Linomide (Roquinimex) is a quinoline derivative immunostimulant which increases NK cell activity and macrophage cytotoxicity. It also inhibits angiogenesis and reduces the secretion of TNF alpha.
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| Elimination half-life | 26-42 hours |
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| ECHA InfoCard | 100.163.758 |
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| Formula | C18H16N2O3 |
| Molar mass | 308.337 g·mol−1 |
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Linomide has been investigated as a treatment for some cancers (including as adjuvant therapy after bone marrow transplantation in acute leukemia) and autoimmune diseases, such as multiple sclerosis[1][2] and recent-onset type I diabetes.[3] Several trials have been terminated due to serious cardiovascular toxicity.
Synthesis
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Ethyl 2-(methylamino)benzoate is condensed with ethyl malonate. Amine-ester interchange of that compound with N-methylaniline results in formation of the amide linomide.
References
edit- ^ Weilbach EX, Hartung HP (August 1996). "[Immune modulation in multiple sclerosis: linomide]". Der Nervenarzt (in German). 67 (8): 701–5. doi:10.1007/s001150050044. PMID 8805117. S2CID 31845910.701-5&rft.date=1996-08&rft_id=https://api.semanticscholar.org/CorpusID:31845910#id-name=S2CID&rft_id=info:pmid/8805117&rft_id=info:doi/10.1007/s001150050044&rft.aulast=Weilbach&rft.aufirst=EX&rft.au=Hartung, HP&rfr_id=info:sid/en.wikipedia.org:Linomide" class="Z3988">
- ^ Hedlund G, Link H, Zhu J, Xiao BG (June 2001). "Effects of Linomide on immune cells and cytokines inhibit autoimmune pathologies of the central and peripheral nervous system". International Immunopharmacology. 1 (6): 1123–30. doi:10.1016/s1567-5769(01)00041-8. PMID 11407306.1123-30&rft.date=2001-06&rft_id=info:doi/10.1016/s1567-5769(01)50041-8&rft_id=info:pmid/11407306&rft.aulast=Hedlund&rft.aufirst=G&rft.au=Link, H&rft.au=Zhu, J&rft.au=Xiao, BG&rfr_id=info:sid/en.wikipedia.org:Linomide" class="Z3988">
- ^ Gross DJ, Weiss L, Reibstein I, Hedlund G, Dahlén E, Rapoport MJ, Slavin S (June 2001). "The immunomodulator Linomide: role in treatment and prevention of autoimmune diabetes mellitus". International Immunopharmacology. 1 (6): 1131–9. doi:10.1016/s1567-5769(01)00042-x. PMID 11407307.1131-9&rft.date=2001-06&rft_id=info:doi/10.1016/s1567-5769(01)50042-x&rft_id=info:pmid/11407307&rft.aulast=Gross&rft.aufirst=DJ&rft.au=Weiss, L&rft.au=Reibstein, I&rft.au=Hedlund, G&rft.au=Dahlén, E&rft.au=Rapoport, MJ&rft.au=Slavin, S&rfr_id=info:sid/en.wikipedia.org:Linomide" class="Z3988">
- ^ EP 59698, Eriksoo, Edgar; Sandberg, Eva Britt-Marie & Stalhandsk, Lars Johan Torbjörn, "Heterocyclic carboxamides, compositions containing such compounds, processes for their preparation and methods of treatment therewith", published 1982-09-08, assigned to AB Leo; E. Eriksoo et al., U.S. patent 4,738,971 (1988 to AB Leo).
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