Carmegliptin

Carmegliptin is a potent, long-acting, selective, orally bioavailable, pyrrolidinone-based inhibitor of dipeptidyl peptidase 4 (DPP-4), with hypoglycemic activity. Carmegliptin shows extensive tissue distribution and is excreted unchanged in the urine and bile.

General

Type : Drug, Pyrrolidine, Gliptin, Quinolizine

Chemical_Nomenclature : (4S)-1-[(2S,3S,11bS)-2-amino-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizin-3-yl]-4-(fluoromethyl)pyrrolidin-2-one

Canonical SMILES : COC1=C(C=C2C3CC(C(CN3CCC2=C1)N4CC(CC4=O)CF)N)OC

InChI : InChI=1S\/C20H28FN3O3\/c1-26-18-6-13-3-4-23-11-17(24-10-12(9-21)5-20(24)25)15(22)8-16(23)14(13)7-19(18)27-2\/h6-7,12,15-17H,3-5,8-11,22H2,1-2H3\/t12-,15+,16+,17+\/m1\/s1

InChIKey : GUYMHFIHHOEFOA-ZCPGHIKRSA-N

Other name(s) : B1Q  ||  UNII-9Z723VGH7J  ||  R-1579  ||  CHEMBL591118


MW : 377.46

Formula : C20H28FN3O3

CAS_number : 813452-18-5

PubChem : 11417567

UniChem : GUYMHFIHHOEFOA-ZCPGHIKRSA-N

Target

Families : Carmegliptin ligand of proteins in family
DPP4N_Peptidase_S9

Structure :
3KWF

Protein :
human-DPP4

References (5)

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 :
PubMedSearch : Gilibili_2015_J.Pharm.Pharm.Sci_18_434
PubMedID: 26517136

Title : Interaction potential of Carmegliptin with P-glycoprotein (Pgp) transporter in healthy volunteers - Kuhlmann_2014_J.Drug.Assess_3_28
Author(s) : Kuhlmann O , Carlile D , Noe J , Bentley D
Ref : J Drug Assess , 3 :28 , 2014
Abstract :
PubMedSearch : Kuhlmann_2014_J.Drug.Assess_3_28
PubMedID: 27536451

Title : Ligand-based pharmacophore detection, screening of potential gliptins and docking studies to get effective antidiabetic agents - Agrawal_2012_Comb.Chem.High.Throughput.Screen_15_849
Author(s) : Agrawal R , Jain P , Dikshit SN
Ref : Comb Chem High Throughput Screen , 15 :849 , 2012
Abstract :
PubMedSearch : Agrawal_2012_Comb.Chem.High.Throughput.Screen_15_849
PubMedID: 23140189

Title : Pharmacokinetics and metabolism of the dipeptidyl peptidase IV inhibitor carmegliptin in rats, dogs, and monkeys - Kuhlmann_2010_Xenobiotica_40_840
Author(s) : Kuhlmann O , Paehler A , Weick I , Funk C , Pantze M , Zell M , Timm U
Ref : Xenobiotica , 40 :840 , 2010
Abstract :
PubMedSearch : Kuhlmann_2010_Xenobiotica_40_840
PubMedID: 20868265

Title : Discovery of carmegliptin: a potent and long-acting dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes - Mattei_2010_Bioorg.Med.Chem.Lett_20_1109
Author(s) : Mattei P , Boehringer M , Di Giorgio P , Fischer H , Hennig M , Huwyler J , Kocer B , Kuhn B , Loeffler BM , Macdonald A , Narquizian R , Rauber E , Sebokova E , Sprecher U
Ref : Bioorganic & Medicinal Chemistry Lett , 20 :1109 , 2010
Abstract :
PubMedSearch : Mattei_2010_Bioorg.Med.Chem.Lett_20_1109
PubMedID: 20031405
Gene_locus related to this paper: human-DPP4