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CAS 654671-77-9

CAS 654671-77-9

Chemistry

Chemistry

MARKET PLACE

1 APIs

1 APIs

Also known as: 654671-77-9, Januvia, Sitagliptin phosphate hydrate, Glactiv, (r)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8h)-yl)-4-(2,4,5-trifluorophenyl)butan-1-one phosphate hydrate, Sitagliptin monohydrate

Molecular Formula

C₁₆H₂₀F₆N₅O₆P

Molecular Weight

523.32 g/mol

InChI Key

GQPYTJVDPQTBQC-KLQYNRQASA-N

FDA UNII

TS63EW8X6F

A pyrazine-derived DIPEPTIDYL-PEPTIDASE IV INHIBITOR and HYPOGLYCEMIC AGENT that increases the levels of the INCRETIN hormones GLUCAGON-LIKE PEPTIDE-1 (GLP-1) and glucose-dependent insulinotropic polypeptide (GIP). It is used in the treatment of TYPE 2 DIABETES.

1 2D Structure

CAS 654671-77-9

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3R)-3-amino-1-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one;phosphoric acid;hydrate

2.1.2 InChI

InChI=1S/C16H15F6N5O.H3O4P.H2O/c17-10-6-12(19)11(18)4-8(10)3-9(23)5-14(28)26-1-2-27-13(7-26)24-25-15(27)16(20,21)22;1-5(2,3)4;/h4,6,9H,1-3,5,7,23H2;(H3,1,2,3,4);1H2/t9-;;/m1../s1

2.1.3 InChI Key

GQPYTJVDPQTBQC-KLQYNRQASA-N

2.1.4 Canonical SMILES

C1CN2C(=NN=C2C(F)(F)F)CN1C(=O)CC(CC3=CC(=C(C=C3F)F)F)N.O.OP(=O)(O)O

2.1.5 Isomeric SMILES

C1CN2C(=NN=C2C(F)(F)F)CN1C(=O)C[C@@H](CC3=CC(=C(C=C3F)F)F)N.O.OP(=O)(O)O

2.2 Other Identifiers

2.2.1 UNII

TS63EW8X6F

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 0431, Mk

2. 4-oxo-4-(3-(trifluoromethyl)-5,6-dihydro(1,2,4)triazolo(4,3-a)pyrazin-7(8h)-yl)-1-(2,4,5-trifluorophenyl)butan-2-amine

3. Anhydrous, Sitagliptin Phosphate

4. Januvia

5. Mk 0431

6. Mk-0431

7. Mk0431

8. Monohydrate, Sitagliptin Monophosphate

9. Monohydrate, Sitagliptin Phosphate

10. Monophosphate Monohydrate, Sitagliptin

11. Phosphate Anhydrous, Sitagliptin

12. Phosphate Monohydrate, Sitagliptin

13. Phosphate, Sitagliptin

14. Sitagliptin

15. Sitagliptin Monophosphate Monohydrate

16. Sitagliptin Phosphate

17. Sitagliptin Phosphate Anhydrous

2.3.2 Depositor-Supplied Synonyms

1. 654671-77-9

2. Januvia

3. Sitagliptin Phosphate Hydrate

4. Glactiv

5. (r)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8h)-yl)-4-(2,4,5-trifluorophenyl)butan-1-one Phosphate Hydrate

6. Sitagliptin Monohydrate

7. Tesavel

8. Mk-0431

9. Sitagliptin Phosphate [usan]

10. Sitagliptin (phosphate Monohydrate)

11. Ono-5435

12. Sitagliptin Monophosphate Monohydrate

13. Ts63ew8x6f

14. Mk0431

15. Sitagliptin Phosphate Anhydrous

16. 654671-77-9 (phosphate Hydrate)

17. Sitagliptin Phosphate (usan)

18. Sitagliptin Monophosphate

19. (3r)-3-amino-1-[3-(trifluoromethyl)-6,8-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one;phosphoric Acid;hydrate

20. (r)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8h)-yl)-4-(2,4,5-trifluorophenyl)butan-1-one Phosphate Monohydrate.

21. Unii-ts63ew8x6f

22. Januvia (tn)

23. Mfcd10001393

24. Sitagpliptin Monohydrate

25. Schembl1039535

26. Chembl1201174

27. Amy1793

28. Dtxsid50904746

29. Sitagliptin Monophosphate Anhydrous

30. Sitagliptin Phosphate [jan]

31. Hy-13749b

32. Mk-431

33. S4002

34. Sitagliptin Phosphate [vandf]

35. Sitagliptin Phosphate [mart.]

36. Sitagliptin Phosphate Hydrate (jp17)

37. Akos015895530

38. Sitagliptin Phosphate [usp-rs]

39. Ac-1939

40. Ccg-213562

41. Cs-3683

42. As-18643

43. Bs164409

44. Sitagliptin Phosphate [orange Book]

45. Sitagliptin Phosphate Hydrate [jan]

46. Sitagliptin Phosphate [usp Monograph]

47. Janumet Component Sitagliptin Phosphate

48. D06645

49. Stelujan Component Sitagliptin Phosphate

50. Sitagliptin Phosphate Component Of Janumet

51. 671s779

52. Sitagliptin Monophosphate Monohydrate [mi]

53. Sitagliptin Phosphate Component Of Stelujan

54. Sitagliptin Phosphate Monohydrate [who-dd]

55. Q27290248

56. Sitagliptin Phosphate Monohydrate [ep Monograph]

57. (2r)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8h)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine Dihydrogenphosphate Monohydrate

58. (2r)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-alpha]pyrazin-7(8h)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine Dihydrogenphosphate Monohydrate

59. (r)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8h)-yl)-4-(2,4,5-trifluorophenyl)butan-1-one Phosphate Hydra

60. 1,2,4-triazolo(4,3-a)pyrazine, 7-((3r)-3-amino-1-oxo-4-(2,4,5-trifluorophenyl)butyl)-5,6,7,8- Tetrahydro-3-(trifluoromethyl)-, Phosphate (1:1) Monohydrate

61. 1,2,4-triazolo(4,3-a)pyrazine, 7-((3r)-3-amino-1-oxo-4-(2,4,5-trifluorophenyl)butyl)-5,6,7,8-tetrahydro-3-(trifluoromethyl), Phosphate (1:1) Monohydrate

62. 1,2,4-triazolo[4,3-a]pyrazine,7-[(3r)-3-amino-1-oxo-4-(2,4,5-trifluorophenyl)butyl]-5,6,7,8-tetrahydro-3-(trifluoromethyl)-, Phosphate (1:1), Monohydrate

63. 7-((3r)-3-amino-4-(2,4,5-trifluorophenyl)butanoyl)-3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4- Triazolo(4,3-a)pyrazine Monophosphate Monohydrate

64. 7-((3r)-3-amino-4-(2,4,5-trifluorophenyl)butanoyl)-3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4-triazolo(4,3-a)pyrazine Monophosphate Monohydrate

65. 7-(3r)-3-amino-1-oxo-4-(2,4,5-trifluorophenyl)butyl-5,6,7,8-tetrahydro-3-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyrazine Phosphate Hydrate

66. 7-[(3r)-3-amino-1-oxo-4-(2,4,5-trifluorophenyl)butyl]-5,6,7,8-tetrahydro-3-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyrazine Phosphate (1:1) Monohydrate

2.4 Create Date

2006-10-26

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₂₀F₆N₅O₆P
Molecular Weight	523.32 g/mol
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	15
Rotatable Bond Count	4
Exact Mass	523.10553934 g/mol
Monoisotopic Mass	523.10553934 g/mol
Topological Polar Surface Area	156 Å²
Heavy Atom Count	34
Formal Charge	0
Complexity	616
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	3

4 Drug and Medication Information

4.1 Drug Indication

For adult patients with type-2 diabetes mellitus, Xelevia is indicated to improve glycaemic control:

- as monotherapy:

- in patients inadequately controlled by diet and exercise alone and for whom metformin is inappropriate due to contraindications or intolerance;

- as dual oral therapy in combination with:

- metformin when diet and exercise plus metformin alone do not provide adequate glycaemic control;

- a sulphonylurea when diet and exercise plus maximal tolerated dose of a sulphonylurea alone do not provide adequate glycaemic control and when metformin is inappropriate due to contraindications or intolerance;

- a peroxisome proliferator-activated receptor gamma (PPAR) agonist (i. e. a thiazolidinedione) when use of a PPAR agonist is appropriate and when diet and exercise plus the PPAR agonist alone do not provide adequate glycaemic control;

- as triple oral therapy in combination with:

- a sulphonylurea and metformin when diet and exercise plus dual therapy with these medicinal products do not provide adequate glycaemic control;

- a PPAR agonist and metformin when use of a PPAR agonist is appropriate and when diet and exercise plus dual therapy with these medicinal products do not provide adequate glycaemic control.

Xelevia is also indicated as add-on to insulin (with or without metformin) when diet and exercise plus stable dose of insulin do not provide adequate glycaemic control.

For patients with type-2 diabetes mellitus, Tesavel is indicated to improve glycaemic control:

- as monotherapy:

- in patients inadequately controlled by diet and exercise alone and for whom metformin is inappropriate due to contraindications or intolerance;

- as dual oral therapy in combination with:

- metformin when diet and exercise plus metformin alone do not provide adequate glycaemic control;

- a PPAR agonist (i. e. a thiazolidinedione) when use of a PPAR agonist is appropriate and when diet and exercise plus the PPAR agonist alone do not provide adequate glycaemic control;

- as triple oral therapy in combination with

- a sulphonylurea and metformin when diet and exercise plus dual therapy with these agents do not provide adequate glycaemic control;

- a peroxisome-proliferator-activated-receptor-gamma (PPAR) agonist and metformin when use of a PPAR agonist is appropriate and when diet and exercise plus dual therapy with these agents do not provide adequate glycaemic control.

Tesavel is also indicated as add on to insulin (with or without metformin) when diet and exercise plus stable dosage of insulin do not provide adequate glycaemic control.

For adult patients with type-2 diabetes mellitus, Januvia is indicated to improve glycaemic control:

- as monotherapy:

- in patients inadequately controlled by diet and exercise alone and for whom metformin is inappropriate due to contraindications or intolerance;

- as dual oral therapy in combination with:

- metformin when diet and exercise plus metformin alone do not provide adequate glycaemic control;

- a peroxisome-proliferator-activated-receptor-gamma (PPAR) agonist (i. e. a thiazolidinedione) when use of a PPAR agonist is appropriate and when diet and exercise plus the PPAR agonist alone do not provide adequate glycaemic control;

- a PPAR agonist (i. e. a thiazolidinedione) when use of a PPAR agonist is appropriate and when diet and exercise plus the PPAR agonist alone do not provide adequate glycaemic control;

- as triple oral therapy in combination with:

- a sulphonylurea and metformin when diet and exercise plus dual therapy with these medicinal products do not provide adequate glycaemic control;

- a PPAR agonist and metformin when use of a PPAR agonist is appropriate and when diet and exercise plus dual therapy with these medicinal products do not provide adequate glycaemic control.

Januvia is also indicated as add-on to insulin (with or without metformin) when diet and exercise plus stable dose of insulin do not provide adequate glycaemic control.

Treatment of type II diabetes mellitus

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

A10BH01