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Chemistry

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Also known as: 254750-02-2, Idn-6556, Pf-03491390, Pf 03491390, (s)-3-((s)-2-(2-(2-tert-butylphenylamino)-2-oxoacetamido)propanamido)-4-oxo-5-(2,3,5,6-tetrafluorophenoxy)pentanoic acid, Idn 6556
Molecular Formula
C26H27F4N3O7
Molecular Weight
569.5  g/mol
InChI Key
SCVHJVCATBPIHN-SJCJKPOMSA-N
FDA UNII
P0GMS9N47Q

Emricasan
Emricasan is the first caspase inhibitor tested in human which has received orphan drug status by FDA. It is developed by Pfizer and made in such a way that it protects liver cells from excessive apoptosis.
1 2D Structure

Emricasan

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(3S)-3-[[(2S)-2-[[2-(2-tert-butylanilino)-2-oxoacetyl]amino]propanoyl]amino]-4-oxo-5-(2,3,5,6-tetrafluorophenoxy)pentanoic acid
2.1.2 InChI
InChI=1S/C26H27F4N3O7/c1-12(31-24(38)25(39)32-16-8-6-5-7-13(16)26(2,3)4)23(37)33-17(10-19(35)36)18(34)11-40-22-20(29)14(27)9-15(28)21(22)30/h5-9,12,17H,10-11H2,1-4H3,(H,31,38)(H,32,39)(H,33,37)(H,35,36)/t12-,17-/m0/s1
2.1.3 InChI Key
SCVHJVCATBPIHN-SJCJKPOMSA-N
2.1.4 Canonical SMILES
CC(C(=O)NC(CC(=O)O)C(=O)COC1=C(C(=CC(=C1F)F)F)F)NC(=O)C(=O)NC2=CC=CC=C2C(C)(C)C
2.1.5 Isomeric SMILES
C[C@@H](C(=O)N[C@@H](CC(=O)O)C(=O)COC1=C(C(=CC(=C1F)F)F)F)NC(=O)C(=O)NC2=CC=CC=C2C(C)(C)C
2.2 Other Identifiers
2.2.1 UNII
P0GMS9N47Q
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 3-(2-(2-tert-butylphenylaminooxalyl)aminopropionylamino)-4-oxo-5-(2,3,5,6-tetrafluorophenoxy)pentanoic Acid

2. Idn 6556

3. Idn-6556

4. Idn6556

5. Pf 03491390

6. Pf-03491390

7. Pf03491390

2.3.2 Depositor-Supplied Synonyms

1. 254750-02-2

2. Idn-6556

3. Pf-03491390

4. Pf 03491390

5. (s)-3-((s)-2-(2-(2-tert-butylphenylamino)-2-oxoacetamido)propanamido)-4-oxo-5-(2,3,5,6-tetrafluorophenoxy)pentanoic Acid

6. Idn 6556

7. (s)-3-((s)-2-(2-((2-(tert-butyl)phenyl)amino)-2-oxoacetamido)propanamido)-4-oxo-5-(2,3,5,6-tetrafluorophenoxy)pentanoic Acid

8. Vay785

9. Vay-785

10. P0gms9n47q

11. (3s)-3-[[(2s)-2-[[2-(2-tert-butylanilino)-2-oxoacetyl]amino]propanoyl]amino]-4-oxo-5-(2,3,5,6-tetrafluorophenoxy)pentanoic Acid

12. L-alaninamide, N-(2-(1,1-dimethylethyl)phenyl)-2-oxoglycyl-n-((1s)-1-(carboxymethyl)-2-oxo-3-(2,3,5,6-tetrafluorophenoxy)propyl)-

13. Emricasan [usan]

14. Emricasan [usan:inn]

15. Unii-p0gms9n47q

16. C26h27f4n3o7

17. Emricasan [inn]

18. Emricasan(idn6556)

19. Emricasan (usan/inn)

20. Emricasan [who-dd]

21. Chembl197672

22. Gtpl6508

23. Schembl3288801

24. Dtxsid10180160

25. Amy36447

26. Bcp07463

27. Ex-a1659

28. Bdbm50461533

29. S7775

30. Zinc14191207

31. Akos016009462

32. Ccg-270089

33. Cs-0599

34. Db05408

35. Ncgc00346477-01

36. Ac-31507

37. As-75073

38. Hy-10396

39. Pf03491390

40. Emricasan(idn6556,pf03491390)

41. J3.566.323a

42. D10004

43. Emricasan (idn-6556, Pf-03491390)

44. A857136

45. Q27077178

46. (3s)-3-((2s)-2-((n-(2-tert-butyl)phenyl)carbamoyl)carbonylamino) Propanoylamino)-4-oxo-5-(2,3,5,6-tetrafluorophenoxy)pentanoic Acid

47. (3s)-3-(n2-((2-tert-butylphenyl)oxamoyl)-l-alaninamido)-4-oxo-5-(2,3,5,6- Tetrafluorophenoxy)pentanoic Acid

48. (3s)-3-(n2-((2-tert-butylphenyl)oxamoyl)-l-alaninamido)-4-oxo-5-(2,3,5,6-tetrafluorophenoxy)pentanoic Acid

49. (3s)-3-[(2s)-2-{[(2-tert-butylphenyl)carbamoyl]formamido}propanamido]-4-oxo-5-(2,3,5,6-tetrafluorophenoxy)pentanoic Acid

50. (3s)-3-[[(2s)-2-[[2-(2-tert-butylanilino)-2-oxo-acetyl]amino]propanoyl]amino]-4-oxo-5-(2,3,5,6-tetrafluorophenoxy)pentanoic Acid

51. (3s)-3-[[(2s)-2-[[2-[(2-tert-butylphenyl)amino]-2-oxoacetyl]amino]propanoyl]amino]-4-oxo-5-(2,3,5,6-tetrafluorophenoxy)pentanoic Acid

52. (s)-3-((s)-2-(2-((2-(tert-butyl)phenyl)amino)-2-oxoacetamido)propanamido)-4-oxo-5-(2,3,5,6-tetrafluorophenoxy)pentanoicacid

2.4 Create Date
2007-02-05
3 Chemical and Physical Properties
Molecular Weight 569.5 g/mol
Molecular Formula C26H27F4N3O7
XLogP33.6
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count11
Rotatable Bond Count11
Exact Mass569.17851286 g/mol
Monoisotopic Mass569.17851286 g/mol
Topological Polar Surface Area151 Ų
Heavy Atom Count40
Formal Charge0
Complexity934
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Investigated for use/treatment in hepatitis (viral, C), liver disease, and transplantation (organ or tissue).


Treatment of non-alcoholic steatohepatitis (NASH)


5 Pharmacology and Biochemistry
5.1 Mechanism of Action

IDN-6556 significantly improves markers of liver damage in patients infected with the Hepatitis C virus (HCV), an infection that affects up to 170m patients worldwide. IDN-6556 represents a new class of drugs that protect the liver from inflammation and cellular damage induced by viral infections and other causes. Various studies have also shown that it significantly lowers aminotransferase activity in HCV patients and appeared to be well tolerated.


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