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Sitagliptin information


Sitagliptin
Clinical data
Pronunciation/sɪtəˈɡlɪptɪn/
Trade namesJanuvia, Zituvio, others
AHFS/Drugs.comMonograph
MedlinePlusa606023
License data
  • US DailyMed: Sitagliptin
Pregnancy
category
  • AU: B3
Routes of
administration
By mouth
ATC code
  • A10BH01 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only[1]
  • UK: POM (Prescription only)
  • US: ℞-only[2][3][4]
  • EU: Rx-only[5]
Pharmacokinetic data
Bioavailability87%
Protein binding38%
MetabolismLiver (CYP3A4- and CYP2C8-mediated)
Elimination half-life8 to 14 h[6]
ExcretionKidney (80%)[6]
Identifiers
IUPAC name
  • (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
  • 486460-32-6 checkY
PubChem CID
  • 4369359
IUPHAR/BPS
  • 6286
DrugBank
  • DB01261 checkY
ChemSpider
  • 3571948 checkY
UNII
  • QFP0P1DV7Z
KEGG
  • D08516
  • as salt: D06645
ChEBI
  • CHEBI:40237 checkY
ChEMBL
  • ChEMBL1422 checkY
CompTox Dashboard (EPA)
  • DTXSID70197572 Edit this at Wikidata
ECHA InfoCard100.217.948 Edit this at Wikidata
Chemical and physical data
FormulaC16H15F6N5O
Molar mass407.320 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • Fc1cc(c(F)cc1F)C[C@@H](N)CC(=O)N3Cc2nnc(n2CC3)C(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 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.[7] In the United Kingdom it is listed as less preferred than metformin or a sulfonylurea.[8] It is taken by mouth.[7] It is also available in the fixed-dose combination medication sitagliptin/metformin (Janumet, Janumet XR).[7]

Common side effects include headaches, swelling of the legs, and upper respiratory tract infections.[7] Serious side effects may include angioedema, low blood sugar, kidney problems, pancreatitis, and joint pain.[7] Whether use in pregnancy or breastfeeding is safe is unclear.[9] 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.[7]

Sitagliptin was developed by Merck & Co. and approved for medical use in the United States in 2006.[7] In 2021, it was the 83rd most commonly prescribed medication in the United States, with more than 8 million prescriptions.[10][11] It is available as a generic medication in Canada but not the United States.[12][13]

  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. ^ 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.
  7. ^ 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.
  8. ^ Cite error: The named reference BNF76 was invoked but never defined (see the help page).
  9. ^ "Sitagliptin Pregnancy and Breastfeeding Warnings". Drugs.com. Archived from the original on March 6, 2019. Retrieved March 3, 2019.
  10. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on January 15, 2024. Retrieved January 14, 2024.
  11. ^ "Sitagliptin - Drug Usage Statistics". ClinCalc. Retrieved January 14, 2024.
  12. ^ "Generic Januvia Availability". Drugs.com. Retrieved December 1, 2023.
  13. ^ "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.

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