikidata Q422252
      S03BA01 Wikidata Q422252
      Warning Alfa Aesar A17590
    • Target Organs:

      Annexin A agonist;NR stimulator;MRP inhibitor;iNOS negative modulator;Glucocorticoid receptor agonist;IL antagonist TargetMol T1076
    • Chemical Class:

      A fluorinated steroid that is 9-fluoropregna-1,4-diene substituted by hydroxy groups at positions 11, 17 and 21, a methyl group at position 16 and oxo groups at positions 3 and 20. It is a synthetic m ember of the class of glucocorticoids. ChEBI, CHEBI:41879
    • Therapeutical Effect:

      Antiemetics,Glucocorticoids Sean Ekins
    • Bio Activity:

      <p>Synthetic glucocorticoid.&nbsp;Differentiates mesenchymal stem cells (MSCs) into adipogenic, chondrogenic and osteogenic lineages.</p> <p>Commonly used with <a href=/l-ascorbic-acid.html title=Ascorbic acid for stem cell differentiation | Hello Bio target=_self>ascorbic acid</a> and &beta;-Gly for osteogenic differentiation of stem cells.</p> <p>Also shows potent anti-inflammatory and immunospressant effects. Active <em>in vivo</em>.</p> <p><a href=/dexamethasone-water-soluble.html title=Water soluble dexamethasone | Hello Bio target=_self>Water soluble dexamethasone</a> also available.</p> Hello Bio HB2521
      <p>Synthetic glucocorticoid. Differentiates mesenchymal stem cells (MSCs) into adipogenic, chondrogenic and osteogenic lineages.</p> <p>Commonly used with <a title="Ascorbic acid for stem cell differentiation | Hello Bio" href="/l-ascorbic-acid.html" target="_self">ascorbic acid</a> and ?-Gly for osteogenic differentiation of stem cells.</p> <p>Also shows potent anti-inflammatory and immunospressant effects. Active <em>in vivo</em>.</p> <p>Recently investigated as part of COVID-19 compound repurposing.</p> <p>Apoptosis inducer.</p> <p><a title="Water soluble dexamethasone | Hello Bio" href="/dexamethasone-water-soluble.html" target="_self">Water soluble dexamethasone</a> also available.</p> Hello Bio HB2521
      Annexin A1;NR;MRP1;iNOS;Glucocorticoid receptor;IL receptor TargetMol T1076
      Biochemicals & small molecules/Agonists & activators Hello Bio HB2521
      Cell process/Stem cells/Differentiation Hello Bio HB2521
      Dexamethasone(MK 125; NSC 34521; Prednisolone F) is a potent synthetic member of the glucocorticoid class of steroid drugs that has anti-inflammatory and immunosuppressant properties.; IC50 Value: 58 nM (HECM-induced eosinophil survival) [1]; Target: ; in vitro: DEX in concentrations from 1 to 100?M did not change LDH release but exposure to 10?M and 100?M DEX for 24, 48 and 72h caused a significa nt reduction in cell viability and proliferation as confirmed by MTT reduction and BrdU ELISA assays, respectively [2]. MedChem Express HY-14648
      Endocrinology/ Hormones TargetMol T1076
      Glucocorticoid Receptor MedChem Express HY-14648
      GPCR/G protein MedChem Express HY-14648
      GPCR/G protein; MedChem Express HY-14648
      Receptors & Transporters/Nuclear hormone/Glucocorticoid Hello Bio HB2521
      Synthetic glucocorticoid. Induces hMSC differentiation. Hello Bio HB2521

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.3±0.1 g/cm3
Boiling Point: 568.2±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.5 mmHg at 25°C
Enthalpy of Vaporization: 98.0±6.0 kJ/mol
Flash Point: 297.5±30.1 °C
Index of Refraction: 1.592
Molar Refractivity: 100.2±0.4 cm3
#H bond acceptors: 5
#H bond donors: 3
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 1.87
ACD/LogD (pH 5.5): 1.92
ACD/BCF (pH 5.5): 16.85
ACD/KOC (pH 5.5): 262.77
ACD/LogD (pH 7.4): 1.92
ACD/BCF (pH 7.4): 16.85
ACD/KOC (pH 7.4): 262.76
Polar Surface Area: 95 Å2
Polarizability: 39.7±0.5 10-24cm3
Surface Tension: 56.6±5.0 dyne/cm
Molar Volume: 296.2±5.0 cm3

Predicted data is generated using the US Environmental Protection Agency�s EPISuite™

 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  1.72
    Log Kow (Exper. database match) =  1.83
       Exper. Ref:  Hansch,C et al. (1995)
    Log Kow (Exper. database match) =  1.94
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  508.92  (Adapted Stein & Brown method)
    Melting Pt (deg C):  216.77  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.81E-014  (Modified Grain method)
    MP  (exp database):  232 deg C
    Subcooled liquid VP: 9.82E-012 mm Hg (25 deg C, Mod-Grain method)

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  75.14
       log Kow used: 1.94 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  89 mg/L (25 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)
     Water Sol (Exper. database match) =  66.5 mg/L (25 deg C)
        Exper. Ref:  EPA

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  58.572 mg/L
    Wat Sol (Exper. database match) =  89.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)
    Wat Sol (Exper. database match) =  66.50
       Exper. Ref:  EPA

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Vinyl/Allyl Ketones

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   7.15E-008  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.993E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.94  (exp database)
  Log Kaw used:  -5.534  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  7.474
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.1561
   Biowin2 (Non-Linear Model)     :   0.0003
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.7584  (months      )
   Biowin4 (Primary Survey Model) :   2.8822  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5880
   Biowin6 (MITI Non-Linear Model):   0.0015
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.7746
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  1.31E-009 Pa (9.82E-012 mm Hg)
  Log Koa (Koawin est  ): 7.474
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.29E+003 
       Octanol/air (Koa) model:  7.31E-006 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.000585 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  69.5010 E-12 cm3/molecule-sec
      Half-Life =     0.154 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.847 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.312500 E-17 cm3/molecule-sec
      Half-Life =     0.873 Days (at 7E11 mol/cm3)
      Half-Life =     20.955 Hrs
   Fraction sorbed to airborne particulates (phi): 1 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  95.97
      Log Koc:  1.982 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
    Rate constants can NOT be estimated for this structure!

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.794 (BCF = 6.22)
       log Kow used: 1.94 (expkow database)

 Volatilization from Water:
    Henry LC:  7.15E-008 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.622E+004  hours   (676 days)
    Half-Life from Model Lake : 1.772E+005  hours   (7382 days)

 Removal In Wastewater Treatment:
    Total removal:               2.20  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.10  percent
    Total to Air:                0.00  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.122           3.14         1000       
   Water     30.6            1.44e+003    1000       
   Soil      69.1            2.88e+003    1000       
   Sediment  0.113           1.3e+004     0          
     Persistence Time: 1.11e+003 hr


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