ChemSpider 2D Image | (+)-S,S-Ethambutol | C10H24N2O2

(+)-S,S-Ethambutol

  • Molecular FormulaC10H24N2O2
  • Average mass204.310 Da
  • Monoisotopic mass204.183777 Da
  • ChemSpider ID13433

  • defined stereocentres - 2 of 2 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

(+)-S,S-Ethambutol
(+)-(S,S)-2,2'-(1,2-Ethylenediimino)-di-1-butanol
(+)-2,2'-(Ethylenediimino)di-1-butanol
(+)-ethambutol
(2S,2'S)-2,2'-(1,2-Ethandiyldiimino)di(1-butanol) [German] [ACD/IUPAC Name]
(2S,2'S)-2,2'-(1,2-Ethanediyldiimino)di(1-butanol) [ACD/IUPAC Name]
(2S,2'S)-2,2'-(1,2-Éthanediyldiimino)di(1-butanol) [French] [ACD/IUPAC Name]
(2S,2'S)-2,2'-(Ethane-1,2-diyldiimino)dibutan-1-ol
(2S,7S)-2,7-Diethyl-3,6-diazaoctane-1,8-diol
(S,S)-ethambutol
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

1074 [DBID]
8G167061QZ [DBID]
6312870 [DBID]
AIDS007655 [DBID]
AIDS-007655 [DBID]
AIDS032284 [DBID]
AIDS-032284 [DBID]
AIDS088822 [DBID]
AIDS-088822 [DBID]
C06984 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Safety:

      J04AK02 Wikidata Q412318

    • Chemical Class:

      An ethylenediamine derivative that is ethane-1,2-diamine in which one hydrogen attached to each of the nitrogens is sutstituted by a 1-hydroxybutan-2-yl group (<stereo>S</stereo>,<stereo>S</stereo>-co nfiguration). It is a bacteriostatic antimycobacterial drug, effective against <ital>Mycobacterium tuberculosis</ital> and some other mycobacteria. It is used (as the dihydrochloride salt) in combinat ion with other antituberculous drugs in the treatment of pulmonary and extrapulmonary tuberculosis; resistant strains of <ital>M. tuberculosis</ital> are readily produced if ethambutol is used alone. ChEBI CHEBI:4877
      An ethylenediamine derivative that is ethane-1,2-diamine in which one hydrogen attached to each of the nitrogens is sutstituted by a 1-hydroxybutan-2-yl group (S,S-co; nfiguration). It is a bacteriost atic antimycobacterial drug, effective against Mycobacterium tuberculosis and some other mycobacteria. It is used (as the dihydrochloride salt) in combinat; ion with other antituberculous drugs in the treatment of pulmonary and extrapulmonary tuberculosis; resistant strains of M. tuberculosis are readily produced if ethambutol is used alone. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4877
      An ethylenediamine derivative that is ethane-1,2-diamine in which one hydrogen attached to each of the nitrogens is sutstituted by a 1-hydroxybutan-2-yl group (S,S-configuration). It is a bacteriostat ic antimycobacterial drug, effective against Mycobacterium tuberculosis and some other mycobacteria. It is used (as the dihydrochloride salt) in combination with other antituberculous drugs in the tre atment of pulmonary and extrapulmonary tuberculosis; resistant strains of M. tuberculosis are readily produced if ethambutol is used alone. ChEBI CHEBI:4877

    • Bio Activity:

      Antibacterial MedChem Express HY-B0535
      Anti-infection MedChem Express HY-B0535
      Anti-infection; MedChem Express HY-B0535
      Ethambutol is a bacteriostatic antimycobacterial agent, which obstructs the formation of cell wall by inhibiting arabinosyl transferases. MedChem Express
      Ethambutol is a bacteriostatic antimycobacterial agent, which obstructs the formation of cell wall by inhibiting arabinosyl transferases.; Target: Antibacterial; Ethambutol directly affects two polymers, arabinogalactan (AG) and lipoarabinomannan (LAM) in Mycobacterium smegmatis. MedChem Express HY-B0535
      Ethambutol is a bacteriostatic antimycobacterial agent, which obstructs the formation of cell wall by inhibiting arabinosyl transferases.;Target: AntibacterialEthambutol directly affects two polymers, arabinogalactan (AG) and lipoarabinomannan (LAM) in Mycobacterium smegmatis. In M. smegmatis, Ethambutol inhibits synthesis of arabinan completely and inhibits AG synthesis most likely as a consequence of this; more than 50% of the cell arabinan is released from the bacteria following Ethambutol treatment, whereas no galactan is released. Ethambutol main targets against embB gene product in M. avium. Ethambutol induces 60% changes in the embB gene in M. tuberculosis resistant mutants [1]. Ethambutol is effective against actively growing microorganisms of the genus Mycobacterium, including M. tuberculosis. Nearly all strains of M. tuberculosis and M. kansasii as well as a number of strains of the M. aviumcomplex (MAC) are sensitive to Ethambutol. [1] Ethambutol is potency against M. tu MedChem Express HY-B0535

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

Density: 1.0±0.1 g/cm3
Boiling Point: 345.3±22.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.7 mmHg at 25°C
Enthalpy of Vaporization: 68.3±6.0 kJ/mol
Flash Point: 113.7±12.9 °C
Index of Refraction: 1.478
Molar Refractivity: 58.6±0.3 cm3
#H bond acceptors: 4
#H bond donors: 4
#Freely Rotating Bonds: 9
#Rule of 5 Violations: 0
ACD/LogP: -0.05
ACD/LogD (pH 5.5): -3.35
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -2.13
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 65 Å2
Polarizability: 23.2±0.5 10-24cm3
Surface Tension: 38.1±3.0 dyne/cm
Molar Volume: 207.0±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) =  -0.41

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  334.27  (Adapted Stein & Brown method)
    Melting Pt (deg C):  96.43  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.82E-006  (Modified Grain method)
    MP  (exp database):  88 deg C
    Subcooled liquid VP: 7.32E-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):  9.488e+005
       log Kow used: -0.41 (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:
       Aliphatic Amines

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.65E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.157E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.41  (KowWin est)
  Log Kaw used:  -11.826  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.416
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.2754
   Biowin2 (Non-Linear Model)     :   0.9897
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.1165  (weeks       )
   Biowin4 (Primary Survey Model) :   3.8984  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.6891
   Biowin6 (MITI Non-Linear Model):   0.6184
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  1.1213
 Ready Biodegradability Prediction:   YES

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  0.000976 Pa (7.32E-006 mm Hg)
  Log Koa (Koawin est  ): 11.416
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00307 
       Octanol/air (Koa) model:  0.064 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0999 
       Mackay model           :  0.197 
       Octanol/air (Koa) model:  0.837 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 212.9135 E-12 cm3/molecule-sec
      Half-Life =     0.050 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.603 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.149 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  10
      Log Koc:  1.000 

 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 = 0.500 (BCF = 3.162)
       log Kow used: -0.41 (estimated)

 Volatilization from Water:
    Henry LC:  3.65E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.293E+010  hours   (9.554E+008 days)
    Half-Life from Model Lake : 2.501E+011  hours   (1.042E+010 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.76  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       9.42e-007       1.21         1000       
   Water     38.8            360          1000       
   Soil      61.1            720          1000       
   Sediment  0.0712          3.24e+003    0          
     Persistence Time: 580 hr

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