Laquinimod
This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Name
- Laquinimod
- Accession Number
- DB06685
- Description
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.
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- 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 Unlock Additional DataAbametapir The serum concentration of Laquinimod can be increased when it is combined with Abametapir. Cenobamate The serum concentration of Laquinimod can be decreased when it is combined with Cenobamate. Haloperidol The serum concentration of Haloperidol can be increased when it is combined with Laquinimod. Metreleptin The metabolism of Laquinimod can be increased when combined with Metreleptin. Pitolisant The serum concentration of Laquinimod can be decreased when it is combined with Pitolisant. Ritonavir The serum concentration of Laquinimod can be increased when it is combined with Ritonavir. Satralizumab The serum concentration of Laquinimod can be decreased when it is combined with Satralizumab. Tucatinib The metabolism of Tucatinib can be decreased when combined with Laquinimod. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
Products
- 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
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. [PubMed:15764719]
- 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. [PubMed:18572078]
- 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. [PubMed:15465591]
- 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 Disseminated 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 Multiple Sclerosis, Primary Progressive 1 2 Completed Treatment Nephritis, Lupus 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. [PubMed:15764719]
- Fernandez O: Oral laquinimod treatment in multiple sclerosis. Neurologia. 2011 Mar;26(2):111-7. doi: 10.1016/j.nrl.2010.07.027. [PubMed:21163185]
Drug created on March 19, 2008 10:49 / Updated on June 12, 2020 10:52
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