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    Sitagliptin phosphate monohydrate
    Sitagliptin phosphate monohydrate

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    InvivoChem Cat #: V0741
    CAS #: 654671-77-9Purity ≥98%

    Description: Sitagliptin phosphate (formerly also known as MK-431; trade name Januvia) monohydrate, an antihyperglycemic agent and antidiabetic drug, is a potent, orally bioavailable inhibitor of DPP-IV (dipeptidyl peptidase-4) with IC50 of 19 nM in Caco-2 cell extracts. It is an enzyme-inhibiting drug that is used either alone or in combination with other oral antihyperglycemic agents (such as metformin or a thiazolidinedione) for treatment of diabetes mellitus type 2. The benefit of this medicine is its lower side-effects (e.g., less hypoglycemia, less weight gain) in the control of blood glucose values. Exenatide (Byetta) also works by its effect on the incretin system. 

    References: J Pharmacol Exp Ther. 2008 Apr;325(1):175-82; Diabetes. 2009 Mar;58(3):641-51. 

    Related CAS: 486460-32-6 (free base); 654671-78-0 (Phosphate)  

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    Molecular Weight (MW)523.32
    FormulaC16H15F6N5O.H3PO4.H2O
    CAS No.654671-77-9  (Phosphate hydrate); 
    Storage-20℃ for 3 years in powder form
    -80℃ for 2 years in solvent
    Solubility (In vitro)DMSO: 100 mg/mL (191.1 mM)
    Water: 41 mg/mL (78.3 mM)
    Ethanol: <1 mg/mL
    Solubility (In vivo)Saline: 30 mg/mL
    SynonymsMK-0431; MK0431; MK 0431; MK-431; MK431; MK 431; Sitagliptin Phosphate; Sitagliptin Phosphate Monohydrate; trade name: Januvia Xelevia Janumet 

    Chemical Name: (R)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butan-1-one Phosphate Monohydrate.

    InChi Key: GQPYTJVDPQTBQC-KLQYNRQASA-N

    InChi Code: InChI=1S/C16H15F6N5O.H3O4P.H2O/c17-10-6-12(19)11(18)4-8(10)3-9(23)5-14(28)26-1-2-27-13(7-26)24-25-15(27)16(20,21)22;1-5(2,3)4;/h4,6,9H,1-3,5,7,23H2;(H3,1,2,3,4);1H2/t9-;;/m1../s1

    SMILES Code: O=C(N1CC2=NN=C(C(F)(F)F)N2CC1)C[C@H](N)CC3=CC(F)=C(F)C=C3F.O=P(O)(O)O.[H]O[H]


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    In Vitro

    In vitro activity: As an orally active agent, Sitagliptin phosphate exhibits a potent inhibitory effect on DPP-4 with IC50 of 19 nM from Caco-2 cell extracts. MK0431 reduces in vitro migration of isolated splenic CD4 T-cells through a pathway involving cAMP/PKA/Rac1 activation. A recent study demonstrates that sitagliptin exerts a novel, direct action in order to stimulate GLP-1 secretion by the intestinal L cell through a DPP-4-independent, protein kinase A- and MEK-ERK1/2-dependent pathway. It therefore reduces the effect of autoimmunity on graft survival.


    Kinase Assay: DPP-4 is extracted from confluent Caco-2 cells. After 5 minutes of incubation at room temperature with lysis buffer (10 mM Tris-HCl, 150 mM NaCl, 0.04 U/mL aprotinin, 0.5% Nonidet P40, pH 8.0), cells are centrifuged at 35,000 g at 4 °C for 30 minutes, and the supernatant is stored at -80°C. Assays are performed by mixing 20 μL of appropriate compound dilutions with 50 μL of the substrate for the DPP-4 enzyme, H-Ala-Pro-7-amido-4-trifluoromethylcoumarin (final concentration in the assay, 100 μM) and 30 μL of the Caco-2 cell extract (diluted 1000-fold with 100 mM Tris-HCl, 100 mM NaCl, pH 7.8). Plates are incubated at room temperature for 1 hour, and fluorescence is measured at excitation/emission wavelengths of 405/535 nm using a SpectraMax GeminiXS. Dissociation kinetics of inhibitors from the DPP-4 enzyme is determined after a 1-hour preincubation of Caco-2 cell extracts with high inhibitor concentrations (30 nM for BI 1356, 3 μM for vildagliptin). The enzymatic reaction is started by adding the substrate H-Ala-Pro-7-amido-4-trifluoromethylcoumarin after a 3000-fold dilution of the preincubation mixture with assay buffer. Under these conditions, the difference in DPP-4 activity at a certain time point in the presence or absence of an inhibitor reflects the amount of this inhibitor still bound to the DPP-4 enzyme. Maximal reaction rates (fluorescence units/seconds × 1000) at 10-minute intervals are calculated using the SoftMax software of the SpectraMax and corrected for the rate of an uninhibited reaction [(vcontrol-vinhibitor)/vcontrol]. 


    Cell Assay: CD4T-cells are plated on membrane inserts in serum-free RPMI 1640, and cell migration is assayed using Transwell chambers (Corning), in the presence or absence of purified porcine kidney DPP-4 (32.1 units/mg; 100 mU/mL final concentration) and DPP-4 inhibitor (100 μM). After 1 hour, cells on the upper surface are removed mechanically, and cells that have migrated into the lower compartment are counted. The extent of migration is expressed relative to the control sample.

    In VivoIn vivo, the ED50 value of Sitagliptin phosphate for inhibition of plasma DPP-4 activity is calculated to be 2.3 mg/kg 7 hour postdose and 30 mg/kg 24 hour postdose in freely fed Han-Wistar rats. The streptozotocin-induced type 1 diabetes mouse model exhibits elevated DPP-4 levels in the plasma that can be substantially inhibited in mice on an Sitagliptin phosphate diet. This is achieved by a positive effect on the regulation of hyperglycemia, potentially through prolongation of islet graft survival. The plasma clearance and volume of distribution of Sitagliptin phosphate are higher in rats (40-48 mL/min/kg, 7-9 L/kg) than in dogs (9 mL/min/kg, 3 L/kg); and its half-life is shorter in rats,2 hours compared with 4 hours in dogs.
    Animal modelFreely fed Han-Wistar rats
    Formulation & DosageDissolved in 0.5% aqueous hyroxyethylcellulose; 30 mg/kg; p.o. administration
    References

    J Pharmacol Exp Ther. 2008 Apr;325(1):175-82; Diabetes. 2009 Mar;58(3):641-51. 


    These protocols are for reference only. InvivoChem does not independently validate these methods.

    Sitagliptin phosphate monohydrate

    The effects of MK0431 in diabetic NOD mice after islet transplantation. Diabetes. 2009 Mar;58(3):641-51. 
     
     

    Sitagliptin phosphate monohydrate

    MK0431 regulates the migration of CD4+ T-cells. Diabetes. 2009 Mar;58(3):641-51. 
     

    Sitagliptin phosphate monohydrate

    Time-course monitoring of glucose responses, plasma chemistry, and islet graft survival after islet transplantation. Diabetes. 2009 Mar;58(3):641-51. 

    Sitagliptin phosphate monohydrate

    Sitagliptin phosphate monohydrate

    Sitagliptin phosphate monohydrate


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