# Linomide

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Chemical compound

Pharmaceutical compound

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 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 NY (what is this?) (verify)

**Linomide** (Roquinimex) is a [quinoline](/source/Quinoline) derivative [immunostimulant](/source/Immunostimulant) which increases [NK cell](/source/Natural_killer_cell) activity and [macrophage](/source/Macrophage) [cytotoxicity](/source/Cytotoxicity). It also inhibits [angiogenesis](/source/Angiogenesis) and reduces the secretion of [TNF alpha](/source/Tumor_necrosis_factor-alpha).

Linomide has been investigated as a treatment for some cancers (including as adjuvant therapy after [bone marrow transplantation](/source/Hematopoietic_stem_cell_transplantation) in acute [leukemia](/source/Leukemia)) and autoimmune diseases, such as [multiple sclerosis](/source/Multiple_sclerosis)[1][2] and recent-onset [type I diabetes](/source/Diabetes_mellitus_type_1).[3] Several trials have been terminated due to serious cardiovascular toxicity.

## Synthesis

Linomide synthesis:[4]

Ethyl 2-(methylamino)benzoate is condensed with [ethyl malonate](/source/Ethyl_malonate). Amine-ester interchange of that compound with [N-methylaniline](/source/N-methylaniline) results in formation of the amide linomide.

## References

1. **[^](#cite_ref-pmid8805117_1-0)** Weilbach EX, Hartung HP (August 1996). "[Immune modulation in multiple sclerosis: linomide]". *Der Nervenarzt* (in German). **67** (8): 701–5. [doi](/source/Doi_(identifier)):[10.1007/s001150050044](https://doi.org/10.1007%2Fs001150050044). [PMID](/source/PMID_(identifier)) [8805117](https://pubmed.ncbi.nlm.nih.gov/8805117). [S2CID](/source/S2CID_(identifier)) [31845910](https://api.semanticscholar.org/CorpusID:31845910).

1. **[^](#cite_ref-pmid11407306_2-0)** 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](/source/Doi_(identifier)):[10.1016/s1567-5769(01)00041-8](https://doi.org/10.1016%2Fs1567-5769%2801%2900041-8). [PMID](/source/PMID_(identifier)) [11407306](https://pubmed.ncbi.nlm.nih.gov/11407306).

1. **[^](#cite_ref-pmid11407307_3-0)** 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](/source/Doi_(identifier)):[10.1016/s1567-5769(01)00042-x](https://doi.org/10.1016%2Fs1567-5769%2801%2900042-x). [PMID](/source/PMID_(identifier)) [11407307](https://pubmed.ncbi.nlm.nih.gov/11407307).

1. **[^](#cite_ref-4)** [EP 59698](https://worldwide.espacenet.com/textdoc?DB=EPODOC&IDX=EP59698), 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](https://patents.google.com/patent/US4738971) (1988 to AB Leo).

v t e Immunostimulants (L03) Endogenous Cytokines Colony-stimulating factors G-CSF Efbemalenograstim alfa Eflapegrastim Filgrastim / Lipegfilgrastim / Pegfilgrastim Lenograstim GM-CSF Molgramostim Sargramostim SCF Ancestim Interferons alpha: Albinterferon Interferon alfa natural Interferon alfa 2a / Peginterferon alfa-2a Interferon alfa 2b / Peginterferon alfa-2b / Ropeginterferon alfa-2b Interferon alfa n1 Interferon alfacon-1 Interferon alpha-n3 feline "omega" beta: Interferon beta natural Interferon beta 1a Interferon beta 1b Interferon gamma Interleukins Aldesleukin Nogapendekin alfa inbakicept Oprelvekin Other protein / peptide Growth hormone Immunocyanin Pegademase Prolactin Tasonermin Other Female sex steroids Histamine dihydrochloride Poly ICLC Vitamin D Exogenous beta-glucan Lentinan heterocyclic compound Plerixafor hydroxyquinoline Roquinimex Mifamurtide oligopeptides Glatiramer acetate Thymopentin Thymosin α1 Thymulin polyribonucleotide Polyinosinic:polycytidylic acid thiazolidine Pidotimod Inosine pranobex vaccines Bacillus Calmette–Guérin Melanoma vaccine Sipuleucel-T Cridanimod

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Adapted from the Wikipedia article [Linomide](https://en.wikipedia.org/wiki/Linomide) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Linomide?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.