ChemSpider 2D Image | spironolactone | C24H32O4S

spironolactone

  • Molecular FormulaC24H32O4S
  • Average mass416.573 Da
  • Monoisotopic mass416.202118 Da
  • ChemSpider ID5628

  • defined stereocentres - 7 of 7 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

(7a,17a)-7-(Acetylthio)-17-hydroxy-3-oxopregn-4-ene-21-carboxylic acid g-lactone
17-Hydroxy-7a-mercapto-3-oxo-17a-pregn-4-ene-21-carboxylic Acid g-Lactone Acetate
200-133-6 [EINECS]
27O7W4T232
3-(3-Oxo-7a-acetylthio-17b-hydroxy-4-androsten-17a-yl)propionic Acid g-Lactone
4-Pregnen-21-oic acid-17α-ol-3-one-7α-thiol γ-lactone 7-acetate
52-01-7 [RN]
7α-(Acetylthio)-17α-hydroxy-3-oxopregn-4-ene-21-carboxylic acid γ-lactone
Aldace [Trade name]
Aldactone [Trade name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

987 [DBID]
BRN 0057767 [DBID]
C07310 [DBID]
D00443 [DBID]
HSDB 3184 [DBID]
NSC 150399 [DBID]
NSC150399 [DBID]
Prestwick0_000128 [DBID]
Prestwick1_000128 [DBID]
S3378_SIGMA [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Toxicity:

      Organic Compound; Ether; Ester; Drug; Diuretic; Metabolite; Synthetic Compound; Mineralocorticoid Receptor Antagonist Toxin, Toxin-Target Database T3D4753

    • Safety:

      C03DA01 Wikidata Q422188

    • Target Organs:

      Androgen Receptor antagonist;Calcium Channel;Estrogen/progestogen Receptor agonist;Glucocorticoid Receptor antagonist TargetMol T0476

    • Chemical Class:

      A steroid lactone that is 17<stereo>alpha</stereo>-pregn-4-ene-21,17-carbolactone substituted by an oxo group at position 3 and an <stereo>alpha</stereo>-acetylsulfanyl group at position 7. ChEBI CHEBI:9241
      A steroid lactone that is 17alpha-pregn-4-ene-21,17-carbolactone substituted by an oxo group at position 3 and an alpha-acetylsulfanyl group at position 7. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9241, CHEBI:9241

    • Therapeutical Effect:

      Aldosterone Antagonists,Diuretics Sean Ekins

    • Bio Activity:

      Androgen Receptor MedChem Express HY-B0561
      Androgen Receptor ;Calcium Channel;Estrogen/progestogen Receptor;Glucocorticoid Receptor TargetMol T0476
      Biochemicals & small molecules/Antagonists & inhibitors Hello Bio [HB2799]
      Competitive mineralocorticoid (aldosterone) receptor antagonist that exhibits antihypertensive activity in vivo. Also displays antiandrogen activity and inhibits steroid hormone biosynthesis. Tocris Bioscience 2968
      Endocrinology/ Hormones; Membrane Transporter/Ion Channel TargetMol T0476
      Mineralocorticoid and androgen receptor antagonist Hello Bio [HB2799]
      Mineralocorticoid Receptor Tocris Bioscience 2968
      Mineralocorticoid receptor (MR) antagonist. Also shows acticity at the androgen receptor (AR) (IC<sub>50</sub> values are 24 and 77 nM at MR and AR resepectively). Shows antihypertensive effects. Hello Bio [HB2799]
      Mineralocorticoid receptor antagonist Tocris Bioscience 2968
      Nuclear Receptors Tocris Bioscience 2968
      Others MedChem Express HY-B0561
      Receptors & Transporters/Nuclear hormone/Mineralocorticoid Hello Bio [HB2799]
      Spironolactone is a potent antagonist of the androgen receptor. MedChem Express http://www.medchemexpress.com/methyclothiazide.html, HY-B0561
      Spironolactone is a potent antagonist of the androgen receptor. ;Target: Androgen ReceptorSpironolactone is a potassium sparing diuretic that acts by antagonism of aldosterone in the distal renal tubules. It is used mainly in the treatment of refractory edema in patients with congestive heart failure, nephrotic syndrome, or hepatic cirrhosis. Its effects on the endocrine system are utilized in the treatments of hirsutism and acne but they can lead to adverse effects. 5% topical spironolactone cream acts as an antiandrogen in human sebaceous glands, competing with DHT receptors and producing a decrease of labelled DHT. At the concentrations used the effect has been only local. No side-effects were recorded during both studies [1]. Patients who received spironolactone had a significant improvement in the symptoms of heart failure, as assessed on the basis of the New York Heart Association functional class (P<0.001). Gynecomastia or breast pain was reported in 10 percent of men who we MedChem Express HY-B0561

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

Density: 1.2±0.1 g/cm3
Boiling Point: 597.0±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.7 mmHg at 25°C
Enthalpy of Vaporization: 88.9±3.0 kJ/mol
Flash Point: 302.3±18.1 °C
Index of Refraction: 1.586
Molar Refractivity: 112.7±0.4 cm3
#H bond acceptors: 4
#H bond donors: 0
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 3.12
ACD/LogD (pH 5.5): 2.78
ACD/BCF (pH 5.5): 76.20
ACD/KOC (pH 5.5): 773.94
ACD/LogD (pH 7.4): 2.78
ACD/BCF (pH 7.4): 76.20
ACD/KOC (pH 7.4): 773.94
Polar Surface Area: 86 Å2
Polarizability: 44.7±0.5 10-24cm3
Surface Tension: 50.9±5.0 dyne/cm
Molar Volume: 335.8±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) =  2.88
    Log Kow (Exper. database match) =  2.78
       Exper. Ref:  Hansch,C et al. (1995)
    Log Kow (Exper. database match) =  2.26
       Exper. Ref:  Hansch,C & Leo,A (1985)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  530.08  (Adapted Stein & Brown method)
    Melting Pt (deg C):  226.65  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.75E-010  (Modified Grain method)
    MP  (exp database):  134.5 deg C
    Subcooled liquid VP: 4.72E-009 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):  28.38
       log Kow used: 2.26 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  22 mg/L (25 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.5645 mg/L
    Wat Sol (Exper. database match) =  22.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.14E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  7.243E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.26  (exp database)
  Log Kaw used:  -8.332  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.592
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.1784
   Biowin2 (Non-Linear Model)     :   0.0115
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.7600  (months      )
   Biowin4 (Primary Survey Model) :   2.9931  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3719
   Biowin6 (MITI Non-Linear Model):   0.0347
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.6212
 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):  6.29E-007 Pa (4.72E-009 mm Hg)
  Log Koa (Koawin est  ): 10.592
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  4.77 
       Octanol/air (Koa) model:  0.00959 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.994 
       Mackay model           :  0.997 
       Octanol/air (Koa) model:  0.434 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 113.4687 E-12 cm3/molecule-sec
      Half-Life =     0.094 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.131 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.137500 E-17 cm3/molecule-sec
      Half-Life =     1.007 Days (at 7E11 mol/cm3)
      Half-Life =     24.179 Hrs
   Fraction sorbed to airborne particulates (phi): 0.996 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1.389E+004
      Log Koc:  4.143 

 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 = 1.040 (BCF = 10.97)
       log Kow used: 2.26 (expkow database)

 Volatilization from Water:
    Henry LC:  1.14E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.048E+007  hours   (4.368E+005 days)
    Half-Life from Model Lake : 1.144E+008  hours   (4.765E+006 days)

 Removal In Wastewater Treatment:
    Total removal:               2.57  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.47  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       0.0145          2.07         1000       
   Water     19.3            1.44e+003    1000       
   Soil      80.6            2.88e+003    1000       
   Sediment  0.109           1.3e+004     0          
     Persistence Time: 1.89e+003 hr

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