ChemSpider 2D Image | Fluocinolone Acetonide | C24H30F2O6

Fluocinolone Acetonide

  • Molecular FormulaC24H30F2O6
  • Average mass452.488 Da
  • Monoisotopic mass452.201050 Da
  • ChemSpider ID5980
  • defined stereocentres - 9 of 9 defined stereocentres


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(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-Difluor-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-
(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-Difluor-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-on
(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-Difluor-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-on [German] [ACD/IUPAC Name]
(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-Difluoro-5-hydroxy-6b-(2-hydroxyacétyl)-4a,6a,8,8-tétraméthyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodécahydro-2H-naphto[2',1':4,5]indéno[1,2-d][1,3]dioxol- 2-one [French] [ACD/IUPAC Name]
(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-difluoro-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
(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-difluoro-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
(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-difluoro-5-hydroxy-6b-(hydroxyacétyl)-4a,6a,8,8-tétraméthyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodécahydro-2H-naphto[2',1':4,5]indéno[1,2-d][1,3]dioxol-2-
(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-difluoro-5-hydroxy-6b-(hydroxyacétyl)-4a,6a,8,8-tétraméthyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodécahydro-2H-naphto[2',1':4,5]indéno[1,2-d][1,3]dioxol-2-one
(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-Difluoro-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 [ACD/IUPAC Name]
(6a,11b,16a)-6,9-Difluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]-pregna-1,4-diene-3,20-dione
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

0CD5FD6S2M [DBID]
AIDS125952 [DBID]
AIDS-125952 [DBID]
CCRIS 3250 [DBID]
D01825 [DBID]
F8880_SIGMA [DBID]
HSDB 3083 [DBID]
MLS000028545 [DBID]
NCI60_042042 [DBID]
NSC 92339 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      WHITE POWDER NIH Clinical Collection [SMR000058329]
    • Safety:

      C05AA10 Wikidata Q924467
      D07AC04 Wikidata Q924467
      GHS07 Biosynth W-104704
      H315; H319; H335 Biosynth W-104704
      P261; P305+P351+P338 Biosynth W-104704
      S01BA15 Wikidata Q924467
      S02BA08 Wikidata Q924467
      Warning Biosynth W-104704
      Xi Abblis Chemicals AB1010906
    • Target Organs:

      Others TargetMol T0367
    • Chemical Class:

      A fluorinated steroid that is flunisolide in which the hydrogen at position 9 is replaced by fluorine. A corticosteroid with glucocorticoid activity, it is used (both as the anhydrous form and as the dihydrate) in creams, gels and ointments for the treatment of various skin disorders. ChEBI CHEBI:31623
    • Bio Activity:

      Fluocinolone Acetonide is a glucocorticoid derivative used topically in the treatment of various skin disorders. MedChem Express
      Fluocinolone Acetonide is a glucocorticoid derivative used topically in the treatment of various skin disorders.; Target: Glucocorticoid Receptor; Fluocinolone acetonide is a corticosteroid primarily used in dermatology to reduce skin inflammation and relieve itching. MedChem Express HY-B0415
      Fluocinolone Acetonide is a glucocorticoid derivative used topically in the treatment of various skin disorders.;Target: Glucocorticoid ReceptorFluocinolone acetonide is a corticosteroid primarily used in dermatology to reduce skin inflammation and relieve itching. It is a synthetic hydrocortisone derivative. The fluorine substitution at position 9 in the steroid nucleus greatly enhances its activity. A typical dosage strength used in dermatology is 0.01-0.025%. One such cream is sold under the brand name Flucort-N and includes the antibiotic neomycin. The Glucocorticoid Receptor(GR) binding affinity (IC50) for Fluocinolone Acetonide(FA) was 2.0 nM, respectively. The values is similar to the GR transactivation EC50 of 0.7 nM for FA, respectively [1, 2]. MedChem Express HY-B0415
      Glucocorticoid Receptor MedChem Express HY-B0415
      GPCR/G protein MedChem Express HY-B0415
      GPCR/G protein; MedChem Express HY-B0415
      Others TargetMol T0367

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density: 1.4±0.1 g/cm3
Boiling Point: 578.5±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.6 mmHg at 25°C
Enthalpy of Vaporization: 99.4±6.0 kJ/mol
Flash Point: 303.7±30.1 °C
Index of Refraction: 1.577
Molar Refractivity: 109.5±0.4 cm3
#H bond acceptors: 6
#H bond donors: 2
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 2.24
ACD/LogD (pH 5.5): 2.39
ACD/BCF (pH 5.5): 38.57
ACD/KOC (pH 5.5): 475.39
ACD/LogD (pH 7.4): 2.39
ACD/BCF (pH 7.4): 38.57
ACD/KOC (pH 7.4): 475.38
Polar Surface Area: 93 Å2
Polarizability: 43.4±0.5 10-24cm3
Surface Tension: 52.7±5.0 dyne/cm
Molar Volume: 330.3±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) =  2.56
    Log Kow (Exper. database match) =  2.48
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  520.94  (Adapted Stein & Brown method)
    Melting Pt (deg C):  222.38  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.02E-014  (Modified Grain method)
    MP  (exp database):  265-266 deg C
    Subcooled liquid VP: 1.29E-011 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):  10.95
       log Kow used: 2.48 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  9.821 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.96E-012  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.642E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.48  (exp database)
  Log Kaw used:  -10.096  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  12.576
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.7511
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.3962  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.6227  (weeks-months)
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4905
   Biowin6 (MITI Non-Linear Model):   0.0000
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -2.5435
 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):  1.72E-009 Pa (1.29E-011 mm Hg)
  Log Koa (Koawin est  ): 12.576
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.74E+003 
       Octanol/air (Koa) model:  0.925 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.987 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  78.0459 E-12 cm3/molecule-sec
      Half-Life =     0.137 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.645 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    :  10
      Log Koc:  1.000 

 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 = 1.210 (BCF = 16.2)
       log Kow used: 2.48 (expkow database)

 Volatilization from Water:
    Henry LC:  1.96E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 6.354E+008  hours   (2.648E+007 days)
    Half-Life from Model Lake : 6.932E+009  hours   (2.888E+008 days)

 Removal In Wastewater Treatment:
    Total removal:               3.04  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.94  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       0.0414          2.84         1000       
   Water     15.9            4.32e+003    1000       
   Soil      83.9            8.64e+003    1000       
   Sediment  0.138           3.89e+004    0          
     Persistence Time: 2.8e+003 hr




                    

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