Roquinimex

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

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
PubChem CID	55197
ChemSpider	10619239
UNII	372T2944C0
CompTox Dashboard (EPA)	DTXSID4045680
ECHA InfoCard	100.163.758
Chemical and physical data
Formula	C18H16N2O3
Molar mass	308.337 g·mol^−1
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 Key:SGOOQMRIPALTEL-UHFFFAOYSA-N
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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 interchange of that compound with N-methylaniline results in formation of the amide roquinimex.

References

1. E. Eriksoo et al., EP 59698; eidem, U.S. Patent 4,738,971 (1982, 1988 both to AB Leo).