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Chemistry

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Also known as: 262352-17-0, Cp-529414, Cp 529414, Cp-529,414, (2r,4s)-4-((3,5-bis-trifluoromethylbenzyl)methoxycarbonylamino)-2-ethyl-6-trifluoromethyl-3,4-dihydro-2h-quinoline-1-carboxylic acid ethyl ester, Chembl479527
Molecular Formula
C26H25F9N2O4
Molecular Weight
600.5  g/mol
InChI Key
CMSGWTNRGKRWGS-NQIIRXRSSA-N
FDA UNII
4N4457MV2U

Torcetrapib
Torcetrapib is a cholesteryl ester transfer protein (CETP) inhibitor that reduces the heterotypic transfer of cholesteryl ester from HDL to LDL and/or VLDL. Torcetrapib failed in phase III trials due to excess deaths.
1 2D Structure

Torcetrapib

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
ethyl (2R,4S)-4-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-2-ethyl-6-(trifluoromethyl)-3,4-dihydro-2H-quinoline-1-carboxylate
2.1.2 InChI
InChI=1S/C26H25F9N2O4/c1-4-18-12-21(19-11-15(24(27,28)29)6-7-20(19)37(18)23(39)41-5-2)36(22(38)40-3)13-14-8-16(25(30,31)32)10-17(9-14)26(33,34)35/h6-11,18,21H,4-5,12-13H2,1-3H3/t18-,21+/m1/s1
2.1.3 InChI Key
CMSGWTNRGKRWGS-NQIIRXRSSA-N
2.1.4 Canonical SMILES
CCC1CC(C2=C(N1C(=O)OCC)C=CC(=C2)C(F)(F)F)N(CC3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)C(=O)OC
2.1.5 Isomeric SMILES
CC[C@@H]1C[C@@H](C2=C(N1C(=O)OCC)C=CC(=C2)C(F)(F)F)N(CC3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)C(=O)OC
2.2 Other Identifiers
2.2.1 UNII
4N4457MV2U
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Cp 529,414

2. Cp 529414

3. Cp-529,414

4. Cp-529414

5. Cp529,414

6. Cp529414

2.3.2 Depositor-Supplied Synonyms

1. 262352-17-0

2. Cp-529414

3. Cp 529414

4. Cp-529,414

5. (2r,4s)-4-((3,5-bis-trifluoromethylbenzyl)methoxycarbonylamino)-2-ethyl-6-trifluoromethyl-3,4-dihydro-2h-quinoline-1-carboxylic Acid Ethyl Ester

6. Chembl479527

7. Ethyl (2r,4s)-4-((3,5-bis(trifluoromethyl)benzyl)(methoxycarbonyl)amino)-2-ethyl-6-(trifluoromethyl)-3,4-dihydroquinoline-1(2h)-carboxylate

8. Ethyl (2r,4s)-4-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-2-ethyl-6-(trifluoromethyl)-3,4-dihydro-2h-quinoline-1-carboxylate

9. Ethyl (2r,4s)-4-{[3,5-bis(trifluoromethyl)benzyl](methoxycarbonyl)amino}-2-ethyl-6-(trifluoromethyl)-3,4-dihydroquinoline-1(2h)-carboxylate

10. Chebi:49203

11. 4n4457mv2u

12. Torcetrapib [usan]

13. 1(2h)-quinolinecarboxylic Acid, 4-[[[3,5-bis(trifluoromethyl)phenyl]methyl](methoxycarbonyl)amino]-2-ethyl-3,4-dihydro-6-(trifluoromethyl)-, Ethyl Ester, (2r,4s)-

14. (2r,4s)-ethyl 4-((3,5-bis(trifluoromethyl)benzyl)(methoxycarbonyl)amino)-2-ethyl-6-(trifluoromethyl)-3,4-dihydroquinoline-1(2h)-carboxylate

15. (2r,4s)-rel-ethyl 4-((3,5-bis(trifluoromethyl)benzyl)(methoxycarbonyl)amino)-2-ethyl-6-(trifluoromethyl)-3,4-dihydroquinoline-1(2h)-carboxylate

16. 262350-59-4

17. Torcetrapib (usan/inn)

18. Torcetrapib [usan:inn]

19. Unii-4n4457mv2u

20. Torcetrapib [mi]

21. Torcetrapib [inn]

22. Torcetrapib [mart.]

23. Schembl49081

24. Torcetrapib [who-dd]

25. Mls006010664

26. Torcetrapib (cp-529414)

27. Torcetrapib, >=98% (hplc)

28. Dtxsid20180873

29. Ex-a081

30. Amy24146

31. Zinc8214714

32. Bdbm50312718

33. Mfcd09260777

34. S2792

35. Akos024458018

36. Ccg-270197

37. Cs-3497

38. Db06281

39. Ncgc00346703-01

40. Ncgc00346703-03

41. 1(2h)-quinolinecarboxylic Acid, 4-(((3,5-bis(trifluoromethyl)phenyl)methyl) (methoxycarbonyl)amino)-2-ethyl-3,4-dihydro-6-(trifluoromethyl)-, Ethyl Ester, (2r,4s)-

42. Ac-35371

43. As-16356

44. Ethyl (2r,4s)-4-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonyl-amino]-2-ethyl-6-(trifluoromethyl)-3,4-dihydro-2h-quinoline-1-carboxylate

45. Hy-12089

46. Smr004701649

47. D06195

48. A818334

49. Sr-01000944945

50. Q7825530

51. Sr-01000944945-1

52. W-202112

53. Brd-k55675242-001-03-0

54. (2r, 4s)-4-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-2-ethyl-6-trifluoromethyl-3,4-dihydro-2h-quinoline-1-carboxylic Acid Ethyl Ester

55. (2r,4s)-4-[[[3,5-bis(trifluoromethyl)phenyl]methyl](methoxycarbonyl)amino]-2-ethyl-6-(trifluoromethyl)-1,2,3,4-tetrahydroquinoline-1-carboxylic Acid Ethyl Ester

56. (2r,4s)-4-{[3,5-bis(trifluoromethyl)benzyl](methoxycarbonyl)amino}-2-ethyl-6-(trifluoromethyl)-3,4-dihydroquinoline-1(2h

57. 0rp

58. 1(2h)-quinolinecarboxylic Acid, 4-(((3,5-bis(trifluoromethyl)phenyl)methyl) (methoxycarbonyl)amino)-2-ethyl-3,4-dihydro-6-(trifluoromethyl)-, Ethyl Ester, (2r,4s)-

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 600.5 g/mol
Molecular Formula C26H25F9N2O4
XLogP37
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count13
Rotatable Bond Count7
Exact Mass600.16706074 g/mol
Monoisotopic Mass600.16706074 g/mol
Topological Polar Surface Area59.1 Ų
Heavy Atom Count41
Formal Charge0
Complexity889
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 peripheral vascular disease and hyperlipidemia.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Anticholesteremic Agents

Substances used to lower plasma cholesterol levels. (See all compounds classified as Anticholesteremic Agents.)


5.2 Mechanism of Action

Torcetrapib is an inhibitor of cholesteryl ester-transfer protein (CETP) that increases high-density lipoprotein (HDL) cholesterol levels. The drug increases HDL-cholesterol and apolipoprotein A-I levels and decreases LDL-cholesterol and apolipoprotein B levels. The effect is showed in monotherapy and when administered in combination with statins.


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