ChemSpider 2D Image | Isotretinoin | C20H28O2

Isotretinoin

  • Molecular FormulaC20H28O2
  • Average mass300.435 Da
  • Monoisotopic mass300.208923 Da
  • ChemSpider ID4445539
  • Double-bond stereo - Double-bond stereo


More details:



Featured data source



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

(13cis)-Retinoic acid [ACD/IUPAC Name]
(13cis)-Rétinoïque acide [French] [ACD/IUPAC Name]
(13Z)-Retinoic Acid
(2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
(2Z,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraensäure [German]
13-cis-Retinoic acid
225-296-0 [EINECS]
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-cis-4-trans-6-trans-8-trans-nonatetraenoic acid
4617
4759-48-2 [RN]
More...

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

DRG 0213 [DBID]
AGN 190013 [DBID]
AIDS196303 [DBID]
AIDS-196303 [DBID]
BRN 1885770 [DBID]
CCRIS 4286 [DBID]
D00348 [DBID]
DRG-0213 [DBID]
EU-0101081 [DBID]
HSDB 3929 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Safety:

      D10AD04 Wikidata Q287029
      D10BA01 Wikidata Q287029
    • Target Organs:

      RXR/RAR inhibitor TargetMol T1611
    • Chemical Class:

      A retinoic acid that is <stereo>all-trans</stereo>-retinoic acid in which the double bond which is <stereo>alpha</stereo>,<stereo>beta</stereo>- to the carboxy group is isomerised to <stereo>Z</stereo > configuration. A synthetic retinoid, it is used for the treatment of severe cases of acne and other skin diseases. ChEBI CHEBI:6067
    • Compound Source:

      semisynthetic Microsource [01502013]
    • Bio Activity:

      Endogenous agonist for retinoic acid receptors. Promotes neurite outgrowth, cell differentiation and inhibits proliferation in a neuroblastoma cell line. Also increases protein expression levels of MY CN and retinoic acid receptor-?. Anti-inflammatory. Tocris Bioscience 5513
      Endogenous agonist for retinoic acid receptors. Promotes neurite outgrowth, cell differentiation and inhibits proliferation in a neuroblastoma cell line. Also increases protein expression levels of MYCN and retinoic acid receptor-?. Anti-inflammatory. Tocris Bioscience 5513
      Endogenous agonist for retinoic acid receptors. Promotes neurite outgrowth, cell differentiation and inhibits proliferation in a neuroblastoma cell line. Also increases protein expression levels of MYCN and retinoic acid receptor-beta. Anti-inflammatory. Tocris Bioscience 5513
      Endogenous agonist for retinoic acid receptors; inducer of neuronal differentiation Tocris Bioscience 5513
      Isotretinoin(13-cis-Retinoic acid) is a medication used for the treatment of severe acne. MedChem Express HY-15127, http://www.medchemexpress.com/Balicatib.html
      Isotretinoin(13-cis-Retinoic acid) is a medication used for the treatment of severe acne. It was first developed to be used as a chemotherapy medication for the treatment of brain cancer, pancreatic cancer and more.;Target: RAR/RXR;Isotretinoin has been the most effective and long-lasting drug for the treatment of severe acne for more than 30 years and can achieve long-term remission in 70-80% of patients after a single course. The new evidence-based European S3-guideline recommends the use of Isotretinoin as a first-line medication for the treatment of severe papulopustular or conglobate acne, especially when prognostically unfavorable factors are present: family history of acne, early onset, marked seborrhea, localization on the trunk, scarring, psychosocial disability or persistent/late-type acne [1]. Five patients with pityriasis rubra pilaris were treated with isotretinoin from September 1982 through 1985. Isotretinoin at an average dose of 1.16 mg/kg/day for 16 to 24 weeks cau MedChem Express HY-15127
      Metabolism TargetMol T1611
      Nuclear Receptors Tocris Bioscience 5513
      Others MedChem Express HY-15127
      RAR TargetMol T1611
      RAR/RXR MedChem Express HY-15127
      Retinoic Acid Receptors Tocris Bioscience 5513

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

Density: 1.0±0.1 g/cm3
Boiling Point: 462.8±14.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.5 mmHg at 25°C
Enthalpy of Vaporization: 79.3±6.0 kJ/mol
Flash Point: 350.6±11.0 °C
Index of Refraction: 1.556
Molar Refractivity: 95.5±0.3 cm3
#H bond acceptors: 2
#H bond donors: 1
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 1
ACD/LogP: 6.83
ACD/LogD (pH 5.5): 5.09
ACD/BCF (pH 5.5): 2769.47
ACD/KOC (pH 5.5): 5968.40
ACD/LogD (pH 7.4): 3.29
ACD/BCF (pH 7.4): 44.30
ACD/KOC (pH 7.4): 95.47
Polar Surface Area: 37 Å2
Polarizability: 37.9±0.5 10-24cm3
Surface Tension: 39.1±3.0 dyne/cm
Molar Volume: 297.2±3.0 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) =  7.85
    Log Kow (Exper. database match) =  6.30
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  411.79  (Adapted Stein & Brown method)
    Melting Pt (deg C):  147.95  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.02E-007  (Modified Grain method)
    MP  (exp database):  181 deg C
    Subcooled liquid VP: 4.29E-006 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):  0.1263
       log Kow used: 6.30 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.23409 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Neutral Organics-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   9.50E-006  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.193E-007 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  6.30  (exp database)
  Log Kaw used:  -3.411  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  9.711
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4933
   Biowin2 (Non-Linear Model)     :   0.0880
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6877  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.6464  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1655
   Biowin6 (MITI Non-Linear Model):   0.0257
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.5104
 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):  0.000572 Pa (4.29E-006 mm Hg)
  Log Koa (Koawin est  ): 9.711
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00524 
       Octanol/air (Koa) model:  0.00126 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.159 
       Mackay model           :  0.296 
       Octanol/air (Koa) model:  0.0917 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 292.5375 E-12 cm3/molecule-sec
      Half-Life =     0.037 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    26.325 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    24.180000 E-17 cm3/molecule-sec
      Half-Life =     0.047 Days (at 7E11 mol/cm3)
      Half-Life =      1.137 Hrs
   Fraction sorbed to airborne particulates (phi): 0.227 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  9987
      Log Koc:  3.999 

 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 = 1.750 (BCF = 56.23)
       log Kow used: 6.30 (expkow database)

 Volatilization from Water:
    Henry LC:  9.5E-006 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:      108.6  hours   (4.525 days)
    Half-Life from Model Lake :       1330  hours   (55.42 days)

 Removal In Wastewater Treatment:
    Total removal:              93.09  percent
    Total biodegradation:        0.77  percent
    Total sludge adsorption:    92.31  percent
    Total to Air:                0.01  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.0088          0.495        1000       
   Water     3.08            900          1000       
   Soil      32.3            1.8e+003     1000       
   Sediment  64.6            8.1e+003     0          
     Persistence Time: 2.7e+003 hr




                    

Click to predict properties on the Chemicalize site





Feedback Form