A potent DPP-4 inhibitor
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Linagliptin

Item No. 23306

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
8-[(3R)-3-amino-1-piperidinyl]-7-(2-butyn-1-yl)-3,7-dihydro-3-methyl-1-[(4-methyl-2-quinazolinyl)methyl]-1H-purine-2,6-dione
CAS Number
668270-12-0
Synonyms
  • BI-1356
Molecular Formula
C25H28N8O2
Formula Weight
472.5
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 2 mg/mlEthanol: 0.2 mg/ml
λmax
203, 226, 293 nm
SMILES
CC1=NC(CN2C(N(C)C(N=C(N3C[C@H](N)CCC3)N4CC#CC)=C4C2=O)=O)=NC5=CC=CC=C51
InChi Code
InChI=1S/C25H28N8O2/c1-4-5-13-32-21-22(29-24(32)31-12-8-9-17(26)14-31)30(3)25(35)33(23(21)34)15-20-27-16(2)18-10-6-7-11-19(18)28-20/h6-7,10-11,17H,8-9,12-15,26H2,1-3H3/t17-/m1/s1
InChi Key
LTXREWYXXSTFRX-QGZVFWFLSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 mg

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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    Linagliptin is a potent inhibitor of dipeptidyl peptidase 4 (DPP-4) with an IC50 value of 1 nM for human recombinant DPP-4.1 It is selective, with ≥10,000-fold selectivity for DPP-4 over a panel of 11 peptidases and proteases. Linagliptin (3 mg/kg) inhibits 90% of plasma DPP-4 activity in rat. It also dose-dependently decreases plasma glucose and increases plasma levels of glucagon-like peptide 1 (GLP-1) and insulin in Zucker diabetic fatty rats. Oral administration of linagliptin reduces HbA1c levels in mice with high-fat diet- and low-dose streptozotocin-induced diabetes.2 Formulations containing linagliptin have been used for the treatment of type 2 diabetes mellitus.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Thomas, L., Eckhardt, M., Langkopf, E., et al. (R)-8-(3-amino-piperidin-1-yl)-7-but-2-ynyl-3-methyl-1-(4-methyl-quinazolin-2-ylmethyl)-3,7-dihydro-purine-2,6-dione (BI 1356), a novel xanthine-based dipeptidyl peptidase 4 inhibitor, has a superior potency and longer duration of action compared with other dipeptidyl peptidase-4 inhibitors. J. Pharmacol. Exp. Ther. 325(1), 175-182 (2008).

    2. Thomas, L., tadayyon, M., and Mark, M. Chronic treatment with the dipeptidyl peptidase-4 inhibitor BI 1356 [(R)-8-(3-amino-piperidin-1-yl)-7-but-2-ynyl-3-methyl-1-(4-methyl-quinazolin-2-ylmethyl)-3,7-dihydro-purine-2,6-dione] increases basal glucagon-like peptide-1 and improves glycemic control in diabetic rodent models. J. Pharmacol. Exp. Ther. 328(2), 556-563 (2009).

    3. Ning, G., Bandgar, T., Hehnke, U., et al. Efficacy and safety of linagliptin in 2681 Asian patients stratified by age, obesity, and renal function: A pooled analysis of randomized clinical trials. Adv. Ther. 34(9), 2150-2162 (2017).