Laquinimod
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MedKoo CAT#: 206167

CAS#: 248281-84-7

Description: Laquinimod, also known as, is an experimental immunomodulator developed by Active Biotech and Teva. It is being investigated as an oral treatment for multiple sclerosis (MS). Laquinimod is the successor of Active Biotech's failed experimental immunomodulator linomide. Laquinimod seems to be able to reduce the MS disease activity on MRI. In 2011, Teva announced its clinical trials involving laquinimod had failed, being unable to significantly reduce relapses into MS among patients beyond a placebo. However, the final results of above-mentioned phase III trial proved oral laquinimod administered once daily slowed the progression of disability and reduced the rate of relapse in patients with relapsing–remitting multiple sclerosis.


Chemical Structure

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Laquinimod
CAS# 248281-84-7

Theoretical Analysis

MedKoo Cat#: 206167
Name: Laquinimod
CAS#: 248281-84-7
Chemical Formula: C19H17ClN2O3
Exact Mass: 356.09277
Molecular Weight: 356.8
Elemental Analysis: C, 63.96; H, 4.80; Cl, 9.94; N, 7.85; O, 13.45

Price and Availability

Size Price Availability Quantity
100.0mg USD 150.0 Same day
200.0mg USD 250.0 Same day
500.0mg USD 450.0 Same day
1.0g USD 650.0 Same day
2.0g USD 1050.0 Same day
5.0g USD 1950.0 Same day
10.0g USD 2950.0 2 Weeks
20.0g USD 4950.0 2 Weeks
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Synonym: Laquinimod; ABR 215062; ABR-215062; ABR215062; SAIK-MS; TV-5600; TV5600; TV 5600.

IUPAC/Chemical Name: 5-chloro-N-ethyl-4-hydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide

InChi Key: GKWPCEFFIHSJOE-UHFFFAOYSA-N

InChi Code: InChI=1S/C19H17ClN2O3/c1-3-22(12-8-5-4-6-9-12)19(25)16-17(23)15-13(20)10-7-11-14(15)21(2)18(16)24/h4-11,23H,3H2,1-2H3

SMILES Code: O=C(C1=C(O)C2=C(N(C)C1=O)C=CC=C2Cl)N(CC)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 356.8 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: D'Haens G, Sandborn WJ, Colombel JF, Rutgeerts P, Brown K, Barkay H, Sakov A, Haviv A, Feagan BG; on behalf of the Laquinimod for Crohn's Disease Investigators. A phase II study of laquinimod in Crohn's disease. Gut. 2014 Oct 3. pii: gutjnl-2014-307118. doi: 10.1136/gutjnl-2014-307118. [Epub ahead of print] PubMed PMID: 25281416.

2: Kelland EE, Gilmore W, Hayardeny L, Weiner LP, Lund BT. In vitro assessment of the direct effect of laquinimod on basic functions of human neural stem cells and oligodendrocyte progenitor cells. J Neurol Sci. 2014 Aug 4. pii: S0022-510X(14)00504-8. doi: 10.1016/j.jns.2014.07.058. [Epub ahead of print] PubMed PMID: 25125045.

3: Gil-Ad I, Amit BH, Hayardeni L, Tarasenko I, Taler M, Uzan Gueta R, Weizman A. Effects of the Anti-Multiple Sclerosis Immunomodulator Laquinimod on Anxiety and Depression in Rodent Behavioral Models. J Mol Neurosci. 2014 Jul 27. [Epub ahead of print] PubMed PMID: 25064496.

4: Pitarokoili K, Ambrosius B, Schrewe L, Hayardeny L, Hayden M, Gold R. Laquinimod exerts strong clinical and immunomodulatory effects in Lewis rat experimental autoimmune neuritis. J Neuroimmunol. 2014 Sep 15;274(1-2):38-45. doi: 10.1016/j.jneuroim.2014.06.012. Epub 2014 Jun 24. PubMed PMID: 25005118.

5: Kieseier BC. Defining a role for laquinimod in multiple sclerosis. Ther Adv Neurol Disord. 2014 Jul;7(4):195-205. doi: 10.1177/1756285614529615. Review. PubMed PMID: 25002907; PubMed Central PMCID: PMC4082303.

6: Varrin-Doyer M, Zamvil SS, Schulze-Topphoff U. Laquinimod, an up-and-coming immunomodulatory agent for treatment of multiple sclerosis. Exp Neurol. 2014 Apr 13. pii: S0014-4886(14)00097-1. doi: 10.1016/j.expneurol.2014.04.002. [Epub ahead of print] Review. PubMed PMID: 24731945; PubMed Central PMCID: PMC4195809.

7: Lourenço EV, Wong M, Hahn BH, Palma-Diaz MF, Skaggs BJ. Laquinimod delays and suppresses nephritis in lupus-prone mice and affects both myeloid and lymphoid immune cells. Arthritis Rheumatol. 2014 Mar;66(3):674-85. doi: 10.1002/art.38259. PubMed PMID: 24574228.

8: Vollmer TL, Sorensen PS, Selmaj K, Zipp F, Havrdova E, Cohen JA, Sasson N, Gilgun-Sherki Y, Arnold DL; BRAVO Study Group. A randomized placebo-controlled phase III trial of oral laquinimod for multiple sclerosis. J Neurol. 2014 Apr;261(4):773-83. doi: 10.1007/s00415-014-7264-4. Epub 2014 Feb 18. PubMed PMID: 24535134.

9: Moore S, Khalaj AJ, Yoon J, Patel R, Hannsun G, Yoo T, Sasidhar M, Martinez-Torres L, Hayardeny L, Tiwari-Woodruff SK. Therapeutic laquinimod treatment decreases inflammation, initiates axon remyelination, and improves motor deficit in a mouse model of multiple sclerosis. Brain Behav. 2013 Nov;3(6):664-82. doi: 10.1002/brb3.174. Epub 2013 Sep 23. PubMed PMID: 24363970; PubMed Central PMCID: PMC3868172.

10: Brück W, Vollmer T. Multiple sclerosis: Oral laquinimod for MS--bringing the brain into focus. Nat Rev Neurol. 2013 Dec;9(12):664-5. doi: 10.1038/nrneurol.2013.234. Epub 2013 Nov 26. PubMed PMID: 24275930.

11: Haggiag S, Ruggieri S, Gasperini C. Efficacy and safety of laquinimod in multiple sclerosis: current status. Ther Adv Neurol Disord. 2013 Nov;6(6):343-52. doi: 10.1177/1756285613499424. PubMed PMID: 24228070; PubMed Central PMCID: PMC3825117.

12: Thöne J, Gold R. Review of laquinimod and its therapeutic potential in multiple sclerosis. Expert Opin Pharmacother. 2013 Dec;14(18):2545-52. doi: 10.1517/14656566.2013.848855. Epub 2013 Nov 11. Review. PubMed PMID: 24215556.

13: Tur C. Oral laquinimod for multiple sclerosis: beyond the anti-inflammatory effect. J Neurol Neurosurg Psychiatry. 2014 Aug;85(8):832. doi: 10.1136/jnnp-2013-306326. Epub 2013 Sep 17. PubMed PMID: 24046393.

14: Filippi M, Rocca MA, Pagani E, De Stefano N, Jeffery D, Kappos L, Montalban X, Boyko AN, Comi G; ALLEGRO Study Group. Placebo-controlled trial of oral laquinimod in multiple sclerosis: MRI evidence of an effect on brain tissue damage. J Neurol Neurosurg Psychiatry. 2014 Aug;85(8):851-8. doi: 10.1136/jnnp-2013-306132. Epub 2013 Sep 12. PubMed PMID: 24029546.

15: He D, Han K, Gao X, Dong S, Chu L, Feng Z, Wu S. Laquinimod for multiple sclerosis. Cochrane Database Syst Rev. 2013 Aug 6;8:CD010475. doi: 10.1002/14651858.CD010475.pub2. Review. PubMed PMID: 23922214.

16: Lund BT, Kelland EE, Hayardeny L, Barilan O, Gilmore W, Weiner LP. Assessment of changes in immune measures of multiple sclerosis patients treated with laquinimod. J Neuroimmunol. 2013 Oct 15;263(1-2):108-15. doi: 10.1016/j.jneuroim.2013.07.008. Epub 2013 Aug 6. PubMed PMID: 23920036.

17: Boĭko AN, Gusev EI. [Laquinimod is an oral drug with a marked neuroprotective effect for pathogenetic treatment of multiple sclerosis(review)]. Zh Nevrol Psikhiatr Im S S Korsakova. 2013;113(2 Pt 2):93-9. Review. Russian. PubMed PMID: 23675607.

18: Jolivel V, Luessi F, Masri J, Kraus SH, Hubo M, Poisa-Beiro L, Klebow S, Paterka M, Yogev N, Tumani H, Furlan R, Siffrin V, Jonuleit H, Zipp F, Waisman A. Modulation of dendritic cell properties by laquinimod as a mechanism for modulating multiple sclerosis. Brain. 2013 Apr;136(Pt 4):1048-66. doi: 10.1093/brain/awt023. Epub 2013 Mar 20. PubMed PMID: 23518712.

19: Ruffini F, Rossi S, Bergamaschi A, Brambilla E, Finardi A, Motta C, Studer V, Barbieri F, De Chiara V, Hayardeny L, Comi G, Centonze D, Martino G. Laquinimod prevents inflammation-induced synaptic alterations occurring in experimental autoimmune encephalomyelitis. Mult Scler. 2013 Jul;19(8):1084-94. doi: 10.1177/1352458512469698. Epub 2012 Dec 11. PubMed PMID: 23232603.

20: Toubi E, Nussbaum S, Staun-Ram E, Snir A, Melamed D, Hayardeny L, Miller A. Laquinimod modulates B cells and their regulatory effects on T cells in multiple sclerosis. J Neuroimmunol. 2012 Oct 15;251(1-2):45-54. doi: 10.1016/j.jneuroim.2012.07.003. Epub 2012 Jul 28. PubMed PMID: 22846497.

Laquinimod

100.0mg / USD 150.0


Additional Information

  Related CAS#
248281-84-7(Laquinimod) 248282-07-7(Laquinimod Sodium)