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Sitagliptin phosphate monohydrate

In stock
Catalog No.
A4036
Potent DPP-4 inhibitor
Grouped product items
SizePriceStock Qty
10mM (in 1mL DMSO)
$55.00
In stock
Evaluation Sample
$28.00
In stock
200mg
$60.00
In stock
500mg
$110.00
In stock

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Sitagliptin phosphate monohydrate is the phosphate salt of its active component, sitagliptin, with one molecule of water. Sitagliptin is a potent inhibitor of dipeptidyl peptidase 4 (DPP-4), an enzyme catalyzing the cleavage of peptides with an N-terminal alanine or proline amino acid residue, that selectively inhibits DPP-4 with 50% inhibition concentration IC50 value of 18 nM and shows no affinity towards other DDP enzymes (such as DDP-8 and DDP-9). The inhibition of DPP4 by sitagliptin has been found to be mediated by increasing levels of two DPP-4 substrates, including glucagon-like peptide-1 (GLP-1) and gastric inhibitory polypeptide (GIP). Sitagliptin is currently being investigated in the treatment of type II diabetes.

Reference

Gallwitz B. Review of sitagliptin phosphate: a novel treatment for type 2 diabetes. Vasc Health Risk Manag. 2007;3(2):203-10.

Product Citation

Chemical Properties

Physical AppearanceA solid
StorageStore at -20°C
M.Wt523.3
Cas No.654671-77-9
FormulaC16H15F6N5O.H3PO4.H2O
SynonymsTesavel, MK-0431,MK0431
Solubility≥23.8 mg/mL in DMSO, <2.41 mg/mL in EtOH, ≥30.6 mg/mL in H2O with ultrasonic
Chemical 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;phosphoric acid;hydrate
SDFDownload SDF
Canonical SMILES[HH].C1CN2C(=NN=C2C(F)(F)F)CN1C(=O)CC(CC3=CC(=C(C=C3F)F)F)N.O.OOP(=O)=O
Shipping ConditionEvaluation sample solution : ship with blue ice.All other available size: ship with RT , or blue ice upon request
General tipsFor obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.

Protocol

Cell experiment [1]:

Cell lines

Endothelial progenitor cells (EPCs) and bone marrow mesenchymalstem cells(MSC)

Preparation method

The solubility of this compound in DMSO is >10 mM. General tips for obtaining a higher concentration: Please warm the tube at 37 °C for 10 minutes and/or shake it in the ultrasonic bath for a while.Stock solution can be stored below -20°C for several months.

Reaction Conditions

14 d; 25 μmol/L

Applications

To determine whether sitagliptin treatment participated in enhancing the differentiation of EPCs and MSCs and cells expressing its ligand, SDF-1α, adipose tissues were co-cultured with sitagliptin (25 μmol/L) in M199 culture medium for 14 d and examined by flow cytometric analysis. The results show that compared with the 7 d cell culture, the numbers of EPCs [CD31/Sca-1+(double-stained) and CXCR4+ (single-stained)] were remarkably higher at day 14 in both the non-sitagliptin-treated (Si-T) group and the Si-T group

Animal experiment [2]:

Animal models

ApoE−/−mice with the C57BL/6 genetic background

Dosage form

200 mg/kg/day; oral taken

Applications

In ApoE−/−mice, the sitagliptin group showed fewer atherosclerotic plaques than in controls (7.64±1.98% [range 4.62–10.13%] vs 12.91±1.15% [range 11.55–14.37%], p<0.001). Compared with control mice, atherosclerotic plaque areas decreased respectively 1.92- and 2.74-fold in the aortic root and abdominal aorta of mice fed sitagliptin (p=0.011 and p=0.006). Our data show that sitagliptin can inhibit the formation of atherosclerotic areas in entire aorta, aortic root and abdominal aorta of ApoE−/− mice.

Other notes

Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal.

References:

[1] Chua S, Sheu J J, Chen Y L, et al. Sitagliptin therapy enhances the number of circulating angiogenic cells and angiogenesis—evaluations< i> in vitro and in the rat critical limb ischemia model[J]. Cytotherapy, 2013, 15(9): 1148-1163.

[2] Zeng Y, Li C, Guan M, et al. The DPP-4 inhibitor sitagliptin attenuates the progress of atherosclerosis in apolipoprotein-E-knockout mice via AMPK-and MAPK-dependent mechanisms[J]. Cardiovascular diabetology, 2014, 13(1): 32.

Biological Activity

Description Sitagliptin phosphate is a potent inhibitor of DPP-IV with IC50 of 19 nM in Caco-2 cell extracts.
Targets DPP-4          
IC50 19 nM          

Quality Control

Research Update

1. Simultaneous Determination of Sitagliptin Phosphate Monohydrate and Metformin Hydrochloride in Tablets by a Validated UPLC Method. Sci Pharm. 2012;80(1):139-52. doi: 10.3797/scipharm.1110-13. Epub 2011 Dec 12.
Abstract
The reverse phase UPLC is a method to simultaneously measure Sitagliptin phosphate monohydrate and Metformin hydrochloride in pharmaceutical dosage forms with LOD and LOQ of 0.2 μg/mL and 0.7 μg/mL respectively for Sitagliptin phosphate monohydrate.
3. Efficacy and safety of initial combination treatment with sitagliptin and pioglitazone-a factorial study. Diabetes Obes Metab. 2014 Mar;16(3):223-30. doi: 10.1111/dom.12194. Epub 2013 Aug 29.
Abstract
The combination of sitagliptin and pioglitazone has been assessed for safety and efficacy in patients with type 2 diabetes.
4. Effects of short-term sitagliptin treatment on immune parameters in healthy individuals, a randomized placebo-controlled study. Clin Exp Immunol. 2013 Oct;174(1):120-8. doi: 10.1111/cei.12144.
Abstract
Sitagliptin is a DPP-4 inhibitor that inhibits the cleavage of GLP-1 leading to improved blood glucose control in patients with type 2 diabetes. Although it initially increased the percentage of cells expressing high levels of CD26, sitagliptin failed to alter systemic immune function in healthy volunteers at the end of 28-day treatment.