ChemSpider 2D Image | Prednisone | C21H26O5

Prednisone

  • Molecular FormulaC21H26O5
  • Average mass358.428 Da
  • Monoisotopic mass358.178009 Da
  • ChemSpider ID5656

  • defined stereocentres - 6 of 6 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

(8S,9S,10R,13S,14S,17R)-17-Hydroxy-17-(hydroxyacetyl)-10,13-dimethyl-7,8,9,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-3,11(6H)-dion
(8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(hydroxyacetyl)-10,13-dimethyl-7,8,9,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthrene-3,11(6H)-dione
(8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(hydroxyacétyl)-10,13-diméthyl-7,8,9,10,12,13,14,15,16,17-décahydro-3H-cyclopenta[a]phénanthrène-3,11(6H)-dione
1,4-Pregnadiene-17a,21-diol-3,11,20-trione
1,4-Pregnadiene-17α,21-diol-3,11,20-trione
17,21-Dihydroxypregna-1,4-dien-3,11,20-trion [German] [ACD/IUPAC Name]
17,21-Dihydroxypregna-1,4-diene-3,11,20-trione [ACD/IUPAC Name]
17,21-Dihydroxyprégna-1,4-diène-3,11,20-trione [French] [ACD/IUPAC Name]
17α,21-Dihydroxy-1,4-pregnadiene-3,11,20-trione
1-Cortisone
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

536 [DBID]
DRG 0227 [DBID]
81552_FLUKA [DBID]
AI3-52939 [DBID]
AIDS184445 [DBID]
AIDS-184445 [DBID]
C07370 [DBID]
CCRIS 2646 [DBID]
DRG-0227 [DBID]
HSDB 3168 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Appearance:

      white crystalline powder OU Chemical Safety Data (No longer updated) More details

    • Stability:

      Stable. Incompatible with strong oxidizing agents. OU Chemical Safety Data (No longer updated) More details

    • Toxicity:

      IPR-MUS LD50 135 mg kg-1 OU Chemical Safety Data (No longer updated) More details
      Organic Compound; Ester; Drug; Anti-Inflammatory Agent; Antineoplastic Agent, Hormonal; Metabolite; Synthetic Compound; Glucocorticoid Toxin, Toxin-Target Database T3D4710

    • Safety:

      A07EA03 Wikidata Q424972
      H02AB07 Wikidata Q424972
      Safety glasses. Do not breathe dust. OU Chemical Safety Data (No longer updated) More details

    • Target Organs:

      Glucocorticoid Receptor agonist;MRP inhibitor TargetMol T1018

    • Chemical Class:

      A synthetic glucocorticoid drug that is particularly effective as an immunosuppressant, and affects virtually all of the immune system. Prednisone is a prodrug that is converted by the liver into pred nisolone (a <stereo>beta</stereo>-hydroxy group instead of the oxo group at position 11), which is the active drug and also a steroid. ChEBI CHEBI:8382
      A synthetic glucocorticoid drug that is particularly effective as an immunosuppressant, and affects virtually all of the immune system. Prednisone is a prodrug that is converted by the liver into pred nisolone (a beta-hydroxy group instead of the oxo group at position 11), which is the active drug and also a steroid. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8382, CHEBI:8382

    • Bio Activity:

      Endocrinology/ Hormones TargetMol T1018
      Glucocorticoid receptor;MRP1 TargetMol T1018
      Others MedChem Express HY-B0214
      Prednisone (Adasone) is a synthetic corticosteroid agent that is particularly effective as an immunosuppressant compound. MedChem Express
      Prednisone (Adasone) is a synthetic corticosteroid agent that is particularly effective as an immunosuppressant compound.; Target: Others; Prednisone is a synthetic corticosteroid drug that is particu larly effective as an immunosuppressant drug. MedChem Express HY-B0214
      Prednisone (Adasone) is a synthetic corticosteroid agent that is particularly effective as an immunosuppressant compound.;Target: Prednisone is a synthetic corticosteroid drug that is particularly effective as an immunosuppressant drug. It is used to treat certain inflammatory diseases (such as moderate allergic reactions) and (at higher doses) some types of cancer, but has significant adverse effects. Because it suppresses the immune system, it leaves patients more susceptible to infections.Prednisone can also be used in the treatment of decompensated heart failure to potentiate renal responsiveness to diuretics, especially in heart failure patients with refractory diuretic resistance with large dose of loop diuretics. The mechanism is prednisone, as a glucocorticoid, can improve renal responsiveness to atrial natriuretic peptide by increasing the density of natriuretic peptide receptor type A in the renal inner medullary collecting duct, inducing a potent diuresis. MedChem Express HY-B0214

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

Density: 1.3±0.1 g/cm3
Boiling Point: 573.7±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.6 mmHg at 25°C
Enthalpy of Vaporization: 98.7±6.0 kJ/mol
Flash Point: 314.8±26.6 °C
Index of Refraction: 1.604
Molar Refractivity: 94.1±0.4 cm3
#H bond acceptors: 5
#H bond donors: 2
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 1.57
ACD/LogD (pH 5.5): 1.64
ACD/BCF (pH 5.5): 10.42
ACD/KOC (pH 5.5): 186.31
ACD/LogD (pH 7.4): 1.64
ACD/BCF (pH 7.4): 10.42
ACD/KOC (pH 7.4): 186.31
Polar Surface Area: 92 Å2
Polarizability: 37.3±0.5 10-24cm3
Surface Tension: 58.6±5.0 dyne/cm
Molar Volume: 273.6±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) =  1.59
    Log Kow (Exper. database match) =  1.46
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  502.06  (Adapted Stein & Brown method)
    Melting Pt (deg C):  213.56  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.89E-013  (Modified Grain method)
    MP  (exp database):  234 dec deg C
    Subcooled liquid VP: 5.17E-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):  312
       log Kow used: 1.46 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  274.18 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 :   2.83E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.369E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.46  (exp database)
  Log Kaw used:  -7.937  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  9.397
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.2043
   Biowin2 (Non-Linear Model)     :   0.0006
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.8632  (months      )
   Biowin4 (Primary Survey Model) :   2.9331  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5678
   Biowin6 (MITI Non-Linear Model):   0.1452
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -2.0450
 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):  6.89E-009 Pa (5.17E-011 mm Hg)
  Log Koa (Koawin est  ): 9.397
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  435 
       Octanol/air (Koa) model:  0.000612 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.0467 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  67.9149 E-12 cm3/molecule-sec
      Half-Life =     0.157 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.890 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    :  36.36
      Log Koc:  1.561 

 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 = 0.424 (BCF = 2.656)
       log Kow used: 1.46 (expkow database)

 Volatilization from Water:
    Henry LC:  2.83E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.917E+006  hours   (1.632E+005 days)
    Half-Life from Model Lake : 4.273E+007  hours   (1.78E+006 days)

 Removal In Wastewater Treatment:
    Total removal:               1.96  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.87  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       0.138           3.2          1000       
   Water     41.2            1.44e+003    1000       
   Soil      58.6            2.88e+003    1000       
   Sediment  0.103           1.3e+004     0          
     Persistence Time: 940 hr

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