Alogliptin benzoate

An orally administered antidiabetic drug used to improve glycemic control in adults with type 2 diabetes mellitus, either alone or in combination with other glucose-lowering agents. Alogliptin selectively inhibits DPP-4, reducing the degradation of incretin hormones GLP-1 and GIP. This enhances glucose-dependent insulin secretion and suppresses glucagon release, thereby lowering blood glucose concentrations. Alogliptin is administered as its benzoate salt and is eliminated predominantly through the kidneys, requiring dose adjustment in patients with renal impairment. Potential adverse effects include pancreatitis, hypersensitivity reactions, and heart failure-related concerns

CAS Number: 850649-62-6

Molecular Mass: 461.5 g/mol

Formula: C₂₅H₂₇N₅O₄

Smiles: Cn1c(=O)cc(N2CCC[C@@H](N)C2)n(Cc2ccccc2C#N)c1=O.O=C(O)c1ccccc1

Synonymes:

Alogliptin benzoate, 850649-62-6, Nesina, SYR-322, SYR 322, Alogliptin (as benzoate), EEN99869SC, CHEBI:72324, OSENI COMPONENT ALOGLIPTIN BENZOATE, KAZANO COMPONENT ALOGLIPTIN BENZOATE, Benzonitrile, 2-((6-((3R)-3-amino-1-piperidinyl)-3,4-dihydro-3-methyl-2,4-dioxo-1(2H)-pyrimidinyl)methyl)-, monobenzoate, SYR322, 2-((6-((3R)-3-AMINOPIPERIDIN-1-YL)-3-METHYL-2,4-DIOXO-3,4-DIHYDROPYRIMIDIN-1(2H)-YL)METHYL)BENZONITRILE MONOBENZOATE, 2-({6-[(3R)-3-Aminopiperidin-1-yl]-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl}methyl)benzonitrile monobenzoate, RefChem:57143, 691-730-4, (R)-2-((6-(3-aminopiperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrile benzoate, MFCD09833195, Alogliptin (Benzoate), 2-[[6-[(3R)-3-aminopiperidin-1-yl]-3-methyl-2,4-dioxopyrimidin-1-yl]methyl]benzonitrile, benzoic acid, Benzonitrile, 2-[[6-[(3R)-3-amino-1-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-, benzoate (1:1), Benzonitrile,2-[[6-[(3R)-3-amino-1-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-, monobenzoate, 2-((6-((3R)-3-amino-1-piperidinyl)-3,4-dihydro-3-methyl-2,4-dioxo-1(2H)- pyrimidinyl)methyl)benzonitrile monobenzoate, 6-((3R)-3-aminopiperidin-1-yl)-1-(2-cyanobenzyl)-3-methylpyrimidin-2,4(1H,3H)-dione monobenzoate, Alogliptin, benzoate, 850649-62-6 (benzoate), Alogliptin benzoate [USAN], UNII-EEN99869SC, C25H27N5O4, Alogliptin benzoate [USAN:JAN], Vipidia (TN), Alogliptin Benzoate?, Nesina (TN), alogliptin monobenzoate, 2-[[6-[(3R)-3-Amino-1-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-1(2H)-pyrimidinyl]methyl]benzonitrile benzoate, SCHEMBL476231, CHEMBL227529, orb1305540, ALOGLIPTIN BENZOATE [MI], SCHEMBL30216225, Alogliptin benzoate (JAN/USAN), HY-A0023R, ALOGLIPTIN BENZOATE [JAN], DTXSID20582095, Alogliptin (Benzoate) (Standard), GLXC-07088, ALOGLIPTIN BENZOATE [VANDF], ALOGLIPTIN BENZOATE [MART.], HY-A0023, AC-021, ALOGLIPTIN BENZOATE [WHO-DD], EBC-80277, AKOS015917686, CS-0761, FA61528, ALOGLIPTIN BENZOATE [ORANGE BOOK], AS-14073, SY098405, D06553, Q27888443, (3R)-1-[3-(2-cyanobenzyl)-1-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl]piperidin-3-aminium benzoate, 2-({6-[(3R)-3-Amino-1-piperidinyl]-3-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl}methyl)benzonitrile benzoate, 2-({6-[(3R)-3-aminopiperidin-1-yl]-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl}methyl)benzonitrile benzoate, 2-[[6-[(3R)-3-amino-1-piperidyl]-3-methyl-2,4-dioxo-pyrimidin-1-yl]methyl]benzonitrile, benzoic acid, Benzoic acid--2-({6-[(3R)-3-aminopiperidin-1-yl]-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl}methyl)benzonitrile (1/1)

Bioactivity: Potent, selective dipeptidyl peptidase-4 (DPP-4) inhibitor; incretin-based oral antidiabetic agent

Solubility in Different Solvents

Solvent	Temperature [K]	Crystal form	Solubility [mg/mL]	Reference
1-Propanol	278.15	-	0.382	[143]
1-Propanol	283.15	-	0.511	[143]
1-Propanol	288.15	-	0.7008	[143]
1-Propanol	293.15	-	0.9627	[143]
1-Propanol	298.15	-	1.284	[143]
1-Propanol	303.15	-	1.699	[143]
1-Propanol	308.15	-	2.232	[143]
1-Propanol	313.15	-	2.886	[143]
1-Propanol	318.15	-	3.738	[143]
Acetone	278.15	-	16.63	[143]
Acetone	283.15	-	18.72	[143]
Acetone	288.15	-	21.01	[143]
Acetone	293.15	-	23.49	[143]
Acetone	298.15	-	26.23	[143]
Acetone	303.15	-	29.2	[143]
Acetone	308.15	-	32.46	[143]
Acetone	313.15	-	35.98	[143]
Acetone	318.15	-	39.82	[143]
Acetonitrile	278.15	-	0.9161	[143]
Acetonitrile	283.15	-	1.293	[143]
Acetonitrile	288.15	-	1.55	[143]
Acetonitrile	293.15	-	2.006	[143]
Acetonitrile	298.15	-	2.551	[143]
Acetonitrile	303.15	-	3.192	[143]
Acetonitrile	308.15	-	4.092	[143]
Acetonitrile	313.15	-	4.987	[143]
Acetonitrile	318.15	-	6.156	[143]
Dimethylformamide	278.15	-	34.73	[143]
Dimethylformamide	283.15	-	41.81	[143]
Dimethylformamide	288.15	-	50.04	[143]
Dimethylformamide	293.15	-	59.54	[143]
Dimethylformamide	298.15	-	70.45	[143]
Dimethylformamide	303.15	-	82.99	[143]
Dimethylformamide	308.15	-	97.35	[143]
Dimethylformamide	313.15	-	113.7	[143]
Dimethylformamide	318.15	-	132.3	[143]
Ethanol	278.15	-	2.855	[143]
Ethanol	283.15	-	3.573	[143]
Ethanol	288.15	-	4.405	[143]
Ethanol	293.15	-	5.398	[143]
Ethanol	298.15	-	6.473	[143]
Ethanol	303.15	-	7.995	[143]
Ethanol	308.15	-	9.508	[143]
Ethanol	313.15	-	11.36	[143]
Ethanol	318.15	-	13.54	[143]
Isopropanol	278.15	-	0.117	[143]
Isopropanol	283.15	-	0.18	[143]
Isopropanol	288.15	-	0.255	[143]
Isopropanol	293.15	-	0.38	[143]
Isopropanol	298.15	-	0.528	[143]
Isopropanol	303.15	-	0.7579	[143]
Isopropanol	308.15	-	1.039	[143]
Isopropanol	313.15	-	1.44	[143]
Isopropanol	318.15	-	1.96	[143]
Methanol	278.15	-	27.76	[143]
Methanol	283.15	-	31.06	[143]
Methanol	288.15	-	34.73	[143]
Methanol	293.15	-	38.73	[143]
Methanol	298.15	-	43.08	[143]
Methanol	303.15	-	47.84	[143]
Methanol	308.15	-	53.02	[143]
Methanol	313.15	-	58.65	[143]
Methanol	318.15	-	64.78	[143]
Water	278.15	-	21.48	[143]
Water	283.15	-	23.45	[143]
Water	288.15	-	25.59	[143]
Water	293.15	-	27.88	[143]
Water	298.15	-	30.35	[143]
Water	303.15	-	33.0	[143]
Water	308.15	-	35.83	[143]
Water	313.15	-	38.87	[143]
Water	318.15	-	42.15	[143]

Molecule 3D descriptors

Descriptor	Value
PMI1	2523.1222
PMI2	2707.5956
PMI3	4141.9970
NPR1	0.6092
NPR2	0.6537
RadiusOfGyration	3.1866
InertialShapeFactor	0.0003
Eccentricity	0.7931
Asphericity	0.1073
SpherocityIndex	0.3874
PBF	1.0630