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evacetrapib

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evacetrapib

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Evacetrapib was a drug under development by Eli Lilly and Company (investigational name LY2484595) that inhibits cholesterylester transfer protein (CETP inhibitor). CETP collects triglycerides from very low-density lipoproteins (VLDL) or low-density lipoproteins (LDL) and exchanges them for cholesteryl esters from high-density lipoproteins (HDL), and vice versa, but primarily increasing high-density lipoprotein and lowering low-density lipoprotein. It is thought that modifying lipoprotein levels modifies the risk of cardiovascular disease. The first CETP inhibitor, torcetrapib, was unsuccessfu

Chemical data

Formula
C31H36F6N6O2
Molecular weight
638.6 g/mol
IUPAC name
4-[[(5S)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-7,9-dimethyl-2,3,4,5-tetrahydro-1-benzazepin-1-yl]methyl]cyclohexane-1-carboxylic acid
SMILES
CC1=CC(=C2C(=C1)[C@H](CCCN2CC3CCC(CC3)C(=O)O)N(CC4=CC(=CC(=C4)C(F)(F)F)C(F)(F)F)C5=NN(N=N5)C)C
InChIKey
IHIUGIVXARLYHP-UXNJHFGPSA-N
XLogP
7.7
Polar surface area
87.4 Ų
H-bond donors
1
H-bond acceptors
13
Formal charge
0

via PubChem

Drug data · ChEMBL

Max clinical phase
Phase 3
Molecule type
Small molecule
Indications
cardiovascular disease, Disorder of lipid metabolism, Hypercholesterolemia, hyperlipidemia

via ChEMBL · EBI

Wikidata facts

Subclass of
carboxylic acid
Mass
638.280394
Show 3 more facts
isomeric SMILES
OC(=O)C1CCC(CC1)CN2CCC[C@@H](C3=C2C(C)=CC(=C3)C)N(C=4N=NN(N4)C)CC5=CC(=CC(=C5)C(F)(F)F)C(F)(F)F
canonical SMILES
OC(=O)C1CCC(CC1)CN2CCCC(C3=C2C(C)=CC(=C3)C)N(C=4N=NN(N4)C)CC5=CC(=CC(=C5)C(F)(F)F)C(F)(F)F
chemical formula
C₃₁H₃₆F₆N₆O₂
Sources (1)

via Wikidata · CC0

~3 min read

Encyclopedic overview

3 sections
Contents
  • Trials
  • ACCELERATE
  • References

{{Chembox | Verifiedfields = changed | verifiedrevid = 461280529 | ImageFile = Evacetrapib.svg | ImageClass = skin-invert-image | ImageSize=150px | IUPACName=Trans-4-({(5S)-5-[{[3,5-bis(trifluoromethyl)phenyl]methyl}(2-methyl-2H-tetrazol-5- yl)amino]-7,9-dimethyl-2,3,4,5-tetrahydro-1H-benzazepin-1-yl}methyl) cyclohexanecarboxylic acid | OtherNames = LY2484595 |Section1= |Section2= |Section3= }}

Evacetrapib was a drug under development by Eli Lilly and Company (investigational name LY2484595) that inhibits cholesterylester transfer protein (CETP inhibitor). CETP collects triglycerides from very low-density lipoproteins (VLDL) or low-density lipoproteins (LDL) and exchanges them for cholesteryl esters from high-density lipoproteins (HDL), and vice versa, but primarily increasing high-density lipoprotein and lowering low-density lipoprotein. It is thought that modifying lipoprotein levels modifies the risk of cardiovascular disease. The first CETP inhibitor, torcetrapib, was unsuccessful because it increased levels of the hormone aldosterone and increased blood pressure, which led to excess cardiac events when it was studied. Evacetrapib does not have the same effect. When studied in a small clinical trial in people with elevated LDL and low HDL, significant improvements were noted in their lipid profile.

Excerpted from Wikipedia’s “evacetrapib” article, available under the CC BY-SA 4.0 licence.

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