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Anagliptin

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Chemistry

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Also known as: 739366-20-2, Suiny, Sk-0403, Anagliptin [inn], (s)-n-(2-((2-(2-cyanopyrrolidin-1-yl)-2-oxoethyl)amino)-2-methylpropyl)-2-methylpyrazolo[1,5-a]pyrimidine-6-carboxamide, Cwp-403

Molecular Formula

C₁₉H₂₅N₇O₂

Molecular Weight

383.4 g/mol

InChI Key

LDXYBEHACFJIEL-HNNXBMFYSA-N

FDA UNII

K726J96838

Anagliptin is an orally available, potent, selective inhibitor of dipeptidyl peptidase 4 (DPP-4), with hypoglycemic activity. Compared to vildagliptin, anagliptin caused longer lasting inhibition of DPP-4 activity.

1 2D Structure

Anagliptin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-[2-[[2-[(2S)-2-cyanopyrrolidin-1-yl]-2-oxoethyl]amino]-2-methylpropyl]-2-methylpyrazolo[1,5-a]pyrimidine-6-carboxamide

2.1.2 InChI

InChI=1S/C19H25N7O2/c1-13-7-16-21-9-14(11-26(16)24-13)18(28)22-12-19(2,3)23-10-17(27)25-6-4-5-15(25)8-20/h7,9,11,15,23H,4-6,10,12H2,1-3H3,(H,22,28)/t15-/m0/s1

2.1.3 InChI Key

LDXYBEHACFJIEL-HNNXBMFYSA-N

2.1.4 Canonical SMILES

CC1=NN2C=C(C=NC2=C1)C(=O)NCC(C)(C)NCC(=O)N3CCCC3C#N

2.1.5 Isomeric SMILES

CC1=NN2C=C(C=NC2=C1)C(=O)NCC(C)(C)NCC(=O)N3CCC[C@H]3C#N

2.2 Other Identifiers

2.2.1 UNII

K726J96838

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (s)-n-(2-((2-(2-cyanopyrrolidin-1-yl)-2-oxoethyl)amino)-2-methylpropyl)-2-methylpyrazolo(1,5-a)pyrimidine-6-carboxamide

2. Anagliptin Hydrochloride

3. N-(2-((2-((2s)-2-cyanopyrrolidin-1-yl)-2-oxoethyl)amino)-2-methylpropyl)-2-methyl Pyrazolo(1,5-a)pyrimidine-6-carboxamide Hydrochloride

2.3.2 Depositor-Supplied Synonyms

1. 739366-20-2

2. Suiny

3. Sk-0403

4. Anagliptin [inn]

5. (s)-n-(2-((2-(2-cyanopyrrolidin-1-yl)-2-oxoethyl)amino)-2-methylpropyl)-2-methylpyrazolo[1,5-a]pyrimidine-6-carboxamide

6. Cwp-403

7. N-[2-[[2-[(2s)-2-cyanopyrrolidin-1-yl]-2-oxoethyl]amino]-2-methylpropyl]-2-methylpyrazolo[1,5-a]pyrimidine-6-carboxamide

8. Chembl1929396

9. Pyrazolo(1,5-a)pyrimidine-6-carboxamide, N-(2-((2-((2s)-2-cyano-1-pyrrolidinyl)-2-oxoethyl)amino)-2-methylpropyl)-2-methyl-

10. K726j96838

11. Chembl1929387

12. Unii-k726j96838

13. N-(2-((2-((2s)-2-cyanopyrrolidin-1-yl)-2-oxoethyl)amino)-2-methylpropyl)-2-methylpyrazolo(1,5-a)pyrimidine-6-carboxamide

14. N-[2-({2-[(2s)-2-cyanopyrrolidin-1-yl]-2-oxoethyl}amino)-2-methylpropyl]-2-methylpyrazolo[1,5-a]pyrimidine-6-carboxamide

15. Anagliptin [mi]

16. Anagliptin (jan/inn)

17. Anagliptin [jan]

18. Anagliptin [who-dd]

19. Schembl905393

20. Gtpl11582

21. Chebi:136043

22. Dtxsid401045689

23. Bdbm50359366

24. Mfcd19443729

25. S5909

26. Sk0403

27. Zinc70647144

28. Akos027325601

29. Cs-4510

30. Db12417

31. Compound 4a [pmid: 22019046]

32. Ncgc00484798-01

33. Hy-14877

34. D09780

35. A916481

36. Q15269682

2.4 Create Date

2009-12-22

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₂₅N₇O₂
Molecular Weight	383.4 g/mol
XLogP3	0
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	6
Exact Mass	383.20697307 g/mol
Monoisotopic Mass	383.20697307 g/mol
Topological Polar Surface Area	115 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	643
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 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.)

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