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
  • 875446-37-0 checkY
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL1800807 ☒N
ChemSpider
  • 9731205 checkY
KEGG
  • D08855 checkY
PubChem CID
  • 11556427
UNII
  • P7T269PR6S checkY
CompTox Dashboard (EPA)
  • DTXSID90236452 Edit this at Wikidata
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
  • 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).
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Infobox references
Chemical compound

Anacetrapib is a CETP inhibitor which was being developed to treat elevated cholesterol levels in an effort to 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:[citation needed]

  • 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. 
  • v
  • t
  • e
GI tract
Cholesterol absorption inhibitors, NPC1L1
Bile acid sequestrants/resins (LDL)
Liver
Statins (HMG-CoA reductase, LDL)
Niacin and derivatives (HDL and LDL)
MTTP inhibitors (VLDL)
ATP citrate lyase inhibitors (LDL)
Thyromimetics (VLDL)
Blood vessels
PPAR agonists (LDL)
Fibrates
Others
CETP inhibitors (HDL)
PCSK9 inhibitors (LDL)
ANGPTL3 inhibitors (LDL/HDL)
CombinationsOther