Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0918)
Drug Name
TV-5600
Synonyms
Laquinimod; Laquinimod (ABR-215062); 248281-84-7; 5-CHLORO-N-ETHYL-4-HYDROXY-1-METHYL-2-OXO-N-PHENYL-1,2-DIHYDROQUINOLINE-3-CARBOXAMIDE; 5-Chloro-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid ethyl-phenyl-amide; 5-chloro-n-ethyl-2-hydroxy-1-methyl-4-oxo-n-phenyl-1,4-dihydroquinoline-3-carboxamide; 908SY76S4G; ABR 215062; ABR-215062; C19H17ClN2O3; MFCD08689859; N-Ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxoquinoline-3-carboxamide; UNII-908SY76S4G
Indication Lupus erythematosus [ICD11: 4A40] Phase 3 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 356.8 Topological Polar Surface Area 60.8
Heavy Atom Count 25 Rotatable Bond Count 3
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
54677946
PubChem SID
14876590 ; 30420153 ; 39226871 ; 53789660 ; 55415688 ; 57399789 ; 80696753 ; 93309883 ; 103144721 ; 103258758 ; 109693522 ; 113461713 ; 117465054 ; 125580534 ; 126659568 ; 126671487 ; 127968532 ; 135135025 ; 135684163 ; 136375556 ; 136920402 ; 136946440 ; 137003754 ; 137267594 ; 142657125 ; 144116129 ; 152159598 ; 152254807 ; 152258415 ; 152343588 ; 160817546 ; 162011445 ; 162036243 ; 162192335 ; 163090687 ; 163686051 ; 164761535 ; 170503204 ; 172092778 ; 174007071 ; 174477470 ; 174528534 ; 179150222 ; 180672675 ; 185974774 ; 185974775 ; 185974776 ; 198987470 ; 204386312 ; 223365974
ChEBI ID
CHEBI:134738
CAS Number
248281-84-7
TTD Drug ID
D0JN5N
Formula
C19H17ClN2O3
Canonical SMILES
CCN(C1=CC=CC=C1)C(=O)C2=C(C3=C(C=CC=C3Cl)N(C2=O)C)O
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
5-chloro-4-hydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide DM006019
434122491
Oxidation - N-dealkylation 1 [3]
5-chloro-N-ethyl-4,6-dihydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide DM006023
434123016
Oxidation - Aromatic hydroxylation 1 [3]
5-chloro-N-ethyl-4,7-dihydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide DM006022
434123079
Oxidation - Aromatic hydroxylation 1 [3]
5-chloro-N-ethyl-4,8-dihydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide DM006021
434123122
Oxidation - Aromatic hydroxylation 1 [3]
5-chloro-N-ethyl-4-hydroxy-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide DM006020
434123559
Oxidation - N-dealkylation 1 [3]
5-chloro-N-ethyl-4-hydroxy-N-(4-hydroxyphenyl)-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide DM006018
434122851
Oxidation - Aromatic hydroxylation 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006479 TV-5600 5-chloro-N-ethyl-4-hydroxy-N-(4-hydroxyphenyl)-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide Oxidation - Aromatic hydroxylation CYP3A4 [3]
MR006480 TV-5600 5-chloro-4-hydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide Oxidation - N-dealkylation CYP3A4 [3]
MR006481 TV-5600 5-chloro-N-ethyl-4-hydroxy-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide Oxidation - N-dealkylation CYP3A4 [3]
MR006482 TV-5600 5-chloro-N-ethyl-4,8-dihydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide Oxidation - Aromatic hydroxylation CYP3A4 [3]
MR006483 TV-5600 5-chloro-N-ethyl-4,7-dihydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide Oxidation - Aromatic hydroxylation CYP3A4 [3]
MR006484 TV-5600 5-chloro-N-ethyl-4,6-dihydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide Oxidation - Aromatic hydroxylation CYP3A4 [3]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
References
1 ClinicalTrials.gov (NCT01047319) A Study to Evaluate the Long-term Safety, Tolerability and Effect of Daily Oral Laquinimod 0.6 mg on Disease Course in Subjects With Relapsing Multiple Sclerosis.
2 Oral laquinimod treatment in multiple sclerosis. Neurologia. 2011 Mar;26(2):111-7.
3 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.

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