Trelagliptin (SYR472; Zafatek)

Alias: SYR 472; Trelagliptin; SYR-472; SYR472; trade name: Zafatek
Cat No.:V0746 Purity: ≥98%
Trelagliptin (formerly also known as SYR-472; trade name Zafatek) is a potent, highly selective, long-acting DPP-4 (dipeptidyl peptidase-4) inhibitor with potential anti-hyperglycemicactivity.
Trelagliptin (SYR472; Zafatek) Chemical Structure CAS No.: 865759-25-7
Product category: DPP-4
This product is for research use only, not for human use. We do not sell to patients.
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Other Forms of Trelagliptin (SYR472; Zafatek):

  • Trelagliptin succinate (SYR-472)
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Trelagliptin (formerly also known as SYR-472; trade name Zafatek) is a potent, highly selective, long-acting inhibitor of DPP-4 (dipeptidyl peptidase-4) that may have hypoglycemic effects. Takeda was developing it, and Japan had approved it for the management of type 2 diabetes (T2D). Trelagliptin has an advantage over other approved medications of the same class in that it can be given once a week rather than once daily as is typically the case.

Biological Activity I Assay Protocols (From Reference)
Targets
DPP-4 (IC50 = 4 nM)
ln Vitro
Dipeptidyl peptidase-4 (DPP-4) is one of the extensively studied novel targets for the type 2 diabetes mellitus (T2DM) strategy that inhibits the DPP-4 action in order to maintain the endogenous glucagon-like peptide (GLP)-1 activity[1].
Trelagliptin has a strong inhibitory effect on DPP-4 that is prepared from Caco-2 cells, with an IC50 value of 5.4 nM. Additionally, trelagliptin inhibits the plasma DPP-4 activity of rats, dogs, and humans with IC50 values of 4.2 nM, 6.2 nM, and 9.7 nM, respectively[2].
Trelagliptin exhibits >10,000-fold selectivity over DPP-2, DPP-8, DPP-9, PEP, and FAPα activities, and it is highly selective for DPP-4, with IC50 values >100,000 nM. Trelagliptin is approximately 4- and 12-fold more potent than sitagliptin and alogliptin in terms of DPP4 selectivity[2].
ln Vivo
Trelagliptin (oral gavage; 7 mg/kg; single dose) inhibits DPP-4 activity >80% of the time even after 24 hours in dogs, demonstrating a sustained Parkinson's disease effect[1]. Trelagliptin (oral gavage; 3 mg/kg; single dose; 60 min prior to oral glucose) reduces the AUC0−120min of 19.3% in ob/ob mice when compared to the vehicle group, greatly improving the glucose tolerance capacity[3]. Trelagliptin (oral gavage; 10 mg/kg; once a week; 8 weeks) significantly lowered fasting blood glucose (FBG) levels; over the course of the treatment period, the average decrease was 16.8% lower than in the control group.Additionally, it raises insulin levels, which in ob/ob mice are raised by 1.7-fold in AUC0−120min[3].
Animal Protocol
ICR ob/ob mice[3]
10 mg/kg
Oral gavage; 10 mg/kg; once a week; 8 weeks
References

[1]. Recent approaches to medicinal chemistry and therapeutic potential of dipeptidyl peptidase-4 (DPP-4) inhibitors. Eur J Med Chem. 2014 Mar 3;74:574-605.

[2]. Trelagliptin (SYR-472, Zafatek), Novel Once-Weekly Treatment for Type 2 Diabetes, Inhibits Dipeptidyl Peptidase-4 (DPP-4) via a Non-Covalent Mechanism. PLoS One. 2016 Jun 21;11(6):e0157509.

[3]. Discovery of a Natural-Product-Derived Preclinical Candidate for Once-Weekly Treatment of Type 2 Diabetes. J Med Chem. 2019 Mar 14;62(5):2348-2361.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C18H20FN5O2
Molecular Weight
357.38
Exact Mass
357.16
Elemental Analysis
C, 60.49; H, 5.64; F, 5.32; N, 19.60; O, 8.95
CAS #
865759-25-7
Appearance
Solid powder
SMILES
CN1C(=O)C=C(N(C1=O)CC2=C(C=CC(=C2)F)C#N)N3CCC[C@H](C3)N
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
Chemical Name
2-[[6-[(3R)-3-aminopiperidin-1-yl]-3-methyl-2,4-dioxopyrimidin-1-yl]methyl]-4-fluorobenzonitrile
Synonyms
SYR 472; Trelagliptin; SYR-472; SYR472; trade name: Zafatek
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: ~71 mg/mL (~198.7 mM)
Water: <1 mg/mL
Ethanol: ~3 mg/mL warmed (~8.4 mM)
Solubility (In Vivo)

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

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.7981 mL 13.9907 mL 27.9814 mL
5 mM 0.5596 mL 2.7981 mL 5.5963 mL
10 mM 0.2798 mL 1.3991 mL 2.7981 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT03555591 Completed Drug: Trelagliptin Type 2 Diabetes Mellitus Takeda May 1, 2016
NCT02512068 Completed Drug: Trelagliptin 25 mg
Drug: Placebo
Type 2 Diabetes Mellitus Takeda August 7, 2015 Phase 3
NCT04285983 Completed Drug: Trelagliptin Type 2 Diabetes Mellitus Takeda March 1, 2020
NCT03014479 Completed Drug: Trelagliptin
Drug: Daily DPP-4 inhibitor
Type 2 Diabetes Takeda February 18, 2017 Phase 4
NCT02771093 Completed Drug: Trelagliptin
Drug: Alogliptin
Type 2 Diabetes Mellitus Takeda September 8, 2016 Phase 4
Biological Data
  • Concentration response curves of DPP-4 inhibitory activities by trelagliptin, alogliptin and sitagliptin. PLoS One . 2016 Jun 21;11(6):e0157509.
  • Double-reciprocal plot showing competitive inhibition of DPP-4 by trelagliptin. PLoS One . 2016 Jun 21;11(6):e0157509.
  • Time course of the reaction of DPP-4 in the absence or presence of different concentrations of trelagliptin. PLoS One . 2016 Jun 21;11(6):e0157509.
  • Time course of the recovery of DPP-4 activity following dissociation of trelagliptin from the preformed DPP-4-inhibitor complex. PLoS One . 2016 Jun 21;11(6):e0157509.
  • Potential fluorine atom interactions in trelagliptin x-ray crystal structure. PLoS One . 2016 Jun 21;11(6):e0157509.
  • Relationship between trelagliptin pharmacokinetics and pharmacodynamics in T2DM patients in phase 2 dose-ranging study. PLoS One . 2016 Jun 21;11(6):e0157509.
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