Roquinimex

Roquinimex

Clinical data
ATC code	L03AX02 (WHO)
Pharmacokinetic data
Elimination half-life	26-42 hours
Identifiers
IUPAC name 4-hydroxy-N,1-dimethyl-2-oxo-N- phenyl-1,2-dihydroquinoline-3-carboxamide
CAS Number	84088-42-6 Y
PubChem CID	55197
ChemSpider	10619239 N
UNII	372T2944C0
ECHA InfoCard	100.163.758
Chemical and physical data
Formula	C18H16N2O3
Molar mass	308.331 g/mol
3D model (JSmol)	Interactive image
SMILES CN1C2=CC=CC=C2C(=C(C1=O)C(=O)N(C)C3=CC=CC=C3)O
InChI 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 N Key:SGOOQMRIPALTEL-UHFFFAOYSA-N N
NY (what is this?)  (verify)

Roquinimex (Linomide) is a quinoline derivative immunostimulant which increases NK cell activity and macrophage cytotoxicity. It also inhibits angiogenesis and reduces the secretion of TNF alpha.

Roquinimex 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 and recent-onset type I diabetes. Several trials have been terminated due to serious cardiovascular toxicity.

Synthesis

Roquinimex synthesis:^[1]

Ethyl 2-(methylamino)benzoate is condensed with ethyl malonate. Amine-ester ineterchange of that compound with N-methylaniline results in formation of the amide roquinimex.

References