356

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

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is present as a standalone ligand in 2 entries

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Chemical Component Summary
Name	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
Synonyms	Linagliptin
Identifiers	8-[(3R)-3-aminopiperidin-1-yl]-7-but-2-ynyl-3-methyl-1-[(4-methylquinazolin-2-yl)methyl]purine-2,6-dione
Formula	C₂₅ H₂₈ N₈ O₂
Molecular Weight	472.542
Type	NON-POLYMER
Isomeric SMILES	CC#CCn1c2c(nc1N3CCC[C@H](C3)N)N(C(=O)N(C2=O)Cc4nc(c5ccccc5n4)C)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

Chemical Details
Formal Charge	0
Atom Count	63
Chiral Atom Count	1
Bond Count	67
Aromatic Bond Count	16

Drug Info: DrugBank

DrugBank ID	DB08882
Name	Linagliptin
Groups	approved
Description	Linagliptin is a DPP-4 inhibitor developed by Boehringer Ingelheim for the treatment of type II diabetes [L9557]. Linagliptin differs from other DPP-4 inhibitors in that it has a non-linear pharmacokinetic profile, is not primarily eliminated by the renal system, and obeys concentration dependant protein binding[A37050]. Linagliptin was approved by the FDA on May 2, 2011[L9557].
Synonyms	(R)-8-(3-aminopiperidin-1-yl)-7-but-2-ynyl-3-methyl-1-(4-methylquinazolin-2-ylmethyl)-3,7-dihydro-purine-2,6-dione Linagliptina Linagliptin
Brand Names	Tradjenta Trajenta Glyxambi Jentadueto Trijardy XR Jentadueto XR
Indication	Linagliptin is indicated for the treatment of type II diabetes in addition to diet and exercise[L9557]. It should not be used to treat type I diabetes or in diabetic ketoacidosis.[L9557] An extended-release combination product containing empagliflozin, linagliptin, and metformin was approved by the FDA in January 2020 for the improvement of glycemic control in adults with type 2 diabetes mellitus when used adjunctively with diet and exercise.[L11479]
Categories	Agents causing angioedema Alimentary Tract and Metabolism Blood Glucose Lowering Agents Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (moderate) Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A4 Substrates (strength unknown) Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates DPP-IV Inhibitors Drugs Used in Diabetes Enzyme Inhibitors Heterocyclic Compounds, Fused-Ring Hormones Hormones, Hormone Substitutes, and Hormone Antagonists Incretins OCT1 inhibitors OCT2 Inhibitors OCT2 Substrates Oral Hypoglycemics P-glycoprotein inhibitors P-glycoprotein substrates Protease Inhibitors Purines Quinazolines
ATC-Code	A10BH05 A10BD19 A10BD11 A10BD27
CAS number	668270-12-0

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Dipeptidyl peptidase 4	MKTPWKVLLGLLGAAALVTIITVPVVLLNKGTDDATADSRKTYTLTDYLK...	unknown	inhibitor
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate,inhibitor
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	substrate
Solute carrier family 22 member 1	MPTVDDILEQVGESGWFQKQAFLILCLLSAAFAPICVGIVFLGFTPDHHC...	unknown	inhibitor
Solute carrier family 22 member 2	MPTTVDDVLEHGGEFHFFQKQMFFLLALLSATFAPIYVGIVFLGFTPDHR...	unknown	substrate,inhibitor
Solute carrier family 22 member 3	MPSFDEALQRVGEFGRFQRRVFLLLCLTGVTFAFLFVGVVFLGTQPDHYW...	unknown	inhibitor
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682