Linomide: Difference between revisions

{{short description|Chemical compound}}

| Verifiedfields = changed

| verifiedrevid = 447995846

| routes_of_administration =

| excretion =

| CAS_number_Ref = {{cascite|correct|??}}

| PubChem = 54676478

| DrugBank_Ref =

| DrugBank = DB11366

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 10619239

| KEGG = D05756

| ChEBI = 92056

| ChEMBL = 11672

| smiles = CN1C2=CC=CC=C2C(=C(C1=O)C(=O)N(C)C3=CC=CC=C3)O

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = SGOOQMRIPALTEL-UHFFFAOYSA-N

'''Linomide''' (Roquinimex) is a [[quinoline]] derivative [[immunostimulant]] which increases [[Natural killer cell|NK cell]] activity and [[macrophage]] [[cytotoxicity]]. It also inhibits [[angiogenesis]] and reduces the secretion of [[Tumor necrosis factor-alpha|TNF alpha]].

Linomide has been investigated as a treatment for some cancers (including as adjuvant therapy after [[Hematopoietic stem cell transplantation|bone marrow transplantation]] in acute [[leukemia]]) and autoimmune diseases, such as [[multiple sclerosis]]<ref name="pmid8805117">{{cite journal | vauthors = Weilbach EX, Hartung HP | title = [Immune modulation in multiple sclerosis: linomide] | language = German | journal = Der Nervenarzt | volume = 67 | issue = 8 | pages = 701–5 | date = August 1996 | pmid = 8805117 | doi = 10.1007/s001150050044 | s2cid = 31845910 }}</ref><ref name="pmid11407306">{{cite journal | vauthors = Hedlund G, Link H, Zhu J, Xiao BG | title = Effects of Linomide on immune cells and cytokines inhibit autoimmune pathologies of the central and peripheral nervous system | journal = International Immunopharmacology | volume = 1 | issue = 6 | pages = 1123–30 | date = June 2001 | pmid = 11407306 | doi = 10.1016/s1567-5769(01)00041-8 }}</ref> and recent-onset [[Diabetes mellitus type 1|type I diabetes]].<ref name="pmid11407307">{{cite journal | vauthors = Gross DJ, Weiss L, Reibstein I, Hedlund G, Dahlén E, Rapoport MJ, Slavin S | title = The immunomodulator Linomide: role in treatment and prevention of autoimmune diabetes mellitus | journal = International Immunopharmacology | volume = 1 | issue = 6 | pages = 1131–9 | date = June 2001 | pmid = 11407307 | doi = 10.1016/s1567-5769(01)00042-x }}</ref> Several trials have been terminated due to serious cardiovascular toxicity.

==Synthesis==

[[File:Roquinimex synthesis.svg|thumb|center|700px|Linomide synthesis:<ref>{{Cite patent|country=EP|number=59698|title=Heterocyclic carboxamides, compositions containing such compounds, processes for their preparation and methods of treatment therewith|pubdate=1982-09-08|assign=AB Leo|inventor1-last=Eriksoo|inventor1-first=Edgar|inventor2-last=Sandberg|inventor2-first=Eva Britt-Marie|inventor3-last=Stalhandsk|inventor3-first=Lars Johan Torbjörn}}; E. Eriksoo et al., {{US patent|4738971}} (1988 to AB Leo).</ref>]]

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==

{{Reflist}}

{{Immunostimulants}}

[[Category:Immunostimulants]]

[[Category:2-Quinolones]]

[[Category:Quinolinols]]

[[Category:Carboxamides]]

[[Category:Anilides]]

[[Category:3-Hydroxypropenals]]