Linagliptin

  • CAT Number: A000890
  • CAS Number: 668270-12-0
  • Molecular Formula: C₂₅H₂₆N₈O₂
  • Molecular Weight: 472.54
  • Purity: ≥95%
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Linagliptin, also known as BI-1356, is a DPP-4 inhibitor developed by Boehringer Ingelheim for treatment of type II diabetes. Linagliptin (once-daily) was approved by the US FDA on 2 May 2011 for treatment of type II diabetes. It is being marketed by Boehringer Ingelheim and Lilly.

Catalog Number A000890
CAS Number 668270-12-0
Molecular Formula

C₂₅H₂₆N₈O₂

Purity 95%
Target DPP-4
Solubility >17.9mg/mL in DMSO
Storage -20°C
InChI 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
InChIKey LTXREWYXXSTFRX-QGZVFWFLSA-N
SMILES CC#CCN1C2=C(N=C1N3CCCC(C3)N)N(C(=O)N(C2=O)CC4=NC5=CC=CC=C5C(=N4)C)C
Reference

1: Li YR, Tsai SS, Chen DY, Chen ST, Sun JH, Chang HY, Liou MJ, Chen TH.
Linagliptin and cardiovascular outcomes in type 2 diabetes after acute coronary
syndrome or acute ischemic stroke. Cardiovasc Diabetol. 2018 Jan 4;17(1):2. doi:
10.1186/s12933-017-0655-y. PubMed PMID: 29301579; PubMed Central PMCID:
PMC5753457.
<br>

2: Umpierrez GE, Cardona S, Chachkhiani D, Fayfman M, Saiyed S, Wang H, Vellanki
P, Haw JS, Olson DE, Pasquel FJ, Johnson TM 2nd. A Randomized Controlled Study
Comparing a DPP4 Inhibitor (Linagliptin) and Basal Insulin (Glargine) in Patients
With Type 2 Diabetes in Long-Term Care and Skilled Nursing Facilities:
Linagliptin-LTC Trial. J Am Med Dir Assoc. 2017 Dec 27. pii:
S1525-8610(17)30629-1. doi: 10.1016/j.jamda.2017.11.002. [Epub ahead of print]
PubMed PMID: 29289540.
<br>

3: Zhang Y, Fava GE, Wu M, Htun W, Klein T, Fonseca VA, Wu H. Effects of
Linagliptin on Pancreatic α Cells of Type 1 Diabetic Mice. J Endocr Soc. 2017 Aug
31;1(10):1224-1234. doi: 10.1210/js.2017-00253. eCollection 2017 Oct 1. PubMed
PMID: 29264448; PubMed Central PMCID: PMC5686619.
<br>

4: Rizos CV, Filippatos TD, Elisaf MS. Pharmacokinetic drug evaluation of
empagliflozin plus linagliptin for the treatment of type 2 diabetes. Expert Opin
Drug Metab Toxicol. 2018 Jan;14(1):117-125. doi: 10.1080/17425255.2018.1418325.
Epub 2017 Dec 19. Review. PubMed PMID: 29241374.
<br>

5: Bahirat UA, Shenoy RR, Talwar R, Goel RN, Nemmani KVS. Co-administration of
APD668, a G protein-coupled receptor 119 agonist and linagliptin, a DPPIV
inhibitor, prevents progression of steatohepatitis in mice fed on a high
trans-fat diet. Biochem Biophys Res Commun. 2018 Jan 8;495(2):1608-1613. doi:
10.1016/j.bbrc.2017.12.004. Epub 2017 Dec 5. PubMed PMID: 29203247.
<br>

6: Hasegawa Y, Hayashi K, Takemoto Y, Cheng C, Takane K, Lin B, Komohara Y,
Kim-Mitsuyama S. DPP-4 inhibition with linagliptin ameliorates the progression of
premature aging in klotho-/- mice. Cardiovasc Diabetol. 2017 Dec 1;16(1):154.
doi: 10.1186/s12933-017-0639-y. PubMed PMID: 29195509; PubMed Central PMCID:
PMC5709858.
<br>

7: Tamborlane WV, Laffel LM, Weill J, Gordat M, Neubacher D, Retlich S, Hettema
W, Hoesl CE, Kaspers S, Marquard J. Randomized, double-blind, placebo-controlled
dose-finding study of the dipeptidyl peptidase-4 inhibitor linagliptin in
pediatric patients with type 2 diabetes. Pediatr Diabetes. 2017 Nov 24. doi:
10.1111/pedi.12616. [Epub ahead of print] PubMed PMID: 29171139.

<br>
8: Catic T, Lekic L, Zah V, Tabakovic V. Budget Impact of Introducing Linagliptin
into Bosnia and Herzegovina Health Insurance Drug Reimbursement List in
2016-2018. Mater Sociomed. 2017 Sep;29(3):176-181. doi:
10.5455/msm.2017.29.176-181. PubMed PMID: 29109662; PubMed Central PMCID:
PMC5644199.
<br>

9: Keshavarz K, Lotfi F, Sanati E, Salesi M, Hashemi-Meshkini A, Jafari M,
Mojahedian MM, Najafi B, Nikfar S. Linagliptin versus sitagliptin in patients
with type 2 diabetes mellitus: a network meta-analysis of randomized clinical
trials. Daru. 2017 Oct 25;25(1):23. doi: 10.1186/s40199-017-0189-6. Review.
PubMed PMID: 29070077; PubMed Central PMCID: PMC5655990.
<br>

10: Satoh H, Ohira T, Moriya C, Inoue I, Kuribayashi S, Seino H, Hirai H, Hiyoshi
T, Watada H; L-CGM Study Group. Effects of linagliptin vs. voglibose on daily
glucose excursions during continuous glucose monitoring of Japanese type 2
diabetes patients (L-CGM): A randomized, open-label, two-arm, parallel
comparative trial. Diabetes Metab. 2017 Dec;43(6):550-553. doi:
10.1016/j.diabet.2017.07.010. Epub 2017 Sep 22. PubMed PMID: 28947255.

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