ChemSpider 2D Image | Ceftibuten | C15H14N4O6S2

Ceftibuten

  • Molecular FormulaC15H14N4O6S2
  • Average mass410.425 Da
  • Monoisotopic mass410.035461 Da
  • ChemSpider ID4445419
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 2 of 2 defined stereocentres


More details:



Featured data source



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

(6R,7R)-7-{[(2Z)-2-(2-Amino-1,3-thiazol-4-yl)-4-carboxy-2-butenoyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-2-carbonsäure [German] [ACD/IUPAC Name]
(6R,7R)-7-{[(2Z)-2-(2-Amino-1,3-thiazol-4-yl)-4-carboxy-2-butenoyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid [ACD/IUPAC Name]
(6R,7R)-7-{[(2Z)-2-(2-Amino-1,3-thiazol-4-yl)-4-carboxybut-2-enoyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
[6R-[6a,7b(Z)]]-7-[[2-(2-Amino-4-thiazolyl)-4-carboxy-1-oxo-2-butenyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-3-carboxylic Acid
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2Z)-2-(2-amino-4-thiazolyl)-4-carboxy-1-oxo-2-buten-1-yl]amino]-8-oxo-, (6R,7R)- [ACD/Index Name]
6335
7432 S
7b-[(Z)-2-(2-Aminothiazol-4-yl)-4-carboxy-2-butenoylamino]-3-cephem-4-carboxylic Acid
97519-39-6 [RN]
Acide (6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxy-2-butenoyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ène-2-carboxylique [French] [ACD/IUPAC Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

S 7432 [DBID]
Sch 39720 [DBID]
Sch-39720 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      J01DD14 Wikidata Q419521
    • Chemical Class:

      A third-generation cephalosporin antibiotic with a [(2<stereo>Z</stereo>)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enoyl]amino substituent at the 7 position of the cephem skeleton. An orally-admini stered agent, ceftibuten is used as the dihydrate to treat urinary-tract and respiratory-tract infections. ChEBI CHEBI:3510
    • Compound Source:

      semisynthetic Microsource [01505207]
    • Bio Activity:

      Antibacterial MedChem Express HY-B0698
      Anti-infection MedChem Express HY-B0698
      Anti-infection; MedChem Express HY-B0698
      Ceftibuten(Sch39720) is a third-generation cephalosporin antibiotic. MedChem Express
      Ceftibuten(Sch39720) is a third-generation cephalosporin antibiotic.; IC50:; Target: Antibacterial; Ceftibuten displayed high activity against Haemophilus influenzae and Branhamella catarrhalis. MedChem Express HY-B0698
      Ceftibuten(Sch39720) is a third-generation cephalosporin antibiotic.;IC50:;Target: AntibacterialCeftibuten displayed high activity against Haemophilus influenzae and Branhamella catarrhalis. There was reduced activity against Streptococcus pneumoniae (MIC90 16 mg/l). The protein binding of Ceftibuten was 77% and the primary target site PBP 3. A high degree of stability to beta-lactamase hydrolysis was observed. [1] MedChem Express HY-B0698

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

Density: 1.8±0.1 g/cm3
Boiling Point: 966.4±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.3 mmHg at 25°C
Enthalpy of Vaporization: 147.5±3.0 kJ/mol
Flash Point: 538.3±34.3 °C
Index of Refraction: 1.762
Molar Refractivity: 96.2±0.4 cm3
#H bond acceptors: 10
#H bond donors: 5
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 2
ACD/LogP: -0.96
ACD/LogD (pH 5.5): -5.33
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -5.79
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 216 Å2
Polarizability: 38.1±0.5 10-24cm3
Surface Tension: 112.2±5.0 dyne/cm
Molar Volume: 233.3±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) =  -1.42

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  727.92  (Adapted Stein & Brown method)
    Melting Pt (deg C):  319.07  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.45E-017  (Modified Grain method)
    Subcooled liquid VP: 2.97E-014 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):  2125
       log Kow used: -1.42 (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:
       Aromatic Amines-acid
       Acrylamides-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   7.36E-027  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.685E-021 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.42  (KowWin est)
  Log Kaw used:  -24.522  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  23.102
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8841
   Biowin2 (Non-Linear Model)     :   0.8746
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.7780  (weeks       )
   Biowin4 (Primary Survey Model) :   4.3292  (hours-days  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0637
   Biowin6 (MITI Non-Linear Model):   0.0027
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.4615
 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):  3.96E-012 Pa (2.97E-014 mm Hg)
  Log Koa (Koawin est  ): 23.102
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  7.58E+005 
       Octanol/air (Koa) model:  3.1E+010 
   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 = 142.8496 E-12 cm3/molecule-sec
      Half-Life =     0.075 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.899 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    14.787499 E-17 cm3/molecule-sec
      Half-Life =     0.077 Days (at 7E11 mol/cm3)
      Half-Life =      1.860 Hrs
   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    :  796.5
      Log Koc:  2.901 

 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: -1.42 (estimated)

 Volatilization from Water:
    Henry LC:  7.36E-027 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.612E+023  hours   (6.715E+021 days)
    Half-Life from Model Lake : 1.758E+024  hours   (7.325E+022 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.75  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       1.33e-011       0.914        1000       
   Water     39              360          1000       
   Soil      60.9            720          1000       
   Sediment  0.0713          3.24e+003    0          
     Persistence Time: 579 hr




                    

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