Review on Chemistry, Analysis and Pharmacology of Teneligliptin: A Novel DPP-4 Inhibitor

Author(s): Sanjay Sharma*, Raksha Sharma, Ketan Hatware, Kiran Patil

Journal Name: Mini-Reviews in Medicinal Chemistry

Volume 20 , Issue 12 , 2020


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Abstract:

This article provides comprehensive and collective facts about teneligliptin. Teneligliptin is a dipeptide peptidase-4 (DPP-4) inhibitor that belongs to the third generation, used in the management of type 2 diabetes. It inhibits human DPP-4 enzyme activity. This drug falls under class 3; it interacts with S1, S2, and S2E extensive sub-sites. Teneligliptin and its metabolites are mainly determined in the human plasma matrix by hyphenated chromatographic methods. These developed methods could be foreseen for their clinical applications. Moreover, the stress degradation studies of Teneligliptin under different stress conditions provide an insight into degradation pathways and help in the elucidation of the structure of the degradation products by liquid mass spectroscopy. These methods are also used for routine quality control analysis of teneligliptin in pharmaceutical dosage forms.

Keywords: Teneligliptin, identification, pharmacokinetics, pharmacodynamics, chemistry, analysis.

[1]
Patil, M.; Jani, H.D.; Khoja, S.S.; Pirani, N.A.; Khoja, S.S. A Review on Chemistry and Pharmacological Activity of Metformin Hydrochloride and Teneligliptin Hydrobromide Hydrate in Combined Dosage Form., 2017, 5, 24-30.
[2]
Kaul, K.; Tarr, J.M.; Ahmad, S.I.; Kohner, E.M.; Chibber, R. Introduction to Diabetes Mellitus.Diabetes; Springer, 2013, pp. 1-11.
[http://dx.doi.org/10.1007/978-1-4614-5441-0_1]
[3]
Chitlange, S.S.; Rawat, D.G.; Chandani, S. Estimation of Anti-Diabetic Teneligliptin Hydrobromide Hydrate by RP-HPLC and Derivative Spectroscopy Method. Indo Am. J. Pharm. Res., 2016, 6, 6144-6153.
[4]
Li, X.; Huang, X.; Bai, C.; Qin, D.; Cao, S.; Mei, Q.; Ye, Y.; Wu, J. Efficacy and Safety of Teneligliptin in Patients With Type 2 Diabetes Mellitus: A Systematic Review and Meta-Analysis of Randomized Controlled Trials. Front. Pharmacol., 2018, 9, 449.
[http://dx.doi.org/10.3389/fphar.2018.00449] [PMID: 29780322]
[5]
Theodorakis, M.J.; Carlson, O.; Michopoulos, S.; Doyle, M.E.; Juhaszova, M.; Petraki, K.; Egan, J.M. Human duodenal enteroendocrine cells: source of both incretin peptides, GLP-1 and GIP. Am. J. Physiol. Endocrinol. Metab., 2006, 290(3), E550-E559.
[http://dx.doi.org/10.1152/ajpendo.00326.2004] [PMID: 16219666]
[6]
Fukuda-Tsuru, S.; Anabuki, J.; Abe, Y.; Yoshida, K.; Ishii, S. A novel, potent, and long-lasting dipeptidyl peptidase-4 inhibitor, teneligliptin, improves postprandial hyperglycemia and dyslipidemia after single and repeated administrations. Eur. J. Pharmacol., 2012, 696(1-3), 194-202.
[http://dx.doi.org/10.1016/j.ejphar.2012.09.024] [PMID: 23022337]
[7]
Patel, B.D.; Ghate, M.D. Recent approaches to medicinal chemistry and therapeutic potential of dipeptidyl peptidase-4 (DPP-4) inhibitors. Eur. J. Med. Chem., 2014, 74, 574-605.
[http://dx.doi.org/10.1016/j.ejmech.2013.12.038] [PMID: 24531198]
[8]
Rajanikanth, B.; Shamanna, M.; M, K.K. An Open Label , 2 Year Long Term Follow-Up Study to Assess the Efficacy , Safety and Tolerability of Teneligliptin in Indian Subjects with Type 2 Diabetes Mellitus. 2019, 3, 8-13.
[9]
Min, S.H.; Yoon, J-H.; Hahn, S.; Cho, Y.M. Efficacy and safety of combination therapy with an α-glucosidase inhibitor and a dipeptidyl peptidase-4 inhibitor in patients with type 2 diabetes mellitus: A systematic review with meta-analysis. J. Diabetes Investig., 2018, 9(4), 893-902.
[http://dx.doi.org/10.1111/jdi.12754] [PMID: 28950431]
[10]
Min, S.H.; Yoon, J-H.; Moon, S.J.; Hahn, S.; Cho, Y.M. Combination of sodium-glucose cotransporter 2 inhibitor and dipeptidyl peptidase-4 inhibitor in type 2 diabetes: a systematic review with meta-analysis. Sci. Rep., 2018, 8(1), 4466.
[http://dx.doi.org/10.1038/s41598-018-22658-2] [PMID: 29535389]
[11]
Maladkar, M.; Sankar, S.; Kamat, K. Teneligliptin: Heralding Change in Type 2 Diabetes. J. Diabetes Mellitus, 2016, 6, 113-131.
[http://dx.doi.org/10.4236/jdm.2016.62012]
[12]
Sen, A.K.; Hinsu, D.N.; Sen, D.B.; Zanwar, A.S.; Maheshwari, R.A. Analytical Method Development and Validation for Simultaneous Estimation of Teneligliptin Hydrobromide Hydrate and Metformin Hydrochloride from It’s Pharmaceutical Dosage Form by Three Different UV Spectrophotometric Methods., 2016.
[http://dx.doi.org/10.7324/JAPS.2016.60924]
[13]
Ganesh Kumar, T.N.V.; Vidyadhara, S.; Narkhede, N.A.; Sai Silpa, Y.; Rajya Lakshmi, M. Method Development, Validation, and Stability Studies of Teneligliptin by RP-HPLC and Identification of Degradation Products by UPLC Tandem Mass Spectroscopy. J. Anal. Sci. Technol., 2016, 7, 18.
[http://dx.doi.org/10.1186/s40543-016-0099-0]
[14]
Kishimoto, M. Teneligliptin: A DPP-4 Inhibitor for the Treatment of Type 2 Diabetes; Diabetes, Metab. Syndr. Obes. Targets Ther, 2013, p. 187.
[15]
Kiran, D.M.; Dalia, D.H.B.C.; Yadav, D.P. Teneligliptin – The Newest DPP4 Inhibitor. Int. J. Pharma Bio Sci., 2017, 8.
[16]
Shantikumar, S.; Satheeshkumar, N.; Srinivas, R. Pharmacokinetic and protein binding profile of peptidomimetic DPP-4 inhibitor - Teneligliptin in rats using liquid chromatography-tandem mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 2015, 1002, 194-200.
[http://dx.doi.org/10.1016/j.jchromb.2015.08.023] [PMID: 26340762]
[17]
Luhar, S.V.; Pandya, K.R.; Jani, G.K.; Narkhed, S.B. Simultaneous Estimation of Teneligliptin Hydrobromide Hydrate and Its Degradation Product by RP-HPLC Method., 2016, 6, 254-261.
[18]
Irache, G.S.; Bhajipale, N.S.; Gandhi, L.R. RP-HPLC Method Development and Validation of Tenegliptin and Metformin in Pharmaceutical Dosage Forms. Int. Res. J. Pharm., 2017, 8, 52-55.
[http://dx.doi.org/10.7897/2230-8407.088144]
[19]
Patil, D.; Ahmad, S.; Shastry, V.M.; Mujawar, T.; Thakare, L. Analytical Method Development and Validation for the Simultaneous Estimation of Metformin and Teneligliptin by RP-HPLC in Bulk and Tablet Dosage Forms. J. Pharm. Res. Vol., 2017, 11, 676-681.
[20]
Paul, D.; Allakonda, L.; Satheeshkumar, N. A validated UHPLC-QTOF-MS method for quantification of metformin and teneligliptin in rat plasma: Application to pharmacokinetic interaction study. J. Pharm. Biomed. Anal., 2017, 143, 1-8.
[http://dx.doi.org/10.1016/j.jpba.2017.05.026] [PMID: 28544884]
[21]
Ali, F.; Nandi, U.; Trivedi, M.; Prakash, A.; Dahiya, M.; Sahu, P.L.; Kumar, R.; Singh, G.N. Quantitative Characterization and Pharmaceutical Compatibility between Teneligliptin and Widely Used Excipients by Using Thermal and Liquid Chromatography Tandem Mass Spectrometry Techniques. J. Therm. Anal. Calorim., 2018, 132, 385-396.
[http://dx.doi.org/10.1007/s10973-018-6962-z]
[22]
Haranadha, R.; Chunduri, B.; Dannana, G.S. Development and Validation of Lc-Ms / Ms Method for Simultaneous Quantification of Pramipexole, Ropinirole and Rasagiline in Human Plasma and Its. World J. Pharm. Pharm. Sci., 2015, 4, 1390-1408.
[23]
Shantikumar, S.; Satheeshkumar, N.; Prasanth, B.; Lingesh, A.; Paul, D.; Srinivas, R. A Sensitive and Selective Liquid Chromatography Mass Spectrometry Method for Simultaneous Estimation of Anti-Diabetic Drugs Inhibiting DPP-4 Enzyme in Human Plasma: Overcoming Challenges Associated with Low Recovery and Sensitivity. Anal. Methods, 2015, 7, 6198-6206.
[http://dx.doi.org/10.1039/C5AY00342C]
[24]
Shah, P.A.; Shrivastav, P.S.; Vanol, P.G.; Sanyal, M. Mechanistic study for the simultaneous determination of metformin and teneligliptin in human plasma using hydrophilic interaction liquid chromatography-MS/MS. Bioanalysis, 2018, 10(7), 475-488.
[http://dx.doi.org/10.4155/bio-2018-0007] [PMID: 29561645]
[25]
Poliakoff, M.; Licence, P. Sustainable technology: green chemistry. Nature, 2007, 450(7171), 810-812.
[http://dx.doi.org/10.1038/450810a] [PMID: 18064000]
[26]
Gaikwad, J.; Sharma, S.; Hatware, K.V. Review on Characteristics and Analytical Methods of Tazarotene: An Update. Crit. Rev. Anal. Chem., 2019, 1-7.
[PMID: 30942085]
[27]
Nakamaru, Y.; Hayashi, Y.; Ikegawa, R.; Kinoshita, S.; Perez Madera, B.; Gunput, D.; Kawaguchi, A.; Davies, M.; Mair, S.; Yamazaki, H.; Kume, T.; Suzuki, M. Metabolism and disposition of the dipeptidyl peptidase IV inhibitor teneligliptin in humans. Xenobiotica, 2014, 44(3), 242-253.
[http://dx.doi.org/10.3109/00498254.2013.816891] [PMID: 23855261]
[28]
Sharma, S.K.; Panneerselvam, A.; Singh, K.P.; Parmar, G.; Gadge, P.; Swami, O.C. Teneligliptin in management of type 2 diabetes mellitus. Diabetes Metab. Syndr. Obes., 2016, 9, 251-260.
[http://dx.doi.org/10.2147/DMSO.S106133] [PMID: 27574456]
[29]
Miyagawa, K.; Kondo, T.; Goto, R.; Matsuyama, R.; Ono, K.; Kitano, S.; Kawasaki, S.; Igata, M.; Kawashima, J.; Matsumura, T.; Motoshima, H.; Araki, E. Effects of combination therapy with vildagliptin and valsartan in a mouse model of type 2 diabetes. Cardiovasc. Diabetol., 2013, 12, 160.
[http://dx.doi.org/10.1186/1475-2840-12-160] [PMID: 24188631]
[30]
Danao, K.R.; Shende, M.V.; Gupta, R.A.; Dumore, N.G.; Mahajan, U.N. Teneligliptin: DPP-4 Inhibitor in the Treatment of Type II Diabetes Mellitus. Int. J. Phytopharm., 2017, 7, 30-35.
[31]
Nabeno, M.; Akahoshi, F.; Kishida, H.; Miyaguchi, I.; Tanaka, Y.; Ishii, S.; Kadowaki, T. A comparative study of the binding modes of recently launched dipeptidyl peptidase IV inhibitors in the active site. Biochem. Biophys. Res. Commun., 2013, 434(2), 191-196.
[http://dx.doi.org/10.1016/j.bbrc.2013.03.010] [PMID: 23501107]
[32]
Yao, G.; Quan, G.; Lin, S.; Peng, T.; Wang, Q.; Ran, H.; Chen, H.; Zhang, Q.; Wang, L.; Pan, X.; Wu, C. Novel dissolving microneedles for enhanced transdermal delivery of levonorgestrel: In vitro and in vivo characterization. Int. J. Pharm., 2017, 534(1-2), 378-386.
[http://dx.doi.org/10.1016/j.ijpharm.2017.10.035] [PMID: 29051119]
[33]
Patel, M.R.; Patel, R.B.; Parikh, J.R.; Patel, B.G. Novel microemulsion-based gel formulation of tazarotene for therapy of acne. Pharm. Dev. Technol., 2016, 21(8), 921-932.
[http://dx.doi.org/10.3109/10837450.2015.1081610] [PMID: 26334480]
[34]
Kim, D. Solid-Phase Colorimetric Sensor Based on Gold Nanoparticle-Loaded Polymer Brushes: Lead Detection as a Case Study. 2013.
[35]
Liu, R.; Cheng, J.; Wu, H. Discovery of food-derived dipeptidyl peptidase IV inhibitory peptides: A review. Int. J. Mol. Sci., 2019, 20(3), 20.
[http://dx.doi.org/10.3390/ijms20030463] [PMID: 30678216]
[36]
Kadowaki, T.; Marubayashi, F.; Yokota, S.; Katoh, M.; Iijima, H. Safety and efficacy of teneligliptin in Japanese patients with type 2 diabetes mellitus: a pooled analysis of two Phase III clinical studies. Expert Opin. Pharmacother., 2015, 16(7), 971-981.
[http://dx.doi.org/10.1517/14656566.2015.1032249] [PMID: 25861982]
[37]
Goda, M.; Kadowaki, T. Teneligliptin for the treatment of type 2 diabetes. Drugs Today (Barc), 2013, 49(10), 615-629.
[http://dx.doi.org/10.1358/dot.2013.49.10.2035882] [PMID: 24191255]
[38]
Morishita, R.; Nakagami, H. Teneligliptin : expectations for its pleiotropic action. Expert Opin. Pharmacother., 2015, 16(3), 417-426.
[http://dx.doi.org/10.1517/14656566.2015.1000301] [PMID: 25597385]
[39]
Eto, T.; Inoue, S.; Kadowaki, T. Effects of once-daily teneligliptin on 24-h blood glucose control and safety in Japanese patients with type 2 diabetes mellitus: a 4-week, randomized, double-blind, placebo-controlled trial. Diabetes Obes. Metab., 2012, 14(11), 1040-1046.
[http://dx.doi.org/10.1111/j.1463-1326.2012.01662.x] [PMID: 22776014]
[40]
Kutoh, E.; Hirate, M.; Ikeno, Y. Teneligliptin as an initial therapy for newly diagnosed, drug naive subjects with type 2 diabetes. J. Clin. Med. Res., 2014, 6(4), 287-294.
[http://dx.doi.org/10.14740/jocmr1841e] [PMID: 24883155]
[41]
Hashikata, T.; Yamaoka-Tojo, M.; Kakizaki, R.; Nemoto, T.; Fujiyoshi, K.; Namba, S.; Kitasato, L.; Hashimoto, T.; Kameda, R.; Maekawa, E.; Shimohama, T.; Tojo, T.; Ako, J. Erratum to: Teneligliptin improves left ventricular diastolic function and endothelial function in patients with diabetes. Heart Vessels, 2016, 31(8), 1311-1312.
[http://dx.doi.org/10.1007/s00380-016-0810-5] [PMID: 26892529]
[42]
Fisman, E.Z.; Tenenbaum, A. Antidiabetic treatment with gliptins: focus on cardiovascular effects and outcomes. Cardiovasc. Diabetol., 2015, 14, 129.
[http://dx.doi.org/10.1186/s12933-015-0294-0] [PMID: 26415691]
[43]
Kishimoto. The effect of alogliptin and metformin combination therapy in type 2 diabetes: A pilot study. J. Endocrinol. Metab., 2013.
[44]
Díaz-Soto, G.; de Luis, D.A.; Conde-Vicente, R.; Izaola-Jauregui, O.; Ramos, C.; Romero, E. Beneficial effects of liraglutide on adipocytokines, insulin sensitivity parameters and cardiovascular risk biomarkers in patients with Type 2 diabetes: a prospective study. Diabetes Res. Clin. Pract., 2014, 104(1), 92-96.
[http://dx.doi.org/10.1016/j.diabres.2014.01.019] [PMID: 24530118]
[45]
Moriya, C.; Satoh, H. Teneligliptin Decreases Uric Acid Levels by Reducing Xanthine Dehydrogenase Expression in White Adipose Tissue of Male Wistar Rats. J. Diabetes Res., 2016, 2016, 3201534
[http://dx.doi.org/10.1155/2016/3201534] [PMID: 27652270]
[46]
Takahara, Y.; Tokunou, T.; Ichiki, T. Suppression of Abdominal Aortic Aneurysm Formation in Mice by Teneligliptin, a Dipeptidyl Peptidase-4 Inhibitor. J. Atheroscler. Thromb., 2018, 25(8), 698-708.
[http://dx.doi.org/10.5551/jat.42481] [PMID: 29321388]
[47]
Zhang, Z.; Jin, X.; Yang, C.; Li, Y. Teneligliptin protects against hypoxia/reoxygenation-induced endothelial cell injury. Biomed. Pharmacother., 2019, 109, 468-474.
[http://dx.doi.org/10.1016/j.biopha.2018.10.016] [PMID: 30399583]


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Article Details

VOLUME: 20
ISSUE: 12
Year: 2020
Published on: 28 February, 2020
Page: [1091 - 1100]
Pages: 10
DOI: 10.2174/1389557520666200228144148
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