carotegrast   Click here for help

GtoPdb Ligand ID: 10511

Synonyms: HCA2969
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Carotegrast (HCA2969) is the active metabolite of carotegrast methyl [1,4]. It acts as an antagonist of α4 integrin-mediated transmigration of leukocytes to sites of inflammation. The chemical structure of carotegrast is claimed as example 108 in EA Pharma patent US20110065918A1 which claims phenylalanine derivatives as α4 integrin antagonists for use as clinical therapeutics [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 113.12
Molecular weight 554.11
XLogP 6.12
No. Lipinski's rules broken 1
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Canonical SMILES CN(c1ccc2c(c1)c(=O)n(c(=O)n2C)c1ccc(cc1)CC(C(=O)O)NC(=O)c1c(Cl)cccc1Cl)C
Isomeric SMILES CN(c1ccc2c(c1)c(=O)n(c(=O)n2C)c1ccc(cc1)C[C@@H](C(=O)O)NC(=O)c1c(Cl)cccc1Cl)C
InChI InChI=1S/C27H24Cl2N4O5/c1-31(2)17-11-12-22-18(14-17)25(35)33(27(38)32(22)3)16-9-7-15(8-10-16)13-21(26(36)37)30-24(34)23-19(28)5-4-6-20(23)29/h4-12,14,21H,13H2,1-3H3,(H,30,34)(H,36,37)/t21-/m0/s1
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. Makino S, Okuzumi T, Yoshimura T, Satake Y, Suzuki N, Izawa H, Sagi K, Chiba A, Nakanishi E, Murata M et al.. (2011)
New phenylalanine derivatives.
Patent number: US20110065918A1. Assignee: EA Pharma Co Ltd. Priority date: 18/08/2000. Publication date: 17/03/2011.
3. Shukla T, Sands BE. (2019)
Novel Non-biologic Targets for Inflammatory Bowel Disease.
Curr Gastroenterol Rep, 21 (5): 22. [PMID:31016396]
4. Sugiura T, Kageyama S, Andou A, Miyazawa T, Ejima C, Nakayama A, Dohi T, Eda H. (2013)
Oral treatment with a novel small molecule alpha 4 integrin antagonist, AJM300, prevents the development of experimental colitis in mice.
J Crohns Colitis, 7 (11): e533-42. [PMID:23623333]
5. 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]
6. 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]