sitagliptin   Click here for help

GtoPdb Ligand ID: 6286

Synonyms: Januvia® | MK-0431
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
SMILES / InChI / InChIKey
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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
InChI Key MFFMDFFZMYYVKS-SECBINFHSA-N
References
1. Davis JA, Singh S, Sethi S, Roy S, Mittra S, Rayasam G, Bansal V, Sattigeri J, Ray A. (2010)
Nature of action of Sitagliptin, the dipeptidyl peptidase-IV inhibitor in diabetic animals.
Indian J Pharmacol, 42 (4): 229-33. [PMID:20927248]
2. Kieffer TJ, McIntosh CH, Pederson RA. (1995)
Degradation of glucose-dependent insulinotropic polypeptide and truncated glucagon-like peptide 1 in vitro and in vivo by dipeptidyl peptidase IV.
Endocrinology, 136 (8): 3585-96. [PMID:7628397]
3. Tewary S, Lucas ES, Fujihara R, Kimani PK, Polanco A, Brighton PJ, Muter J, Fishwick KJ, Da Costa MJMD, Ewington LJ et al.. (2020)
Impact of sitagliptin on endometrial mesenchymal stem-like progenitor cells: A randomised, double-blind placebo-controlled feasibility trial.
EBioMedicine, 51: 102597. DOI: 10.1016/j.ebiom.2019.102597 [PMID:31928963]