ChemSpider 2D Image | Triamcinolone | C21H27FO6

Triamcinolone

  • Molecular FormulaC21H27FO6
  • Average mass394.434 Da
  • Monoisotopic mass394.179169 Da
  • ChemSpider ID29046

  • defined stereocentres - 8 of 8 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

(11β,16α)-9-Fluor-11,16,17,21-tetrahydroxypregna-1,4-dien-3,20-dion [German] [ACD/IUPAC Name]
(11β,16α)-9-Fluoro-11,16,17,21-tetrahydroxypregna-1,4-diene-3,20-dione [ACD/IUPAC Name]
(11β,16α)-9-Fluoro-11,16,17,21-tétrahydroxyprégna-1,4-diène-3,20-dione [French] [ACD/IUPAC Name]
(8S,9R,10S,11S,13S,14S,16R,17S)-9-Fluor-11,16,17-trihydroxy-17-(hydroxyacetyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-on
(8S,9R,10S,11S,13S,14S,16R,17S)-9-fluoro-11,16,17-trihydroxy-17-(hydroxyacetyl)-10,13-dimethyl-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,16R,17S)-9-fluoro-11,16,17-trihydroxy-17-(hydroxyacétyl)-10,13-diméthyl-6,7,8,9,10,11,12,13,14,15,16,17-dodécahydro-3H-cyclopenta[a]phénanthrén-3-one
(8S,9R,10S,11S,13S,14S,16R,17S)-9-Fluoro-17-glycoloyl-11,16,17-trihydroxy-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one
124-94-7 [RN]
16a-Hydroxy-9a-fluoroprednisolone
1ZK20VI6TY
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

755 [DBID]
287334_ALDRICH [DBID]
AIDS124117 [DBID]
AIDS-124117 [DBID]
BRN 2341955 [DBID]
CL 19823 [DBID]
D00385 [DBID]
EU-0101179 [DBID]
HSDB 3194 [DBID]
MLS000028542 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Toxicity:

      Organic Compound; Organofluoride; Ester; Drug; Anti-Inflammatory Agent; Metabolite; Synthetic Compound; Glucocorticoid Toxin, Toxin-Target Database T3D4756

    • Safety:

      A01AC01 Wikidata Q1074056
      C05AA12 Wikidata Q1074056
      D07AB09 Wikidata Q1074056
      D07XB02 Wikidata Q1074056
      H02AB08 Wikidata Q1074056
      R01AD11 Wikidata Q1074056
      R03BA06 Wikidata Q1074056
      S01BA05 Wikidata Q1074056

    • Target Organs:

      COX inhibitor;Glucocorticoid Receptor antagonist TargetMol T0798

    • Chemical Class:

      A C<smallsub>21</smallsub>-steroid hormone that is 1,4-pregnadiene-3,20-dione carrying four hydroxy substituents at positions 11<stereo>beta</stereo>, 16<stereo>alpha</stereo>, 17<stereo>alpha</stereo > and 21 as well as a fluoro substituent at position 9. Used in the form of its 16,17-acetonide to treat various skin infections. ChEBI CHEBI:9667
      A C21-steroid hormone that is 1,4-pregnadiene-3,20-dione carrying four hydroxy substituents at positions 11beta, 16alpha, 17alpha and 21 as well as a fluoro substituent at position 9. Used in the form of its 16,17-acetonide to treat various skin infections. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9667, CHEBI:9667

    • Bio Activity:

      Glucocorticoid Receptor MedChem Express HY-B0328
      GPCR/G protein MedChem Express HY-B0328
      GPCR/G protein; MedChem Express HY-B0328
      Neuroscience TargetMol T0798
      Prostaglandin G/H synthase ;Glucocorticoid receptor TargetMol T0798
      Triamcinolone is a long-acting synthetic corticosteroid. MedChem Express
      Triamcinolone is a long-acting synthetic corticosteroid.; Target: Glucocorticoid Receptor; Dimethyl fumarate is an anti-inflammatory. MedChem Express HY-B0328
      Triamcinolone is a long-acting synthetic corticosteroid.;Target: Glucocorticoid ReceptorDimethyl fumarate is an anti-inflammatory. It is indicated for multiple sclerosis patients with relapsing forms and is also being investigated for the treatment of psoriasis. The mechanism of action of dimethyl fumarate in multiple sclerosis is not well understood. It is thought to involve dimethyl fumarate degradation to its active metabolite monomethyl fumarate (MMF) then MMF up-regulates the Nuclear factor (erythroid-derived 2)-like 2 (Nrf2) pathway that is activated in response to oxidative stress [1]. ;The mean duration of follow-up was 40 months. The rate of decline in the FEV1 after bronchodilator use was similar in the 559 participants in the triamcinolone group and the 557 participants in the placebo group (44.2+/-2.9 vs. 47.0+/-3.0 ml per year, P= 0.50). Members of the triamcinolone group had fewer respiratory symptoms during the course of the study (21.1 per 100 person-years vs. 28.2 MedChem Express HY-B0328

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

Density: 1.4±0.1 g/cm3
Boiling Point: 587.5±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.7 mmHg at 25°C
Enthalpy of Vaporization: 100.7±6.0 kJ/mol
Flash Point: 309.1±30.1 °C
Index of Refraction: 1.618
Molar Refractivity: 97.1±0.4 cm3
#H bond acceptors: 6
#H bond donors: 4
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 0.83
ACD/LogD (pH 5.5): 0.92
ACD/BCF (pH 5.5): 2.92
ACD/KOC (pH 5.5): 75.01
ACD/LogD (pH 7.4): 0.92
ACD/BCF (pH 7.4): 2.92
ACD/KOC (pH 7.4): 75.00
Polar Surface Area: 115 Å2
Polarizability: 38.5±0.5 10-24cm3
Surface Tension: 65.6±5.0 dyne/cm
Molar Volume: 277.4±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) =  0.96
    Log Kow (Exper. database match) =  1.16
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  537.02  (Adapted Stein & Brown method)
    Melting Pt (deg C):  229.89  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.32E-015  (Modified Grain method)
    MP  (exp database):  270 deg C
    Subcooled liquid VP: 1.15E-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):  338.7
       log Kow used: 1.16 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  80 mg/L (25 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  4924.7 mg/L
    Wat Sol (Exper. database match) =  80.00
       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 :   1.97E-009  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.555E-018 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.16  (exp database)
  Log Kaw used:  -7.094  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  8.254
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.3139
   Biowin2 (Non-Linear Model)     :   0.0009
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.9140  (months      )
   Biowin4 (Primary Survey Model) :   3.0088  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.7429
   Biowin6 (MITI Non-Linear Model):   0.0037
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.5623
 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):  1.53E-010 Pa (1.15E-012 mm Hg)
  Log Koa (Koawin est  ): 8.254
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.96E+004 
       Octanol/air (Koa) model:  4.41E-005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.00351 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  84.3636 E-12 cm3/molecule-sec
      Half-Life =     0.127 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.521 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 = 0.193 (BCF = 1.56)
       log Kow used: 1.16 (expkow database)

 Volatilization from Water:
    Henry LC:  1.97E-009 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 5.903E+005  hours   (2.459E+004 days)
    Half-Life from Model Lake : 6.439E+006  hours   (2.683E+005 days)

 Removal In Wastewater Treatment:
    Total removal:               1.90  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.81  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       0.131           2.66         1000       
   Water     46.9            1.44e+003    1000       
   Soil      52.8            2.88e+003    1000       
   Sediment  0.105           1.3e+004     0          
     Persistence Time: 849 hr

Click to predict properties on the Chemicalize site


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