carotegrast methyl   Click here for help

GtoPdb Ligand ID: 10510

Synonyms: AJM-300 | AJM300
Immunopharmacology Ligand
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].
2D Structure
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Physico-chemical Properties
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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
SMILES / InChI / InChIKey
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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
References
1. Fukase H, Kajioka T, Oikawa I, Ikeda N, Furuie H. (2020)
AJM300, a novel oral antagonist of α4-integrin, sustains an increase in circulating lymphocytes: A randomised controlled trial in healthy male subjects.
Br J Clin Pharmacol, 86 (3): 591-600. [PMID:31658381]
2. Shukla T, Sands BE. (2019)
Novel Non-biologic Targets for Inflammatory Bowel Disease.
Curr Gastroenterol Rep, 21 (5): 22. [PMID:31016396]
3. Vetter M, Neurath MF. (2017)
Emerging oral targeted therapies in inflammatory bowel diseases: opportunities and challenges.
Therap Adv Gastroenterol, 10 (10): 773-790. [PMID:29051788]
4. White JR, Phillips F, Monaghan T, Fateen W, Samuel S, Ghosh S, Moran GW. (2018)
Review article: novel oral-targeted therapies in inflammatory bowel disease.
Aliment. Pharmacol. Ther., 47 (12): 1610-1622. [PMID:29672874]
5. Yoshimura N, Watanabe M, Motoya S, Tominaga K, Matsuoka K, Iwakiri R, Watanabe K, Hibi T, AJM300 Study Group. (2015)
Safety and Efficacy of AJM300, an Oral Antagonist of α4 Integrin, in Induction Therapy for Patients With Active Ulcerative Colitis.
Gastroenterology, 149 (7): 1775-1783.e2. [PMID:26327130]