ChemSpider 2D Image | Linagliptin | C25H28N8O2

Linagliptin

  • Molecular FormulaC25H28N8O2
  • Average mass472.542 Da
  • Monoisotopic mass472.233521 Da
  • ChemSpider ID8271879
  • defined stereocentres - 1 of 1 defined stereocentres


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8-[(3R)-3-Amino-1-piperidinyl]-7-(2-butin-1-yl)-3-methyl-1-[(4-methyl-2-chinazolinyl)methyl]-3,7-dihydro-1H-purin-2,6-dion [German] [ACD/IUPAC Name]
8-[(3R)-3-Amino-1-piperidinyl]-7-(2-butyn-1-yl)-3-methyl-1-[(4-methyl-2-quinazolinyl)methyl]-3,7-dihydro-1H-purine-2,6-dione [ACD/IUPAC Name]
8-[(3R)-3-Amino-1-pipéridinyl]-7-(2-butyn-1-yl)-3-méthyl-1-[(4-méthyl-2-quinazolinyl)méthyl]-3,7-dihydro-1H-purine-2,6-dione [French] [ACD/IUPAC Name]
(R)-8-(3-aminopiperidin-1-yl)-7-(but-2-yn-1-yl)-3-methyl-1-((4-methylquinazolin-2-yl)methyl)-3,7-dihydro-1H-purine-2,6-dione
(R)-8-(3-aminopiperidin-1-yl)-7-(but-2-ynyl)-3-methyl-1-((4-methylquinazolin-2-yl)methyl)-1H-purine-2,6(3H,7H)-dione
(R)-8-(3-aminopiperidin-1-yl)-7-but-2-ynyl-3-methyl-1-(4-methylquinazolin-2-ylmethyl)-3,7-dihydro-purine-2,6-dione
[668270-12-0]
1H-Purine-2,6-dione, 8-[(3R)-3-amino-1-piperidinyl]-7-(2-butyn-1-yl)-3,7-dihydro-3-methyl-1-[(4-methyl-2-quinazolinyl)methyl]- [ACD/Index Name]
356
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

BI-1356 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      5 Axon Medchem 2354
      A10BH05 Wikidata Q909745
      H303;H313;H317;H333;H334;H335;H373 Axon Medchem 2354
      no pictogram Axon Medchem 2354
      P101;P102;P103;P260;P262;P263;P264;P270;P280;P304;P312;P340 Axon Medchem 2354
      Warning Axon Medchem 2354
    • Chemical Class:

      A xanthine that is 7<element>H</element>-xanthine bearing (4-methylquinazolin-2-yl)methyl, methyl, but-2-yn-1-yl and 3-aminopiperidin-1-yl substituents at positions 1, 3, 7 and 8 respectively (the <st ereo>R</stereo>-enantiomer). Used for treatment of type II diabetes. ChEBI CHEBI:68610
    • Bio Activity:

      DPP4 MedChem Express HY-10284
      Linagliptin is a highly potent, selective DPP-4 inhibitor with IC50 of 1 nM. MedChem Express
      Linagliptin is a highly potent, selective DPP-4 inhibitor with IC50 of 1 nM.;IC50 value: 1 nM [1];Target: DPP-4;In vitro: Linagliptin shows a potent inhibition effect against DPP-4 in vitro and a low affinity for hERG channel and M1 receptor (IC50 295 nM) [1]. Linagliptin acts as a competitive inhibitor with a Ki of 1 nM, and also shows 10,000-fold more selectivity for DPP-4 than DPP-8, DPP-9, amino-peptidases N and P, prolyloligopeptidase, trypsin, plasmin, and thrombin, and 90-fold more selectivity than fibroblast activation protein in vitro [2].;In vivo: In male Wistar rats, Beagle dogs, and Rhesus monkeys, Linagliptin shows a highly efficacious, long-lasting, and potent inhibitory activity against DPP-4 by more than 70% inhibition for all three species after oral administration of 1 mg/kg. Oral administration of Linagliptin to db/db mice 45 min before an oral glucose tolerance test reduces plasma glucose excursion in a dose-dependent manner from 0.1 mg/kg (15% inhibition) to 1 MedChem Express HY-10284
      Metabolism/Protease; MedChem Express HY-10284

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

Density: 1.4±0.1 g/cm3
Boiling Point: 661.2±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.0 mmHg at 25°C
Enthalpy of Vaporization: 97.3±3.0 kJ/mol
Flash Point: 353.7±34.3 °C
Index of Refraction: 1.717
Molar Refractivity: 133.1±0.5 cm3
#H bond acceptors: 10
#H bond donors: 2
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 1
ACD/LogP: 1.99
ACD/LogD (pH 5.5): -0.91
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -0.16
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.70
Polar Surface Area: 113 Å2
Polarizability: 52.8±0.5 10-24cm3
Surface Tension: 59.1±7.0 dyne/cm
Molar Volume: 338.0±7.0 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) =  2.85

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  759.10  (Adapted Stein & Brown method)
    Melting Pt (deg C):  333.63  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.35E-018  (Modified Grain method)
    Subcooled liquid VP: 4.26E-015 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):  3.977
       log Kow used: 2.85 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  40.798 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.15E-023  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.111E-019 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.85  (KowWin est)
  Log Kaw used:  -20.770  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  23.620
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5258
   Biowin2 (Non-Linear Model)     :   0.0142
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.8497  (months      )
   Biowin4 (Primary Survey Model) :   2.8527  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.5850
   Biowin6 (MITI Non-Linear Model):   0.0000
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.3961
 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):  5.68E-013 Pa (4.26E-015 mm Hg)
  Log Koa (Koawin est  ): 23.620
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  5.28E+006 
       Octanol/air (Koa) model:  1.02E+011 
   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 = 148.3080 E-12 cm3/molecule-sec
      Half-Life =     0.072 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.865 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.003000 E-17 cm3/molecule-sec
      Half-Life =   382.000 Days (at 7E11 mol/cm3)
   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    :  1.415E+004
      Log Koc:  4.151 

 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 = 1.492 (BCF = 31.02)
       log Kow used: 2.85 (estimated)

 Volatilization from Water:
    Henry LC:  4.15E-023 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.067E+019  hours   (1.278E+018 days)
    Half-Life from Model Lake : 3.346E+020  hours   (1.394E+019 days)

 Removal In Wastewater Treatment:
    Total removal:               4.60  percent
    Total biodegradation:        0.11  percent
    Total sludge adsorption:     4.48  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       1.28e-007       1.73         1000       
   Water     11.5            1.44e+003    1000       
   Soil      88.3            2.88e+003    1000       
   Sediment  0.204           1.3e+004     0          
     Persistence Time: 2.61e+003 hr




                    

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