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Linomide

Chemical compound From Wikipedia, the free encyclopedia

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.

ATC code
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Linomide
Clinical data
ATC code
Pharmacokinetic data
Elimination half-life26-42 hours
Identifiers
  • 4-hydroxy-N,1-dimethyl-2-oxo-N-
    phenyl-1,2-dihydroquinoline-3-carboxamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.163.758 Edit this at Wikidata
Chemical and physical data
FormulaC18H16N2O3
Molar mass308.337 g·mol−1
3D model (JSmol)
  • CN1C2=CC=CC=C2C(=C(C1=O)C(=O)N(C)C3=CC=CC=C3)O
  • InChI=1S/C18H16N2O3/c1-19(12-8-4-3-5-9-12)17(22)15-16(21)13-10-6-7-11-14(13)20(2)18(15)23/h3-11,21H,1-2H3 X markN
  • Key:SGOOQMRIPALTEL-UHFFFAOYSA-N X markN
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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

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.

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