ChemSpider 2D Image | Cefalexin | C16H17N3O4S

Cefalexin

  • Molecular FormulaC16H17N3O4S
  • Average mass347.389 Da
  • Monoisotopic mass347.093964 Da
  • ChemSpider ID25541
  • defined stereocentres - 3 of 3 defined stereocentres


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Cefalexin [JP15] [Wiki]
(6R,7R)-7-{[(2R)-2-Amino-2-phenylacetyl]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-2-carbonsäure [German] [ACD/IUPAC Name]
(6R,7R)-7-{[(2R)-2-Amino-2-phenylacetyl]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid [ACD/IUPAC Name]
105879-42-3 [RN]
15686-71-2 [RN]
239-773-6 [EINECS]
2400
254-192-8 [EINECS]
5SFF1W6677
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-methyl-8-oxo-, (6R,7R)- [ACD/Index Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AIDS070031 [DBID]
AIDS-070031 [DBID]
BRN 0965503 [DBID]
C06895 [DBID]
CCRIS 937 [DBID]
D00263 [DBID]
HSDB 3022 [DBID]
Lilly 66873 [DBID]
Prestwick0_000358 [DBID]
Prestwick1_000358 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      J01DB01 Wikidata Q411417
    • Chemical Class:

      A semisynthetic first-generation cephalosporin antibiotic having methyl and <stereo>beta</stereo>-(2<stereo>R</stereo>)-2-amino-2-phenylacetamido groups at the 3- and 7- of the cephem skeleton, respec tively. It is effective against both Gram-negative and Gram-positive organisms, and is used for treatment of infections of the skin, respiratory tract and urinary tract. ChEBI CHEBI:3534
    • Bio Activity:

      Antibacterial MedChem Express HY-B0200
      Anti-infection MedChem Express HY-B0200
      Anti-infection; MedChem Express HY-B0200
      Cefalexin is a cephalosporin antibiotic. MedChem Express
      Cefalexin is a cephalosporin antibiotic.; Target: Antibacterial; Cefalexin (INN, BAN) or cephalexin (USAN, AAN) is a first-generation cephalosporin antibiotic introduced in 1967 by Eli Lilly and Company. MedChem Express HY-B0200
      Cefalexin is a cephalosporin antibiotic.;Target: AntibacterialCefalexin (INN, BAN) or cephalexin (USAN, AAN) is a first-generation cephalosporin antibiotic introduced in 1967 by Eli Lilly and Company. It is an orally administered agent with a similar antimicrobial spectrum to the intravenous agents cefalotin and cefazolin. It was first marketed as Keflex (Lilly), and is marketed under several other trade names. As of 2008, cefalexin was the most popular cephalosporin antibiotic in the United States, with more than 25 million prescriptions of its generic versions alone, for US$255 million in sales (though less popular than two other antibiotics, amoxicillin and azithromycin, each with 50 million prescriptions per year).Cefalexin is marketed by generic pharmaceutical manufacturers under a wide range of brand names, including: Apo-Cephalex, Biocef, Cefanox, Ceforal, Cephabos, Cephalexin, Cephorum, Ceporex, Cilex, Ialex, Ibilex, Kefexin, Keflet, Keflex, Rekosporin, Keforal, Keftab, K MedChem Express HY-B0200

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

Density: 1.5±0.1 g/cm3
Boiling Point: 727.4±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.5 mmHg at 25°C
Enthalpy of Vaporization: 111.5±3.0 kJ/mol
Flash Point: 393.7±32.9 °C
Index of Refraction: 1.700
Molar Refractivity: 89.4±0.4 cm3
#H bond acceptors: 7
#H bond donors: 4
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 0.65
ACD/LogD (pH 5.5): -2.83
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -3.63
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 138 Å2
Polarizability: 35.4±0.5 10-24cm3
Surface Tension: 78.5±5.0 dyne/cm
Molar Volume: 231.3±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) =  0.40
    Log Kow (Exper. database match) =  0.65
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  636.05  (Adapted Stein & Brown method)
    Melting Pt (deg C):  326.81  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.24E-015  (Modified Grain method)
    Subcooled liquid VP: 8.36E-012 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):  1789
       log Kow used: 0.65 (expkow database)
       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-acid
       Benzyl Amines-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.77E-017  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  8.278E-019 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.65  (exp database)
  Log Kaw used:  -14.946  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.596
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.3571
   Biowin2 (Non-Linear Model)     :   0.9991
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.7341  (weeks-months)
   Biowin4 (Primary Survey Model) :   4.1911  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2227
   Biowin6 (MITI Non-Linear Model):   0.0176
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.2822
 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):  1.11E-009 Pa (8.36E-012 mm Hg)
  Log Koa (Koawin est  ): 15.596
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.69E+003 
       Octanol/air (Koa) model:  968 
   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 = 153.2022 E-12 cm3/molecule-sec
      Half-Life =     0.070 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.838 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     7.393750 E-17 cm3/molecule-sec
      Half-Life =     0.155 Days (at 7E11 mol/cm3)
      Half-Life =      3.720 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    :  663.4
      Log Koc:  2.822 

 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: 0.65 (expkow database)

 Volatilization from Water:
    Henry LC:  2.77E-017 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  3.94E+013  hours   (1.641E+012 days)
    Half-Life from Model Lake : 4.298E+014  hours   (1.791E+013 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       0.000107        1.16         1000       
   Water     43.6            900          1000       
   Soil      56.3            1.8e+003     1000       
   Sediment  0.0874          8.1e+003     0          
     Persistence Time: 1.01e+003 hr




                    

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