Vildagliptin
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MedKoo CAT#: 315140

CAS#: 274901-16-5

Description: Vildagliptin (also known as LAF237 and Zomelis) is an oral anti-hyperglycemic agent (anti-diabetic drug) of the new dipeptidyl peptidase-4 (DPP-4) inhibitor class of drugs. Vildagliptin inhibits the inactivation of GLP-1 and GIP by DPP-4, allowing GLP-1 and GIP to potentiate the secretion of insulin in the beta cells and suppress glucagon release by the alpha cells of the islets of Langerhans in the pancreas. Vildagliptin has been shown to reduce hyperglycemia in type 2 diabetes mellitus. Novartis has since withdrawn its intent to submit vildagliptin to the FDA, as of July 2008. T it was approved in Feb 2008 by European Medicines Agency for use within the EU and is listed on the Australian PBS with certain restrictions.

Chemical Structure

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Vildagliptin
CAS# 274901-16-5
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 315140
Name: Vildagliptin
CAS#: 274901-16-5
Chemical Formula: C17H25N3O2
Exact Mass: 303.19
Molecular Weight: 303.410
Elemental Analysis: C, 67.30; H, 8.31; N, 13.85; O, 10.55

Price and Availability

Size Price Availability Quantity
1g USD 150 Ready to ship
2g USD 225 Ready to ship
5g USD 450 Ready to ship
10g USD 750 Ready to ship
25g USD 1250 Ready to ship
50g USD 1950 Ready to ship
100g USD 2950 Ready to ship
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Synonym: LAF237; LAF-237; LAF 237; DSP 7238; DSP-7238; DSP7238; Vildagliptin; Zomelis

IUPAC/Chemical Name: (S)-1-(2-(((1s,3R,5R,7S)-3-hydroxyadamantan-1-yl)amino)acetyl)pyrrolidine-2-carbonitrile

InChi Key: SYOKIDBDQMKNDQ-AUOOEQCUSA-N

InChi Code: InChI=1S/C17H25N3O2/c18-9-14-2-1-3-20(14)15(21)10-19-16-5-12-4-13(6-16)8-17(22,7-12)11-16/h12-14,19,22H,1-8,10-11H2/t12-,13+,14-,16-,17-/m0/s1

SMILES Code: N#C[C@H]1N(C(CN[C@@]23C[C@@]4(O)C[C@](C3)([H])C[C@@](C4)([H])C2)=O)CCC1

Appearance: White to off-white solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO.

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target: Vildagliptin (LAF237) is a potent, stable, selective dipeptidyl peptidase IV (DPP-IV) inhibitor with an IC50 of 3.5 nM in human Caco-2 cells.
In vitro activity: To evaluate the direct efficacy of vildagliptin in inhibiting LPS-induced EndMT in HMVEC-Ls, in vitro experiments were conducted to test whether vildagliptin inhibited EndMT in the absence of immune cells or GLP-1.While LPS exposure induced morphological change to a spindle-shaped phenotype, vildagliptin treatment attenuated the degree (Fig. 4a). In addition, FCM analyses revealed that vildagliptin treatment decreased upregulation of α-SMA and S100A4 expression in HMVEC-Ls (Fig.4b). Immunocytochemistry also showed an increase in the number of α-SMA+-HMVEC-Ls 144 h after LPS challenge, whereas vildagliptin suppressed this increase. Since GLP-1 is produced and secreted by intestinal enteroendocrine epithelial cells, the experiments performed in vitro using a single vascular cell type provided results independent of GLP-1 participation. These data demonstrated that vildagliptin can attenuate the mesenchymal transition of endotoxin-treated PVECs partly independent of GLP-1 (Fig.4c). Next, it was evaluated if vildagliptin attenuated ROS production in HMVEC-Ls independent of GLP-1. Interestingly, expression of ROS was significantly decreased in LPS-HMVEC-Ls treated with vildagliptin in the absence of GLP-1 (Fig.5b). Vildagliptin might play a beneficial role in ameliorating pulmonary fibrosis by inhibiting EndMT even in the absence of GLP-1. Respir Res. 2017; 18: 177. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5644255/
In vivo activity: This study aimed to identify whether vildagliptin modifies the gut microbiota structure during T2D treatment. Diabetic SpragueDawley (SD) rats were induced by a high-fat diet and streptozotocin injection (HFD/STZ). Diabetic rats were orally administered a low dose of vildagliptin (LV, 0.01 g/kg/d vildagliptin), high dose of vildagliptin (HV, 0.02 g/kg/d vildagliptin), or normal saline for 12 weeks. Fasting blood glucose, blood glucose after glucose loading, and serum insulin levels were significantly reduced in the LV and HV groups compared with those in the T2D group. The serum GLP-1 level increased more in the vildagliptin-treated group than in the T2D group. Pyrosequencing of the V3-V4 regions of 16S rRNA genes revealed that vildagliptin significantly altered the gut microbiota. The operational taxonomic units (OTUs) and community richness (Chao1) index were significantly reduced in the vildagliptin and diabetic groups compared with those in the control group. At the phylum level, a higher relative abundance of Bacteroidetes, lower abundance of Firmicutes, and reduced ratio of Fimicutes/Bacteroidetes were observed in the vildagliptin-treated group. Moreover, vildagliptin treatment increased butyrate-producing bacteria, including Baceroides and Erysipelotrichaeae, in the diabetic rats. In conclusion, vildagliptin treatment could benefit the communities of the gut microbiota. PLoS One. 2017; 12(10): e0184735. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5643055/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 38.0 125.24
H2O 55.0 181.27

Preparing Stock Solutions

The following data is based on the product molecular weight 303.41 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Suzuki T, Tada Y, Gladson S, Nishimura R, Shimomura I, Karasawa S, Tatsumi K, West J. Vildagliptin ameliorates pulmonary fibrosis in lipopolysaccharide-induced lung injury by inhibiting endothelial-to-mesenchymal transition. Respir Res. 2017 Oct 16;18(1):177. doi: 10.1186/s12931-017-0660-4. PMID: 29037205; PMCID: PMC5644255. 2. Bi J, Cai W, Ma T, Deng A, Ma P, Han Y, Lou C, Wu L. Protective effect of vildagliptin on TNF-α-induced chondrocyte senescence. IUBMB Life. 2019 Jul;71(7):978-985. doi: 10.1002/iub.2049. Epub 2019 Apr 26. PMID: 31026379. 3.Suzuki T, Tada Y, Gladson S, Nishimura R, Shimomura I, Karasawa S, Tatsumi K, West J. Vildagliptin ameliorates pulmonary fibrosis in lipopolysaccharide-induced lung injury by inhibiting endothelial-to-mesenchymal transition. Respir Res. 2017 Oct 16;18(1):177. doi: 10.1186/s12931-017-0660-4. PMID: 29037205; PMCID: PMC5644255 4. Zhang Q, Xiao X, Li M, Yu M, Ping F, Zheng J, Wang T, Wang X. Vildagliptin increases butyrate-producing bacteria in the gut of diabetic rats. PLoS One. 2017 Oct 16;12(10):e0184735. doi: 10.1371/journal.pone.0184735. PMID: 29036231; PMCID: PMC5643055.
In vitro protocol: 1. Suzuki T, Tada Y, Gladson S, Nishimura R, Shimomura I, Karasawa S, Tatsumi K, West J. Vildagliptin ameliorates pulmonary fibrosis in lipopolysaccharide-induced lung injury by inhibiting endothelial-to-mesenchymal transition. Respir Res. 2017 Oct 16;18(1):177. doi: 10.1186/s12931-017-0660-4. PMID: 29037205; PMCID: PMC5644255. 2. Bi J, Cai W, Ma T, Deng A, Ma P, Han Y, Lou C, Wu L. Protective effect of vildagliptin on TNF-α-induced chondrocyte senescence. IUBMB Life. 2019 Jul;71(7):978-985. doi: 10.1002/iub.2049. Epub 2019 Apr 26. PMID: 31026379.
In vivo protocol: 1. Suzuki T, Tada Y, Gladson S, Nishimura R, Shimomura I, Karasawa S, Tatsumi K, West J. Vildagliptin ameliorates pulmonary fibrosis in lipopolysaccharide-induced lung injury by inhibiting endothelial-to-mesenchymal transition. Respir Res. 2017 Oct 16;18(1):177. doi: 10.1186/s12931-017-0660-4. PMID: 29037205; PMCID: PMC5644255. 2. Zhang Q, Xiao X, Li M, Yu M, Ping F, Zheng J, Wang T, Wang X. Vildagliptin increases butyrate-producing bacteria in the gut of diabetic rats. PLoS One. 2017 Oct 16;12(10):e0184735. doi: 10.1371/journal.pone.0184735. PMID: 29036231; PMCID: PMC5643055.

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1: Aziz KM. Fasting during Ramadan: efficacy, safety, and patient acceptability of vildagliptin in diabetic patients. Diabetes Metab Syndr Obes. 2015 Apr 16;8:207-11. doi: 10.2147/DMSO.S54683. eCollection 2015. Review. PubMed PMID: 25931826; PubMed Central PMCID: PMC4404947.

2: Forst T, Bramlage P. Vildagliptin , a DPP-4 inhibitor for the twice-daily treatment of type 2 diabetes mellitus with or without metformin. Expert Opin Pharmacother. 2014 Jun;15(9):1299-313. doi: 10.1517/14656566.2014.920009. Review. PubMed PMID: 24837407.

3: Stein SA, Lamos EM, Davis SN. Vildagliptin, a dipeptidyl peptidase-4 inhibitor, for the treatment of type 2 diabetes. Expert Opin Drug Metab Toxicol. 2014 Apr;10(4):599-608. doi: 10.1517/17425255.2014.889683. Epub 2014 Feb 19. Review. PubMed PMID: 24547938.

4: Kožnarová R. [Use of vildagliptin from an internal disease specialists point of view]. Vnitr Lek. 2013 Apr;59(4):322-4. Review. Czech. PubMed PMID: 23711060.

5: Khan S, Khan S, Imran M, Pillai KK, Akhtar M, Najmi AK. Effects of pioglitazone and vildagliptin on coagulation cascade in diabetes mellitus--targeting thrombogenesis. Expert Opin Ther Targets. 2013 Jun;17(6):627-39. doi: 10.1517/14728222.2013.764991. Epub 2013 Jan 28. Review. PubMed PMID: 23356568.

6: Dejager S, Schweizer A, Foley JE. Evidence to support the use of vildagliptin monotherapy in the treatment of type 2 diabetes mellitus. Vasc Health Risk Manag. 2012;8:339-48. doi: 10.2147/VHRM.S31758. Epub 2012 May 18. Review. PubMed PMID: 22661900; PubMed Central PMCID: PMC3363148.

7: Guarino E, Nigi L, Patti A, Fondelli C, Dotta F. Combination therapy with metformin plus vildagliptin in type 2 diabetes mellitus. Expert Opin Pharmacother. 2012 Jun;13(9):1377-84. doi: 10.1517/14656566.2012.667078. Epub 2012 Mar 7. Review. PubMed PMID: 22397507.

8: He YL. Clinical pharmacokinetics and pharmacodynamics of vildagliptin. Clin Pharmacokinet. 2012 Mar 1;51(3):147-62. doi: 10.2165/11598080-000000000-00000. Review. PubMed PMID: 22339447.

9: Cai L, Cai Y, Lu ZJ, Zhang Y, Liu P. The efficacy and safety of vildagliptin in patients with type 2 diabetes: a meta-analysis of randomized clinical trials. J Clin Pharm Ther. 2012 Aug;37(4):386-98. doi: 10.1111/j.1365-2710.2011.01323.x. Epub 2011 Dec 22. Review. PubMed PMID: 22191695.

10: Kalra S. Emerging role of dipeptidyl peptidase-IV (DPP-4) inhibitor vildagliptin in the management of type 2 diabetes. J Assoc Physicians India. 2011 Apr;59:237-45. Review. PubMed PMID: 21755761.