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Overview

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SCHEMBL476231
PharmaCompass
  • Chemistry
SCHEMBL476231
Also known as: 850649-62-6, Nesina, Alogliptin (benzoate), Syr 322, Syr-322, Unii-een99869sc
Molecular Formula
C25H27N5O4
Molecular Weight
461.522  g/mol
InChI Key
KEJICOXJTRHYAK-XFULWGLBSA-N
FDA UNII
EEN99869SC

1 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 Depositor-Supplied Synonyms

1. 850649-62-6

2. Nesina

3. Alogliptin (benzoate)

4. Syr 322

5. Syr-322

6. Unii-een99869sc

7. Alogliptin, Benzoate

8. Een99869sc

9. Chebi:72324

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

11. C18h21n5o2.c7h6o2

12. 2-[[6-[(3r)-3-amino-1-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-1(2h)-pyrimidinyl]methyl]benzonitrile Benzoate

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

14. Alogliptin Benzoate [usan:jan]

15. Vipidia (tn)

16. Nesina (tn)

17. Alogliptin Monobenzoate

18. Alogliptin?syr-322

19. Schembl476231

20. Chembl227529

21. Alogliptin Benzoate (jan/usan)

22. Dtxsid20582095

23. Molport-005-933-064

24. 850649-62-6 (benzoate)

25. 2-[6-[3(r)-aminopiperidin-1-yl]-3-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-ylmethyl]benzonitrile Benzoate

26. Hy-a0023

27. Ac-021

28. Akos015917686

29. An-6359

30. Api0004995

31. Cs-0761

32. Ak143301

33. As-14073

34. Bc202597

35. Ab1008522

36. Am20090704

37. Ft-0686730

38. X4993

39. D06553

40. J90037

41. I14-8828

42. (3r)-1-[3-(2-cyanobenzyl)-1-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl]piperidin-3-aminium Benzoate

43. 2-((6-((3r)-3-amino-1-piperidinyl)-3,4-dihydro-3-methyl-2,4-dioxo-1(2h)- Pyrimidinyl)methyl)benzonitrile Monobenzoate

44. 2-({6-[(3r)-3-aminopiperidin-1-yl]-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl}methyl)benzonitrile Benzoate

45. 2-[[6-[(3r)-3-amino-1-piperidyl]-3-methyl-2,4-dioxo-pyrimidin-1-yl]methyl]benzonitrile; Benzoic Acid

46. 2-[[6-[(3r)-3-aminopiperidin-1-yl]-3-methyl-2,4-dioxopyrimidin-1-yl]methyl]benzonitrile;benzoic Acid

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

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

49. 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 461.522 g/mol
Molecular Formula C25H27N5O4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count4
Exact Mass461.206 g/mol
Monoisotopic Mass461.206 g/mol
Topological Polar Surface Area131 A^2
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 3  
Drug NameNESINA
Active IngredientALOGLIPTIN BENZOATE
CompanyTAKEDA PHARMS USA (Application Number: N022271. Patents: 6890898, 7078381, 7459428, 7807689, 8173663, 8288539, 8697125)

2 of 3  
Drug NameKAZANO
Active IngredientALOGLIPTIN BENZOATE; METFORMIN HYDROCHLORIDE
CompanyTAKEDA PHARMS USA (Application Number: N203414. Patents: 6890898, 7078381, 7459428, 7807689, 8173663, 8288539, 8900638)

3 of 3  
Drug NameOSENI
Active IngredientALOGLIPTIN BENZOATE; PIOGLITAZONE HYDROCHLORIDE
CompanyTAKEDA PHARMS USA (Application Number: N022426. Patents: 6329404, 6890898, 7078381, 7459428, 7807689, 8173663, 8288539, 8637079)

5 Pharmacology and Biochemistry
5.1 Pharmacology

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.


5.2 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.


Hypoglycemic Agents

Substances which lower blood glucose levels.


Incretins

Peptides which stimulate INSULIN release from the PANCREATIC BETA CELLS following oral nutrient ingestion, or postprandially.


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