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Danegaptide

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2 Drugs in Development

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Also known as: 943134-39-2, Gap-134, (2s,4r)-1-(2-aminoacetyl)-4-benzamidopyrrolidine-2-carboxylic acid, Danegaptida, Zp1609, Pa0y7735at

Molecular Formula

C₁₄H₁₇N₃O₄

Molecular Weight

291.30 g/mol

InChI Key

BIZKIHUJGMSVFD-MNOVXSKESA-N

FDA UNII

PA0Y7735AT

an antiarrhythmia agent with cytoprotective activity

1 2D Structure

Danegaptide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S,4R)-1-(2-aminoacetyl)-4-benzamidopyrrolidine-2-carboxylic acid

2.1.2 InChI

InChI=1S/C14H17N3O4/c15-7-12(18)17-8-10(6-11(17)14(20)21)16-13(19)9-4-2-1-3-5-9/h1-5,10-11H,6-8,15H2,(H,16,19)(H,20,21)/t10-,11+/m1/s1

2.1.3 InChI Key

BIZKIHUJGMSVFD-MNOVXSKESA-N

2.2 Other Identifiers

2.2.1 UNII

PA0Y7735AT

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Zp1609

2.3.2 Depositor-Supplied Synonyms

1. 943134-39-2

2. Gap-134

3. (2s,4r)-1-(2-aminoacetyl)-4-benzamidopyrrolidine-2-carboxylic Acid

4. Danegaptida

5. Zp1609

6. Pa0y7735at

7. Zp-1609

8. Glycyl-(4r)-4-(benzoylamino)-l-proline

9. L-proline, Glycyl-4-(benzoylamino)-, (4r)-

10. Dtxsid201026039

11. (2s,4r)-1-(aminoacetyl)-4-(benzoylamino)pyrrolidine-2-carboxylic Acid

12. Danegaptidum

13. [2s,4r]-1-(2-aminoacetyl)-4-benzamidopyrrolidine-2-carboxylic Acid

14. Refchem:919625

15. Dtxcid301510295

16. 943134-39-2 (free Base)

17. (2s,4r)-4-benzamido-1-glycylpyrrolidine-2-carboxylic Acid

18. Mfcd16619374

19. Danegaptide [usan]

20. Danegaptide [usan:inn]

21. Unii-pa0y7735at

22. (2s,4r)-1-(2-aminoacetyl)-4-benzamidopyrrolidine-2-carboxylicacid

23. Danegaptide [inn]

24. Danegaptide (usan/inn)

25. Danegaptide [who-dd]

26. Chembl560592

27. Schembl2399763

28. Bizkihujgmsvfd-mnovxskesa-n

29. Chebi:177853

30. Akos030527026

31. Cs-1100

32. Db11821

33. Hy-10913

34. Db-289821

35. Ns00072457

36. D09599

37. D95155

38. 134a392

39. Brd-k35589454-003-01-1

40. Q27286426

41. (2s,4r) 1-(2-amino-acetyl)-4-benzoylamino-pyrrolidine-2-carboxylic Acid

42. (2s,4r)-1-(2-azanylethanoyl)-4-benzamido-pyrrolidine-2-carboxylic Acid

43. (2s4r) 1-(2-amino-acetyl)-4-benzoylamino-pyrrolidine-2-carboxylic Acid

44. (2s4r)1-(2-amino-acetyl)-4-benzoylamino-pyrrolidine-2-carboxylic Acid

2.4 Create Date

2007-08-09

3 Chemical and Physical Properties

Molecular Formula	C₁₄H₁₇N₃O₄
Molecular Weight	291.30 g/mol
XLogP3	-2.7
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	4
Exact Mass	Da
Monoisotopic Mass	Da
Topological Polar Surface Area	113
Heavy Atom Count	21
Formal Charge	0
Complexity	420
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
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 Mechanism of Action

Danegaptide, a small modified dipeptide, is a selective second generation gap junction modifier with oral bioavailability. Danegaptide prevents postoperative atrial fibrillation (AF) and chronic AF in large animal models. In a canine model of acute sterile pericarditis, Danegaptide significantly reduced AF duration and overall AF burden. Danegaptide has a similar mechanism of action to its parent compound rotigaptide. Rotigaptide is a synthetic antiarrhythmic peptide (AAP) analogue which has been tested in vitro which shows prevention of prevents metabolic stress-induced atrial conduction velocity (CV) and rapidly reverts established atrial CV slowing. Rogitapeptide enhances gap junction conductance and coupling, increasing the amount of small molecules such as ions, metabolites and secondary messengers passing from one cell to another.

Drugs in Development