Anacetrapib

Anacetrapib
Names
Preferred IUPAC name
(4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-3-{[4′-fluoro-2′-methoxy-5′-(propan-2-yl)-4-(trifluoromethyl)[1,1′-biphenyl]-2-yl]methyl}-4-methyl-1,3-oxazolidin-2-one
Other names
MK-0859
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
InChI
  • InChI=1S/C30H25F10NO3/c1-14(2)22-11-23(25(43-4)12-24(22)31)21-6-5-18(28(32,33)34)9-17(21)13-41-15(3)26(44-27(41)42)16-7-19(29(35,36)37)10-20(8-16)30(38,39)40/h5-12,14-15,26H,13H2,1-4H3/t15-,26-/m0/s1 checkY
    Key: MZZLGJHLQGUVPN-HAWMADMCSA-N checkY
  • InChI=1/C30H25F10NO3/c1-14(2)22-11-23(25(43-4)12-24(22)31)21-6-5-18(28(32,33)34)9-17(21)13-41-15(3)26(44-27(41)42)16-7-19(29(35,36)37)10-20(8-16)30(38,39)40/h5-12,14-15,26H,13H2,1-4H3/t15-,26-/m0/s1
    Key: MZZLGJHLQGUVPN-HAWMADMCBN
SMILES
  • O=C2O[C@H](c1cc(cc(c1)C(F)(F)F)C(F)(F)F)[C@@H](N2Cc4c(c3cc(c(F)cc3OC)C(C)C)ccc(c4)C(F)(F)F)C
Properties
Chemical formula
 C30H25F10NO3
Molar mass 637.51 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Anacetrapib is a CETP inhibitor which was being developed to treat elevated cholesterol levels in an effort prevent cardiovascular disease.[1] In 2017 its development was abandoned by Merck.[2]

Evidence

In 2017 REVEAL trial anacetrapib was shown to decrease the risk of repeat heart attacks in high-risk patients with previous acute coronary events.[3]

See also

Other CETP inhibitors:

  • Torcetrapib was developed by Pfizer until December 2006 but caused unacceptable increases in blood pressure and had net cardiovascular detriment.
  • Dalcetrapib was developed by Hoffmann–La Roche until May 2012. It did not raise blood pressure and did raise HDL, but it showed no clinically meaningful efficacy.
  • Evacetrapib was developed by Eli Lilly & Company until October 2015.

References

  1. ↑ Gutstein DE, Krishna R, Johns D, et al. (2012). "Anacetrapib, a Novel CETP Inhibitor: Pursuing a New Approach to Cardiovascular Risk Reduction". Clinical Pharmacology & Therapeutics. 91 (1): 109–122. doi:10.1038/clpt.2011.271. PMID 22130116. S2CID 36510986.
  2. ↑ "Merck says will not seek approval of cholesterol treatment". Reuters. 2017. Retrieved 18 October 2017.
  3. ↑ Filippatos, TD; Kei, A; Elisaf, MS (29 September 2017). "Anacetrapib, a New CETP Inhibitor: The New Tool for the Management of Dyslipidemias?". Diseases. 5 (4): 21. doi:10.3390/diseases5040021. PMC 5750532. PMID 28961179.

Further reading

  • WO 2007005572, Miller, Ross A. & Cote, Aaron S., "Process for synthesizing a CETP inhibitor", published 2007-01-11, assigned to Merck & Co. Inc. 
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