ChemSpider 2D Image | Capecitabine | C15H22FN3O6

Capecitabine

  • Molecular FormulaC15H22FN3O6
  • Average mass359.350 Da
  • Monoisotopic mass359.149261 Da
  • ChemSpider ID54916

  • defined stereocentres - 4 of 4 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

{1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-méthyltétrahydrofuran-2-yl]-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl}carbamate de pentyle
154361-50-9 [RN]
5'-Deoxy-5-fluoro-N-[(pentyloxy)carbonyl]cytidine [ACD/IUPAC Name]
5'-Deoxy-5-fluoro-N-[hydroxy(pentyloxy)methylene]cytidine [ACD/IUPAC Name]
5'-Desoxy-5-fluor-N-[(pentyloxy)carbonyl]cytidin [German] [ACD/IUPAC Name]
5'-Desoxy-5-fluor-N-[hydroxy(pentyloxy)methylen]cytidin [German] [ACD/IUPAC Name]
5'-Désoxy-5-fluoro-N-[(pentyloxy)carbonyl]cytidine [French] [ACD/IUPAC Name]
5'-Désoxy-5-fluoro-N-[hydroxy(pentyloxy)méthylène]cytidine [French] [ACD/IUPAC Name]
capecitabina [Spanish] [INN]
Capecitabine [JAN] [USAN] [Wiki]
More...

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

6804DJ8Z9U [DBID]
7317 [DBID]
154361-50-9,158798-73-3 [DBID]
C12650 [DBID]
D01223 [DBID]
R-340 [DBID]
UNII:6804DJ8Z9U [DBID]
UNII-6804DJ8Z9U [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Toxicity:

      Organic Compound; Amine; Organofluoride; Ether; Ester; Drug; Antineoplastic Agent; Antimetabolite; Antimetabolite, Antineoplastic; Metabolite; Prodrug; Synthetic Compound Toxin, Toxin-Target Database T3D3507

    • Safety:

      L01BC06 Wikidata Q420207

    • Target Organs:

      DNA/RNA Synthesis inhibitor TargetMol T1408

    • Chemical Class:

      A carbamate ester that is cytidine in which the hydrogen at position 5 is replaced by fluorine and in which the amino group attached to position 4 is converted to its <element>N</element>-(penyloxy)ca rbonyl derivative. Capecitabine is a antineoplastic agent used in the treatment of cancers. ChEBI CHEBI:31348

    • Bio Activity:

      Capecitabine is an anti-cancer chemotherapy drug. MedChem Express http://www.medchemexpress.com/Flutamide.html, HY-B0016
      Capecitabine is an anti-cancer chemotherapy drug. It is classified as an antimetabolite.;IC50 Value:;Target: Nucleoside antimetabolite/analogCapecitabine is an orally-administered chemotherapeutic agent used in the treatment of metastatic breast and colorectal cancers. Capecitabine is a prodrug, that is enzymatically converted to 5-fluorouracil in the tumor, where it inhibits DNA synthesis and slows growth of tumor tissue. The activation of capecitabine follows a pathway with three enzymatic steps and two intermediary metabolites, 5'-deoxy-5-fluorocytidine (5'-DFCR) and 5'-deoxy-5-fluorouridine (5'-DFUR), to form 5-fluorouracil. From Wikipedia. MedChem Express HY-B0016
      Cell Biology Tocris Bioscience 4799
      Cell Cycle/DNA Damage MedChem Express HY-B0016
      Cell Cycle/DNA Damage; MedChem Express HY-B0016
      Cell Metabolism Tocris Bioscience 4799
      DNA Damage/DNA Repair TargetMol T1408
      DNA, RNA and Protein Synthesis Tocris Bioscience 4799
      Nucleoside antimetabolite/analog MedChem Express HY-B0016
      Prodrug of 5-Fluorouracil (5-FU) (Cat. No. 3257). Selectively activated in tumor cells by thymidine phosphorylase; inhibits DNA synthesis upon conversion to 5-FU. Orally available. Tocris Bioscience 4799
      Prodrug of 5-Fluorouracil (Cat. No. 3257). Inhibits DNA synthesis Tocris Bioscience 4799
      Thymidylate synthase TargetMol T1408

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

Density: 1.5±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.600
Molar Refractivity: 82.3±0.5 cm3
#H bond acceptors: 9
#H bond donors: 3
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 0
ACD/LogP: 0.97
ACD/LogD (pH 5.5): 0.39
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 28.84
ACD/LogD (pH 7.4): -0.96
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.28
Polar Surface Area: 121 Å2
Polarizability: 32.6±0.5 10-24cm3
Surface Tension: 51.3±7.0 dyne/cm
Molar Volume: 240.5±7.0 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) =  0.56

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  492.85  (Adapted Stein & Brown method)
    Melting Pt (deg C):  209.26  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.12E-012  (Modified Grain method)
    Subcooled liquid VP: 1.01E-010 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):  1821
       log Kow used: 0.56 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.92E-019  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.908E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.56  (KowWin est)
  Log Kaw used:  -16.923  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  17.483
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7345
   Biowin2 (Non-Linear Model)     :   0.3930
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.9679  (weeks       )
   Biowin4 (Primary Survey Model) :   4.0411  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1952
   Biowin6 (MITI Non-Linear Model):   0.0003
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.5557
 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):  1.35E-008 Pa (1.01E-010 mm Hg)
  Log Koa (Koawin est  ): 17.483
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  223 
       Octanol/air (Koa) model:  7.46E+004 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  82.7123 E-12 cm3/molecule-sec
      Half-Life =     0.129 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.552 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.070000 E-17 cm3/molecule-sec
      Half-Life =    16.371 Days (at 7E11 mol/cm3)
   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    :  16.65
      Log Koc:  1.221 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  4.928E-006  L/mol-sec
  Kb Half-Life at pH 8:    4456.481  years  
  Kb Half-Life at pH 7: 4.456E+004  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: 0.56 (estimated)

 Volatilization from Water:
    Henry LC:  2.92E-019 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.801E+015  hours   (1.584E+014 days)
    Half-Life from Model Lake : 4.147E+016  hours   (1.728E+015 days)

 Removal In Wastewater Treatment:
    Total removal:               1.86  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.77  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       8.15e-008       3.08         1000       
   Water     37.2            360          1000       
   Soil      62.8            720          1000       
   Sediment  0.0703          3.24e+003    0          
     Persistence Time: 591 hr

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