ChemSpider 2D Image | doripenem | C15H24N4O6S2

doripenem

  • Molecular FormulaC15H24N4O6S2
  • Average mass420.504 Da
  • Monoisotopic mass420.113739 Da
  • ChemSpider ID66040

  • defined stereocentres - 6 of 6 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

(4R,5S,6S)-6-[(1R)-1-Hydroxyethyl]-4-methyl-7-oxo-3-({(3S,5S)-5-[(sulfamoylamino)methyl]-3-pyrrolidinyl}sulfanyl)-1-azabicyclo[3.2.0]hept-2-en-2-carbonsäure [German] [ACD/IUPAC Name]
(4R,5S,6S)-6-[(1R)-1-Hydroxyethyl]-4-methyl-7-oxo-3-({(3S,5S)-5-[(sulfamoylamino)methyl]-3-pyrrolidinyl}sulfanyl)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid [ACD/IUPAC Name]
(4R,5S,6S)-6-[(1R)-1-Hydroxyethyl]-4-methyl-7-oxo-3-({(3S,5S)-5-[(sulfamoylamino)methyl]pyrrolidin-3-yl}sulfanyl)-1-azabicyclo[3.2.0]hept-2-en-2-carbonsäure [German]
148016-81-3 [RN]
1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[[(3S,5S)-5-[[(aminosulfonyl)amino]methyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-, (4R,5S,6S)- [ACD/Index Name]
Acide (4R,5S,6S)-6-[(1R)-1-hydroxyéthyl]-4-méthyl-7-oxo-3-({(3S,5S)-5-[(sulfamoylamino)méthyl]-3-pyrrolidinyl}sulfanyl)-1-azabicyclo[3.2.0]hept-2-ène-2-carboxylique [French] [ACD/IUPAC Name]
acide (4R,5S,6S)-6-[(1R)-1-hydroxyéthyl]-4-méthyl-7-oxo-3-({(3S,5S)-5-[(sulfamoylamino)méthyl]pyrrolidin-3-yl}sulfanyl)-1-azabicyclo[3.2.0]hept-2-ène-2-carboxylique [French]
BHV525JOBH
doripenem [INN] [USAN] [Wiki]
doripenem [Spanish] [INN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

7975 [DBID]
S-4661 [DBID]
148016-81-3; 364622-82-2 [DBID]
15340136 [DBID]
D03895 [DBID]
S 4661 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Bio Activity:

      Antibacterial MedChem Express HY-B0187
      Anti-infection MedChem Express HY-B0187
      Anti-infection; MedChem Express HY-B0187
      Doripenem is a new member of the carbapenem class of beta-lactam antibiotics with broad-spectrum coverage of Gram-positive, Gram-negative and anaerobic pathogens. MedChem Express
      Doripenem is a new member of the carbapenem class of beta-lactam antibiotics with broad-spectrum coverage of Gram-positive, Gram-negative and anaerobic pathogens.; Target: Antibacterial; Doripenem is an ultra-broad-spectrum injectable antibiotic. MedChem Express HY-B0187
      Doripenem is a new member of the carbapenem class of beta-lactam antibiotics with broad-spectrum coverage of Gram-positive, Gram-negative and anaerobic pathogens.;Target: AntibacterialDoripenem is an ultra-broad-spectrum injectable antibiotic. It is a beta-lactam and belongs to the subgroup of carbapenems. It was launched by Shionogi Co. of Japan under the brand name Finibax in 2005 and is being marketed outside Japan by Johnson & Johnson. It is particularly active against Pseudomonas aeruginosa. It is recommended that those allergic to doripenem or to any type of beta-lactam antibiotics such as cephalosporin or other Carbapenems not receive doripenem.Doripenem appears as crystalline powder anywhere from a white to somewhat yellowish colour.Doripenem is moderately soluble in water, slightly soluble in methanol, and virtually insoluble in ethanol. Doripenem is also solution in N,N-dimethylformamide. Doripenem's chemical configuration has 6 asymmetrical carbon atoms (6 stereocentre MedChem Express HY-B0187

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

Density: 1.6±0.1 g/cm3
Boiling Point: 694.8±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±4.9 mmHg at 25°C
Enthalpy of Vaporization: 116.4±6.0 kJ/mol
Flash Point: 374.0±34.3 °C
Index of Refraction: 1.681
Molar Refractivity: 99.6±0.4 cm3
#H bond acceptors: 10
#H bond donors: 6
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 2
ACD/LogP: -3.65
ACD/LogD (pH 5.5): -4.55
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -4.53
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 196 Å2
Polarizability: 39.5±0.5 10-24cm3
Surface Tension: 84.7±5.0 dyne/cm
Molar Volume: 263.5±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) =  -2.42

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  685.18  (Adapted Stein & Brown method)
    Melting Pt (deg C):  333.98  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  8.86E-020  (Modified Grain method)
    Subcooled liquid VP: 2.83E-016 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):  1.3e+004
       log Kow used: -2.42 (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:
       Aliphatic Amines-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.82E-027  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.771E-024 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -2.42  (KowWin est)
  Log Kaw used:  -25.128  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  22.708
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.1428
   Biowin2 (Non-Linear Model)     :   0.9308
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.7647  (weeks       )
   Biowin4 (Primary Survey Model) :   4.0048  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0646
   Biowin6 (MITI Non-Linear Model):   0.0013
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.4233
 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):  3.77E-014 Pa (2.83E-016 mm Hg)
  Log Koa (Koawin est  ): 22.708
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  7.95E+007 
       Octanol/air (Koa) model:  1.25E+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 = 223.7036 E-12 cm3/molecule-sec
      Half-Life =     0.048 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.574 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    13.650000 E-17 cm3/molecule-sec
      Half-Life =     0.084 Days (at 7E11 mol/cm3)
      Half-Life =      2.015 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    :  31.23
      Log Koc:  1.495 

 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: -2.42 (estimated)

 Volatilization from Water:
    Henry LC:  1.82E-027 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 6.597E+023  hours   (2.749E+022 days)
    Half-Life from Model Lake : 7.196E+024  hours   (2.998E+023 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       3.83e-010       0.731        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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