Details of the Drug

General Information of Drug (ID: DM3IWS8)

Drug Name
Laquinimod
Synonyms
Laquinimod; 248281-84-7; 5-CHLORO-N-ETHYL-4-HYDROXY-1-METHYL-2-OXO-N-PHENYL-1,2-DIHYDROQUINOLINE-3-CARBOXAMIDE; ABR-215062; ABR 215062; 5-Chloro-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid ethyl-phenyl-amide; UNII-908SY76S4G; CIVENTICHEM CV-4057; Laquinimod (ABR-215062); 908SY76S4G; N-Ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxoquinoline-3-carboxamide; 5-chloro-n-ethyl-2-hydroxy-1-methyl-4-oxo-n-phenyl-1,4-dihydroquinoline-3-carboxamide; C19H17ClN2O3
Indication
Disease Entry ICD 11 Status REF
Lupus 4A40 Phase 3 [1]
Multiple sclerosis 8A40 Phase 3 [2]
Huntington disease 8A01.10 Phase 2 [3]
Primary progressive multiple sclerosis 8A40.1 Phase 2 [2]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 356.8
Logarithm of the Partition Coefficient (xlogp) 3.7
Rotatable Bond Count (rotbonds) 3
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 3
ADMET Property
Metabolism
The drug is metabolized via the hepatic []
Chemical Identifiers
Formula
C19H17ClN2O3
IUPAC Name
5-chloro-N-ethyl-4-hydroxy-1-methyl-2-oxo-N-phenylquinoline-3-carboxamide
Canonical SMILES
CCN(C1=CC=CC=C1)C(=O)C2=C(C3=C(C=CC=C3Cl)N(C2=O)C)O
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
InChIKey
GKWPCEFFIHSJOE-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
54677946
ChEBI ID
CHEBI:134738
CAS Number
248281-84-7
DrugBank ID
DB06685
TTD ID
D0JN5N
INTEDE ID
DR0918
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Nuclear factor NF-kappa-B (NFKB) TTSXVID NFKB1_HUMAN ; NFKB2_HUMAN ; TF65_HUMAN ; RELB_HUMAN ; REL_HUMAN Modulator [4]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cytochrome P450 1A1 (CYP1A1) OTE4EFH8 CP1A1_HUMAN Gene/Protein Processing [6]
Cytochrome P450 1B1 (CYP1B1) OTYXFLSD CP1B1_HUMAN Gene/Protein Processing [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Lupus
ICD Disease Classification 4A40
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Nuclear factor NF-kappa-B (NFKB) DTT NFKB1; NFKB2; RELA; RELB; REL 5.39E-01 0.16 0.27
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 7.29E-03 -3.47E-02 -1.80E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7639).
2 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
3 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
4 Reduced astrocytic NF- B activation by laquinimod protects from cuprizone-induced demyelination. Acta Neuropathol. 2012 Sep;124(3):411-24.
5 Oral laquinimod treatment in multiple sclerosis. Neurologia. 2011 Mar;26(2):111-7.
6 Assessing anti-estrogenic effects of AHR ligands in primary human and rat endometrial epithelial cells. Reprod Toxicol. 2020 Sep;96:202-208. doi: 10.1016/j.reprotox.2020.07.003. Epub 2020 Jul 12.