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
Structure for Laquinimod (DB06685)
- Weight
- Average: 356.81
Monoisotopic: 356.0927701 - Chemical Formula
- C19H17ClN2O3
- Synonyms
- Laquinimod
- External IDs
- ABR 215062
- ABR-215062
Pharmacology
- Indication
Investigated for use/treatment in multiple sclerosis.
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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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.
Hover over products below to view reaction partners
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Laquinimod can be increased when it is combined with Abametapir. Amiodarone The metabolism of Laquinimod can be decreased when combined with Amiodarone. Amprenavir The metabolism of Laquinimod can be decreased when combined with Amprenavir. Apalutamide The metabolism of Laquinimod can be increased when combined with Apalutamide. Aprepitant The metabolism of Laquinimod can be decreased when combined with Aprepitant. Atazanavir The metabolism of Laquinimod can be decreased when combined with Atazanavir. Berotralstat The metabolism of Laquinimod can be decreased when combined with Berotralstat. Boceprevir The metabolism of Laquinimod can be decreased when combined with Boceprevir. Carbamazepine The metabolism of Laquinimod can be increased when combined with Carbamazepine. Cenobamate The serum concentration of Laquinimod can be decreased when it is combined with Cenobamate. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Laquinimod sodium 4H914M0CSP 248282-07-7 JWHPPWBIIQMBQC-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
- 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]
- 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]
- 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]
- External Links
- PubChem Compound
- 54677946
- PubChem Substance
- 347827782
- ChemSpider
- 11444966
- ChEBI
- 134738
- ChEMBL
- CHEMBL66092
- ZINC
- ZINC000100004621
- Wikipedia
- Laquinimod
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Treatment Multiple Sclerosis 3 3 Terminated Treatment Relapsing Multiple Sclerosis (RMS) 2 3 Withdrawn Treatment Relapsing Remitting Multiple Sclerosis (RRMS) 1 2 Completed Treatment Crohn's Disease (CD) 1 2 Completed Treatment Huntington's Disease (HD) 1 2 Completed Treatment Lupus Arthritis 1 2 Completed Treatment Lupus Nephritis 1 2 Completed Treatment Multiple Sclerosis, Primary Progressive 1 2 Completed Treatment Relapsing Remitting Multiple Sclerosis (RRMS) 1 2 Terminated Treatment Relapsing Remitting Multiple Sclerosis (RRMS) 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
Property Value Source Water Solubility 0.0438 mg/mL ALOGPS logP 2.77 ALOGPS logP 2.55 ChemAxon logS -3.9 ALOGPS pKa (Strongest Acidic) 5.02 ChemAxon pKa (Strongest Basic) -2.2 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 60.85 Å2 ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 97.31 m3·mol-1 ChemAxon Polarizability 35.31 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.983 Blood Brain Barrier + 0.8819 Caco-2 permeable + 0.6474 P-glycoprotein substrate Non-substrate 0.6369 P-glycoprotein inhibitor I Non-inhibitor 0.8987 P-glycoprotein inhibitor II Inhibitor 0.6333 Renal organic cation transporter Non-inhibitor 0.8013 CYP450 2C9 substrate Non-substrate 0.7842 CYP450 2D6 substrate Non-substrate 0.8278 CYP450 3A4 substrate Substrate 0.5998 CYP450 1A2 substrate Non-inhibitor 0.5961 CYP450 2C9 inhibitor Inhibitor 0.506 CYP450 2D6 inhibitor Non-inhibitor 0.8592 CYP450 2C19 inhibitor Inhibitor 0.5187 CYP450 3A4 inhibitor Non-inhibitor 0.6712 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7445 Ames test Non AMES toxic 0.6719 Carcinogenicity Non-carcinogens 0.7705 Biodegradation Not ready biodegradable 0.9957 Rat acute toxicity 2.2971 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9702 hERG inhibition (predictor II) Non-inhibitor 0.6325
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Enzymes
- 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
- 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]
- 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