lomitapide   Click here for help

GtoPdb Ligand ID: 7439

Synonyms: AEGR-733 | BMS-201038 | Juxtapid® | Lojuxta®
Approved drug
lomitapide is an approved drug (FDA (2012), EMA (2013))
Compound class: Synthetic organic
Comment: Lomitapide is a lipid-lowering agent for the treatment of familial hypercholesterolemia.
Click here for help

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: lomitapide

2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 14
Topological polar surface area 61.44
Molecular weight 693.28
XLogP 10.09
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

✖
Canonical SMILES O=C(c1ccccc1c1ccc(cc1)C(F)(F)F)NC1CCN(CC1)CCCCC1(C(=O)NCC(F)(F)F)c2ccccc2c2c1cccc2
Isomeric SMILES O=C(c1ccccc1c1ccc(cc1)C(F)(F)F)NC1CCN(CC1)CCCCC1(C(=O)NCC(F)(F)F)c2ccccc2c2c1cccc2
InChI InChI=1S/C39H37F6N3O2/c40-38(41,42)25-46-36(50)37(33-13-5-3-10-30(33)31-11-4-6-14-34(31)37)21-7-8-22-48-23-19-28(20-24-48)47-35(49)32-12-2-1-9-29(32)26-15-17-27(18-16-26)39(43,44)45/h1-6,9-18,28H,7-8,19-25H2,(H,46,50)(H,47,49)
InChI Key MBBCVAKAJPKAKM-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2012), EMA (2013))
IUPAC Name Click here for help
N-(2,2,2-trifluoroethyl)-9-[4-[4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]piperidin-1-yl]butyl]fluorene-9-carboxamide
International Nonproprietary Names Click here for help
INN number INN
9120 lomitapide
Synonyms Click here for help
AEGR-733 | BMS-201038 | Juxtapid® | Lojuxta®
Database Links Click here for help
CAS Registry No. 82431-12-5
ChEBI CHEBI:72297
ChEMBL Ligand CHEMBL354541
DrugBank Ligand DB08827
DrugCentral Ligand 4721
GtoPdb PubChem SID 178104011
PubChem CID 9853053
Search Google for chemical match using the InChIKey MBBCVAKAJPKAKM-UHFFFAOYSA-N
Search Google for chemicals with the same backbone MBBCVAKAJPKAKM
Search PubMed clinical trials lomitapide
Search PubMed titles lomitapide
Search PubMed titles/abstracts lomitapide
UniChem Compound Search for chemical match using the InChIKey MBBCVAKAJPKAKM-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey MBBCVAKAJPKAKM-UHFFFAOYSA-N
Wikipedia Lomitapide