ChemSpider 2D Image | Niclosamide | C13H8Cl2N2O4

Niclosamide

  • Molecular FormulaC13H8Cl2N2O4
  • Average mass327.120 Da
  • Monoisotopic mass325.986115 Da
  • ChemSpider ID4322

More details:

Featured data source
The Merck Index Online

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

Niclosamide [BSI] [INN] [ISO] [USAN] [Wiki]
2',5-Dichlor-4'-nitro-salizylsaeureanilid [German]
2',5-Dichloro-4'-nitrosalicylanilide
200-056-8 [EINECS]
50-65-7 [RN]
5-Chlor-N-(2-chlor-4-nitrophenyl)-2-hydroxybenzamid [German] [ACD/IUPAC Name]
5-Chlor-N-(2-chlor-4-nitrophenyl)-2-hydroxybenzolcarboxamid
5-Chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide [ACD/IUPAC Name]
5-Chloro-N-(2-chloro-4-nitrophényl)-2-hydroxybenzamide [French] [ACD/IUPAC Name]
8KK8CQ2K8G
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

1532 [DBID]
2820605 [DBID]
36177_RIEDEL [DBID]
AI3-25823 [DBID]
AIDS092503 [DBID]
AIDS-092503 [DBID]
B 2353 [DBID]
BAY 2353 [DBID]
Bayer 2353 [DBID]
Bayer 73 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Appearance:

      yellow solid OU Chemical Safety Data (No longer updated) More details

    • Stability:

      Stable. Hydrolyzes in concentrated acidic or basic solutions. OU Chemical Safety Data (No longer updated) More details

    • Toxicity:

      No detailed toxicological data available beyond the LD50s shown below., ORL-RAT LD50 500 mg kg-1, IPR-RAT LD50 250 mg kg-1 OU Chemical Safety Data (No longer updated) More details
      Organic Compound; Organochloride; Pesticide; Amine; Amide; Ester; Drug; Metabolite; Synthetic Compound Toxin, Toxin-Target Database T3D3891

    • Safety:

      P02DA01 Wikidata Q418523
      Treat as potentially harmful. OU Chemical Safety Data (No longer updated) More details

    • Target Organs:

      STAT inhibitor; Autophagy activator TargetMol T0711

    • Chemical Class:

      A secondary carboxamide resulting from the formal condensation of the carboxy group of 5-chlorosalicylic acid with the amino group of 2-chloro-4-nitroaniline. It is an oral anthelmintic drug approved for use against tapeworm infections. ChEBI CHEBI:7553

    • Bio Activity:

      <p>STAT3 signaling pathway inhibitor which inhibits the activation and transcriptional function of STAT3 and induces cell growth inhibition, apoptosis, and cell cycle arrest of cancer cells with constitutively active STAT3. Shows selectivity for STAT3 over STAT1, STAT5, JAK1, JAK2 and Src kinases.</p> <p>Also inhibits mTORC and Wnt/&beta;-catenin pathways. Antineoplastic against AML stem cells.</p> <p>Shows antiproliferative, anticancer, antidiabetic actions. Shows antiparasitic actions and recently investigated as part of COVID-19 compound repurposing.</p> Hello Bio HB1435
      Anti-infection MedChem Express HY-B0497
      Anti-infection; MedChem Express HY-B0497
      Antiparasitic MedChem Express HY-B0497
      Biochemicals & small molecules/Antagonists & inhibitors Hello Bio HB1435
      Cell Biology Tocris Bioscience 4079
      Cell process/Stem cells/Stem cell signaling Hello Bio HB1435
      Cytokine and NF-kB Signaling Tocris Bioscience 4079
      Inhibitor of the STAT3 signaling pathway; inhibits the activation, nuclear translocation and transactivation of STAT3. Displays selectivity for STAT3 over STAT1, STAT5, JAK1, JAK2 and Src kinases. Inh ibits the transcription of STAT3 target genes and induces cell growth inhibition, apoptosis and cell cycle arrest of cancer cells with constitutively active STAT3. Also reversibly inhibits mTORC1 sign aling and stimulates autophagy in vitro; displays antineoplastic effects in acute myelogenous leukemia (AML) stem cells. Tocris Bioscience 4079
      Inhibitor of the STAT3 signaling pathway; inhibits the activation, nuclear translocation and transactivation of STAT3. Displays selectivity for STAT3 over STAT1, STAT5, JAK1, JAK2 and Src kinases. Inhibits the transcription of STAT3 target genes and induces cell growth inhibition, apoptosis and cell cycle arrest of cancer cells with constitutively active STAT3. Also reversibly inhibits mTORC1 signaling and stimulates autophagy in vitro; displays antineoplastic effects in acute myelogenous leukemia (AML) stem cells. Tocris Bioscience 4079
      JAK/STAT Signaling; Ubiquitination TargetMol T0711
      Niclosamide(BAY2353) is used for the treatment of most tapeworm infections by inhibiting DNA replication.; Target: Antiparasitic; Niclosamide (< 5 ?M) dose dependently inhibits STAT3-mediated luciferase reporter activity with IC50 of 0.25 ?M in HeLa cells. MedChem Express HY-B0497
      Proteins - Other/STAT Hello Bio HB1435
      Signal Transduction Tocris Bioscience 4079
      STAT Tocris Bioscience 4079
      STAT3 inhibitor; also inhibits mTORC1 signaling Tocris Bioscience 4079
      STAT3 signaling pathway inhibitor and also inhibits mTORC and Wnt/&beta;-catenin pathways. Antineoplastic against AML stem cells. Shows antiproliferative, anticancer, antidiabetic and anthelmintic actions. Hello Bio HB1435
      STAT3 signaling pathway inhibitor. Antineoplastic against AML stem cells. Hello Bio HB1435
      STAT3; Autophagy TargetMol T0711
  • Gas Chromatography

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

Density: 1.6±0.1 g/cm3
Boiling Point: 424.5±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.0 mmHg at 25°C
Enthalpy of Vaporization: 70.5±3.0 kJ/mol
Flash Point: 210.5±28.7 °C
Index of Refraction: 1.709
Molar Refractivity: 79.0±0.3 cm3
#H bond acceptors: 6
#H bond donors: 2
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 1
ACD/LogP: 5.41
ACD/LogD (pH 5.5): 4.72
ACD/BCF (pH 5.5): 2253.26
ACD/KOC (pH 5.5): 8718.00
ACD/LogD (pH 7.4): 4.48
ACD/BCF (pH 7.4): 1318.25
ACD/KOC (pH 7.4): 5100.37
Polar Surface Area: 95 Å2
Polarizability: 31.3±0.5 10-24cm3
Surface Tension: 71.7±3.0 dyne/cm
Molar Volume: 202.5±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) =  4.56

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  506.40  (Adapted Stein & Brown method)
    Melting Pt (deg C):  215.59  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.49E-011  (Modified Grain method)
    MP  (exp database):  230 deg C
    VP  (exp database):  1.49E-11 mm Hg at 20 deg C
    Subcooled liquid VP: 1.59E-009 mm Hg (20 deg C, exp database VP )

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  1.685
       log Kow used: 4.56 (estimated)
       no-melting pt equation used
     Water Sol (Exper. database match) =  1.6 mg/L (20 deg C)
        Exper. Ref:  TOMLIN,C (1997)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  30.197 mg/L
    Wat Sol (Exper. database match) =  1.60
       Exper. Ref:  TOMLIN,C (1997)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.47E-013  atm-m3/mole
   Group Method:   Incomplete
   Exper Database: 4.00E-12  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  3.806E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.56  (KowWin est)
  Log Kaw used:  -9.786  (exp database)
      Log Koa (KOAWIN v1.10 estimate):  14.346
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.2479
   Biowin2 (Non-Linear Model)     :   0.0102
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.8956  (months      )
   Biowin4 (Primary Survey Model) :   3.1818  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.1961
   Biowin6 (MITI Non-Linear Model):   0.0005
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.2423
 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):  2.12E-007 Pa (1.59E-009 mm Hg)
  Log Koa (Koawin est  ): 14.346
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  14.2 
       Octanol/air (Koa) model:  54.5 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.998 
       Mackay model           :  0.999 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =   9.4634 E-12 cm3/molecule-sec
      Half-Life =     1.130 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    13.563 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.999 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1854
      Log Koc:  3.268 

 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 = 2.410 (BCF = 256.9)
       log Kow used: 4.56 (estimated)

 Volatilization from Water:
    Henry LC:  4E-012 atm-m3/mole  (Henry experimental database)
    Half-Life from Model River: 2.647E+008  hours   (1.103E+007 days)
    Half-Life from Model Lake : 2.888E+009  hours   (1.203E+008 days)

 Removal In Wastewater Treatment:
    Total removal:              59.15  percent
    Total biodegradation:        0.55  percent
    Total sludge adsorption:    58.60  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       0.0129          27.1         1000       
   Water     7.64            1.44e+003    1000       
   Soil      83.7            2.88e+003    1000       
   Sediment  8.67            1.3e+004     0          
     Persistence Time: 3.07e+003 hr

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