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Synopsis

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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 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 Formula	C₂₆H₂₅F₉N₂O₄
Molecular Weight	600.5 g/mol
XLogP3	7
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	13
Rotatable Bond Count	7
Exact Mass	600.16706074 g/mol
Monoisotopic Mass	600.16706074 g/mol
Topological Polar Surface Area	59.1 Å²
Heavy Atom Count	41
Formal Charge	0
Complexity	889
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 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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