ChemSpider 2D Image | Betamethasone | C22H29FO5

Betamethasone

  • Molecular FormulaC22H29FO5
  • Average mass392.461 Da
  • Monoisotopic mass392.199890 Da
  • ChemSpider ID9399
  • defined stereocentres - 8 of 8 defined stereocentres


More details:



Featured data source



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

(11b,16b)-9-fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione
(11β,16β)-9-Fluor-11,17,21-trihydroxy-16-methylpregna-1,4-dien-3,20-dion [German] [ACD/IUPAC Name]
(11β,16β)-9-Fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione [ACD/IUPAC Name]
(11β,16β)-9-Fluoro-11,17,21-trihydroxy-16-méthylprégna-1,4-diène-3,20-dione [French] [ACD/IUPAC Name]
(8S,9R,10S,11S,13S,14S,16S,17R)-9-Fluor-11,17-dihydroxy-17-(hydroxyacetyl)-10,13,16-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-on [German]
(8S,9R,10S,11S,13S,14S,16S,17R)-9-fluoro-11,17-dihydroxy-17-(hydroxyacetyl)-10,13,16-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one
(8S,9R,10S,11S,13S,14S,16S,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]
1045
16b-Methyl-9a-fluoro-D1-hydrocortisone
16b-Methyl-9a-fluoroprednisolone
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

9842X06Q6M [DBID]
UNII-9842X06Q6M [DBID]
34166_RIEDEL [DBID]
AIDS070523 [DBID]
AIDS-070523 [DBID]
B7005_SIAL [DBID]
B9675_SIAL [DBID]
BRN 3176546 [DBID]
D00244 [DBID]
HSDB 3015 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Safety:

      A07EA04 Wikidata Q416132
      C05AA05 Wikidata Q416132
      D07AC01 Wikidata Q416132
      D07XC01 Wikidata Q416132
      H02AB01 Wikidata Q416132
      Irritant SynQuest 2420-1-03, 85147
      R01AD06 Wikidata Q416132
      R03BA04 Wikidata Q416132
      S01BA06 Wikidata Q416132
      S01CB04 Wikidata Q416132
      S02BA07 Wikidata Q416132
      S03BA03 Wikidata Q416132
    • Target Organs:

      Glucocorticoid Receptor agonist TargetMol T1652
    • Therapeutical Effect:

      Glucocorticoids Sean Ekins
    • Drug Status:

      approved BIONET-Key Organics KS-5302
    • Bio Activity:

      Betamethasone is a glucocorticoid steroid with anti-inflammatory and immunosuppressive properties. MedChem Express
      Betamethasone is a glucocorticoid steroid with anti-inflammatory and immunosuppressive properties.; Target: Glucocorticoid Receptor; Betamethasone is a potent glucocorticoid steroid with anti-inflamma tory and immunosuppressive properties. MedChem Express HY-13570
      Betamethasone is a glucocorticoid steroid with anti-inflammatory and immunosuppressive properties.;Target: Glucocorticoid ReceptorBetamethasone is a potent glucocorticoid steroid with anti-inflammatory and immunosuppressive properties. Unlike other drugs with these effects, betamethasone does not cause water retention. The median (range) IC50 value for betamethasone butyrate propionate evaluated in the streptococcal pyrogenic enterotoxin A-stimulated peripheral-blood mononuclear cells was 291.6 (0.001-1171.5) ng/ml, which was significantly higher than the value 0.072 (0.01-222.5) ng/ml found in concanavalin A-stimulated peripheral-blood mononuclear cells (P=0.0245) [1]. Children exposed prenatally to betamethasone (n = 121) did not differ in systolic or diastolic blood pressure from children exposed to placebo (n = 102) (mean difference: systolic: -1.6 mm Hg; 95% confidence interval: -4.1 to 0.8 mm Hg; diastolic: -0.3 mm Hg; 95% confidence interval: -2.5 to 1.8 mm Hg) [2]. Intra-ar MedChem Express HY-13570
      Endocrinology/ Hormones TargetMol T1652
      Glucocorticoid Receptor MedChem Express HY-13570
      Glucocorticoid Receptor TargetMol T1652
      GPCR/G protein MedChem Express HY-13570
      GPCR/G protein; MedChem Express HY-13570

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

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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