Chemistry:Linomide

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Short description: Chemical compound
Linomide
Roquinimex.svg
Clinical data
ATC code
Pharmacokinetic data
Elimination half-life26-42 hours
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC18H16N2O3
Molar mass308.337 g·mol−1
3D model (JSmol)
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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.

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

Linomide synthesis:[4]

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

  1. "[Immune modulation in multiple sclerosis: linomide]" (in German). Der Nervenarzt 67 (8): 701–5. August 1996. doi:10.1007/s001150050044. PMID 8805117. 
  2. "Effects of Linomide on immune cells and cytokines inhibit autoimmune pathologies of the central and peripheral nervous system". International Immunopharmacology 1 (6): 1123–30. June 2001. doi:10.1016/s1567-5769(01)00041-8. PMID 11407306. 
  3. "The immunomodulator Linomide: role in treatment and prevention of autoimmune diabetes mellitus". International Immunopharmacology 1 (6): 1131–9. June 2001. doi:10.1016/s1567-5769(01)00042-x. PMID 11407307. 
  4. Eriksoo, Edgar; Eva Britt-Marie Sandberg & Lars Johan Torbjörn Stalhandsk, "Heterocyclic carboxamides, compositions containing such compounds, processes for their preparation and methods of treatment therewith", EP patent 59698, published 1982-09-08; E. Eriksoo et al., U.S. Patent 4,738,971 (1988 to AB Leo).