Structure via PubChem · Public domain (PubChem)
sitagliptin
Sign in to saveAlso known as Januvia®, MK-0431, Sitagliptine, (2R)-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, Sitagliptina, Sitagliptin phosphate, Sitagliptan
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).
Key facts
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 464392221
- Drug.image
- Sitagliptin.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 254
- Drug.image2
- Sitagliptin 3D.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Januvia, Zituvio, others
- Drug.MedlinePlus
- a606023
- Drug.DailyMedID
- Sitagliptin
- Drug.pregnancy_AU
- B3
- Drug.routes_of_administration
- By mouth
- Drug.ATC_prefix
- A10
- Drug.ATC_suffix
- BH01
- Drug.legal_AU
- S4
- Drug.legal_CA
- Rx-only
- Drug.legal_UK
- POM
- Drug.legal_US
- Rx-only
via Wikipedia infobox
Chemical data
- Formula
- C16H15F6N5O
- Molecular weight
- 407.31 g/mol
- IUPAC name
- (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
- SMILES
- C1CN2C(=NN=C2C(F)(F)F)CN1C(=O)C[C@@H](CC3=CC(=C(C=C3F)F)F)N
- InChIKey
- MFFMDFFZMYYVKS-SECBINFHSA-N
- XLogP
- 0.7
- Polar surface area
- 77 Ų
- H-bond donors
- 1
- H-bond acceptors
- 10
- Formal charge
- 0
via PubChem
Research
3,591 papers- Efficacy and Safety of Sitagliptin in the Treatment of COVID-19.Journal of pharmacy practice · 2023
- Efficacy and safety of sitagliptin treatment in older adults with moderately controlled type 2 diabetes: the STREAM study.Scientific reports · 2023
- Sitagliptin: A Review in Type 2 Diabetes.Drugs · 2017
- Is sitagliptin effective for SARS-CoV-2 infection: false or true prophecy?Inflammopharmacology · 2022
- Sitagliptin to Prevent Acute Graft-versus-Host Disease.The New England journal of medicine · 2021
via PubMed
Wikidata facts
- Mass
- 407.118
Show 7 more facts
- chemical formula
- C₁₆H₁₅F₆N₅O
- canonical SMILES
- C1CN2C(=NN=C2C(F)(F)F)CN1C(=O)CC(CC3=CC(=C(C=C3F)F)F)N
- isomeric SMILES
- C1CN2C(=NN=C2C(F)(F)F)CN1C(=O)C[C@@H](CC3=CC(=C(C=C3F)F)F)N
- World Health Organisation international non-proprietary name
- sitagliptin
- defined daily dose
- 0.1
- stylized name
- SITagliptin
- Commons category
- Sitagliptin
Sources (7)
via Wikidata · CC0
~5 min read
Article
6 sectionsContents
- Medical uses
- Adverse effects
- Mechanism of action
- History
- External links
- References
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.