laquinimod   Click here for help

GtoPdb Ligand ID: 7639

Synonyms: ABR-215062 | TV-5600
Compound class: Synthetic organic
Comment: Laquinimod is an experimental immunomodulator being investigated as an oral treatment for multiple sclerosis (MS) [2-5].
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 62.54
Molecular weight 356.09
XLogP 5.05
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CCN(C(=O)c1c(O)c2c(Cl)cccc2n(c1=O)C)c1ccccc1
Isomeric SMILES CCN(C(=O)c1c(O)c2c(Cl)cccc2n(c1=O)C)c1ccccc1
InChI 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
InChI Key GKWPCEFFIHSJOE-UHFFFAOYSA-N
References
1. Brunmark C, Runström A, Ohlsson L, Sparre B, Brodin T, Aström M, Hedlund G. (2002)
The new orally active immunoregulator laquinimod (ABR-215062) effectively inhibits development and relapses of experimental autoimmune encephalomyelitis.
J Neuroimmunol, 130 (1-2): 163-72. [PMID:12225898]
2. Comi G, Jeffery D, Kappos L, Montalban X, Boyko A, Rocca MA, Filippi M, ALLEGRO Study Group. (2012)
Placebo-controlled trial of oral laquinimod for multiple sclerosis.
N Engl J Med, 366 (11): 1000-9. [PMID:22417253]
3. Comi G, Pulizzi A, Rovaris M, Abramsky O, Arbizu T, Boiko A, Gold R, Havrdova E, Komoly S, Selmaj K et al.. (2008)
Effect of laquinimod on MRI-monitored disease activity in patients with relapsing-remitting multiple sclerosis: a multicentre, randomised, double-blind, placebo-controlled phase IIb study.
Lancet, 371 (9630): 2085-92. [PMID:18572078]
4. Jönsson S, Andersson G, Fex T, Fristedt T, Hedlund G, Jansson K, Abramo L, Fritzson I, Pekarski O, Runström A et al.. (2004)
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, 47 (8): 2075-88. [PMID:15056005]
5. Keegan BM, Weinshenker BG. (2008)
Laquinimod, a new oral drug for multiple sclerosis.
Lancet, 371 (9630): 2059-60. [PMID:18572062]
6. Zou LP, Abbas N, Volkmann I, Nennesmo I, Levi M, Wahren B, Winblad B, Hedlund G, Zhu J. (2002)
Suppression of experimental autoimmune neuritis by ABR-215062 is associated with altered Th1/Th2 balance and inhibited migration of inflammatory cells into the peripheral nerve tissue.
Neuropharmacology, 42 (5): 731-9. [PMID:11985832]