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MedKoo Cat#: 314244 | Name: Trelagliptin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Trelagliptin, also known as SYR-472, is a long acting dipeptidyl peptidase-4 (DPP-4) inhibitor that is being developed by Takeda for the treatment of type 2 diabetes (T2D). Once-weekly SYR-472 treatment produced clinically and statistically significant improvements in glycaemic control in patients with type 2 diabetes. It was well tolerated and might be a new treatment option for patients with this disease. Trelagliptin (Zafatek(®)) was approved in Japan for the treatment of type 2 diabetes mellitus (T2DM).

Chemical Structure

Trelagliptin
Trelagliptin
CAS#865759-25-7 (free base)

Theoretical Analysis

MedKoo Cat#: 314244

Name: Trelagliptin

CAS#: 865759-25-7 (free base)

Chemical Formula: C18H20FN5O2

Exact Mass: 357.1601

Molecular Weight: 357.38

Elemental Analysis: C, 60.49; H, 5.64; F, 5.32; N, 19.60; O, 8.95

Price and Availability

Size Price Availability Quantity
25mg USD 90.00 Ready to ship
50mg USD 150.00 Ready to Ship
100mg USD 250.00 Ready to ship
200mg USD 450.00 Ready to ship
500mg USD 950.00 Ready to ship
1g USD 1,650.00 Ready to ship
2g USD 2,950.00 2 Weeks
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Related CAS #
1029877-94-8 (succinate) 865759-25-7 (free base)
Synonym
SYR472; SYR472; SYR 472; Trelagliptin, brand name: Zafatek.
IUPAC/Chemical Name
(R)-2-((6-(3-aminopiperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)-4-fluorobenzonitrile.
InChi Key
IWYJYHUNXVAVAA-OAHLLOKOSA-N
InChi Code
InChI=1S/C18H20FN5O2/c1-22-17(25)8-16(23-6-2-3-15(21)11-23)24(18(22)26)10-13-7-14(19)5-4-12(13)9-20/h4-5,7-8,15H,2-3,6,10-11,21H2,1H3/t15-/m1/s1
SMILES Code
N#CC1=CC=C(F)C=C1CN(C(N2C)=O)C(N3C[C@H](N)CCC3)=CC2=O
Appearance
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
Related CAS# 865759-25-7 (free base); 1029877-94-8 (succinate).

Preparing Stock Solutions

The following data is based on the product molecular weight 357.38 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
1: Kondo Y, Satoh S, Terauchi Y. Effects of dulaglutide and trelagliptin on beta-cell function in patients with type 2 diabetes: a randomized controlled study: DUET-beta study. Diabetol Int. 2024 Apr 3;15(3):474-482. doi: 10.1007/s13340-024-00717-6. PMID: 39101164; PMCID: PMC11291836. 2: Abdullah Ali M, Naji Alhassani A, Kareem Hamad B. Impacts of trelagliptin and remogliflozin alone and in combination with Alpha Lipoic Acid on cardiac function in streptozotocin-induced diabetes mellitus in rats. Cell Mol Biol (Noisy-le-grand). 2023 Sep 30;69(9):106-112. doi: 10.14715/cmb/2023.69.9.15. PMID: 37807327. 3: Lei M, Guo X, Yao Y, Shu T, Ren Z, Yang X, Ouyang C, Chen Q, Liu C, Liu X. Trelagliptin relieved cognitive impairment of diabetes mellitus rats: Involvement of PI3K/Akt/GSK-3β and inflammation pathway. Exp Gerontol. 2023 Oct 15;182:112307. doi: 10.1016/j.exger.2023.112307. Epub 2023 Oct 7. PMID: 37804920. 4: Kumar S, Balaya RDA, Kanekar S, Raju R, Prasad TSK, Kandasamy RK. Computational tools for exploring peptide-membrane interactions in gram-positive bacteria. Comput Struct Biotechnol J. 2023 Mar 2;21:1995-2008. doi: 10.1016/j.csbj.2023.02.051. PMID: 36950221; PMCID: PMC10025024. 5: Ogura T, Shiraishi C. Comparison of Adverse Events Occurred During Administration of Dipeptidyl Peptidase-4 Inhibitor in Patients with Diabetes Using FDA Adverse Event Reporting System. Clin Drug Investig. 2023 Feb;43(2):129-140. doi: 10.1007/s40261-022-01242-7. Epub 2023 Jan 13. PMID: 36637688. 6: Wu C, Liu H, Yu S, Ren C, Zhang J, Wang G, Li B, Liu Y. Prediction of pharmacokinetics and pharmacodynamics of trelagliptin and omarigliptin in healthy humans and in patients with renal impairment using physiologically based pharmacokinetic combined DPP-4 occupancy modeling. Biomed Pharmacother. 2022 Sep;153:113509. doi: 10.1016/j.biopha.2022.113509. Epub 2022 Aug 4. PMID: 36076596. 7: Zhou Y, Sun Y, Xu C, Liu F, Gao Y, Liu C, Qiao Y, Yang J, Li G. ABCC8-related maturity-onset diabetes of the young: Clinical features and genetic analysis of one case. Pediatr Diabetes. 2022 Aug;23(5):588-596. doi: 10.1111/pedi.13388. Epub 2022 Jul 8. PMID: 35757975. 8: Dutta D, Mohindra R, Surana V, Sharma M. Safety and efficacy of once weekly dipeptidyl-peptidase-4 inhibitor trelagliptin in type-2 diabetes: A meta- analysis. Diabetes Metab Syndr. 2022 Apr;16(4):102469. doi: 10.1016/j.dsx.2022.102469. Epub 2022 Mar 21. PMID: 35344848. 9: Mowaka S, Ashoush N, Tadros MM, Ayoub BM. Investigation of Pharmacokinetic Parameters of Trelagliptin in Egyptian Volunteers Using Sensitive LC-MS/MS: A Comparative Study with a Japanese Population. J Anal Methods Chem. 2021 Dec 9;2021:9664099. doi: 10.1155/2021/9664099. PMID: 34925935; PMCID: PMC8677398. 10: Zhang YS, Zheng YD, Yuan Y, Chen SC, Xie BC. Effects of Anti-Diabetic Drugs on Fracture Risk: A Systematic Review and Network Meta-Analysis. Front Endocrinol (Lausanne). 2021 Oct 14;12:735824. doi: 10.3389/fendo.2021.735824. PMID: 34721294; PMCID: PMC8553257. 11: Liu J, Zuo Q, Li Z, Chen J, Liu F. Trelagliptin ameliorates IL-1β-impaired chondrocyte function via the AMPK/SOX-9 pathway. Mol Immunol. 2021 Dec;140:70-76. doi: 10.1016/j.molimm.2021.09.009. Epub 2021 Oct 16. PMID: 34666245. 12: Zhang Y, Li C, Pei Y, Zheng L, Sun X, Zhao Z, Wang S. Trelagliptin ameliorates oxygen-glucose deprivation/reperfusion (OGD/R)-induced mitochondrial dysfunction and metabolic disturbance of endothelial cells. Hum Cell. 2021 Nov;34(6):1717-1726. doi: 10.1007/s13577-021-00594-0. Epub 2021 Aug 25. PMID: 34435315. 13: Mannucci E, Nreu B, Montereggi C, Ragghianti B, Gallo M, Giaccari A, Monami M; SID-AMD joint panel for Italian Guidelines on Treatment of Type 2 Diabetes. Cardiovascular events and all-cause mortality in patients with type 2 diabetes treated with dipeptidyl peptidase-4 inhibitors: An extensive meta-analysis of randomized controlled trials. Nutr Metab Cardiovasc Dis. 2021 Sep 22;31(10):2745-2755. doi: 10.1016/j.numecd.2021.06.002. Epub 2021 Jul 5. PMID: 34364771. 14: Heo R, Seo MS, An JR, Kang M, Park H, Han ET, Han JH, Chun W, Park WS. The anti-diabetic drug trelagliptin induces vasodilation via activation of Kv channels and SERCA pumps. Life Sci. 2021 Oct 15;283:119868. doi: 10.1016/j.lfs.2021.119868. Epub 2021 Aug 3. PMID: 34358551. 15: Sun Y, Hu B, Jing Y, Wu J, Zhou M, Chen M, Hao F, Zhang C, Sun F. Preparation of (R)-3-aminopiperidine by resolution with optically active cyclic phosphoric acids. Chirality. 2021 Jul;33(7):379-384. doi: 10.1002/chir.23312. Epub 2021 May 3. PMID: 33942379. 16: Zhou J, Peng Z, Wang J. Trelagliptin Alleviates Lipopolysaccharide (LPS)-Induced Inflammation and Oxidative Stress in Acute Lung Injury Mice. Inflammation. 2021 Aug;44(4):1507-1517. doi: 10.1007/s10753-021-01435-w. Epub 2021 Mar 10. PMID: 33751359. 17: Shao H, Wu R, Cao L, Gu H, Chai F. Trelagliptin stimulates osteoblastic differentiation by increasing runt-related transcription factor 2 (RUNX2): a therapeutic implication in osteoporosis. Bioengineered. 2021 Dec;12(1):960-968. doi: 10.1080/21655979.2021.1900633. PMID: 33734011; PMCID: PMC8291811. 18: Zang L, Yang B, Zhang M, Cui J, Ma X, Wei L. Trelagliptin Mitigates Macrophage Infiltration by Preventing the Breakdown of the Blood-Brain Barrier in the Brain of Middle Cerebral Artery Occlusion Mice. Chem Res Toxicol. 2021 Apr 19;34(4):1016-1023. doi: 10.1021/acs.chemrestox.0c00323. Epub 2021 Mar 17. PMID: 33728903. 19: Wang G, Wu B, Zhang L, Jin X, Wang K, Xu W, Zhang B, Wang H. The protective effects of trelagliptin on high-fat diet-induced nonalcoholic fatty liver disease in mice. J Biochem Mol Toxicol. 2021 Apr;35(4):e22696. doi: 10.1002/jbt.22696. Epub 2021 Jan 9. PMID: 33421258. 20: Meng J, Zhang W, Wang C, Xiong S, Wang Q, Li H, Liu G, Hao Z. The dipeptidyl peptidase (DPP)-4 inhibitor trelagliptin inhibits IL-1β-induced endothelial inflammation and monocytes attachment. Int Immunopharmacol. 2020 Dec;89(Pt B):106996. doi: 10.1016/j.intimp.2020.106996. Epub 2020 Oct 10. PMID: 33049493.