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Linagliptin

Linagliptin Structure
Linagliptin structure
CAS No.
668270-12-0
Chemical Name:
Linagliptin
Synonyms
Linagliptin API;Linaglitpin;Linagliptin (BI-1356);8-[(3R)-3-Amino-1-piperidinyl]-7-(2-butynyl)-3,7-dihydro-3-methyl-1-[(4-methyl-2-quinazolinyl)methyl]-1H-purine-2,6-dione;inag;iptin;inagL;Ondero;CS-494;Bi 1356
CBNumber:
CB71518518
Molecular Formula:
C25H28N8O2
Molecular Weight:
472.54
MDL Number:
MFCD14635356
MOL File:
668270-12-0.mol
MSDS File:
SDS
Last updated:2024-11-19 20:33:22
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Linagliptin Properties

Melting point 202 ºC
Boiling point 661.2±65.0 °C(Predicted)
Density 1.39
storage temp. Refrigerator
solubility Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly)
pka 10.01±0.20(Predicted)
form Solid
color White to Orange
InChIKey LTXREWYXXSTFRX-QGZVFWFLSA-N
SMILES N1(CC#CC)C2=C(N(C)C(=O)N(CC3=NC(C)=C4C(=N3)C=CC=C4)C2=O)N=C1N1CCC[C@@H](N)C1
FDA UNII 3X29ZEJ4R2
ATC code A10BH05
NCI Drug Dictionary linagliptin

Pharmacokinetic data

Protein binding 75-99 (concentration dependent)
Excreted unchanged in urine 5%
Volume of distribution 1110 Litres
Biological half-life 12 / -

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H319-H335-H315
Precautionary statements  P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362
HS Code  29335990
NFPA 704
0
2 0

Linagliptin price More Price(36)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Cayman Chemical 23306 Linagliptin ≥98% 668270-12-0 100mg $62 2024-03-01 Buy
Cayman Chemical 23306 Linagliptin ≥98% 668270-12-0 500mg $120 2024-03-01 Buy
Cayman Chemical 23306 Linagliptin ≥98% 668270-12-0 1g $225 2024-03-01 Buy
TRC L465900 Linagliptin 668270-12-0 500mg $120 2021-12-16 Buy
Medical Isotopes, Inc. D47119 Linagliptin-d3 668270-12-0 25mg $5450 2021-12-16 Buy
Product number Packaging Price Buy
23306 100mg $62 Buy
23306 500mg $120 Buy
23306 1g $225 Buy
L465900 500mg $120 Buy
D47119 25mg $5450 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

dipeptidypeptidase inhibitor, antidiabetic

Uses

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

Uses

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

Uses

highly potent CD26 inhibitor

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

Clinical Use

Type 2 diabetes mellitus

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.

Synthesis_668270-12-0

target

DDP-4

storage

+4°C

Linagliptin Preparation Products And Raw materials

Raw materials

Preparation Products

Linagliptin Suppliers

Global( 637)Suppliers
Supplier Tel Email Country ProdList Advantage
Protheragen-ING 		+16313385890 info@protheragen-ing.com United States 3868 58
ShenZhen H&D Pharmaceutical Technology Co., LTD
+8618627948422 sale@hdimpurity.com China 3389 58
Hebei Weibang Biotechnology Co., Ltd 		+8615531157085 abby@weibangbio.com China 8811 58
Shaanxi Dideu Medichem Co. Ltd 		+86-29-81148696 +86-15536356810 1022@dideu.com China 3882 58
Hebei Chuanghai Biotechnology Co,.LTD 		+86-13131129325 sales1@chuanghaibio.com China 5893 58
Sinoway Industrial co., ltd. 		0592-5800732; +8613806035118 xie@china-sinoway.com China 988 58
Henan Fengda Chemical Co., Ltd 		+86-371-86557731 +86-13613820652 info@fdachem.com China 20287 58
Hangzhou Hyper Chemicals Limited 		+86-0086-57187702781 +8613675893055 info@hyper-chem.com China 295 58
Shaanxi TNJONE Pharmaceutical Co., Ltd 		+8618092446649 sarah@tnjone.com China 1143 58
Hebei Ganmiao New material Technology Co., LTD 		+86-17332992504 +86-17332992504 sales8@hbganmiao.com China 299 58
Supplier Advantage
Protheragen-ING 		58
ShenZhen H&D Pharmaceutical Technology Co., LTD
58
Hebei Weibang Biotechnology Co., Ltd 		58
Shaanxi Dideu Medichem Co. Ltd 		58
Hebei Chuanghai Biotechnology Co,.LTD 		58
Sinoway Industrial co., ltd. 		58
Henan Fengda Chemical Co., Ltd 		58
Hangzhou Hyper Chemicals Limited 		58
Shaanxi TNJONE Pharmaceutical Co., Ltd 		58
Hebei Ganmiao New material Technology Co., LTD 		58

Related articles

  • What is Linagliptin?
  • Linagliptin (TrajentaR, TradjentaTM, TrazentaTM, TrayentaTM) is an oral, highly selective inhibitor of dipeptidyl peptidase-4 ....
  • Feb 10，2020

View Lastest Price from Linagliptin manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Linagliptin pictures 2024-11-25 Linagliptin
668270-12-0
 US $0.00-0.00 / g/Bag 100g/Bag 99% up, High Density 20 tons Sinoway Industrial co., ltd.
Linagliptin pictures 2024-11-22 Linagliptin
668270-12-0
 US $0.00 / Kg/Bag 1KG 98%min 50kg WUHAN FORTUNA CHEMICAL CO., LTD
linagliptin pictures 2024-11-22 linagliptin
668270-12-0
 US $0.00-0.00 / kg 1kg 99%，single impurity＜0.1 1 ton Nanjing Fred Technology Co., Ltd
  • Linagliptin pictures
  • Linagliptin
    668270-12-0
  • US $0.00-0.00 / g/Bag
  • 99% up, High Density
  • Sinoway Industrial co., ltd.
  • Linagliptin pictures
  • Linagliptin
    668270-12-0
  • US $0.00 / Kg/Bag
  • 98%min
  • WUHAN FORTUNA CHEMICAL CO., LTD
  • linagliptin pictures
  • linagliptin
    668270-12-0
  • US $0.00-0.00 / kg
  • 99%，single impurity＜0.1
  • Nanjing Fred Technology Co., Ltd

668270-12-0(Linagliptin)Related Search:

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Linagliptin Impurity I Linagliptin Impurity 8 8-bromo-7-(but-2-ynyl)-3-methyl-1H-purine-2,6(3H,7H)-dione

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linagliptin (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 1H-Purine-2,6-dione, 8-((3R)-3-amino-1-piperidinyl)-7-(2-butynyl)-3,7-dihydro-3-methyl-1-((4-methyl-2-quinazolinyl)methyl)- Bi 1356 Ondero 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 8-[(3R)-3-AMino-1-piperidinyl]-7-(2-butynyl)-3,7-dihydro-3-Methyl-1-[(4-Methyl-2-quinazolinyl)Methyl]-1H-purine-2,6-d 8-[(3R)-3-aMinopiperidin-1-yl]-7-(but-2-yn-1-yl)-3-Methyl-1-[(4-Methylquinazolin-2-yl)Methyl]-2,3,6,7-tetrahydro-1H-purine-2,6-dione Tradjenta Linagliptin-D4 Linaglitine (R)-8-(3-aMinopiperidin-1-yl)-7-(but-2-yn-1-yl)-3-Methyl-1-((4-Methylquinazolin-2-yl)Methyl)-1H-purine-2,6(3H,7H)-dione 1H-Purine-2,6-dione,8-[(3R)-3-aMino-1-piperidinyl]-7-(2-butyn-1-yl)-3,7-dihydro-3-Methyl-1-[(4-Methyl-2-quinazolinyl)Methyl]- (R)-8-(3-aminopiperidin-1-yl)-7-(but-2-ynyl)-3-methyl-1-((4-methylquinazolin-2-yl)methyl)-1H-purine-2,6(3H,7H)-dione Linagliptin 8-[(3R)-3-Amino-1-piperidinyl]-7-(2-butynyl)-3,7-dihydro-3-methyl-1-[(4-methyl-2-quinazolinyl)methyl]-1H-purine-2,6-dione Linagliptin, >=98% linagliptin / 1H-Purine-2,6-dione, 8-[(3R)-3-amino-1-piperidinyl]-7-(2-butyn-1-yl)-3,7-dihydro-3-methyl-1-[(4-methyl-2-quinazolinyl)methyl]- Linagliptin (668270-12-0) 8-[(3R)-3-AMino-1-piperidinyl]-7-(2-butyn-1-yl)-3,7-dihydro-3-Met Lillidine CS-1974 CS-494 BI1356; BI 1356 Lilalitine inag iptin inagL Linagliptin ISO 9001：2015 REACH Linagliptin Impurity 81 Linagliptin Impurity 79 (R)-8-(3-aminopiperidin-1-yl)-7-(but-2-yn-1-yl)-3-methyl-1-((4-methylquinazolin-2-yl)methyl)-1H-purine-2,6(3H,8H)-dione LinagliptinQ: What is Linagliptin Q: What is the CAS Number of Linagliptin Q: What is the storage condition of Linagliptin Q: What are the applications of Linagliptin Azelastina Azelastinum 8-[(3R)-3-Amino-1-piperidinyl]-7-(2-butynyl)-3,7-dihydro-3-methyl-1-[(4-methyl-2-quinazolinyl)methyl]-1H-purine-2,6-dione Linagliptin (BI-1356) Linagliptin API Linaglitpin Benzene,1,2-dichloro-9-methoxy- 2-Pyrrolidinone,10-(hydroxymethyl)- LIGLIPTIN Liggliptin Linagliptin (R)-8-(3-aminopiperidin-1-yl)-7-(but-2-yn-1-yl)-3-methyl-1-((4- methylquinazolin-2-yl)methyl)-3,7-dihydro-1H-purine-2,6-dione Liraglutine 668270-12-0 6668270-12-0 68270-12-0 C25H28N8O2 TRADJENTA Linagliptin Inhibitor Pharmaceutical raw material API Amines Aromatics Heterocycles Intermediates & Fine Chemicals Pharmaceuticals