Structure via PubChem · Public domain (PubChem)
torcetrapib
Sign in to saveAlso known as (2R,4S)-4-((3,5-bis-trifluoromethylbenzyl)methoxycarbonylamino)-2-ethyl-6-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester
Torcetrapib (CP-529,414, Pfizer) 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.
Chemical data
- Formula
- C26H25F9N2O4
- Molecular weight
- 600.5 g/mol
- IUPAC name
- ethyl (2R,4S)-4-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-2-ethyl-6-(trifluoromethyl)-3,4-dihydro-2H-quinoline-1-carboxylate
- 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
- InChIKey
- CMSGWTNRGKRWGS-NQIIRXRSSA-N
- XLogP
- 7
- Polar surface area
- 59.1 Ų
- H-bond donors
- 0
- H-bond acceptors
- 13
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 3
- Molecule type
- Small molecule
- Indications
- familial hypercholesterolemia, Combined hyperlipidemia, coronary artery disease, Hypertriglyceridemia
via ChEMBL · EBI
Research
396 papers- Torcetrapib/atorvastatin combination therapy.Expert review of cardiovascular therapy · 2005
- Torcetrapib for animal and human pharmacokinetic studies: applicability of chiral and achiral methodologies.Bioanalysis · 2009
- The end of the road for CETP inhibitors after torcetrapib?Current opinion in cardiology · 2009
- The failure of torcetrapib: is there a case for independent preclinical and clinical testing?Expert opinion on pharmacotherapy · 2008
- JTT-705: is there still future for a CETP inhibitor after torcetrapib?Expert opinion on investigational drugs · 2008
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 600.167
Show 4 more facts
- chemical formula
- C₂₆H₂₅F₉N₂O₄
- 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
- 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
- Commons category
- Torcetrapib
Sources (2)
via Wikidata · CC0
~6 min read
Encyclopedic overview
10 sectionsContents
- Medical uses
- Mechanism
- Development
- Clinical trials
- Early termination of study
- Synthesis
- See also
- References
- Notes
- External links
{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 461752029 | ImageFile = Torcetrapib.svg | ImageSize = | PIN = Ethyl (2R,4S)-4-({[3,5-bis(trifluoromethyl)phenyl]methyl}(methoxycarbonyl)amino)-2-ethyl-6-(trifluoromethyl)-3,4-dihydroquinoline-1(2H)-carboxylate | OtherNames =
| Section1 =
Excerpted from Wikipedia’s “torcetrapib” article, available under the CC BY-SA 4.0 licence.
Gallery (2)
Available in 9 languages
via Wikidata sitelinks · CC0