Alogliptin
Alogliptin is a selective, orally bioavailable, pyrimidinedione-based inhibitor of dipeptidyl peptidase 4 (DPP-4), with hypoglycemic activity. Almost identical to Trelagliptin which is a fluride derivative (Alogliptin cation CID 26322458 in structure 3G0B)
General
Type : Drug,Piperidine,Pyrimidine,Cyanide,Gliptin
Chemical_Nomenclature : 2-[[6-[(3R)-3-aminopiperidin-1-yl]-3-methyl-2,4-dioxopyrimidin-1-yl]methyl]benzonitrile
Canonical SMILES : CN1C(=O)C=C(N(C1=O)CC2=CC=CC=C2C#N)N3CCCC(C3)N
InChI : InChI=1S\/C18H21N5O2\/c1-21-17(24)9-16(22-8-4-7-15(20)12-22)23(18(21)25)11-14-6-3-2-5-13(14)10-19\/h2-3,5-6,9,15H,4,7-8,11-12,20H2,1H3\/t15-\/m1\/s1
InChIKey : ZSBOMTDTBDDKMP-OAHLLOKOSA-N
Other name(s) : Alogliptina,UNII-JHC049LO86,CHEMBL376359,TAK-322,Nesina,SYR-322
MW : 339.39
Formula : C18H21N5O2
CAS_number : 850649-61-5
PubChem : 11450633
UniChem : ZSBOMTDTBDDKMP-OAHLLOKOSA-N
IUPHAR : 6319
Wikipedia : Alogliptin
Target
Families : Alogliptin ligand of proteins in family: DPP4N_Peptidase_S9
Stucture :
Protein : human-DPP4
References (23)
| Title : Fotagliptin monotherapy with alogliptin as an active comparator in patients with uncontrolled type 2 diabetes mellitus: a randomized, multicenter, double-blind, placebo-controlled, phase 3 trial - Xu_2023_BMC.Med_21_388 |
| Author(s) : Xu M , Sun K , Xu W , Wang C , Yan D , Li S , Cong L , Pi Y , Song W , Sun Q , Xiao R , Peng W , Wang J , Peng H , Zhang Y , Duan P , Zhang M , Liu J , Huang Q , Li X , Bao Y , Zeng T , Wang K , Qin L , Wu C , Deng C , Huang C , Yan S , Zhang W , Li M , Sun L , Wang Y , Li H , Wang G , Pang S , Zheng X , Wang H , Wang F , Su X , Ma Y , Li Z , Xie Z , Xu N , Ni L , Zhang L , Deng X , Pan T , Dong Q , Wu X , Shen X , Zhang X , Zou Q , Jiang C , Xi J , Ma J , Sun J , Yan L |
| Ref : BMC Med , 21 :388 , 2023 |
| Abstract : Xu_2023_BMC.Med_21_388 |
| ESTHER : Xu_2023_BMC.Med_21_388 |
| PubMedSearch : Xu_2023_BMC.Med_21_388 |
| PubMedID: 37814306 |
| Title : Alogliptin abates memory injuries of hepatic encephalopathy induced by acute paracetamol intoxication via switching-off autophagy-related apoptosis - Saad_2018_Life.Sci_215_11 |
| Author(s) : Saad MA , Rastanawi AA , El-Yamany MF |
| Ref : Life Sciences , 215 :11 , 2018 |
| Abstract : Saad_2018_Life.Sci_215_11 |
| ESTHER : Saad_2018_Life.Sci_215_11 |
| PubMedSearch : Saad_2018_Life.Sci_215_11 |
| PubMedID: 30391466 |
| 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 : Comparison of effects of anagliptin and alogliptin on serum lipid profile in type 2 diabetes mellitus patients - Kurozumi_2018_J.Diabetes.Investig_9_360 |
| Author(s) : Kurozumi A , Okada Y , Arao T , Kobayashi T , Masuda D , Yamashita S , Tanaka Y |
| Ref : J Diabetes Investig , 9 :360 , 2018 |
| Abstract : Kurozumi_2018_J.Diabetes.Investig_9_360 |
| ESTHER : Kurozumi_2018_J.Diabetes.Investig_9_360 |
| PubMedSearch : Kurozumi_2018_J.Diabetes.Investig_9_360 |
| PubMedID: 28853228 |
| Title : Alogliptin prevents diastolic dysfunction and preserves left ventricular mitochondrial function in diabetic rabbits - Zhang_2018_Cardiovasc.Diabetol_17_160 |
| Author(s) : Zhang X , Zhang Z , Yang Y , Suo Y , Liu R , Qiu J , Zhao Y , Jiang N , Liu C , Tse G , Li G , Liu T |
| Ref : Cardiovasc Diabetol , 17 :160 , 2018 |
| Abstract : Zhang_2018_Cardiovasc.Diabetol_17_160 |
| ESTHER : Zhang_2018_Cardiovasc.Diabetol_17_160 |
| PubMedSearch : Zhang_2018_Cardiovasc.Diabetol_17_160 |
| PubMedID: 30591063 |
| Title : Retrospective and Prospective Human Intravenous and Oral Pharmacokinetic Projection of Dipeptidyl peptidase-IV Inhibitors Using Simple Allometric Principles - Case Studies of ABT-279, ABT-341, Alogliptin, Carmegliptin, Sitagliptin and Vildagliptin - Gilibili_2015_J.Pharm.Pharm.Sci_18_434 |
| Author(s) : Gilibili RR , Bhamidipati RK , Mullangi R , Srinivas NR |
| Ref : J Pharm Pharm Sci , 18 :434 , 2015 |
| Abstract : Gilibili_2015_J.Pharm.Pharm.Sci_18_434 |
| ESTHER : Gilibili_2015_J.Pharm.Pharm.Sci_18_434 |
| PubMedSearch : Gilibili_2015_J.Pharm.Pharm.Sci_18_434 |
| PubMedID: 26517136 |
| Title : Novel pyrrolopyrimidine analogues as potent dipeptidyl peptidase IV inhibitors based on pharmacokinetic property-driven optimization - Xie_2012_Eur.J.Med.Chem_52_205 |
| Author(s) : Xie H , Zeng L , Zeng S , Lu X , Zhang G , Zhao X , Cheng N , Tu Z , Li Z , Xu H , Yang L , Zhang X , Huang M , Zhao J , Hu W |
| Ref : Eur Journal of Medicinal Chemistry , 52 :205 , 2012 |
| Abstract : Xie_2012_Eur.J.Med.Chem_52_205 |
| ESTHER : Xie_2012_Eur.J.Med.Chem_52_205 |
| PubMedSearch : Xie_2012_Eur.J.Med.Chem_52_205 |
| PubMedID: 22475866 |
| Title : Design and synthesis of pyrimidinone and pyrimidinedione inhibitors of dipeptidyl peptidase IV - Zhang_2011_J.Med.Chem_54_510 |
| Author(s) : Zhang Z , Wallace MB , Feng J , Stafford JA , Skene RJ , Shi L , Lee B , Aertgeerts K , Jennings A , Xu R , Kassel DB , Kaldor SW , Navre M , Webb DR , Gwaltney SL |
| Ref : Journal of Medicinal Chemistry , 54 :510 , 2011 |
| Abstract : Zhang_2011_J.Med.Chem_54_510 |
| ESTHER : Zhang_2011_J.Med.Chem_54_510 |
| PubMedSearch : Zhang_2011_J.Med.Chem_54_510 |
| PubMedID: 21186796 |
| Gene_locus related to this paper: human-DPP4 |
| Title : Alogliptin: a review of its use in the management of type 2 diabetes mellitus - Scott_2010_Drugs_70_2051 |
| Author(s) : Scott LJ |
| Ref : Drugs , 70 :2051 , 2010 |
| Abstract : Scott_2010_Drugs_70_2051 |
| ESTHER : Scott_2010_Drugs_70_2051 |
| PubMedSearch : Scott_2010_Drugs_70_2051 |
| PubMedID: 20883057 |
| Title : Pharmacokinetics of alogliptin when administered with food, metformin, or cimetidine: a two-phase, crossover study in healthy subjects - Karim_2010_Int.J.Clin.Pharmacol.Ther_48_46 |
| Author(s) : Karim A , Covington P , Christopher R , Davenport M , Fleck P , Li X , Wann E , Mekki Q |
| Ref : Int J Clinical Pharmacology & Therapeutics , 48 :46 , 2010 |
| Abstract : Karim_2010_Int.J.Clin.Pharmacol.Ther_48_46 |
| ESTHER : Karim_2010_Int.J.Clin.Pharmacol.Ther_48_46 |
| PubMedSearch : Karim_2010_Int.J.Clin.Pharmacol.Ther_48_46 |
| PubMedID: 20040339 |
| Title : DPP-4 (CD26) inhibitor alogliptin inhibits TLR4-mediated ERK activation and ERK-dependent MMP-1 expression by U937 histiocytes - Ta_2010_Atherosclerosis_213_429 |
| Author(s) : Ta NN , Li Y , Schuyler CA , Lopes-Virella MF , Huang Y |
| Ref : Atherosclerosis , 213 :429 , 2010 |
| Abstract : Ta_2010_Atherosclerosis_213_429 |
| ESTHER : Ta_2010_Atherosclerosis_213_429 |
| PubMedSearch : Ta_2010_Atherosclerosis_213_429 |
| PubMedID: 20843518 |
| Title : Alogliptin: a new, highly selective dipeptidyl peptidase-4 inhibitor for the treatment of type 2 diabetes - Pratley_2009_Expert.Opin.Pharmacother_10_503 |
| Author(s) : Pratley RE |
| Ref : Expert Opin Pharmacother , 10 :503 , 2009 |
| Abstract : Pratley_2009_Expert.Opin.Pharmacother_10_503 |
| ESTHER : Pratley_2009_Expert.Opin.Pharmacother_10_503 |
| PubMedSearch : Pratley_2009_Expert.Opin.Pharmacother_10_503 |
| PubMedID: 19191685 |
| Title : DPP4 inhibitors: from sitagliptin monotherapy to the new alogliptin-pioglitazone combination therapy - Argyrakopoulou_2009_Adv.Ther_26_272 |
| Author(s) : Argyrakopoulou G , Doupis J |
| Ref : Adv Ther , 26 :272 , 2009 |
| Abstract : Argyrakopoulou_2009_Adv.Ther_26_272 |
| ESTHER : Argyrakopoulou_2009_Adv.Ther_26_272 |
| PubMedSearch : Argyrakopoulou_2009_Adv.Ther_26_272 |
| PubMedID: 19259628 |
| Title : A novel dipeptidyl peptidase-4 inhibitor, alogliptin (SYR-322), is effective in diabetic rats with sulfonylurea-induced secondary failure - Asakawa_2009_Life.Sci_85_122 |
| Author(s) : Asakawa T , Moritoh Y , Kataoka O , Suzuki N , Takeuchi K , Odaka H |
| Ref : Life Sciences , 85 :122 , 2009 |
| Abstract : Asakawa_2009_Life.Sci_85_122 |
| ESTHER : Asakawa_2009_Life.Sci_85_122 |
| PubMedSearch : Asakawa_2009_Life.Sci_85_122 |
| PubMedID: 19427871 |
| Title : The dipeptidyl peptidase-4 inhibitor alogliptin in combination with pioglitazone improves glycemic control, lipid profiles, and increases pancreatic insulin content in ob\/ob mice - Moritoh_2009_Eur.J.Pharmacol_602_448 |
| Author(s) : Moritoh Y , Takeuchi K , Asakawa T , Kataoka O , Odaka H |
| Ref : European Journal of Pharmacology , 602 :448 , 2009 |
| Abstract : Moritoh_2009_Eur.J.Pharmacol_602_448 |
| ESTHER : Moritoh_2009_Eur.J.Pharmacol_602_448 |
| PubMedSearch : Moritoh_2009_Eur.J.Pharmacol_602_448 |
| PubMedID: 19038243 |
| Title : Efficacy and safety of adding the dipeptidyl peptidase-4 inhibitor alogliptin to metformin therapy in patients with type 2 diabetes inadequately controlled with metformin monotherapy: a multicentre, randomised, double-blind, placebo-controlled study - Nauck_2009_Int.J.Clin.Pract_63_46 |
| Author(s) : Nauck MA , Ellis GC , Fleck PR , Wilson CA , Mekki Q |
| Ref : Int J Clin Pract , 63 :46 , 2009 |
| Abstract : Nauck_2009_Int.J.Clin.Pract_63_46 |
| ESTHER : Nauck_2009_Int.J.Clin.Pract_63_46 |
| PubMedSearch : Nauck_2009_Int.J.Clin.Pract_63_46 |
| PubMedID: 19125992 |
| Title : Efficacy and safety of the dipeptidyl peptidase-4 inhibitor alogliptin in patients with type 2 diabetes inadequately controlled by glyburide monotherapy - Pratley_2009_Diabetes.Obes.Metab_11_167 |
| Author(s) : Pratley RE , Kipnes MS , Fleck PR , Wilson C , Mekki Q |
| Ref : Diabetes Obes Metab , 11 :167 , 2009 |
| Abstract : Pratley_2009_Diabetes.Obes.Metab_11_167 |
| ESTHER : Pratley_2009_Diabetes.Obes.Metab_11_167 |
| PubMedSearch : Pratley_2009_Diabetes.Obes.Metab_11_167 |
| PubMedID: 19125778 |
| Title : Pharmacokinetic, pharmacodynamic, and efficacy profiles of alogliptin, a novel inhibitor of dipeptidyl peptidase-4, in rats, dogs, and monkeys - Lee_2008_Eur.J.Pharmacol_589_306 |
| Author(s) : Lee B , Shi L , Kassel DB , Asakawa T , Takeuchi K , Christopher RJ |
| Ref : European Journal of Pharmacology , 589 :306 , 2008 |
| Abstract : Lee_2008_Eur.J.Pharmacol_589_306 |
| ESTHER : Lee_2008_Eur.J.Pharmacol_589_306 |
| PubMedSearch : Lee_2008_Eur.J.Pharmacol_589_306 |
| PubMedID: 18538760 |
| Title : Chronic administration of alogliptin, a novel, potent, and highly selective dipeptidyl peptidase-4 inhibitor, improves glycemic control and beta-cell function in obese diabetic ob\/ob mice - Moritoh_2008_Eur.J.Pharmacol_588_325 |
| Author(s) : Moritoh Y , Takeuchi K , Asakawa T , Kataoka O , Odaka H |
| Ref : European Journal of Pharmacology , 588 :325 , 2008 |
| Abstract : Moritoh_2008_Eur.J.Pharmacol_588_325 |
| ESTHER : Moritoh_2008_Eur.J.Pharmacol_588_325 |
| PubMedSearch : Moritoh_2008_Eur.J.Pharmacol_588_325 |
| PubMedID: 18499100 |
| Title : Pharmacokinetics, pharmacodynamics, and tolerability of single increasing doses of the dipeptidyl peptidase-4 inhibitor alogliptin in healthy male subjects - Christopher_2008_Clin.Ther_30_513 |
| Author(s) : Christopher R , Covington P , Davenport M , Fleck P , Mekki QA , Wann ER , Karim A |
| Ref : Clin Ther , 30 :513 , 2008 |
| Abstract : Christopher_2008_Clin.Ther_30_513 |
| ESTHER : Christopher_2008_Clin.Ther_30_513 |
| PubMedSearch : Christopher_2008_Clin.Ther_30_513 |
| PubMedID: 18405789 |
| Title : Pharmacokinetic, pharmacodynamic, and tolerability profiles of the dipeptidyl peptidase-4 inhibitor alogliptin: a randomized, double-blind, placebo-controlled, multiple-dose study in adult patients with type 2 diabetes - Covington_2008_Clin.Ther_30_499 |
| Author(s) : Covington P , Christopher R , Davenport M , Fleck P , Mekki QA , Wann ER , Karim A |
| Ref : Clin Ther , 30 :499 , 2008 |
| Abstract : Covington_2008_Clin.Ther_30_499 |
| ESTHER : Covington_2008_Clin.Ther_30_499 |
| PubMedSearch : Covington_2008_Clin.Ther_30_499 |
| PubMedID: 18405788 |
| Title : Alogliptin, a potent and selective dipeptidyl peptidase-IV inhibitor for the treatment of type 2 diabetes - Deacon_2008_Curr.Opin.Investig.Drugs_9_402 |
| Author(s) : Deacon CF |
| Ref : Curr Opin Investig Drugs , 9 :402 , 2008 |
| Abstract : Deacon_2008_Curr.Opin.Investig.Drugs_9_402 |
| ESTHER : Deacon_2008_Curr.Opin.Investig.Drugs_9_402 |
| PubMedSearch : Deacon_2008_Curr.Opin.Investig.Drugs_9_402 |
| PubMedID: 18393107 |
| Title : Discovery of alogliptin: a potent, selective, bioavailable, and efficacious inhibitor of dipeptidyl peptidase IV - Feng_2007_J.Med.Chem_50_2297 |
| Author(s) : Feng J , Zhang Z , Wallace MB , Stafford JA , Kaldor SW , Kassel DB , Navre M , Shi L , Skene RJ , Asakawa T , Takeuchi K , Xu R , Webb DR , Gwaltney SL, 2nd |
| Ref : Journal of Medicinal Chemistry , 50 :2297 , 2007 |
| Abstract : Feng_2007_J.Med.Chem_50_2297 |
| ESTHER : Feng_2007_J.Med.Chem_50_2297 |
| PubMedSearch : Feng_2007_J.Med.Chem_50_2297 |
| PubMedID: 17441705 |
| Gene_locus related to this paper: human-DPP4 |