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Linagliptin

Uses Treatment of Type 2 diabetes Pharmacokinetics
Linagliptin
Linagliptin structure
CAS No.
668270-12-0
Chemical Name:
Linagliptin
Synonyms
inag;iptin;inagL;Ondero;CS-494;Bi 1356;CS-1974;Tradjenta;Lillidine;Lilalitine
CBNumber:
CB71518518
Molecular Formula:
C25H28N8O2
Formula Weight:
472.54
MOL File:
668270-12-0.mol

Linagliptin Properties

Melting point:
202 ºC
Boiling point:
661.2±65.0 °C(Predicted)
Density 
1.39
pka
10.01±0.20(Predicted)
FDA UNII
3X29ZEJ4R2
NCI Drug Dictionary
linagliptin
ATC code
A10BH05
SAFETY
  • Risk and Safety Statements
HS Code  29335990

Linagliptin price More Price(3)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Cayman Chemical 23306 Linagliptin ≥98% 668270-12-0 100mg $49 2021-03-22 Buy
Cayman Chemical 23306 Linagliptin ≥98% 668270-12-0 500mg $98 2021-03-22 Buy
Cayman Chemical 23306 Linagliptin ≥98% 668270-12-0 1g $184 2021-03-22 Buy

Linagliptin Chemical Properties,Uses,Production

Uses

Linagliptin (TrajentaR, TradjentaTM, TrazentaTM, TrayentaTM) is an oral, highly selective inhibitor of dipeptidyl peptidase-4 and is the first agent of its class to be eliminated predominantly via a nonrenal route. Linagliptin is indicated for once daily use for the treatment of adults with type 2 diabetes mellitus.

Treatment of Type 2 diabetes

Linagliptin acts to lower blood glucose levels by inhibiting the enzyme DPP-4, thereby preventing the degradation of the incretin hormones (glucagon-like peptide-1 [GLP-1] and glucose-dependent insulinotropic peptide) and attenuating postprandial glucose excursions. By selectively targeting DPP-4, linagliptin potentially causes a more physiologically based control of glucose-dependent postprandial glucose excursions and of fasting blood glucose, both of which are mediated by effects of glucose on insulin and glucagon secretion. An advantage of linagliptin is that since incretin-stimulated release of insulin is glucose dependent, linagliptin is associated with a low incidence of hypoglycaemia. Moreover, DPP-4 inhibitors have a low potential for drug-drug interactions (with the exception of saxagliptin, which is metabolized by cytochrome P450 [CYP] 3A4/5), are generally well tolerated and have minimal or neutral effects on bodyweight. 

Pharmacokinetics

Linagliptin shows modest oral bioavailability, and it is rapidly absorbed. The maximum plasma concentration at steady state is reached on average 1.5 hours after administration of linagliptin 5 mg, once daily . Linagliptin half-life is 131 hours. No relevant food effects were observed on the absorption profile of linagliptin. Unlike other DPP-4 inhibitors, linagliptin excretion is not performed by the kidneys, but rather through the enterohepatic system.

Description

Linagliptin (trade names Tradjenta and Trajetna) is an inhibitor of dipeptidyl peptidase-4 (DPP-4) that was approved by the U.S. FDA in May 2011 for the treatment of Type 2 diabetes along with diet and exercise. Linagliptin (BI-1356) has been described as a potent highly selective, slow-off rate and long acting inhibitor of DPP-4. Linagliptin arose from optimization efforts of xanthine-based DPP-4 inhibitors with the initial lead identified from an HTS campaign. After optimizing the activity of the initial micromolar lead, two issues that needed to be addressed were activity for hERG and muscarinic receptor M1. Introduction of a butynyl group at the N7 position of the xanthine ring gave much reduced M1 affinity with no measureable hERG activity. Linagliptin inhibits DPP-4 with an IC50=1 nM and is highly selective (>10,000-fold) against DPP-8 and DPP-9. Linagliptin shows no interactions with CYPs up to 50 mM. The described synthesis of linagliptin starts with 8-bromoxanthine, which is alkylated at the N-7 position to introduce the butyne group, followed by alkylation of the N-1 group to introduce the methyl-quinazoline group. Displacement of the bromide with (R)-Boc-3-amino-piperidine followed by deprotection gives linagliptin. When administered to db/db mice orally, linagliptin dose dependently reduced glucose excursion from 0.1 mg/kg (15% inhibition) to 1 mg/kg (66% inhibition).

Originator

Boehringer Ingelheim (United States)

Uses

A novel potent and selective dipeptidyl peptidase-4 (DPP-4) inhibitor with potential use in the treatment of type 2 diabetes.

Uses

dipeptidypeptidase inhibitor, antidiabetic

Uses

highly potent CD26 inhibitor

Uses

Labeled Linagliptin, intended for use as an internal standard for the quantification of Linagliptin by GC- or LC-mass spectrometry.

Definition

ChEBI: A xanthine that is 7H-xanthine bearing (4-methylquinazolin-2-yl)methyl, methyl, but-2-yn-1-yl and 3-aminopiperidin-1-yl substituents at positions 1, 3, 7 and 8 respectively (the R-enantiomer). Used for treatment of type I diabetes.

brand name

Tradjenta

Chemical Synthesis

The synthesis of linagliptin began from commercially available 8-bromo-3-methylxanthine (171). Sequential alkylations of guanine derivative 171 at N-7 with butyn-2-yl bromide in the presence of N,N-diisopropylethylamine and N-1 with 2- (chloromethyl)-4-methylquinazoline (173) in the presence of potassium carbonate, yielded N1,N7-dialkylated xanthine 174 in 85% yield. This material was further condensed with (R)-3-Bocaminopiperidine (175) in the presence of potassium carbonate to give aminopurine dione 176 in 88% yield. Finally, the primary amine of 176 was liberated with trifluoroacetic acid in methylene chloride to produce linagliptin (XV) in 91% yield.

Linagliptin Preparation Products And Raw materials

Raw materials

Preparation Products


Linagliptin Suppliers

Global( 451)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
HubeiwidelychemicaltechnologyCo.,Ltd
18627774460
faith@widelychemical.com CHINA 743 58
Jinan Shengqi pharmaceutical Co,Ltd
86+18663751872
christine@shengqipharm.com CHINA 494 58
Beijing Yibai Biotechnology Co., Ltd
0086-182-6772-3597
sales04@yibaibiotech.com CHINA 420 58
Jinan Ande Pharmaceutical Co.,Ltd.
+8613256107535
andepharm@163.com CHINA 220 58
Hangzhou Huarong Pharm Co., Ltd.
+8613588754946 +86-571-86758373
0086-571-81131109 sales@huarongpharm.com CHINA 3149 58
Jiangsu Monade Biological Technology Co., Ltd.
+8613857751219
gao@mndbio.com CHINA 240 58
Frapp's ChemicalNFTZ Co., Ltd.
+86 (576) 8169-6106
+86 (576) 8169-6105 sales@frappschem.com China 886 50
Henan DaKen Chemical CO.,LTD.
+86-371-66670886
info@dakenchem.com China 20911 58
Beijing Cooperate Pharmaceutical Co.,Ltd
010-60279497
010-60279497 sales01@cooperate-pharm.com CHINA 1817 55
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22607 55

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View Lastest Price from Linagliptin manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-12-03 Linagliptin
668270-12-0
US $1.00 / KG 1KG 98% 1000 Jinan Ande Pharmaceutical Co.,Ltd.
2021-12-01 Linagliptin
668270-12-0
US $5.70 / g/Bag 10g 99% 10000kg Hebei Crovell Biotech Co Ltd
2021-11-27 Linagliptin
668270-12-0
US $0.50 / g 100g 99.99% 5ton/Month Hebei Yirun Sega Biological Technology Co. Ltd

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