Januvia

Sitagliptin
Clinical data


AHFS/Drugs.com	Monograph
MedlinePlus	a606023
License data	EU EMA: Januvia US FDA: Sitagliptin
Pregnancy category	AU: B3 US: B (No risk in non-human studies)
Routes of administration	Oral
ATC code	A10BH01 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	87%
Protein binding	38%
Metabolism	Hepatic (CYP3A4- and CYP2C8-mediated)
Biological half-life	8 to 14 h
Excretion	Renal (80%)
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^Y
PubChem CID	4369359
IUPHAR/BPS	6286
DrugBank	DB01261^Y
ChemSpider	3571948^Y
UNII	QFP0P1DV7Z
ChEBI	CHEBI:40237^Y
ChEMBL	CHEMBL1422^Y
ECHA InfoCard	100.217.948
Chemical and physical data
Formula	C₁₆H₁₅F₆N₅O
Molar mass	407.314 g/mol
3D model (Jmol)	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^Y Key:MFFMDFFZMYYVKS-SECBINFHSA-N^Y

Sitagliptin (INN; ⁱ/sɪtəˈɡlɪptɪn/, previously identified as MK-0431 and marketed as the phosphate salt under the trade name Januvia) is an oral antihyperglycemic (antidiabetic drug) of the dipeptidyl peptidase-4 (DPP-4) inhibitor class. It was developed, and is marketed, by Merck & Co. This enzyme-inhibiting drug is used either alone or in combination with other oral antihyperglycemic agents (such as metformin or a thiazolidinedione) for treatment of diabetes mellitus type 2.

Side effects are as common with sitagliptin (whether used alone or with metformin or pioglitazone) as they were with placebo, except for rare nausea and common cold-like symptoms, including photosensitivity. There is no significant difference in the occurrence of hypoglycemia between placebo and sitagliptin. In those taking sulphonylureas there is an increased risk of low blood sugar.