Roquinimex
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MedKoo CAT#: 202500

CAS#: 84088-42-6

Description: Roquinimex, also known as LS 2616 and FCF89 (brande name: Linomide), is a quinoline-3-carboxamide with potential antineoplastic activity. 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.


Chemical Structure

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Roquinimex
CAS# 84088-42-6

Theoretical Analysis

MedKoo Cat#: 202500
Name: Roquinimex
CAS#: 84088-42-6
Chemical Formula: C18H16N2O3
Exact Mass: 308.11609
Molecular Weight: 308.33
Elemental Analysis: C, 70.12; H, 5.23; N, 9.09; O, 15.57

Price and Availability

Size Price Availability Quantity
100.0mg USD 650.0 2 Weeks
200.0mg USD 1050.0 2 Weeks
500.0mg USD 1950.0 2 Weeks
1.0g USD 2950.0 2 Weeks
2.0g USD 5250.0 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, not in water

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

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.

Recalculate based on batch purity %
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

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1: 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. Epub 2007 Sep 29. PubMed PMID: 17950363.

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. PubMed PMID: 15270847; PubMed Central PMCID: PMC1809122.

3: 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. PubMed PMID: 15035809.

4: Liu Q, Wang Y, Wan MX, Zhang XW, Andersson G, Hedlund G, Thorlacius H. Roquinimex inhibits dextran sodium sulfate-induced murine colitis. Inflamm Res. 2003 Feb;52(2):64-8. PubMed PMID: 12665123.

5: Strandgården K, Höglund P, Grönquist L, Svensson L, Gunnarsson PO. Absorption and disposition including enterohepatic circulation of (14C) roquinimex after oral administration to healthy volunteers. Biopharm Drug Dispos. 2000 Mar;21(2):53-67. PubMed PMID: 11100907.

6: Tuvesson H, Wienkers LC, Gunnarsson PO, Seidegård J, Persson R. Identification of cytochrome P4503A as the major subfamily responsible for the metabolism of roquinimex in man. Xenobiotica. 2000 Sep;30(9):905-14. PubMed PMID: 11055268.

7: Ohsuga Y, Rowe JM, Liesveld J, Burns RP, Gaspari AA. Dermatologic changes associated with roquinimex immunotherapy after autologous bone marrow transplant. J Am Acad Dermatol. 2000 Sep;43(3):437-41. PubMed PMID: 10954654.

8: Simonsson B, Tötterman T, Hokland P, Lauria F, Carella AM, Fernandez MN, Rozman C, Ferrant A, de Witte T, Zander AR, Meier K, Hansson F, Nilsson BI. Roquinimex (Linomide) vs placebo in AML after autologous bone marrow transplantation. Bone Marrow Transplant. 2000 Jun;25(11):1121-7. PubMed PMID: 10849523.

9: Tuvesson H, Strandgården K, Nordle O, Gunnarsson PO, Seidegård J, Persson R. Metabolism of roquinimex in mouse and rat: an in vitro/in vivo comparison. Xenobiotica. 2000 Apr;30(4):371-80. PubMed PMID: 10821166.

10: Strandgârden K, Höglund P, Nordle O, Polacek J, Wännman H, Gunnarsson PO. Dissolution rate-limited absorption and complete bioavailability of roquinimex in man. Biopharm Drug Dispos. 1999 Oct;20(7):347-54. PubMed PMID: 10760843.

11: Rowe JM, Rapoport AP, Ryan DH, Nilsson BI, Duerst RE, Packman CH, Abboud CN, DiPersio JF, Linder T, Wang N, Simonsson B, Liesveld JL. Treatment of chronic myelogenous leukemia with autologous bone marrow transplantation followed by roquinimex. Bone Marrow Transplant. 1999 Nov;24(10):1057-63. PubMed PMID: 10578155.

12: Mackean MJ, Kerr D, Lesko M, Svedberg A, Hansson F, Jodrell D, Cassidy J. A feasibility study of roquinimex (Linomide) and alpha interferon in patients with advanced malignant melanoma or renal carcinoma. Br J Cancer. 1998 Dec;78(12):1620-3. PubMed PMID: 9862573; PubMed Central PMCID: PMC2063243.

13: Tian WZ, Navikas V, Matusevicius D, Söderström M, Fredrikson S, Hedlund G, Link H. Linomide (roquinimex) affects the balance between pro- and anti-inflammatory cytokines in vitro in multiple sclerosis. Acta Neurol Scand. 1998 Aug;98(2):94-101. PubMed PMID: 9724006.

14: Rosenfeld CS, Zeigler ZR, Shadduck RK, Nilsson B. Phase II study of roquinimex in myelodysplastic syndrome. Am J Clin Oncol. 1997 Apr;20(2):189-92. PubMed PMID: 9124198.

15: Bergh JC, Tötterman TH, Termander BC, Strandgarden KA, Gunnarsson PO, Nilsson BI. The first clinical pilot study of roquinimex (Linomide) in cancer patients with special focus on immunological effects. Cancer Invest. 1997;15(3):204-11. PubMed PMID: 9171853.

16: Vaz F, Silva MR, Ascensao JL. Enhanced lymphokine-activated killer cell activity by an immunomodulator, Roquinimex. Br J Cancer. 1995 Dec;72(6):1498-503. PubMed PMID: 8519666; PubMed Central PMCID: PMC2034089.

17: Gaspari AA, Cheng SF, DiPersio JF, Rowe JM. Roquinimex-induced graft-versus-host reaction after autologous bone marrow transplantation. J Am Acad Dermatol. 1995 Nov;33(5 Pt 1):711-7. PubMed PMID: 7593767.

Roquinimex

10.0mg / Not available


Additional Information

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).