sitagliptin   Click here for help

GtoPdb Ligand ID: 6286

Synonyms: Januvia® | MK-0431 | Zituvio®
Approved drug PDB Ligand
sitagliptin is an approved drug (FDA (2006), EMA (2007))
Compound class: Synthetic organic
Comment: Sitagliptin is a dipeptidyl peptidase 4 (DPP4) inhibitor. Marketed formulations may contain sitagliptin phosphate monohydrate (PubChem CID 11591741).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 77.04
Molecular weight 407.12
XLogP 3.85
No. Lipinski's rules broken 0
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Canonical SMILES NC(Cc1cc(F)c(cc1F)F)CC(=O)N1CCn2c(C1)nnc2C(F)(F)F
Isomeric SMILES N[C@H](Cc1cc(F)c(cc1F)F)CC(=O)N1CCn2c(C1)nnc2C(F)(F)F
InChI InChI=1S/C16H15F6N5O/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/h4,6,9H,1-3,5,7,23H2/t9-/m1/s1
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Summary of Clinical Use Click here for help
Used in the treatment of type 2 diabetes, usually as a second-line drug and in combination with other drugs, following the failure of metformin plus diet/exercise to control blood glucose levels.

A small-scale feasibility trial (with EU Clinical Trials Register no. 2016-001120-54) has been performed to assess the ability of sitagliptin (via increasing the bioavailability of the potent chemoattractant stromal cell-derived factor-1α) to elevate recruitment and differentiation of bone marrow-derived cells to endometrial mesenchymal stem-like progenitor cells in the endometrium as a mechanism to increase successful implantation in patients with recurrent pregnancy loss [3]. Positive results suggest that more extensive investigation of the effects of preconception sitagliptin treatment is warranted.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
'Gliptin' class inhibitors improve glucose homoeostasis by blocking DPP4-mediated degradation of the incretin hormones glucagon-like peptide-1 and glucose-dependant insulinotropic polypeptide [2], thereby increasing insulin production and decreasing glucagon production by the pancreas.
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