Compound: Linagliptin
SMILES: O=c1n(c(=O)c2n(CC#CC)c(nc2n1C)N3C[C@H](N)CCC3)Cc4nc5c(cccc5)c(n4)C
InChIKey: LTXREWYXXSTFRX-QGZVFWFLSA-N
Synonyms: Linagliptin, 668270-12-0, Tradjenta, BI-1356, BI 1356, Trazenta, Trajenta, BI-1356-BS, linagliptine, Linagliptina, BS 1356 BS, BI1356, 3X29ZEJ4R2, (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-1356BS, BI 1356 BS, BS-1356-BS, CHEBI:68610, DTXSID201021653, GLYXAMBI COMPONENT LINAGLIPTIN, (R)-8-(3-aminopiperidin-1-yl)-7-but-2-ynyl-3-methyl-1-(4-methylquinazolin-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)-, TRIJARDY XR COMPONENT LINAGLIPTIN, 8-[(3R)-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, linagliptinum, 8-((3R)-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, RefChem:5948, 1356, BI, A10BH05, DTXCID801506661, Ondero, Linagliptin (BI-1356), MFCD14635356, ione, CHEMBL237500, C25H28N8O2, (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, (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, (R)-8-[3-Aminopiperidin-1-yl]-7-(2-butynyl)-3-methyl-1-(4-methylquinazolin-2-ylmethyl)xanthine, 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]-, 8-[(3R)-3-aminopiperidin-1-yl]-7-but-2-ynyl-3-methyl-1-[(4-methylquinazolin-2-yl)methyl]purine-2,6-dione, 8-[(3r)-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, UNII-3X29ZEJ4R2, Linaglitpin, Linagliptin [USAN:INN:JAN], HSDB 8204, Tradjenta (TN), 8-[(3R)-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-d ione, Linagliptin (Standard), LINAGLIPTIN [MI], LINAGLIPTIN [INN], LINAGLIPTIN [JAN], LINAGLIPTIN [USAN], LINAGLIPTIN [VANDF], LINAGLIPTIN [MART.], LINAGLIPTIN [WHO-DD], Linagliptin (BI-1356)?, MLS006010217, SCHEMBL160188, Linagliptin (JAN/USAN/INN), GTPL6318, orb1310851, orb3141336, Linagliptin - Bio-X trade mark, SCHEMBL29359185, EX-A076, LINAGLIPTIN [ORANGE BOOK], LTXREWYXXSTFRX-QGZVFWFLSA-N, GLXC-10521, MSK15589, BDBM50228403, EBC-13284, HY-10284R, s3031, AKOS015951179, AKOS015995251, AC-8761, CCG-269463, CS-0637, DB08882, FL24893, NCGC00346655-01, NCGC00346655-02, NCGC00346655-08, 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-piperidyl]-7-but-2-ynyl-3-methyl-1-[(4-methylquinazolin-2-yl)methyl]purine-2,6-dione, 8-[(3R)-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, 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, AS-35080, BL164627, DA-54932, HY-10284, SMR004701306, NS00098773, SW219813-1, D09566, AB01563307_01, AB01563307_03, EN300-6481354, Q909745, BRD-K96550715-001-02-6, BRD-K96550715-001-03-4, BRD-K96550715-001-04-2, BRD-K96550715-003-01-4, Z2235801970, 1-[(4-methyl-quinazolin-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-(3-(R)-aminopiperidin-1-yl)xanthine, 1-[(4-methyl-quinazolin-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-(3-(R)aminopiperidin-1-yl)xanthine, 1-[(4-methyl-quinazolin-2yl) methyl]-3-methyl-7-(2-butyn-1-yl)-8-[3-(R) amino-piperidin-1-yl]-xanthine, 1-[(4-Methylquinazolin-2-yl)-methyl]-3-methyl-7-(2-butin-1-yl)-8-(3-(R)-aminopiperidin-1-yl)-xanthine, 1-[(4-Methylquinazolin-2-yl)methyl]-3-methyl-7-(2-butin-1-yl)-8-(3-(R)-aminopiperidin-1-yl)-xanthine, 1233245-11-8, 8-[(3R)-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-d
Theoretical properties:
molecular_formula: C25H28N8O2
molecular_weight: 472.5 g/mol
exact_mass: 472.23352217 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 7
rotatable_bond_count: 4
heavy_atom_count: 35
topological_polar_surface_area: 113 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: White to yellow solid; also reported as a crystalline solid
color: White to yellow solid; also reported as a crystalline solid
melting_point: 190-196
solubility: <1 mg/mL
Descriptions:
pubchem: Linagliptin is 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 II diabetes. It has a role as a hypoglycemic agent and an EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor. It is a member of quinazolines and an aminopiperidine. It is functionally related to a 7H-xanthine.
chebi: A xanthine that is 7<em>H</em>-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 <i>R</i>-enantiomer). Used for treatment of type II diabetes.
chembl: LINAGLIPTIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Linagliptin, sold under the brand name Tradjenta among others, is a medication used to treat type 2 diabetes (but not type 1) in conjunction with exercise and diet. Linagliptin is a dipeptidyl peptidase-4 inhibitor that works by increasing the production of insulin and decreasing the production of glucagon by the pancreas. It is generally less preferred than metformin and sulfonylureas as an initial treatment. It is taken by mouth.
Common side effects include inflammation of the nose and throat. Serious side effects may include angioedema, pancreatitis, joint pain. Use in pregnancy and breastfeeding is not recommended.
Linagliptin was approved for medical use in the United States, Japan, the European Union, Canada, and Australia in 2011. In 2023, it was the 254th most commonly prescribed medication in the United States, with more than 1 million prescriptions. From August 2021, linagliptin became available as a generic medicine in the US.