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Sitagliptin Phosphate

Synopsis, Chemistry

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TABLET;ORAL - EQ 100MG BASE, TABLET;ORAL - EQ 25MG BASE, TABLET;ORAL - EQ 50MG BASE, TABLET;ORAL - 1GM;EQ 50MG BASE, TABLET;ORAL - 500MG;EQ 50MG BASE

TABLET;ORAL - EQ 100MG BASE
TABLET;ORAL - EQ 25MG BASE
TABLET;ORAL - EQ 50MG BASE
TABLET;ORAL - 1GM;EQ 50MG BASE
TABLET;ORAL - 500MG;EQ 50MG BASE

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Also known as: 654671-78-0, Sitagliptin (phosphate), Mk-0431, Chembl393336, 494p4635i6, Mk0431

Molecular Formula

C₁₆H₁₈F₆N₅O₅P

Molecular Weight

505.31 g/mol

InChI Key

IQFYVLUXQXSJJN-SBSPUUFOSA-N

FDA UNII

494P4635I6

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

Sitagliptin Phosphate

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

2.1.2 InChI

InChI=1S/C16H15F6N5O.H3O4P/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)/t9-;/m1./s1

2.1.3 InChI Key

IQFYVLUXQXSJJN-SBSPUUFOSA-N

2.1.4 Canonical SMILES

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

2.2 Other Identifiers

2.2.1 UNII

494P4635I6

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 Anhydrous

17. Sitagliptin Phosphate Monohydrate

2.3.2 Depositor-Supplied Synonyms

1. 654671-78-0

2. Sitagliptin (phosphate)

3. Mk-0431

4. Chembl393336

5. 494p4635i6

6. Mk0431

7. (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 Phosphate Salt

8. (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

9. (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

10. 1-butanone, 3-amino-1-[5,6-dihydro-3-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyrazin-7(8h)-yl]-4-(2,4,5-trifluorophenyl)-, (3r)-, Phosphate (1:1)

11. Sitagliptin Monophosphate

12. Sitagliptin Phosphate Anhydrous

13. (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)-1-butanone; Phosphoric Acid

14. Mk 0431

15. Sr-05000001748

16. Unii-494p4635i6

17. (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 Phosphate Salt

18. Mk 431

19. Mk-0431 Phosphate

20. Schembl877069

21. Dtxsid10215789

22. Hy-13749a

23. Mfcd09952339

24. Akos015896098

25. Sitagliptin Phosphate [who-dd]

26. Ks-1214

27. 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 Phosphate

28. Sitagliptin Monophosphate Anhydrous [mi]

29. 671s780

30. A835125

31. Sr-05000001748-2

32. Q27259224

33. Sitagliptin Phosphate Anhydrous Component Of Janumet

34. (3r)-3-amino-1-[5,6-dihydro-3-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyrazin-7(8h)-yl]-4-(2,4,5-trifluorophenyl)-1-butanone Phosphate

35. (3r)-3-azanyl-1-[3-(trifluoromethyl)-6,8-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-[2,4,5-tris(fluoranyl)phenyl]butan-1-one; Phosphoric Acid

36. 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)

37. 1269630-53-6

38. 7-((3r)-3-amino-4-(2,4,5-trifluorophenyl)butanoyl)-3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4-triazolo(4,3-a)pyrazinemonophosphate

39. 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

2.4 Create Date

2006-04-29

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₁₈F₆N₅O₅P
Molecular Weight	505.31 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	14
Rotatable Bond Count	4
Exact Mass	505.09497466 g/mol
Monoisotopic Mass	505.09497466 g/mol
Topological Polar Surface Area	155 Å²
Heavy Atom Count	33
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	2

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Januvia
PubMed Health	Sitagliptin (By mouth)
Drug Classes	Antidiabetic
Drug Label	JANUVIA Tablets contain sitagliptin phosphate, an orally-active inhibitor of the dipeptidyl peptidase-4 (DPP-4) enzyme. Sitagliptin phosphate monohydrate is described chemically as 7-[(3R)-3-amino-1-oxo-4-(2,4,5-trifluorophenyl)butyl]-5,6,7,8-tetrahy...
Active Ingredient	Sitagliptin phosphate
Dosage Form	Tablet
Route	Oral
Strength	eq 100mg base; eq 50mg base; eq 25mg base
Market Status	Prescription
Company	Merck Sharp Dohme

2 of 4
Drug Name	Sitagliptin phosphate
Active Ingredient	Sitagliptin phosphate
Dosage Form	Tablet
Route	oral; Oral
Strength	eq 100mg base; 25mg; eq 50mg base; 100mg; 50mg; eq 25mg base
Market Status	Tentative Approval
Company	Mylan Pharms; Apotex; Sandoz; Sun Pharma Global; Watson Labs

3 of 4
Drug Name	Januvia
PubMed Health	Sitagliptin (By mouth)
Drug Classes	Antidiabetic
Drug Label	JANUVIA Tablets contain sitagliptin phosphate, an orally-active inhibitor of the dipeptidyl peptidase-4 (DPP-4) enzyme. Sitagliptin phosphate monohydrate is described chemically as 7-[(3R)-3-amino-1-oxo-4-(2,4,5-trifluorophenyl)butyl]-5,6,7,8-tetrahy...
Active Ingredient	Sitagliptin phosphate
Dosage Form	Tablet
Route	Oral
Strength	eq 100mg base; eq 50mg base; eq 25mg base
Market Status	Prescription
Company	Merck Sharp Dohme

4 of 4
Drug Name	Sitagliptin phosphate
Active Ingredient	Sitagliptin phosphate
Dosage Form	Tablet
Route	oral; Oral
Strength	eq 100mg base; 25mg; eq 50mg base; 100mg; 50mg; eq 25mg base
Market Status	Tentative Approval
Company	Mylan Pharms; Apotex; Sandoz; Sun Pharma Global; Watson Labs

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

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.)

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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