Torcetrapib
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MedKoo CAT#: 319507

CAS#: 262352-17-0

Description: Torcetrapib, also known as CP-529,414 was a drug being developed to treat hypercholesterolemia (elevated cholesterol levels) and prevent cardiovascular disease. Its development was halted in 2006 when phase III studies showed excessive all-cause mortality in the treatment group receiving a combination of atorvastatin (Lipitor) and torcetrapib. Torcetrapib acts (as a CETP inhibitor) by inhibiting cholesterylester transfer protein (CETP), which normally transfers cholesterol from HDL cholesterol to very low density or low density lipoproteins (VLDL or LDL). Inhibition of this process results in higher HDL levels and reduces LDL levels.


Chemical Structure

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Torcetrapib
CAS# 262352-17-0

Theoretical Analysis

MedKoo Cat#: 319507
Name: Torcetrapib
CAS#: 262352-17-0
Chemical Formula: C26H25F9N2O4
Exact Mass: 600.16706
Molecular Weight: 600.48163
Elemental Analysis: C, 52.01; H, 4.20; F, 28.47; N, 4.67; O, 10.66

Price and Availability

Size Price Availability Quantity
10.0mg USD 250.0 2 Weeks
20.0mg USD 450.0 2 Weeks
50.0mg USD 1025.0 2 Weeks
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Synonym: CP-529414; CP529414; CP 529414; CP-529,414; CP529,414; CP 529,414; Torcetrapib.

IUPAC/Chemical Name: ethyl (2R,4S)-4-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-2-ethyl-6-(trifluoromethyl)-3,4-dihydro-2H-quinoline-1-carboxylate

InChi Key: CMSGWTNRGKRWGS-NQIIRXRSSA-N

InChi Code: 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

SMILES Code: O=C(N1[C@H](CC)C[C@H](N(CC2=CC(C(F)(F)F)=CC(C(F)(F)F)=C2)C(OC)=O)C3=C1C=CC(C(F)(F)F)=C3)OCC

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 600.48163 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Liu Y, Salituro GM, Lee KJ, Bak A, Leung DH. Modulating Drug Release and Enhancing the Oral Bioavailability of Torcetrapib with Solid Lipid Dispersion Formulations. AAPS PharmSciTech. 2015 Feb 18. [Epub ahead of print] PubMed PMID: 25690735.

2: McEvoy CL, Trevaskis NL, Edwards GA, Perlman ME, Ambler CM, Mack MC, Brockhurst B, Porter CJ. In vitro-in vivo evaluation of lipid based formulations of the CETP inhibitors CP-529,414 (torcetrapib) and CP-532,623. Eur J Pharm Biopharm. 2014 Nov;88(3):973-85. doi: 10.1016/j.ejpb.2014.08.006. Epub 2014 Aug 23. PubMed PMID: 25152213.

3: Briand F, Prunet-Marcassus B, Thieblemont Q, Costard C, Muzotte E, Sordello S, Sulpice T. Raising HDL with CETP inhibitor torcetrapib improves glucose homeostasis in dyslipidemic and insulin resistant hamsters. Atherosclerosis. 2014 Apr;233(2):359-62. doi: 10.1016/j.atherosclerosis.2014.01.028. Epub 2014 Jan 23. PubMed PMID: 24530763.

4: Kalgutkar AS, Frederick KS, Hatch HL, Ambler CM, Perry DA, Garigipati RS, Chang GC, Lefker BA, Clark RW, Morehouse LA, Francone O, Hu X. Identification of a novel, non-tetrahydroquinoline variant of the cholesteryl ester transfer protein (CETP) inhibitor torcetrapib, with improved aqueous solubility. Xenobiotica. 2014 Jul;44(7):591-605. doi: 10.3109/00498254.2013.874611. Epub 2013 Dec 31. PubMed PMID: 24380613.

5: Fan S, Geng Q, Pan Z, Li X, Tie L, Pan Y, Li X. Clarifying off-target effects for torcetrapib using network pharmacology and reverse docking approach. BMC Syst Biol. 2012 Dec 10;6:152. doi: 10.1186/1752-0509-6-152. PubMed PMID: 23228038; PubMed Central PMCID: PMC3547811.

6: Verma N, Figueredo VM. HDL cholesterol: all hope is not lost after the torcetrapib setback--emerging therapeutic strategies on the horizon. Am J Ther. 2014 May-Jun;21(3):222-32. doi: 10.1097/MJT.0b013e318249a1b5. Review. PubMed PMID: 22967983.

7: Barter PJ, Rye KA, Beltangady MS, Ports WC, Duggan WT, Boekholdt SM, DeMicco DA, Kastelein JJ, Shear CL. Relationship between atorvastatin dose and the harm caused by torcetrapib. J Lipid Res. 2012 Nov;53(11):2436-42. doi: 10.1194/jlr.P026328. Epub 2012 Sep 2. PubMed PMID: 22941786; PubMed Central PMCID: PMC3466012.

8: Knop FK. Letter by Knop regarding article, "Effect of torcetrapib on glucose, insulin, and hemoglobin A1c in subjects in the investigation of lipid level management to understand its impact in atherosclerotic events (ILLUMINATE) trial". Circulation. 2012 Mar 6;125(9):e428. doi: 10.1161/CIRCULATIONAHA.111.060152. PubMed PMID: 22392871.

9: McGuire DK, Aguilar D. Letter by McGuire and Aguilar regarding article, "Effect of torcetrapib on glucose, insulin, and hemoglobin A1c in subjects in the investigation of lipid level management to understand its impact in atherosclerotic events (ILLUMINATE) trial". Circulation. 2012 Mar 6;125(9):e427. doi: 10.1161/CIRCULATIONAHA.111.057844. PubMed PMID: 22392870.

10: Johns DG, Duffy J, Fisher T, Hubbard BK, Forrest MJ. On- and off-target pharmacology of torcetrapib: current understanding and implications for the structure activity relationships (SAR), discovery and development of cholesteryl ester-transfer protein (CETP) inhibitors. Drugs. 2012 Mar 5;72(4):491-507. doi: 10.2165/11599310-000000000-00000. Review. PubMed PMID: 22356288.

11: Briand F, Thieblemont Q, André A, Ouguerram K, Sulpice T. CETP inhibitor torcetrapib promotes reverse cholesterol transport in obese insulin-resistant CETP-ApoB100 transgenic mice. Clin Transl Sci. 2011 Dec;4(6):414-20. doi: 10.1111/j.1752-8062.2011.00344.x. Epub 2011 Dec 7. PubMed PMID: 22212222.

12: Simic B, Hermann M, Shaw SG, Bigler L, Stalder U, Dörries C, Besler C, Lüscher TF, Ruschitzka F. Torcetrapib impairs endothelial function in hypertension. Eur Heart J. 2012 Jul;33(13):1615-24. doi: 10.1093/eurheartj/ehr348. Epub 2011 Sep 14. PubMed PMID: 21920972.

13: Barter PJ, Rye KA, Tardif JC, Waters DD, Boekholdt SM, Breazna A, Kastelein JJ. Effect of torcetrapib on glucose, insulin, and hemoglobin A1c in subjects in the Investigation of Lipid Level Management to Understand its Impact in Atherosclerotic Events (ILLUMINATE) trial. Circulation. 2011 Aug 2;124(5):555-62. doi: 10.1161/CIRCULATIONAHA.111.018259. Epub 2011 Jul 18. PubMed PMID: 21804130.

14: Osório J. Off-target effects of torcetrapib. Nat Rev Cardiol. 2010 Oct;7(10):541. doi: 10.1038/nrcardio.2010.129. PubMed PMID: 21080555.

15: Meyer O, Jenni R, Greiter-Wilke A, Breidenbach A, Holzgrefe HH. Comparison of telemetry and high-definition oscillometry for blood pressure measurements in conscious dogs: effects of torcetrapib. J Am Assoc Lab Anim Sci. 2010 Jul;49(4):464-71. PubMed PMID: 20819394; PubMed Central PMCID: PMC2919188.

16: Clerc RG, Stauffer A, Weibel F, Hainaut E, Perez A, Hoflack JC, Bénardeau A, Pflieger P, Garriz JM, Funder JW, Capponi AM, Niesor EJ. Mechanisms underlying off-target effects of the cholesteryl ester transfer protein inhibitor torcetrapib involve L-type calcium channels. J Hypertens. 2010 Aug;28(8):1676-86. doi: 10.1097/HJH.0b013e32833b1f8e. PubMed PMID: 20498617.

17: von Eckardstein A. Implications of torcetrapib failure for the future of HDL therapy: is HDL-cholesterol the right target? Expert Rev Cardiovasc Ther. 2010 Mar;8(3):345-58. doi: 10.1586/erc.10.6. Review. PubMed PMID: 20222814.

18: Connelly MA, Parry TJ, Giardino EC, Huang Z, Cheung WM, Chen C, Cools F, Van der Linde H, Gallacher DJ, Kuo GH, Sarich TC, Demarest KT, Damiano BP. Torcetrapib produces endothelial dysfunction independent of cholesteryl ester transfer protein inhibition. J Cardiovasc Pharmacol. 2010 May;55(5):459-68. doi: 10.1097/FJC.0b013e3181cf03cb. PubMed PMID: 20051879.

19: Funder JW. Aldosterone, sodium, and hypertension: lessons from torcetrapib? Hypertension. 2010 Feb;55(2):221-3. doi: 10.1161/HYPERTENSIONAHA.109.146936. Epub 2010 Jan 4. Review. PubMed PMID: 20048191.

20: Polakowski JS, King AJ, Campbell TJ, Nelson RA, Preusser LC, Kempf-Grote AJ, Marsh KC, Gintant GA, Cox BF, Mittelstadt SW. Cardiovascular effects of torcetrapib in conscious and pentobarbital-anesthetized dogs. J Cardiovasc Pharmacol. 2009 Dec;54(6):543-51. doi: 10.1097/FJC.0b013e3181bfb158. PubMed PMID: 19770671.