NAV

Laquinimod

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Laquinimod
DrugBank Accession Number
DB06685
Background

Laquinimod is an immunomodulator developed by Active Biotech and produced by Teva Pharmaceutical Industries. It is currently under development in phase III trials for treatment of multiple sclerosis as an oral therapy, like fingolimod. It has been shown to reduce disease activity on magnetic resonance imaging and to be well tolerated orally.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 356.81
Monoisotopic: 356.0927701
Chemical Formula
C19H17ClN2O3
Synonyms
  • Laquinimod
External IDs
  • ABR 215062
  • ABR-215062
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Pharmacology

Indication

Investigated for use/treatment in multiple sclerosis.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Hepatic. Cytochrome P450 3A4 is the major enzyme responsible for the metabolism of laquinimod.

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Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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AbametapirThe serum concentration of Laquinimod can be increased when it is combined with Abametapir.
AmiodaroneThe metabolism of Laquinimod can be decreased when combined with Amiodarone.
AmprenavirThe metabolism of Laquinimod can be decreased when combined with Amprenavir.
ApalutamideThe serum concentration of Laquinimod can be decreased when it is combined with Apalutamide.
AprepitantThe metabolism of Laquinimod can be decreased when combined with Aprepitant.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Laquinimod sodium4H914M0CSP248282-07-7JWHPPWBIIQMBQC-UHFFFAOYSA-M

Categories

ATC Codes
N07XX10 — Laquinimod
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as aromatic anilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with an aromatic group. They have the general structure RNC(=O)R', where R= benzene, and R = aryl group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Anilides
Direct Parent
Aromatic anilides
Alternative Parents
Quinoline-3-carboxamides / Chloroquinolines / Hydroquinolones / Hydroxyquinolines / Hydroquinolines / Pyridinecarboxylic acids and derivatives / Pyridinones / Hydroxypyridines / Aryl chlorides / Tertiary carboxylic acid amides
show 11 more
Substituents
Aromatic anilide / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Carboxamide group / Carboxylic acid derivative / Chloroquinoline / Dihydroquinoline / Dihydroquinolone
show 23 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
908SY76S4G
CAS number
248281-84-7
InChI Key
GKWPCEFFIHSJOE-UHFFFAOYSA-N
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
IUPAC Name
5-chloro-N-ethyl-4-hydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide
SMILES
CCN(C(=O)C1=C(O)C2=C(C=CC=C2Cl)N(C)C1=O)C1=CC=CC=C1

References

General References
  1. Tuvesson H, Hallin I, Persson R, Sparre B, Gunnarsson PO, Seidegard J: Cytochrome P450 3A4 is the major enzyme responsible for the metabolism of laquinimod, a novel immunomodulator. Drug Metab Dispos. 2005 Jun;33(6):866-72. Epub 2005 Mar 11. [Article]
  2. Comi G, Pulizzi A, Rovaris M, Abramsky O, Arbizu T, Boiko A, Gold R, Havrdova E, Komoly S, Selmaj K, Sharrack B, Filippi M: 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. 2008 Jun 21;371(9630):2085-92. doi: 10.1016/S0140-6736(08)60918-6. [Article]
  3. 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. [Article]
PubChem Compound
54677946
PubChem Substance
347827782
ChemSpider
11444966
ChEBI
134738
ChEMBL
CHEMBL66092
ZINC
ZINC000100004621
Wikipedia
Laquinimod

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
3CompletedTreatmentMultiple Sclerosis3
3TerminatedTreatmentRelapsing Multiple Sclerosis (RMS)2
3WithdrawnTreatmentRelapsing Remitting Multiple Sclerosis (RRMS)1
2CompletedTreatmentCrohn's Disease (CD)1
2CompletedTreatmentHuntington's Disease (HD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0438 mg/mLALOGPS
logP2.77ALOGPS
logP2.55Chemaxon
logS-3.9ALOGPS
pKa (Strongest Acidic)5.02Chemaxon
pKa (Strongest Basic)-2.2Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area60.85 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity97.31 m3·mol-1Chemaxon
Polarizability35.31 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.983
Blood Brain Barrier+0.8819
Caco-2 permeable+0.6474
P-glycoprotein substrateNon-substrate0.6369
P-glycoprotein inhibitor INon-inhibitor0.8987
P-glycoprotein inhibitor IIInhibitor0.6333
Renal organic cation transporterNon-inhibitor0.8013
CYP450 2C9 substrateNon-substrate0.7842
CYP450 2D6 substrateNon-substrate0.8278
CYP450 3A4 substrateSubstrate0.5998
CYP450 1A2 substrateNon-inhibitor0.5961
CYP450 2C9 inhibitorInhibitor0.506
CYP450 2D6 inhibitorNon-inhibitor0.8592
CYP450 2C19 inhibitorInhibitor0.5187
CYP450 3A4 inhibitorNon-inhibitor0.6712
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7445
Ames testNon AMES toxic0.6719
CarcinogenicityNon-carcinogens0.7705
BiodegradationNot ready biodegradable0.9957
Rat acute toxicity2.2971 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9702
hERG inhibition (predictor II)Non-inhibitor0.6325
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0039000000-d3633e10621621c04bfe
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-2029000000-fc6639ecf3be16fd4a4e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0aba-0925000000-35f979de86ae3b38bf2a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0019-9788000000-5cbfc3b7f86c643632d0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fki-1891000000-fb9759fb179a44d02d01
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-4923000000-d7f5cd346e6ad92f27e6
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-183.66238
predicted
DeepCCS 1.0 (2019)
[M+H]+186.02037
predicted
DeepCCS 1.0 (2019)
[M+Na]+193.11382
predicted
DeepCCS 1.0 (2019)

Enzymes

Details1. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Tuvesson H, Hallin I, Persson R, Sparre B, Gunnarsson PO, Seidegard J: Cytochrome P450 3A4 is the major enzyme responsible for the metabolism of laquinimod, a novel immunomodulator. Drug Metab Dispos. 2005 Jun;33(6):866-72. Epub 2005 Mar 11. [Article]
  2. Fernandez O: Oral laquinimod treatment in multiple sclerosis. Neurologia. 2011 Mar;26(2):111-7. doi: 10.1016/j.nrl.2010.07.027. [Article]

Drug created at March 19, 2008 16:49 / Updated at February 21, 2021 18:52