Linagliptin
Linagliptin is a purine and quinazoline derivative that functions as a potentiator of incretin and as long lasting dipeptidyl-peptidase IV inhibitor. It is used as a hypoglycemic agent in the treatment of Type II diabetes mellitus
General
Type : Drug,Purine,Gliptin,Quinazoline
Chemical_Nomenclature : 8-[(3R)-3-aminopiperidin-1-yl]-7-but-2-ynyl-3-methyl-1-[(4-methylquinazolin-2-yl)methyl]purine-2,6-dione. Linagliptin inhibits also fibroblast activation protein (FAP)
Canonical SMILES : CC#CCN1C2=C(N=C1N3CCCC(C3)N)N(C(=O)N(C2=O)CC4=NC5=CC=CC=C5C(=N4)C)C
InChI : InChI=1S\/C25H28N8O2\/c1-4-5-13-32-21-22(29-24(32)31-12-8-9-17(26)14-31)30(3)25(35)33(23(21)34)15-20-27-16(2)18-10-6-7-11-19(18)28-20\/h6-7,10-11,17H,8-9,12-15,26H2,1-3H3\/t17-\/m1\/s1
InChIKey : LTXREWYXXSTFRX-QGZVFWFLSA-N
Other name(s) : Tradjenta,BI-1356,Trajenta,Ondero
MW : 472.54
Formula : C25H28N8O2
CAS_number : 668270-12-0
PubChem : 10096344
UniChem : LTXREWYXXSTFRX-QGZVFWFLSA-N
IUPHAR : 6318
Wikipedia : Linagliptin
Target
Families : Linagliptin ligand of proteins in family: DPP4N_Peptidase_S9
Stucture :
Protein : human-DPP4 || human-FAP
References (23)
| Title : Linagliptin ameliorated cardiac fibrosis and restored cardiomyocyte structure in diabetic mice associated with the suppression of necroptosis - Adhikari_2023_J.Diabetes.Investig__ |
| Author(s) : Adhikari J , Hirai T , Kawakita E , Iwai K , Koya D , Kanasaki K |
| Ref : J Diabetes Investig , : , 2023 |
| Abstract : Adhikari_2023_J.Diabetes.Investig__ |
| ESTHER : Adhikari_2023_J.Diabetes.Investig__ |
| PubMedSearch : Adhikari_2023_J.Diabetes.Investig__ |
| PubMedID: 37092329 |
| Title : A Quantitative Systems Pharmacology Model of the Incretin Hormones GIP and GLP1, Glucagon, Glucose, Insulin, and the Small Molecule DPP-4 Inhibitor, Linagliptin - Wu_2023_J.Pharm.Sci__ |
| Author(s) : Wu N , An G |
| Ref : J Pharm Sci , : , 2023 |
| Abstract : Wu_2023_J.Pharm.Sci__ |
| ESTHER : Wu_2023_J.Pharm.Sci__ |
| PubMedSearch : Wu_2023_J.Pharm.Sci__ |
| PubMedID: 37716531 |
| Title : Targeting DPP4-RBD interactions by sitagliptin and linagliptin delivers a potential host-directed therapy against pan-SARS-CoV-2 infections - Mani_2023_Int.J.Biol.Macromol_245_125444 |
| Author(s) : Mani S , Kaur A , Jakhar K , Kumari G , Sonar S , Kumar A , Das S , Kumar S , Kumar V , Kundu R , Pandey AK , Singh UP , Majumdar T |
| Ref : Int J Biol Macromol , 245 :125444 , 2023 |
| Abstract : Mani_2023_Int.J.Biol.Macromol_245_125444 |
| ESTHER : Mani_2023_Int.J.Biol.Macromol_245_125444 |
| PubMedSearch : Mani_2023_Int.J.Biol.Macromol_245_125444 |
| PubMedID: 37385308 |
| Gene_locus related to this paper: human-DPP4 |
| Title : The dipeptidyl peptidase-4 inhibitor linagliptin ameliorates LPS-induced acute lung injury by maintenance of pulmonary microvascular barrier via activating the Epac1\/AKT pathway - Zhang_2022_Biomed.Pharmacother_155_113704 |
| Author(s) : Zhang N , Tang S , Zhang J , Pei B , Pang T , Sun G |
| Ref : Biomed Pharmacother , 155 :113704 , 2022 |
| Abstract : Zhang_2022_Biomed.Pharmacother_155_113704 |
| ESTHER : Zhang_2022_Biomed.Pharmacother_155_113704 |
| PubMedSearch : Zhang_2022_Biomed.Pharmacother_155_113704 |
| PubMedID: 36115114 |
| Title : Linagliptin, a Selective Dipeptidyl Peptidase-4 Inhibitor, Reduces Physical and Behavioral Effects of Morphine Withdrawal - Listos_2022_Molecules_27_ |
| Author(s) : Listos J , Listos P , Baranowska-Bosiacka I , Karpiuk A , Filarowska J , Lupina M , Slowik T , Zawislak S , Kotlinska J |
| Ref : Molecules , 27 : , 2022 |
| Abstract : Listos_2022_Molecules_27_ |
| ESTHER : Listos_2022_Molecules_27_ |
| PubMedSearch : Listos_2022_Molecules_27_ |
| PubMedID: 35458676 |
| Title : Linagliptin, a DPP-4 inhibitor, ameliorates Abeta (1-42) peptides induced neurodegeneration and brain insulin resistance (BIR) via insulin receptor substrate-1 (IRS-1) in rat model of Alzheimer's disease - Siddiqui_2021_Neuropharmacol__108662 |
| Author(s) : Siddiqui N , Ali J , Parvez S , Zameer S , Najmi AK , Akhtar M |
| Ref : Neuropharmacology , :108662 , 2021 |
| Abstract : Siddiqui_2021_Neuropharmacol__108662 |
| ESTHER : Siddiqui_2021_Neuropharmacol__108662 |
| PubMedSearch : Siddiqui_2021_Neuropharmacol__108662 |
| PubMedID: 34119519 |
| Title : The dipeptidyl peptidase 4 inhibitor linagliptin ameliorates renal injury and accelerated resolution in a rat model of crescentic nephritis - Mayer_2021_Br.J.Pharmacol_178_878 |
| Author(s) : Mayer AL , Scheitacker I , Ebert N , Klein T , Amann K , Daniel C |
| Ref : British Journal of Pharmacology , 178 :878 , 2021 |
| Abstract : Mayer_2021_Br.J.Pharmacol_178_878 |
| ESTHER : Mayer_2021_Br.J.Pharmacol_178_878 |
| PubMedSearch : Mayer_2021_Br.J.Pharmacol_178_878 |
| PubMedID: 33171531 |
| Title : Metformin dose increase versus added linagliptin in non-alcoholic fatty liver disease and type 2 diabetes: An analysis of the J-LINK study - Komorizono_2021_Diabetes.Obes.Metab_23_832 |
| Author(s) : Komorizono Y , Hosoyamada K , Imamura N , Kajiya S , Hashiguchi Y , Ueyama N , Shinmaki H , Koriyama N , Tsukasa M , Kamada T |
| Ref : Diabetes Obes Metab , 23 :832 , 2021 |
| Abstract : Komorizono_2021_Diabetes.Obes.Metab_23_832 |
| ESTHER : Komorizono_2021_Diabetes.Obes.Metab_23_832 |
| PubMedSearch : Komorizono_2021_Diabetes.Obes.Metab_23_832 |
| PubMedID: 33236464 |
| Title : A Single Second Shell Amino Acid Determines Affinity and Kinetics of Linagliptin Binding to Type 4 Dipeptidyl Peptidase and Fibroblast Activation Protein - Schnapp_2021_ChemMedChem_16_630 |
| Author(s) : Schnapp G , Hoevels Y , Bakker RA , Schreiner P , Klein T , Nar H |
| Ref : ChemMedChem , 16 :630 , 2021 |
| Abstract : Schnapp_2021_ChemMedChem_16_630 |
| ESTHER : Schnapp_2021_ChemMedChem_16_630 |
| PubMedSearch : Schnapp_2021_ChemMedChem_16_630 |
| PubMedID: 33030297 |
| Gene_locus related to this paper: human-FAP |
| Title : A comparative study of the binding properties, dipeptidyl peptidase-4 (DPP-4) inhibitory activity and glucose-lowering efficacy of the DPP-4 inhibitors alogliptin, linagliptin, saxagliptin, sitagliptin and vildagliptin in mice - Berger_2018_Endocrinol.Diabetes.Metab_1_e00002 |
| Author(s) : Berger JP , SinhaRoy R , Pocai A , Kelly TM , Scapin G , Gao YD , Pryor KAD , Wu JK , Eiermann GJ , Xu SS , Zhang X , Tatosian DA , Weber AE , Thornberry NA , Carr RD |
| Ref : Endocrinol Diabetes Metab , 1 :e00002 , 2018 |
| Abstract : Berger_2018_Endocrinol.Diabetes.Metab_1_e00002 |
| ESTHER : Berger_2018_Endocrinol.Diabetes.Metab_1_e00002 |
| PubMedSearch : Berger_2018_Endocrinol.Diabetes.Metab_1_e00002 |
| PubMedID: 30815539 |
| Gene_locus related to this paper: human-DPP4 |
| Title : Pharmacokinetic and pharmacodynamic evaluation of linagliptin for the treatment of type 2 diabetes mellitus, with consideration of Asian patient populations - Ceriello_2017_J.Diabetes.Investig_8_19 |
| Author(s) : Ceriello A , Inagaki N |
| Ref : J Diabetes Investig , 8 :19 , 2017 |
| Abstract : Ceriello_2017_J.Diabetes.Investig_8_19 |
| ESTHER : Ceriello_2017_J.Diabetes.Investig_8_19 |
| PubMedSearch : Ceriello_2017_J.Diabetes.Investig_8_19 |
| PubMedID: 27180612 |
| Title : Empagliflozin (an SGLT2 inhibitor), alone or in combination with linagliptin (a DPP-4 inhibitor), prevents steatohepatitis in a novel mouse model of non-alcoholic steatohepatitis and diabetes - Jojima_2016_Diabetol.Metab.Syndr_8_45 |
| Author(s) : Jojima T , Tomotsune T , Iijima T , Akimoto K , Suzuki K , Aso Y |
| Ref : Diabetol Metab Syndr , 8 :45 , 2016 |
| Abstract : Jojima_2016_Diabetol.Metab.Syndr_8_45 |
| ESTHER : Jojima_2016_Diabetol.Metab.Syndr_8_45 |
| PubMedSearch : Jojima_2016_Diabetol.Metab.Syndr_8_45 |
| PubMedID: 27462372 |
| Title : Long-Term Efficacy and Safety of Linagliptin in Patients With Type 2 Diabetes and Severe Renal Impairment: A 1-year, randomized, double-blind, placebo-controlled study - McGill_2013_Diabetes.Care_36_237 |
| Author(s) : McGill JB , Sloan L , Newman J , Patel S , Sauce C , von Eynatten M , Woerle HJ |
| Ref : Diabetes Care , 36 :237 , 2013 |
| Abstract : McGill_2013_Diabetes.Care_36_237 |
| ESTHER : McGill_2013_Diabetes.Care_36_237 |
| PubMedSearch : McGill_2013_Diabetes.Care_36_237 |
| PubMedID: 23033241 |
| Title : Pharmacokinetic, pharmacodynamic, and tolerability profiles of the dipeptidyl peptidase-4 inhibitor linagliptin: a 4-week multicenter, randomized, double-blind, placebo-controlled phase IIa study in Japanese type 2 diabetes patients - Horie_2011_Clin.Ther_33_973 |
| Author(s) : Horie Y , Kanada S , Watada H , Sarashina A , Taniguchi A , Hayashi N , Graefe-Mody EU , Woerle HJ , Dugi KA |
| Ref : Clin Ther , 33 :973 , 2011 |
| Abstract : Horie_2011_Clin.Ther_33_973 |
| ESTHER : Horie_2011_Clin.Ther_33_973 |
| PubMedSearch : Horie_2011_Clin.Ther_33_973 |
| PubMedID: 21723606 |
| Title : Assessment of the pharmacokinetic interaction between the novel DPP-4 inhibitor linagliptin and a sulfonylurea, glyburide, in healthy subjects - Graefe-Mody_2011_Drug.Metab.Pharmacokinet_26_123 |
| Author(s) : Graefe-Mody U , Rose P , Ring A , Zander K , Iovino M , Woerle HJ |
| Ref : Drug Metab Pharmacokinet , 26 :123 , 2011 |
| Abstract : Graefe-Mody_2011_Drug.Metab.Pharmacokinet_26_123 |
| ESTHER : Graefe-Mody_2011_Drug.Metab.Pharmacokinet_26_123 |
| PubMedSearch : Graefe-Mody_2011_Drug.Metab.Pharmacokinet_26_123 |
| PubMedID: 21084763 |
| Title : The dipeptidyl peptidase-4 inhibitor linagliptin exhibits time- and dose-dependent localization in kidney, liver, and intestine after intravenous dosing: results from high resolution autoradiography in rats - Greischel_2010_Drug.Metab.Dispos_38_1443 |
| Author(s) : Greischel A , Binder R , Baierl J |
| Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , 38 :1443 , 2010 |
| Abstract : Greischel_2010_Drug.Metab.Dispos_38_1443 |
| ESTHER : Greischel_2010_Drug.Metab.Dispos_38_1443 |
| PubMedSearch : Greischel_2010_Drug.Metab.Dispos_38_1443 |
| PubMedID: 20538719 |
| Title : Pharmacokinetics and pharmacodynamics of single rising intravenous doses (0.5 mg-10 mg) and determination of absolute bioavailability of the dipeptidyl peptidase-4 inhibitor linagliptin (BI 1356) in healthy male subjects - Retlich_2010_Clin.Pharmacokinet_49_829 |
| Author(s) : Retlich S , Duval V , Ring A , Staab A , Huttner S , Jungnik A , Jaehde U , Dugi KA , Graefe-Mody U |
| Ref : Clinical Pharmacokinetics , 49 :829 , 2010 |
| Abstract : Retlich_2010_Clin.Pharmacokinet_49_829 |
| ESTHER : Retlich_2010_Clin.Pharmacokinet_49_829 |
| PubMedSearch : Retlich_2010_Clin.Pharmacokinet_49_829 |
| PubMedID: 21053992 |
| Title : The metabolism and disposition of the oral dipeptidyl peptidase-4 inhibitor, linagliptin, in humans - Blech_2010_Drug.Metab.Dispos_38_667 |
| Author(s) : Blech S , Ludwig-Schwellinger E , Grafe-Mody EU , Withopf B , Wagner K |
| Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , 38 :667 , 2010 |
| Abstract : Blech_2010_Drug.Metab.Dispos_38_667 |
| ESTHER : Blech_2010_Drug.Metab.Dispos_38_667 |
| PubMedSearch : Blech_2010_Drug.Metab.Dispos_38_667 |
| PubMedID: 20086031 |
| Title : Linagliptin (BI 1356), a potent and selective DPP-4 inhibitor, is safe and efficacious in combination with metformin in patients with inadequately controlled Type 2 diabetes - Forst_2010_Diabet.Med_27_1409 |
| Author(s) : Forst T , Uhlig-Laske B , Ring A , Graefe-Mody U , Friedrich C , Herbach K , Woerle HJ , Dugi KA |
| Ref : Diabet Med , 27 :1409 , 2010 |
| Abstract : Forst_2010_Diabet.Med_27_1409 |
| ESTHER : Forst_2010_Diabet.Med_27_1409 |
| PubMedSearch : Forst_2010_Diabet.Med_27_1409 |
| PubMedID: 21059094 |
| Title : Evaluation of the pharmacokinetic interaction between the dipeptidyl peptidase-4 inhibitor linagliptin and pioglitazone in healthy volunteers - Graefe-Mody_2010_Int.J.Clin.Pharmacol.Ther_48_652 |
| Author(s) : Graefe-Mody EU , Jungnik A , Ring A , Woerle HJ , Dugi KA |
| Ref : Int J Clinical Pharmacology & Therapeutics , 48 :652 , 2010 |
| Abstract : Graefe-Mody_2010_Int.J.Clin.Pharmacol.Ther_48_652 |
| ESTHER : Graefe-Mody_2010_Int.J.Clin.Pharmacol.Ther_48_652 |
| PubMedSearch : Graefe-Mody_2010_Int.J.Clin.Pharmacol.Ther_48_652 |
| PubMedID: 20875371 |
| Title : Pharmacokinetics, pharmacodynamics and tolerability of multiple oral doses of linagliptin, a dipeptidyl peptidase-4 inhibitor in male type 2 diabetes patients - Heise_2009_Diabetes.Obes.Metab_11_786 |
| Author(s) : Heise T , Graefe-Mody EU , Huttner S , Ring A , Trommeshauser D , Dugi KA |
| Ref : Diabetes Obes Metab , 11 :786 , 2009 |
| Abstract : Heise_2009_Diabetes.Obes.Metab_11_786 |
| ESTHER : Heise_2009_Diabetes.Obes.Metab_11_786 |
| PubMedSearch : Heise_2009_Diabetes.Obes.Metab_11_786 |
| PubMedID: 19476474 |
| Title : Binding to dipeptidyl peptidase-4 determines the disposition of linagliptin (BI 1356)--investigations in DPP-4 deficient and wildtype rats - Retlich_2009_Biopharm.Drug.Dispos_30_422 |
| Author(s) : Retlich S , Withopf B , Greischel A , Staab A , Jaehde U , Fuchs H |
| Ref : Biopharmaceutics & Drug Disposition , 30 :422 , 2009 |
| Abstract : Retlich_2009_Biopharm.Drug.Dispos_30_422 |
| ESTHER : Retlich_2009_Biopharm.Drug.Dispos_30_422 |
| PubMedSearch : Retlich_2009_Biopharm.Drug.Dispos_30_422 |
| PubMedID: 19771584 |
| Title : 8-(3-(R)-aminopiperidin-1-yl)-7-but-2-ynyl-3-methyl-1-(4-methyl-quinazolin-2-ylme thyl)-3,7-dihydropurine-2,6-dione (BI 1356), a highly potent, selective, long-acting, and orally bioavailable DPP-4 inhibitor for the treatment of type 2 diabetes - Eckhardt_2007_J.Med.Chem_50_6450 |
| Author(s) : Eckhardt M , Langkopf E , Mark M , Tadayyon M , Thomas L , Nar H , Pfrengle W , Guth B , Lotz R , Sieger P , Fuchs H , Himmelsbach F |
| Ref : Journal of Medicinal Chemistry , 50 :6450 , 2007 |
| Abstract : Eckhardt_2007_J.Med.Chem_50_6450 |
| ESTHER : Eckhardt_2007_J.Med.Chem_50_6450 |
| PubMedSearch : Eckhardt_2007_J.Med.Chem_50_6450 |
| PubMedID: 18052023 |
| Gene_locus related to this paper: human-DPP4 |