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[7]
ExcretionKidney (80%)[7]
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 Edit this at Wikidata
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 checkY
  • Key:MFFMDFFZMYYVKS-SECBINFHSA-N checkY
  (verify)

Sitagliptin, sold under the brand name Januvia among others, is an anti-diabetic medication used to treat type 2 diabetes.[8] In the United Kingdom it is listed as less preferred than metformin or a sulfonylurea.[9] It is taken by mouth.[8] It is also available in the fixed-dose combination medication sitagliptin/metformin (Janumet, Janumet XR).[8]

Common side effects include headaches, swelling of the legs, and upper respiratory tract infections.[8] Serious side effects may include angioedema, low blood sugar, kidney problems, pancreatitis, and joint pain.[8] Whether use in pregnancy or breastfeeding is safe is unclear.[10] 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.[8]

Sitagliptin was developed by Merck & Co. and approved for medical use in the United States in 2006.[8] In 2022, it was the 86th most commonly prescribed medication in the United States, with more than 7 million prescriptions.[11][12] It is available as a generic medication.[13][14][15]

  1. ^ "Product monograph brand safety updates". Health Canada. February 2024. Retrieved March 24, 2024.
  2. ^ "Januvia- sitagliptin tablet, film coated". DailyMed. Archived from the original on October 27, 2021. Retrieved October 15, 2021.
  3. ^ "Zituvio- sitagliptin tablet". DailyMed. November 1, 2023. Retrieved December 25, 2023.
  4. ^ "Zituvio- sitagliptin tablet". DailyMed. November 1, 2023. Retrieved December 25, 2023.
  5. ^ "Januvia EPAR". European Medicines Agency. September 17, 2018. Archived from the original on October 23, 2021. Retrieved October 15, 2021.
  6. ^ "Xelevia EPAR". European Medicines Agency (EMA). March 21, 2007. Retrieved October 19, 2024.
  7. ^ a b Herman GA, Stevens C, van Dyck K, Bergman A, Yi B, De Smet M, et al. (December 2005). "Pharmacokinetics and pharmacodynamics of sitagliptin, an inhibitor of dipeptidyl peptidase IV, in healthy subjects: results from two randomized, double-blind, placebo-controlled studies with single oral doses". Clinical Pharmacology and Therapeutics. 78 (6): 675–688. doi:10.1016/j.clpt.2005.09.002. PMID 16338283. S2CID 20935646.{{cite journal}}: CS1 maint: overridden setting (link)
  8. ^ a b c d e f g "Sitagliptin Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Archived from the original on March 4, 2016. Retrieved March 3, 2019.
  9. ^ Cite error: The named reference BNF76 was invoked but never defined (see the help page).
  10. ^ "Sitagliptin Pregnancy and Breastfeeding Warnings". Drugs.com. Archived from the original on March 6, 2019. Retrieved March 3, 2019.
  11. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on August 30, 2024. Retrieved August 30, 2024.
  12. ^ "Sitagliptin Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved August 30, 2024.
  13. ^ "Generic Januvia Availability". Drugs.com. Retrieved December 1, 2023.
  14. ^ "JAMP Pharma Group receives Health Canada approval for PrJAMP Sitagliptin, a new generic alternative for the treatment of type 2 diabetes" (Press release). JAMP Pharma. January 6, 2023. Retrieved June 19, 2023 – via Newswire.
  15. ^ "Sitagliptin SUN EPAR". European Medicines Agency (EMA). December 9, 2021. Retrieved September 27, 2024.