Roquinimex | CAS#84088-42-6 | immunostimulant

MedKoo Cat#: 202500 | Name: Roquinimex

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Roquinimex (also known as LS 2616, FCF89, and Linomide), is a quinoline-3-carboxamide with potential antineoplastic activity. Roquinimex has been investigated as a treatment for some cancers and autoimmune diseases, such as multiple sclerosis and recent-onset type I diabetes. However, several roquinimex clinical trials have been terminated due to serious cardiovascular toxicity.

Chemical Structure

Roquinimex

CAS#84088-42-6

Theoretical Analysis

MedKoo Cat#: 202500

Name: Roquinimex

CAS#: 84088-42-6

Chemical Formula: C18H16N2O3

Exact Mass: 308.1161

Molecular Weight: 308.33

Elemental Analysis: C, 70.12; H, 5.23; N, 9.09; O, 15.57

Price and Availability

Size	Price	Availability
50mg	USD 450.00	2 Weeks
100mg	USD 750.00	2 Weeks
200mg	USD 1,250.00	2 Weeks
500mg	USD 2,650.00	2 Weeks
1g	USD 3,850.00	2 Weeks

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Synonym

Roquinimex, FCF-89; FCF89; FCF 89; LS-2616; LS2616; LS 2616; Linomide. US brand name: Linomide.

IUPAC/Chemical Name

4-hydroxy-N,1-dimethyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide

InChi Key

SGOOQMRIPALTEL-UHFFFAOYSA-N

InChi Code

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

SMILES Code

O=C(C1=C(O)C2=C(N(C)C1=O)C=CC=C2)N(C)C3=CC=CC=C3

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, DMF, and ethanol

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

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 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. (source: http://en.wikipedia.org/wiki/Roquinimex).

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Roquinimex inhibits endothelial cell proliferation, migration, and basement membrane invasion; reduces the secretion of the angiogenic factor tumor necrosis factor alpha by tumor-associated macrophages (TAMs); and inhibits angiogenesis. This agent is also an immune modulator that appears to alter cytokine profiles and enhance the activity of T cells, natural killer cells, and macrophages.

In vitro activity:

Roquinimex exposure reduced lipopolysaccharide (LPS)-evoked TNF-alpha production in a dose-dependent manner. Roquinimex inhibited LPS-induced NF-kappaB binding to the NF-kappaB consensus oligonucleotide and NF-kappaB-mediated reporter gene expression. Roquinimex inhibited phosphorylation of p38 kinase and c-jun N terminal kinase in LPS-stimulated RAW264.7 cells, a murine macrophage cell line. Reference: Immunol Lett. 2007 Dec 15;114(2):81-5. https://pubmed.ncbi.nlm.nih.gov/17964662/

In vivo activity:

Roquinimex treatment suppressed the production of IFN-gamma and also the production of IL-10 in HSV-infected BALB/c mice. Reference: Clin Exp Immunol. 2004 Aug;137(2):305-12. https://pubmed.ncbi.nlm.nih.gov/15270847/

	Solvent	mg/mL	mM
Solubility
	DMF	5.0	16.21
	DMSO	3.0	9.73
	Ethanol	3.0	9.73

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 308.33 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Xiao ZY, Zhou WX, Zhang YX, Cheng JP, He JF, Yang RF, Yun LH. Inhibitory effect of linomide on lipopolysaccharide-induced proinflammatory cytokine tumor necrosis factor-alpha production in RAW264.7 macrophages through suppression of NF-kappaB, p38, and JNK activation. Immunol Lett. 2007 Dec 15;114(2):81-5. doi: 10.1016/j.imlet.2007.09.001. Epub 2007 Oct 1. PMID: 17964662. 2. Peltoniemi J, Broberg EK, Halenius A, Setala N, Eralinna JP, Salmi AA, Roytta M, Hukkanen V. Immunomodulation by roquinimex decreases the expression of IL-23 (p19) mRNA in the brains of herpes simplex virus type 1 infected BALB/c mice. Clin Exp Immunol. 2004 Aug;137(2):305-12. doi: 10.1111/j.1365-2249.2004.02528.x. PMID: 15270847; PMCID: PMC1809122. 3. Ivarsson K, Sturesson C, Stenram U, Tranberg KG. Linomide improves the effect of interstitial laser thermotherapy in a rat liver tumour model. Anticancer Res. 2003 Mar-Apr;23(2B):1257-63. PMID: 12820380.

In vitro protocol:

In vivo protocol:

1. Peltoniemi J, Broberg EK, Halenius A, Setala N, Eralinna JP, Salmi AA, Roytta M, Hukkanen V. Immunomodulation by roquinimex decreases the expression of IL-23 (p19) mRNA in the brains of herpes simplex virus type 1 infected BALB/c mice. Clin Exp Immunol. 2004 Aug;137(2):305-12. doi: 10.1111/j.1365-2249.2004.02528.x. PMID: 15270847; PMCID: PMC1809122. 2. Ivarsson K, Sturesson C, Stenram U, Tranberg KG. Linomide improves the effect of interstitial laser thermotherapy in a rat liver tumour model. Anticancer Res. 2003 Mar-Apr;23(2B):1257-63. PMID: 12820380.

1: Hasan AM, Gatea FK. Novel effect of topical Roquinimex and its combination with Clobetasol on an imiquimod-induced model of psoriasis in mice. Naunyn Schmiedebergs Arch Pharmacol. 2024 Jul;397(7):5219-5232. doi: 10.1007/s00210-024-02947-6. Epub 2024 Jan 24. PMID: 38265682. 2: Zhou Y, Shao M, Wang W, Cheung CY, Wu Y, Yu H, Hu X, Cook GM, Gong H, Lu X. Discovery of 1-hydroxy-2-methylquinolin-4(1H)-one derivatives as new cytochrome bd oxidase inhibitors for tuberculosis therapy. Eur J Med Chem. 2023 Jan 5;245(Pt 1):114896. doi: 10.1016/j.ejmech.2022.114896. Epub 2022 Nov 4. PMID: 36370551. 3: Rikken G, van den Brink NJM, van Vlijmen-Willems IMJJ, van Erp PEJ, Pettersson L, Smits JPH, van den Bogaard EH. Carboxamide Derivatives Are Potential Therapeutic AHR Ligands for Restoring IL-4 Mediated Repression of Epidermal Differentiation Proteins. Int J Mol Sci. 2022 Feb 4;23(3):1773. doi: 10.3390/ijms23031773. PMID: 35163694; PMCID: PMC8836151. 4: Priolkar RNS, Shingade S, Palkar M, Desai SM. Design, Synthesis, and Characterization of Novel Linomide Analogues and their Evaluation for Anticancer Activity. Curr Drug Discov Technol. 2020;17(2):203-212. doi: 10.2174/1570163815666181008151037. PMID: 30306874. 5: Banu S, Bollu R, Bantu R, Nagarapu L, Polepalli S, Jain N, Vangala R, Manga V. Design, synthesis and docking studies of novel 1,2-dihydro-4-hydroxy-2-oxoquinoline-3-carboxamide derivatives as a potential anti-proliferative agents. Eur J Med Chem. 2017 Jan 5;125:400-410. doi: 10.1016/j.ejmech.2016.09.062. Epub 2016 Sep 21. PMID: 27688193. 6: Constantinescu SE, Constantinescu CS. Laquinimod (ABR-215062) for the treatment of relapsing multiple sclerosis. Expert Rev Clin Pharmacol. 2016;9(1):49-57. doi: 10.1586/17512433.2016.1108189. Epub 2015 Nov 4. PMID: 26536299. 7: Gupta N, Al Ustwani O, Shen L, Pili R. Mechanism of action and clinical activity of tasquinimod in castrate-resistant prostate cancer. Onco Targets Ther. 2014 Feb 12;7:223-34. doi: 10.2147/OTT.S53524. PMID: 24600234; PMCID: PMC3928061. 8: Xiao ZY, Chen SH, Zhou WX, Zhang YX, Cheng JP, Yang RF. H1521, a novel derivative of 4-hydroxyquinoline-3-carboxamide, suppresses the development of lupus in mice by inducing Th1 cytokine profile in T cells. Int Immunopharmacol. 2011 Apr;11(4):435-43. doi: 10.1016/j.intimp.2010.12.011. Epub 2010 Dec 31. PMID: 21195814. 9: Isaacs JT. The long and winding road for the development of tasquinimod as an oral second-generation quinoline-3-carboxamide antiangiogenic drug for the treatment of prostate cancer. Expert Opin Investig Drugs. 2010 Oct;19(10):1235-43. doi: 10.1517/13543784.2010.514262. PMID: 20836618; PMCID: PMC4124623. 10: Xiao ZY, Zhou WX, Zhang YX, Cheng JP, He JF, Yang RF, Yun LH. Inhibitory effect of linomide on lipopolysaccharide-induced proinflammatory cytokine tumor necrosis factor-alpha production in RAW264.7 macrophages through suppression of NF-kappaB, p38, and JNK activation. Immunol Lett. 2007 Dec 15;114(2):81-5. doi: 10.1016/j.imlet.2007.09.001. Epub 2007 Oct 1. PMID: 17964662. 11: Xiao ZY, Zhou WX, Zhang YX, Cheng JP, He JF, Yang RF, Yun LH. Roquinimex- mediated protection effect on the development of chronic graft-versus-host disease in mice is associated with induction of Th1 cytokine production and inhibition of proinflammatory cytokine production. Life Sci. 2007 Oct 27;81(19-20):1403-10. doi: 10.1016/j.lfs.2007.08.044. Epub 2007 Sep 29. PMID: 17950363. 12: Isaacs JT, Pili R, Qian DZ, Dalrymple SL, Garrison JB, Kyprianou N, Björk A, Olsson A, Leanderson T. Identification of ABR-215050 as lead second generation quinoline-3-carboxamide anti-angiogenic agent for the treatment of prostate cancer. Prostate. 2006 Dec 1;66(16):1768-78. doi: 10.1002/pros.20509. PMID: 16955399. 13: Peltoniemi J, Broberg EK, Nygårdas M, Erälinna JP, Waris M, Hukkanen V. Enhancement of Th2 responses to replicative herpes simplex virus type 1 vectors by immunomodulative chemotherapy. Int Immunopharmacol. 2006 May;6(5):817-29. doi: 10.1016/j.intimp.2005.12.003. Epub 2006 Jan 4. PMID: 16546713. 14: He JF, Yun LH, Yang RF, Xiao ZY, Cheng JP, Zhou WX, Zhang YX. Design, synthesis, and biological evaluation of novel 4-hydro-quinoline-3-carboxamide derivatives as an immunomodulator. Bioorg Med Chem Lett. 2005 Jun 15;15(12):2980-5. doi: 10.1016/j.bmcl.2005.04.040. PMID: 15908212. 15: Abdul-Hai A, Hershkoviz R, Weiss L, Lider O, Slavin S. Effect of Linomide on adhesion molecules, TNF-alpha, nitrogen oxide, and cell adhesion. Int Immunopharmacol. 2005 Feb;5(2):231-9. doi: 10.1016/j.intimp.2004.08.007. PMID: 15652754. 16: Li X, Klintman D, Sato T, Hedlund G, Schramm R, Jeppsson B, Thorlacius H. Interleukin-10 mediates the protective effect of Linomide by reducing CXC chemokine production in endotoxin-induced liver injury. Br J Pharmacol. 2004 Dec;143(7):865-71. doi: 10.1038/sj.bjp.0706015. Epub 2004 Oct 18. PMID: 15492015; PMCID: PMC1575945. 17: Yang JS, Xu LY, Xiao BG, Hedlund G, Link H. Laquinimod (ABR-215062) suppresses the development of experimental autoimmune encephalomyelitis, modulates the Th1/Th2 balance and induces the Th3 cytokine TGF-beta in Lewis rats. J Neuroimmunol. 2004 Nov;156(1-2):3-9. doi: 10.1016/j.jneuroim.2004.02.016. PMID: 15465591. 18: Peltoniemi J, Broberg EK, Halenius A, Setala N, Eralinna JP, Salmi AA, Roytta M, Hukkanen V. Immunomodulation by roquinimex decreases the expression of IL-23 (p19) mRNA in the brains of herpes simplex virus type 1 infected BALB/c mice. Clin Exp Immunol. 2004 Aug;137(2):305-12. doi: 10.1111/j.1365-2249.2004.02528.x. PMID: 15270847; PMCID: PMC1809122. 19: Jönsson S, Andersson G, Fex T, Fristedt T, Hedlund G, Jansson K, Abramo L, Fritzson I, Pekarski O, Runström A, Sandin H, Thuvesson I, Björk A. Synthesis and biological evaluation of new 1,2-dihydro-4-hydroxy-2-oxo-3-quinolinecarboxamides for treatment of autoimmune disorders: structure-activity relationship. J Med Chem. 2004 Apr 8;47(8):2075-88. doi: 10.1021/jm031044w. PMID: 15056005. 20: Lindberg P, Billström A, Kinnby B. Reduced gingival fluid flow: a peripheral marker of the pharmacological effect of roquinimex. Inflammopharmacology. 2003;11(3):267-76. doi: 10.1163/156856003322315613. PMID: 15035809.