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carotegrast methyl   Click here for help

GtoPdb Ligand ID: 10510

Synonyms: AJM-300 | AJM300 | Carogra®
Approved drug Immunopharmacology Ligand
carotegrast methyl is an approved drug
Compound class: Synthetic organic
Comment: Carotegrast methyl (AJM300) is an orally administered esterified prodrug α4 integrin inhibitor/antagonist that was developed by EA Pharma for anti-inflammatory potential [1].

carotegrast methyl is commercially available from our sponsors

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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 5
Hydrogen bond donors 1
Rotatable bonds 9
Topological polar surface area 102.12
Molecular weight 568.13
XLogP 6.44
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES COC(=O)C(NC(=O)c1c(Cl)cccc1Cl)Cc1ccc(cc1)n1c(=O)c2cc(ccc2n(c1=O)C)N(C)C
Isomeric SMILES COC(=O)[C@@H](NC(=O)c1c(Cl)cccc1Cl)Cc1ccc(cc1)n1c(=O)c2cc(ccc2n(c1=O)C)N(C)C
InChI InChI=1S/C28H26Cl2N4O5/c1-32(2)18-12-13-23-19(15-18)26(36)34(28(38)33(23)3)17-10-8-16(9-11-17)14-22(27(37)39-4)31-25(35)24-20(29)6-5-7-21(24)30/h5-13,15,22H,14H2,1-4H3,(H,31,35)/t22-/m0/s1
InChI Key MMHHPKCJJIFLBQ-QFIPXVFZSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
AJM300 was advanced to Phase 3 clinical evaluation in patients with active ulcerative colitis (see NCT03531892). The safety and efficacy of AJM300 was first reported in 2015, with results from a Phase 2a study in Japan [5]. First approval was granted in Japan (March 2022) for the treatment of mesalazine-insensitive moderate ulcerative colitis.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT03531892 A Study to Evaluate the Safety and Efficacy of AJM300 in Participants With Active Ulcerative Colitis Phase 3 Interventional Eisai Inc.