milategrast   Click here for help

GtoPdb Ligand ID: 10463

Synonyms: example 9 [US20050261291A1]
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Milategrast (example 9) is claimed in Esai Co.'s patent US20050261291A1 as the hydrochloride salt [1]. The chemical structures in this patent are claimed for their potential to treat inflammatory and autoimmune diseases that are associated with adhesion and infiltration of leukocytes (e.g. inflammatory bowel disease, rheumatoid arthritis, psoriasis, multiple sclerosis, asthma and atopic dermatitis). We show just the parent molecule. In INN proposed list 121 (August 2019) milategrast is described as a non-steroidal anti-inflammatory agent. Review of Esai's epipeline document and other online reports suggests that this might the agent with development code E6007. The association between example 9, E6007 and milategrast is speculative, provided in good faith, and will only be confirmed by open publication of name-to-structure by Esai.
2D Structure
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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.

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Physico-chemical Properties
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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.

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Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 4
Topological polar surface area 6.48
Molecular weight 354.3
XLogP 7.52
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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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.

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Canonical SMILES CC1(C)CC(CC(C1)(C)C)c1ccccc1N1CCN(CC1)CC1CC1
Isomeric SMILES CC1(C)CC(CC(C1)(C)C)c1ccccc1N1CCN(CC1)CC1CC1
InChI InChI=1S/C24H38N2/c1-23(2)15-20(16-24(3,4)18-23)21-7-5-6-8-22(21)26-13-11-25(12-14-26)17-19-9-10-19/h5-8,19-20H,9-18H2,1-4H3
InChI Key PGWIKFFLIJECAM-UHFFFAOYSA-N
Bioactivity Comments
In a cell adhesion assay using Jurkat cells example 9 inhibited adhesion to human fibronectin-coated plates with an IC50 of 3.1 μM. Adhesion of human peripheral blood neutrophils to immobilized HUVEC endothelial cells was inhibited with an IC50 of 6.7 μM. example 9 also inhibited oxazolone-induced neutrophil infiltration of the colon in an in vitro mouse model, and it effectively reduced disease signals in the DSS-induced colitis model [1].