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2D Structure
Also known as: 850649-62-6, Nesina, Syr 322, Syr-322, Alogliptin (benzoate), (r)-2-((6-(3-aminopiperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl)methyl)benzonitrile benzoate
Molecular Formula
C25H27N5O4
Molecular Weight
461.5  g/mol
InChI Key
KEJICOXJTRHYAK-XFULWGLBSA-N
FDA UNII
EEN99869SC

Alogliptin Benzoate is the benzoate salt form of alogliptin, a selective, orally bioavailable, pyrimidinedione-based inhibitor of dipeptidyl peptidase 4 (DPP-4), with hypoglycemic activity. In addition to its effect on glucose levels, alogliptin may inhibit inflammatory responses by preventing the toll-like receptor 4 (TLR-4)-mediated formation of proinflammatory cytokines.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-[[6-[(3R)-3-aminopiperidin-1-yl]-3-methyl-2,4-dioxopyrimidin-1-yl]methyl]benzonitrile;benzoic acid
2.1.2 InChI
InChI=1S/C18H21N5O2.C7H6O2/c1-21-17(24)9-16(22-8-4-7-15(20)12-22)23(18(21)25)11-14-6-3-2-5-13(14)10-19;8-7(9)6-4-2-1-3-5-6/h2-3,5-6,9,15H,4,7-8,11-12,20H2,1H3;1-5H,(H,8,9)/t15-;/m1./s1
2.1.3 InChI Key
KEJICOXJTRHYAK-XFULWGLBSA-N
2.1.4 Canonical SMILES
CN1C(=O)C=C(N(C1=O)CC2=CC=CC=C2C#N)N3CCCC(C3)N.C1=CC=C(C=C1)C(=O)O
2.1.5 Isomeric SMILES
CN1C(=O)C=C(N(C1=O)CC2=CC=CC=C2C#N)N3CCC[C@H](C3)N.C1=CC=C(C=C1)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
EEN99869SC
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-((6-((3r)-3-aminopiperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl)methyl) Benzonitrile

2. Alogliptin

3. Nesina

4. Syr 322

5. Syr-322

6. Syr322

2.3.2 Depositor-Supplied Synonyms

1. 850649-62-6

2. Nesina

3. Syr 322

4. Syr-322

5. Alogliptin (benzoate)

6. (r)-2-((6-(3-aminopiperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl)methyl)benzonitrile Benzoate

7. 850649-62-6 (benzoate)

8. Alogliptin (as Benzoate)

9. Een99869sc

10. Chebi:72324

11. 2-((6-((3r)-3-amino-1-piperidinyl)-3,4-dihydro-3-methyl-2,4-dioxo-1(2h)- Pyrimidinyl)methyl)benzonitrile Monobenzoate

12. 2-[[6-[(3r)-3-aminopiperidin-1-yl]-3-methyl-2,4-dioxopyrimidin-1-yl]methyl]benzonitrile;benzoic Acid

13. 6-((3r)-3-aminopiperidin-1-yl)-1-(2-cyanobenzyl)-3-methylpyrimidin-2,4(1h,3h)-dione Monobenzoate

14. Benzonitrile, 2-((6-((3r)-3-amino-1-piperidinyl)-3,4-dihydro-3-methyl-2,4-dioxo-1(2h)-pyrimidinyl)methyl)-, Monobenzoate

15. Alogliptin, Benzoate

16. Alogliptin Benzoate [usan]

17. Unii-een99869sc

18. Mfcd09833195

19. Alogliptin Benzoate [usan:jan]

20. Vipidia (tn)

21. Nesina (tn)

22. Alogliptin Monobenzoate

23. Alogliptin(syr-322)

24. Schembl476231

25. Chembl227529

26. Alogliptin Benzoate [mi]

27. Alogliptin Benzoate (jan/usan)

28. Alogliptin Benzoate [jan]

29. Dtxsid20582095

30. Alogliptin Benzoate [vandf]

31. Alogliptin Benzoate [mart.]

32. Bcp08885

33. Hy-a0023

34. Ac-021

35. Alogliptin Benzoate [who-dd]

36. Akos015917686

37. Cs-0761

38. Alogliptin Benzoate [orange Book]

39. 2-[[6-[(3r)-3-amino-1-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-1(2h)-pyrimidinyl]methyl]benzonitrile Benzoate

40. As-14073

41. Oseni Component Alogliptin Benzoate

42. Kazano Component Alogliptin Benzoate

43. Alogliptin Pound Syr-322 Pound(c)benzoate

44. Alogliptin Benzoate Component Of Oseni

45. Am20090704

46. Alogliptin Benzoate Component Of Kazano

47. D06553

48. Q27888443

49. Syr 322 Benzoate; Syr-322 Benzoate; Syr322 Benzoate

50. (3r)-1-[3-(2-cyanobenzyl)-1-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl]piperidin-3-aminium Benzoate

51. 2-((6-((3r)-3-aminopiperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl)methyl)benzonitrile Monobenzoate

52. 2-({6-[(3r)-3-aminopiperidin-1-yl]-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl}methyl)benzonitrile Benzoate

53. Benzoic Acid--2-({6-[(3r)-3-aminopiperidin-1-yl]-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl}methyl)benzonitrile (1/1)

54. Benzonitrile, 2-[[6-[(3r)-3-amino-1-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-1(2h)-pyrimidinyl]methyl]-, Benzoate (1:1)

2.4 Create Date
2007-06-18
3 Chemical and Physical Properties
Molecular Weight 461.5 g/mol
Molecular Formula C25H27N5O4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count4
Exact Mass461.20630436 g/mol
Monoisotopic Mass461.20630436 g/mol
Topological Polar Surface Area131 Ų
Heavy Atom Count34
Formal Charge0
Complexity726
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameNesina
PubMed HealthAlogliptin (By mouth)
Drug ClassesAntidiabetic
Drug LabelNESINA tablets contain the active ingredient alogliptin, which is a selective, orally bioavailable inhibitor of the enzymatic activity of dipeptidyl peptidase-4 (DPP-4).Chemically, alogliptin is prepared as a benzoate salt, which is identified as 2-(...
Active IngredientAlogliptin benzoate
Dosage FormTablet
RouteOral
Strengtheq 12.5mg base; eq 6.25mg base; eq 25mg base
Market StatusPrescription
CompanyTakeda Pharms Usa

2 of 2  
Drug NameNesina
PubMed HealthAlogliptin (By mouth)
Drug ClassesAntidiabetic
Drug LabelNESINA tablets contain the active ingredient alogliptin, which is a selective, orally bioavailable inhibitor of the enzymatic activity of dipeptidyl peptidase-4 (DPP-4).Chemically, alogliptin is prepared as a benzoate salt, which is identified as 2-(...
Active IngredientAlogliptin benzoate
Dosage FormTablet
RouteOral
Strengtheq 12.5mg base; eq 6.25mg base; eq 25mg base
Market StatusPrescription
CompanyTakeda Pharms Usa

4.2 Drug Indication

Vipidia is indicated in adults aged 18 years and older with type 2 diabetes mellitus to improve glycaemic control in combination with other glucose lowering medicinal products including insulin, when these, together with diet and exercise, do not provide adequate glycaemic control (see sections 4. 4, 4. 5 and 5. 1 for available data on different combinations).


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Dipeptidyl-Peptidase IV Inhibitors

Compounds that suppress the degradation of INCRETINS by blocking the action of DIPEPTIDYL-PEPTIDASE IV. This helps to correct the defective INSULIN and GLUCAGON secretion characteristic of TYPE 2 DIABETES MELLITUS by stimulating insulin secretion and suppressing glucagon release. (See all compounds classified as Dipeptidyl-Peptidase IV Inhibitors.)


Hypoglycemic Agents

Substances which lower blood glucose levels. (See all compounds classified as Hypoglycemic Agents.)


Incretins

Peptides which stimulate INSULIN release from the PANCREATIC BETA CELLS following oral nutrient ingestion, or postprandially. (See all compounds classified as Incretins.)


5.2 ATC Code

A10BH04