Sitagliptin

Sitagliptin
Clinical data
Pronunciation/sɪtəˈɡlɪptɪn/
Trade namesJanuvia, Zituvio, others
AHFS/Drugs.comMonograph
MedlinePlusa606023
License data
Pregnancy
category
  • AU: B3
Routes of
administration
By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability87%
Protein binding38%
MetabolismLiver (CYP3A4- and CYP2C8-mediated)
Elimination half-life8 to 14 h
ExcretionKidney (80%)
Identifiers
  • (R)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.217.948
Chemical and physical data
FormulaC16H15F6N5O
Molar mass407.320 g·mol−1
3D model (JSmol)
  • Fc1cc(c(F)cc1F)C[C@@H](N)CC(=O)N3Cc2nnc(n2CC3)C(F)(F)F
  • 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 Y
  • Key:MFFMDFFZMYYVKS-SECBINFHSA-N Y
  (verify)

Sitagliptin, sold under the brand name Januvia among others, is an anti-diabetic medication used to treat type 2 diabetes. It is in the dipeptidyl peptidase-4 (DPP-4) inhibitor class and works by increasing the production of insulin and decreasing the production of glucagon by the pancreas. In the United Kingdom it is listed as less preferred than metformin or a sulfonylurea. It is taken by mouth. It is also available in the fixed-dose combination medication sitagliptin/metformin (Janumet, Janumet XR).

Common side effects include headaches, swelling of the legs, and upper respiratory tract infections. Serious side effects may include angioedema, low blood sugar, kidney problems, pancreatitis, and joint pain. Whether use in pregnancy or breastfeeding is safe is unclear.

Sitagliptin was developed by Merck & Co. and approved for medical use in the United States in 2006. In 2022, it was the 86th most commonly prescribed medication in the United States, with more than 7 million prescriptions. It is available as a generic medication, but not in the United States.