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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2006), EMA (2007))
IUPAC Name Click here for help
(3R)-3-amino-1-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one
International Nonproprietary Names Click here for help
INN number INN
8692 sitagliptin
Synonyms Click here for help
Januvia® | MK-0431
Database Links Click here for help
CAS Registry No. 486460-32-6
ChEBI CHEBI:40237
ChEMBL Ligand CHEMBL1422
DrugBank Ligand DB07214
DrugCentral Ligand 2448
GtoPdb PubChem SID 178102906
PubChem CID 4369359
RCSB PDB Ligand 715
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SynPHARM 78465 (in complex with dipeptidyl peptidase 4)
Wikipedia Sitagliptin