ChemSpider 2D Image | Alogliptin | C18H21N5O2

Alogliptin

  • Molecular FormulaC18H21N5O2
  • Average mass339.392 Da
  • Monoisotopic mass339.169525 Da
  • ChemSpider ID9625485

  • defined stereocentres - 1 of 1 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

2-({6-[(3R)-3-Amino-1-piperidinyl]-3-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl}methyl)benzonitril [German] [ACD/IUPAC Name]
2-({6-[(3R)-3-Amino-1-piperidinyl]-3-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl}methyl)benzonitrile [ACD/IUPAC Name]
2-({6-[(3R)-3-Amino-1-pipéridinyl]-3-méthyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl}méthyl)benzonitrile [French] [ACD/IUPAC Name]
2-({6-[(3R)-3-aminopiperidin-1-yl]-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl}methyl)benzonitrile
850649-61-5 [RN]
Alogliptin [INN] [Wiki]
Benzonitrile, 2-[[6-[(3R)-3-amino-1-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-1(2H)-pyrimidinyl]methyl]- [ACD/Index Name]
(R)-2-((6-(3-aminopiperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrile
[850649-61-5] [RN]
1133421-35-8 [RN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

SYR-322 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Safety:

      A10BH04 Wikidata Q4734170

    • Chemical Class:

      A piperidine that is 3-methyl-2,4-dioxo-3,4-dihydropyrimidine carrying additional 2-cyanobenzyl and 3-aminopiperidin-1-yl groups at positions 1 and 2 respectively (the <stereo>R</stereo>-enantiomer). Used in the form of its benzoate salt for treatment of type 2 diabetes. ChEBI CHEBI:72323
      A piperidine that is 3-methyl-2,4-dioxo-3,4-dihydropyrimidine carrying additional 2-cyanobenzyl and 3-aminopiperidin-1-yl groups at positions 1 and 2 respectively (the R-enantiomer). ; Used in the for m of its benzoate salt for treatment of type 2 diabetes. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:72323
      A piperidine that is 3-methyl-2,4-dioxo-3,4-dihydropyrimidine carrying additional 2-cyanobenzyl and 3-aminopiperidin-1-yl groups at positions 1 and 2 respectively (the R-enantiomer). Used in the form of its benzoate salt for treatment of type 2 diabetes. ChEBI CHEBI:72323

    • Bio Activity:

      Alogliptin(SYR-322) is a potent, selective inhibitor of DPP-4 with IC50 of <10 nM, exhibits greater than 10,000-fold selectivity over DPP-8 and DPP-9. MedChem Express
      Alogliptin(SYR-322) is a potent, selective inhibitor of DPP-4 with IC50 of <10 nM, exhibits greater than 10,000-fold selectivity over DPP-8 and DPP-9.;IC50 value: <10 nM;Target: DPP4Alogliptin is an orally administered, anti-diabetic drug in the DPP-4 inhibitor class. A randomized clinical trial reporting in 2011 aimed to determine the efficacy and safety of alogliptin versus placebo and voglibose among newly diagnosed Type 2 diabetes patients in Japan. The main outcome indicated that alogliptin was statistically superior to both comparitors. A randomized clinical trial reporting in 2012 aimed to demonstrate that alogliptin was non-inferior to a very low fat/calorie traditional Japanese diet among newly diagnosed Type 2 diabetes patients in Japan. The outcome indicated that both the drug and dietary treatments comparably impacted indicators of the diabetic condition, such as HbA1c levels and glycemic efficacy. The drug treatment had its impact without changing body mass index MedChem Express HY-A0023A
      DPP4 MedChem Express HY-A0023A
      Metabolism/Protease; MedChem Express HY-A0023A

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

Density: 1.3±0.1 g/cm3
Boiling Point: 519.2±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.4 mmHg at 25°C
Enthalpy of Vaporization: 79.2±3.0 kJ/mol
Flash Point: 267.8±32.9 °C
Index of Refraction: 1.660
Molar Refractivity: 93.3±0.4 cm3
#H bond acceptors: 7
#H bond donors: 2
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 1.84
ACD/LogD (pH 5.5): -2.10
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -1.35
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 94 Å2
Polarizability: 37.0±0.5 10-24cm3
Surface Tension: 70.9±5.0 dyne/cm
Molar Volume: 252.9±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) =  0.49

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  562.56  (Adapted Stein & Brown method)
    Melting Pt (deg C):  241.82  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.11E-012  (Modified Grain method)
    Subcooled liquid VP: 6.92E-010 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):  1491
       log Kow used: 0.49 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  754.37 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aliphatic Amines
       Imides

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.13E-017  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  9.315E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.49  (KowWin est)
  Log Kaw used:  -15.335  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.825
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8415
   Biowin2 (Non-Linear Model)     :   0.8482
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1364  (months      )
   Biowin4 (Primary Survey Model) :   3.0481  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.2023
   Biowin6 (MITI Non-Linear Model):   0.0010
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.0442
 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):  9.23E-008 Pa (6.92E-010 mm Hg)
  Log Koa (Koawin est  ): 15.825
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  32.5 
       Octanol/air (Koa) model:  1.64E+003 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.999 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 156.6818 E-12 cm3/molecule-sec
      Half-Life =     0.068 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.819 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.175000 E-17 cm3/molecule-sec
      Half-Life =     6.549 Days (at 7E11 mol/cm3)
   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    :  4075
      Log Koc:  3.610 

 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: 0.49 (estimated)

 Volatilization from Water:
    Henry LC:  1.13E-017 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 9.545E+013  hours   (3.977E+012 days)
    Half-Life from Model Lake : 1.041E+015  hours   (4.339E+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       2.65e-007       1.62         1000       
   Water     47.3            1.44e+003    1000       
   Soil      52.6            2.88e+003    1000       
   Sediment  0.0948          1.3e+004     0          
     Persistence Time: 1.21e+003 hr

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