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

General Information of Drug (ID: DR1443)
Drug Name
FCF-89
Synonyms
LS 2616; LS-2616; Linomide; PNU-212616; ROQUINIMEX; Roquinimex [USAN:INN]; Roquinimexum; Roquinimexum [Latin]; 1,2-Dihydro-4-hydroxy-N,1-dimethyl-2-oxo-3-quinolinecarboxanilide; 372T2944C0; 4-hydroxy-N,1-dimethyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide; 84088-42-6; C18H16N2O3; CCRIS 7673; DSSTox_CID_25680; DSSTox_GSID_45680; DSSTox_RID_81054; FCF 89; FCF-89; N-phenyl-N-methyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-quinoline-3-carboxamide; NCGC00025172-01; UNII-372T2944C0
Indication Rheumatoid arthritis [ICD11: FA20] Discontinued [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 308.3 Topological Polar Surface Area 60.8
Heavy Atom Count 23 Rotatable Bond Count 2
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
54676478
ChEBI ID
CHEBI:92056
CAS Number
84088-42-6
TTD Drug ID
D0G9ZW
Formula
C18H16N2O3
Canonical SMILES
CN1C2=CC=CC=C2C(=C(C1=O)C(=O)N(C)C3=CC=CC=C3)O
InChI
1S/C18H16N2O3/c1-19(12-8-4-3-5-9-12)17(22)15-16(21)13-10-6-7-11-14(13)20(2)18(15)23/h3-11,21H,1-2H3
InChIKey
SGOOQMRIPALTEL-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
4-hydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide DM005601
54676449
Unclear 1 [2] , [3]
PNU-212679 N-Phenyl-N-methyl-2-oxo-4-hydroxy-1,2-dihydroquinoline-3-carboxamide DM005602
54682853
Unclear 1 [2] , [3]
PNU-212684 4-hydroxy-N-(4-hydroxyphenyl)-N,1-dimethyl-2-oxoquinoline-3-carboxamide DM005600
54717849
Unclear 1 [2] , [3]
PNU-213708 4,6-dihydroxy-N,1-dimethyl-2-oxo-N-phenylquinoline-3-carboxamide DM005597
54717876
Unclear 1 [2] , [3]
PNU-213831 4,8-dihydroxy-N,1-dimethyl-2-oxo-N-phenylquinoline-3-carboxamide DM005599
154699478
Unclear 1 [2] , [3]
PNU-214608 4,7-dihydroxy-N,1-dimethyl-2-oxo-N-phenylquinoline-3-carboxamide DM005598
154699823
Unclear 1 [2] , [3]
R=glucuronic acid OH or sulphate DM005603 N. A. Unclear 1 [2] , [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005966 FCF-89 PNU-213708 4,6-dihydroxy-N,1-dimethyl-2-oxo-N-phenylquinoline-3-carboxamide Unclear CYP3A4 [2], [3]
MR005967 FCF-89 PNU-214608 4,7-dihydroxy-N,1-dimethyl-2-oxo-N-phenylquinoline-3-carboxamide Unclear CYP3A4 [2], [3]
MR005968 FCF-89 PNU-213831 4,8-dihydroxy-N,1-dimethyl-2-oxo-N-phenylquinoline-3-carboxamide Unclear CYP3A4 [2], [3]
MR005969 FCF-89 PNU-212684 4-hydroxy-N-(4-hydroxyphenyl)-N,1-dimethyl-2-oxoquinoline-3-carboxamide Unclear CYP3A4 ... [2], [3]
MR005970 FCF-89 4-hydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide Unclear CYP3A4 [2], [3]
MR005971 FCF-89 PNU-212679 N-Phenyl-N-methyl-2-oxo-4-hydroxy-1,2-dihydroquinoline-3-carboxamide Unclear CYP3A4 [2], [3]
MR005972 FCF-89 R=glucuronic acid OH or sulphate Unclear Unclear [2], [3]
⏷ Show the Full List of 7 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2] , [3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
References
1 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800001478)
2 Absorption and disposition including enterohepatic circulation of (14C) roquinimex after oral administration to healthy volunteers
3 Identification of cytochrome P4503A as the major subfamily responsible for the metabolism of roquinimex in man. Xenobiotica. 2000 Sep;30(9):905-14.

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