trametinib   Click here for help

GtoPdb Ligand ID: 6495

Synonyms: GSK1120212 | GSK1120212B | GSK212 | JTP 74057 | Mekinist® | trametinib dimethyl sulfoxide
Approved drug PDB Ligand
trametinib is an approved drug (FDA (2013), EMA (2014))
Compound class: Synthetic organic
Comment: Trametinib is a Type-3 kinase inhibitor. Marketed formulations contain trametinib dimethyl sulfoxide (PubChem CID 50992434).
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: trametinib

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 6
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 106.61
Molecular weight 615.08
XLogP 6.37
No. Lipinski's rules broken 1
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 CC(=O)Nc1cccc(c1)n1c(=O)n(C2CC2)c(=O)c2c1c(C)c(=O)n(c2Nc1ccc(cc1F)I)C
Isomeric SMILES CC(=O)Nc1cccc(c1)n1c(=O)n(C2CC2)c(=O)c2c1c(C)c(=O)n(c2Nc1ccc(cc1F)I)C
InChI InChI=1S/C26H23FIN5O4/c1-13-22-21(23(31(3)24(13)35)30-20-10-7-15(28)11-19(20)27)25(36)33(17-8-9-17)26(37)32(22)18-6-4-5-16(12-18)29-14(2)34/h4-7,10-12,17,30H,8-9H2,1-3H3,(H,29,34)
InChI Key LIRYPHYGHXZJBZ-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2013), EMA (2014))
IUPAC Name Click here for help
N-[3-[3-cyclopropyl-5-[(2-fluoro-4-iodophenyl)amino]-6,8-dimethyl-2,4,7-trioxopyrido[3,4-e]pyrimidin-1-yl]phenyl]acetamide
International Nonproprietary Names Click here for help
INN number INN
9421 trametinib
Synonyms Click here for help
GSK1120212 | GSK1120212B | GSK212 | JTP 74057 | Mekinist® | trametinib dimethyl sulfoxide
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9653120
Reactome Reaction Reactome logo R-HSA-9657599
Other databases
CAS Registry No. 871700-17-3 (source: SciFinder)
ChEMBL Ligand CHEMBL2103875
DrugBank Ligand DB08911
DrugCentral Ligand 4802
GtoPdb PubChem SID 178103109
PubChem CID 11707110
RCSB PDB Ligand QOM
Search Google for chemical match using the InChIKey LIRYPHYGHXZJBZ-UHFFFAOYSA-N
Search Google for chemicals with the same backbone LIRYPHYGHXZJBZ
Search PubMed clinical trials trametinib
Search PubMed titles trametinib
Search PubMed titles/abstracts trametinib
UniChem Compound Search for chemical match using the InChIKey LIRYPHYGHXZJBZ-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey LIRYPHYGHXZJBZ-UHFFFAOYSA-N
Wikipedia Trametinib