ChemSpider 2D Image | Methylprednisolone | C22H30O5

Methylprednisolone

  • Molecular FormulaC22H30O5
  • Average mass374.471 Da
  • Monoisotopic mass374.209320 Da
  • ChemSpider ID6485
  • defined stereocentres - 8 of 8 defined stereocentres


More details:



Featured data source



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

Methylprednisolone [BAN] [INN] [JAN] [USAN] [Wiki]
(6a,11b)-11,17,21-Trihydroxy-6-methyl-1,4-pregnadiene-3,20-dione
(6S,8S,9S,10R,11S,13S,14S,17R)-11,17-Dihydroxy-17-(hydroxyacetyl)-6,10,13-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-on
(6α)-11,17,21-Trihydroxy-6-methylpregna-1,4-dien-3,20-dion [German] [ACD/IUPAC Name]
(6α)-11,17,21-Trihydroxy-6-methylpregna-1,4-diene-3,20-dione [ACD/IUPAC Name]
(6α)-11,17,21-Trihydroxy-6-méthylprégna-1,4-diène-3,20-dione [French] [ACD/IUPAC Name]
(6α,11β)-11,17,21-Trihydroxy-6-methylpregna-1,4-dien-3,20-dion [German] [ACD/IUPAC Name]
(6α,11β)-11,17,21-Trihydroxy-6-methylpregna-1,4-diene-3,20-dione [ACD/IUPAC Name]
(6α,11β)-11,17,21-Trihydroxy-6-méthylprégna-1,4-diène-3,20-dione [French] [ACD/IUPAC Name]
11b,17a,21-Trihydroxy-6a-methyl-1,4-pregnadiene-3,20-dione
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

DRG 0050 [DBID]
46436_RIEDEL [DBID]
AIDS184446 [DBID]
AIDS-184446 [DBID]
BRN 2340300 [DBID]
D00407 [DBID]
DRG-0050 [DBID]
HSDB 3127 [DBID]
M0639_SIGMA [DBID]
MLS000028541 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      WHITE TO OFF-WHITE NIH Clinical Collection [SMR000058330]
    • Safety:

      5 Axon Medchem 2066
      D07AA01 Wikidata Q417222
      D10AA02 Wikidata Q417222
      GHS07 Biosynth Q-201395
      H02AB04 Wikidata Q417222
      H303;H313;H317;H333;H334;H335;H373 Axon Medchem 2066
      H315; H319; H335 Biosynth Q-201395
      no pictogram Axon Medchem 2066
      P101;P102;P103;P260;P262;P263;P264;P270;P280;P304;P312;P340 Axon Medchem 2066
      P261; P280; P302+P352; P304+P340; P305+P351+P338; P312 Biosynth Q-201395
      Sold for research purposes under agreement from Pfizer Inc. Tocris Bioscience 4819
      Warning Biosynth Q-201395
      Warning Axon Medchem 2066
    • Target Organs:

      Glucocorticoid Receptor agonist TargetMol T1171
    • Chemical Class:

      The 6<stereo>alpha</stereo>-stereoisomer of 6-methylprednisolone. ChEBI CHEBI:6888
    • Drug Status:

      approved BIONET-Key Organics KS-1273
    • Bio Activity:

      Endocrinology/ Hormones TargetMol T1171
      Glucocorticoid Receptor Tocris Bioscience 4819
      Glucocorticoid Receptor MedChem Express HY-B0260
      Glucocorticoid Receptor TargetMol T1171
      Glucocorticoid receptor (GR) agonist. Displays anti-inflammatory and antioxidant properties. Attenuates apoptosis in oligodendrocytes after injury stimuli. Upregulates expression of Bcl-xL via direct binding of the GR/STAT5 complex. Neuroprotective. Tocris Bioscience 4819
      Glucocorticoid receptor (GR) agonist. Displays anti-inflammatory and antioxidant properties. Attenuates apoptosis in oligodendrocytes after injury stimuli. Upregulates expression of Bcl-xL via direct binding of the GR/STAT5 complex. Neuroprotective. Tocris Bioscience 4819
      Glucocorticoid receptor agonist Tocris Bioscience 4819
      GPCR/G protein MedChem Express HY-B0260
      GPCR/G protein; MedChem Express HY-B0260
      Immunomodulator; Zerenex Molecular [ZBioX-0530]
      Methylprednisolone is a synthetic corticosteroid with anti-inflammatory and immunomodulating properties. MedChem Express
      Methylprednisolone is a synthetic corticosteroid with anti-inflammatory and immunomodulating properties.; Target: Glucocorticoid Receptor; Methylprednisolone is typically used for its anti-inflammator y effects. MedChem Express HY-B0260
      Methylprednisolone is a synthetic corticosteroid with anti-inflammatory and immunomodulating properties.;Target: Glucocorticoid ReceptorMethylprednisolone is typically used for its anti-inflammatory effects. Common uses include arthritis therapy and short-term treatment of bronchial inflammation or acute bronchitis due to various respiratory diseases. Methylprednisolone is used both in the treatment of acute periods and long-term management of autoimmune diseases, most notably systemic lupus erythematosus. It is also used for vestibular neuritis [1].After six months the patients who were treated with methylprednisolone within eight hours of their injury had significant improvement as compared with those given placebo in motor function (neurologic change scores of 16.0 and 11.2, respectively; P = 0.03) and sensation to pinprick (change scores of 11.4 and 6.6; P = 0.02) and touch (change scores, 8.9 and 4.3; P = 0.03). Benefit from methylprednisolone was seen in patients whose inju MedChem Express HY-B0260
      Nuclear Receptors Tocris Bioscience 4819

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

Density: 1.3±0.1 g/cm3
Boiling Point: 571.8±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.6 mmHg at 25°C
Enthalpy of Vaporization: 98.5±6.0 kJ/mol
Flash Point: 313.7±26.6 °C
Index of Refraction: 1.603
Molar Refractivity: 100.1±0.4 cm3
#H bond acceptors: 5
#H bond donors: 3
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 1.99
ACD/LogD (pH 5.5): 1.97
ACD/BCF (pH 5.5): 18.39
ACD/KOC (pH 5.5): 279.82
ACD/LogD (pH 7.4): 1.97
ACD/BCF (pH 7.4): 18.39
ACD/KOC (pH 7.4): 279.82
Polar Surface Area: 95 Å2
Polarizability: 39.7±0.5 10-24cm3
Surface Tension: 58.1±5.0 dyne/cm
Molar Volume: 291.5±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) =  1.82

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  513.91  (Adapted Stein & Brown method)
    Melting Pt (deg C):  219.10  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.92E-014  (Modified Grain method)
    MP  (exp database):  232.5 deg C
    Subcooled liquid VP: 6.72E-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):  123.3
       log Kow used: 1.82 (estimated)
       no-melting pt equation used
     Water Sol (Exper. database match) =  120 mg/L (25 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  89.98 mg/L
    Wat Sol (Exper. database match) =  120.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.59E-008  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.567E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.82  (KowWin est)
  Log Kaw used:  -5.833  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  7.653
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.3486
   Biowin2 (Non-Linear Model)     :   0.0021
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.0102  (months      )
   Biowin4 (Primary Survey Model) :   3.0616  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5690
   Biowin6 (MITI Non-Linear Model):   0.0730
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.4010
 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):  8.96E-010 Pa (6.72E-012 mm Hg)
  Log Koa (Koawin est  ): 7.653
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  3.35E+003 
       Octanol/air (Koa) model:  1.1E-005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.000882 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  73.8559 E-12 cm3/molecule-sec
      Half-Life =     0.145 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.738 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    :  60.12
      Log Koc:  1.779 

 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 = 0.700 (BCF = 5.007)
       log Kow used: 1.82 (estimated)

 Volatilization from Water:
    Henry LC:  3.59E-008 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.156E+004  hours   (1315 days)
    Half-Life from Model Lake : 3.445E+005  hours   (1.435E+004 days)

 Removal In Wastewater Treatment:
    Total removal:               2.11  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     2.02  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           2.98         1000       
   Water     33.4            1.44e+003    1000       
   Soil      66.4            2.88e+003    1000       
   Sediment  0.109           1.3e+004     0          
     Persistence Time: 1.05e+003 hr




                    

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