Uses Treatment of Type 2 diabetes Pharmacokinetics
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Linagliptin

Uses Treatment of Type 2 diabetes Pharmacokinetics
Product Name
Linagliptin
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
Formula Weight
472.54
MOL File
668270-12-0.mol
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Linagliptin Property

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
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
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
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Safety

HS Code 
29335990
Hazardous Substances Data
668270-12-0(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

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N-Bromosuccinimide Price

Cayman Chemical
Product number
23306
Product name
Linagliptin
Purity
≥98%
Packaging
100mg
Price
$62
Updated
2024/03/01
Cayman Chemical
Product number
23306
Product name
Linagliptin
Purity
≥98%
Packaging
500mg
Price
$120
Updated
2024/03/01
Cayman Chemical
Product number
23306
Product name
Linagliptin
Purity
≥98%
Packaging
1g
Price
$225
Updated
2024/03/01
TRC
Product number
L465900
Product name
Linagliptin
Packaging
500mg
Price
$120
Updated
2021/12/16
Medical Isotopes, Inc.
Product number
D47119
Product name
Linagliptin-d3
Packaging
25mg
Price
$5450
Updated
2021/12/16
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Linagliptin Chemical Properties,Usage,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

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.

target

DDP-4

storage

+4°C

Linagliptin Preparation Products And Raw materials

Raw materials

Preparation Products

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Linagliptin Suppliers

Canada 2 China 528 China Hong Kong 1 Germany 1 India 66 Israel 1 Poland 1 United Kingdom 2 United States 26 Global 628
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+1-781-999-5354 +1-00000000000
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marketing@targetmol.com
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View Lastest Price from Linagliptin manufacturers

Sinoway Industrial co., ltd.
Product
Linagliptin 668270-12-0
Price
US $0.00-0.00/g/Bag
Min. Order
100g/Bag
Purity
99% up, High Density
Supply Ability
20 tons
Release date
2024-06-27
Nanjing Fred Technology Co., Ltd
Product
linagliptin 668270-12-0
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99%，single impurity＜0.1
Supply Ability
1 ton
Release date
2024-01-04
Hebei Chuanghai Biotechnology Co,.LTD
Product
Linagliptin 668270-12-0
Price
US $5.70/KG
Min. Order
10KG
Purity
99%
Supply Ability
10000kg
Release date
2024-08-21

668270-12-0, LinagliptinRelated Search:

Methyl acrylate Linagliptin Impurity 23 Linagliptin impurity 15 Methanol Dihydromyrcenol Bensulfuron methyl METSULFURON METHYL DROPERIDOL Methylparaben Kresoxim-methyl Methyl cellulose Haloperidol Sulfaquinoxaline Quinazoline Linagliptin Impurity M Linagliptin Impurity I Linagliptin Impurity 8 8-bromo-7-(but-2-ynyl)-3-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
  • (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
  • Linagliptin (BI-1356)
  • Linaglitine
  • Linagliptin (668270-12-0)
  • (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
  • Linagliptin API
  • 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]-
  • 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
  • Linaglitpin
  • 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
  • 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