Sitagliptin

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Cat Number

API486460326

CAS Number

486460-32-6

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CAS Number

486460-32-6

EINECS

690-730-1

Storage

Store at room temperature

Synonyms

Sitagliptin; Januvia; Zituvio; sitagliptina; sitagliptine; LEZ763; sitagliptinum; QFP0P1DV7Z

Molecular Formula

C16H15F6N5O

Molecular Weight

407.31

Smiles

C1CN2C(=NN=C2C(F)(F)F)CN1C(=O)C[C@@H](CC3=CC(=C(C=C3F)F)F)N

Appearance

White to off-white crystalline powder

Melting Point

114.1-115.7°C

Boiling Point

529.9±60.0°C at 760 mmHg (Predicted)

Relative Density

1.61±0.1 (Predicted)

General Description

Sitagliptin is a synthetic triazole derivative with a trifluoromethyl group, belonging to the class of dipeptidyl peptidase-4 (DPP-4) inhibitors. Its chemical structure is (3R)-3-amino-1-[3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)butan-1-one. Sitagliptin is a white to off-white powder, soluble in water. It is a potent and selective inhibitor of DPP-4.

Mechanism of Action

Sitagliptin inhibits the enzyme DPP-4, which is responsible for the degradation of incretin hormones, such as glucagon-like peptide-1 (GLP-1) and glucose-dependent insulinotropic polypeptide (GIP). By preventing the breakdown of these hormones, the drug increases their concentration and activity, leading to enhanced insulin secretion, suppressed glucagon release, and improved glycemic control. The effect is glucose-dependent, reducing the risk of hypoglycemia.

Application

Sitagliptin is indicated as an adjunct to diet and exercise for the treatment of type 2 diabetes mellitus, either as monotherapy or in combination with other antidiabetic agents, such as metformin, sulfonylureas, and insulin. It is effective in reducing fasting and postprandial glucose levels and improving HbA1c. The drug is generally weight-neutral and has a low risk of hypoglycemia.

Sitagliptin, a DPP-4 inhibitor for type 2 diabetes, shows potential neuroprotective effects beyond glycemic control. Experimental studies demonstrate it reduces pro-inflammatory cytokines (TNF-α, IL-6, IL-17) and increases anti-inflammatory IL-10 and TGF-β in the brain. It also exhibits antioxidative and antiapoptotic properties in the hippocampus and reduces β-amyloid accumulation in Alzheimer’s models, possibly via SDF-1α. Clinical observations suggest improved MMSE scores. The paper reviews mechanisms linking sitagliptin to neuroinflammation and Alzheimer’s disease.

Fig. 1 Proposed nonincretin mechanisms of sitagliptin activity. (Wiciński M, et al., 2018)

References

Wiciński M, et al. Neuroprotective Activity of Sitagliptin via Reduction of Neuroinflammation beyond the Incretin Effect: Focus on Alzheimer's Disease. Biomed Res Int. 2018;2018:6091014.

In an open‑label RCT of 46 adolescents with type 1 diabetes and microalbuminuria using the MiniMed 780G system, adding sitagliptin 50 mg daily for 3 months significantly reduced urinary albumin/creatinine ratio (from 7.27 to 1.32 mg/mmol, P<0.001) and SDF‑1 levels, while improving time in range, reducing glycemic variability, and lowering insulin requirements. Sitagliptin is renoprotective in type 1 diabetes with nephropathy.

Fig. 2 CONSORT flow diagram for the enrolled participants with type 1 diabetes and diabetic nephropathy on the MiniMed 780G system. (Elbarbary NS, et al., 2024)

References

Elbarbary NS, et al. The DPP-4 inhibitor sitagliptin improves glycaemic control and early-stage diabetic nephropathy in adolescents with type 1 diabetes using the MiniMed 780G advanced hybrid closed-loop system: a randomised controlled trial. Diabetologia. 2024;67(12):2637-2649.

Does Sitagliptin require protection from moisture during storage?

Yes, it is hygroscopic. The phosphate salt and β‑ketoamide group are susceptible to hydrolysis. Store in tightly sealed, moisture‑proof containers with desiccant.

What is the recommended storage temperature for Sitagliptin?

Store at controlled room temperature (15–25°C). Avoid excessive heat above 30°C, which accelerates degradation and formation of the desfluoro impurity.

Is Sitagliptin stable in tablet formulations with standard excipients?

Yes, when formulated with moisture‑protective packaging (e.g., blisters).

How is the impurity sitagliptin desfluoro (a process‑related impurity) monitored?

This impurity is quantified using a stability‑indicating HPLC method, ensuring it remains within pharmacopoeial limits.