Linomide

Linomide
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	54676478;
DrugBank	DB11366;
ChemSpider	10619239 ;
UNII	372T2944C0;
KEGG	D05756;
ChEBI	CHEBI:92056;
ChEMBL	ChEMBL11672;
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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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

^ 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.
^ 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.
^ 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.
^ 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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[pmid8805117-1] 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.

[pmid11407306-2] 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.

[pmid11407307-3] 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.

[4] 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).

[1]

[2]

[3]

[4]

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	54676478
DrugBank	DB11366
ChemSpider	10619239^N
UNII	372T2944C0
KEGG	D05756
ChEBI	CHEBI:92056
ChEMBL	ChEMBL11672
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^N Key:SGOOQMRIPALTEL-UHFFFAOYSA-N^N
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