Details of the Drug

General Information of Drug (ID: DMDHYM7)

Drug Name
Torcetrapib
Synonyms
Torcetrapib [USAN]; CP 529414; CP-529414; CP-529,414; Torcetrapib (USAN/INN); Ethyl (2R,4S)-4-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-2-ethyl-6-(trifluoromethyl)-3,4-dihydro-2H-quinoline-1-carboxylate; Ethyl (2R,4S)-4-{[3,5-bis(trifluoromethyl)benzyl](methoxycarbonyl)amino}-2-ethyl-6-(trifluoromethyl)-3,4-dihydroquinoline-1(2H)-carboxylate; Ethyl (2R,4S)-4-((3,5-bis(trifluoromethyl)benzyl)(methoxycarbonyl)amino)-2-ethyl-6-(trifluoromethyl)-3,4-dihydroquinoline-1(2H)-carboxylate; (2R,4S)-4-((3,5-Bis-trifluoromethylbenzyl)methoxycarbonylamino)-2-ethyl-6-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester
Indication
Disease Entry ICD 11 Status REF
Hyperlipidaemia 5C80 Discontinued in Phase 2 [1]
Peripheral vascular disease BD4Z Discontinued in Phase 2 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 3 Molecular Weight (mw) 600.5
Logarithm of the Partition Coefficient (xlogp) 7
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 13
Chemical Identifiers
Formula
C26H25F9N2O4
IUPAC Name
ethyl (2R,4S)-4-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-2-ethyl-6-(trifluoromethyl)-3,4-dihydro-2H-quinoline-1-carboxylate
Canonical 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
InChI
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
InChIKey
CMSGWTNRGKRWGS-NQIIRXRSSA-N
Cross-matching ID
PubChem CID
159325
ChEBI ID
CHEMBL479527
CAS Number
262352-17-0
UNII
4N4457MV2U
DrugBank ID
DB06281
TTD ID
D07GDN
INTEDE ID
DR1786
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Cholesteryl ester transfer protein (CETP) TTFQAYR CETP_HUMAN Inhibitor [2]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
1-acyl-sn-glycerol-3-phosphate acyltransferase gamma (AGPAT3) OTAUR5TG PLCC_HUMAN Gene/Protein Processing [4]
17S U2 SnRNP complex component HTATSF1 (HTATSF1) OTLQ1ZLS HTSF1_HUMAN Gene/Protein Processing [4]
26S proteasome non-ATPase regulatory subunit 7 (PSMD7) OT7PZZ4K PSMD7_HUMAN Gene/Protein Processing [4]
3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 2 (HSD3B2) OT02MSKN 3BHS2_HUMAN Gene/Protein Processing [5]
3',5'-cyclic-AMP phosphodiesterase 4B (PDE4B) OTOA8WU2 PDE4B_HUMAN Gene/Protein Processing [4]
3',5'-cyclic-AMP phosphodiesterase 4D (PDE4D) OT1RWFV0 PDE4D_HUMAN Gene/Protein Processing [4]
ADP-ribosylation factor-like protein 5B (ARL5B) OTYYBIDG ARL5B_HUMAN Gene/Protein Processing [4]
AF4/FMR2 family member 2 (AFF2) OTMF1PZW AFF2_HUMAN Gene/Protein Processing [4]
Akirin-1 (AKIRIN1) OTINWTT9 AKIR1_HUMAN Gene/Protein Processing [4]
Amyloid beta precursor protein binding family B member 2 (APBB2) OT1VD51B APBB2_HUMAN Gene/Protein Processing [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Hyperlipidaemia
ICD Disease Classification 5C80
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Cholesteryl ester transfer protein (CETP) DTT CETP 8.86E-01 -0.1 -0.6
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 5.08E-01 -8.08E-02 -5.30E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800015157)
2 Safety and tolerability of dalcetrapib. Am J Cardiol. 2009 Jul 1;104(1):82-91.
3 Pharmacokinetics, metabolism, and excretion of torcetrapib, a cholesteryl ester transfer protein inhibitor, in humans. Drug Metab Dispos. 2008 Nov;36(11):2185-98.
4 Clarifying off-target effects for torcetrapib using network pharmacology and reverse docking approach. BMC Syst Biol. 2012 Dec 10;6:152.
5 Steroid profiling in H295R cells to identify chemicals potentially disrupting the production of adrenal steroids. Toxicology. 2017 Apr 15;381:51-63.