Linomide: Difference between revisions
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Updating {{drugbox}} (changes to watched fields - updated 'ChemSpiderID_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report [[Wikipedia talk:WikiProject_Pha |
Citation bot (talk | contribs) Add: s2cid. | Use this bot. Report bugs. | Suggested by Abductive | Category:Quinolinols | #UCB_Category 17/24 |
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{{short description|Chemical compound}} |
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{{Drugbox |
{{Drugbox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
| Watchedfields = changed |
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| verifiedrevid = |
| verifiedrevid = 447995846 |
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| IUPAC_name = 4-hydroxy-''N'',1-dimethyl-2-oxo-''N''-<br>phenyl-1,2-dihydroquinoline-3-carboxamide |
| IUPAC_name = 4-hydroxy-''N'',1-dimethyl-2-oxo-''N''-<br>phenyl-1,2-dihydroquinoline-3-carboxamide |
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| image = Roquinimex.svg |
| image = Roquinimex.svg |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
| legal_status = |
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| routes_of_administration = |
| routes_of_administration = |
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<!--Pharmacokinetic data--> |
<!--Pharmacokinetic data--> |
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| metabolism = |
| metabolism = |
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| elimination_half-life = 26-42 hours |
| elimination_half-life = 26-42 hours |
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| excretion = |
| excretion = |
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<!--Identifiers--> |
<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 84088-42-6 |
| CAS_number = 84088-42-6 |
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| ATC_prefix = L03 |
| ATC_prefix = L03 |
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| ATC_suffix = AX02 |
| ATC_suffix = AX02 |
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| PubChem = |
| PubChem = 54676478 |
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| DrugBank_Ref = |
| DrugBank_Ref = |
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| DrugBank = |
| DrugBank = DB11366 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 372T2944C0 |
| UNII = 372T2944C0 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 10619239 |
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| KEGG = D05756 |
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| ChEBI = 92056 |
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| ChEMBL = 11672 |
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<!--Chemical data--> |
<!--Chemical data--> |
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| C=18 | H=16 | N=2 | O=3 |
| C=18 | H=16 | N=2 | O=3 |
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| smiles = CN1C2=CC=CC=C2C(=C(C1=O)C(=O)N(C)C3=CC=CC=C3)O |
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| molecular_weight = 308.331 g/mol |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| 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 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = SGOOQMRIPALTEL-UHFFFAOYSA-N |
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}} |
}} |
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''' |
'''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]]. |
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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. |
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==Synthesis== |
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[[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>]] |
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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. |
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==References== |
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[[Category:3-Hydroxypropenals]] |
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{{antineoplastic-drug-stub}} |
{{antineoplastic-drug-stub}} |