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

General Information of Drug (ID: DR1425)
Drug Name
Riluzole
Synonyms
Rilutek; Riluzol; Riluzol [INN-Spanish]; Riluzole (Rilutek); Riluzolum; Riluzolum [INN-Latin]; riluzole; 1744-22-5; PK-26124; RP 54274; RP-54274; 2-Amino-6-(trifluoromethoxy)benzothiazole; 2-Benzothiazolamine, 6-(trifluoromethoxy)-; 2-amino-6-(trifluoromethoxy)benzo[d]thiazole; 2-amino-6-trifluoromethoxybenzothiazole; 6-(trifluoromethoxy)-1,3-benzothiazol-2-amine; 6-(trifluoromethoxy)benzo[d]thiazol-2-amine; 6-Trifluoromethoxy-benzothiazol-2-ylamine; Amino-2 trifluoromethoxy-6 benzothiazole; MLS000069369; UNII-7LJ087RS6F
Indication Amyotrophic lateral sclerosis [ICD11: 8B60] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 234.2 Topological Polar Surface Area 76.4
Heavy Atom Count 15 Rotatable Bond Count 1
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
5070
PubChem SID
10139 ; 855844 ; 866566 ; 3158794 ; 7379879 ; 7735262 ; 7847840 ; 7980518 ; 8153119 ; 11111722 ; 11111723 ; 11113346 ; 11120296 ; 11120784 ; 11121272 ; 11466195 ; 11467315 ; 11484335 ; 11485690 ; 11488366 ; 12013649 ; 14773880 ; 17405620 ; 24278006 ; 26679689 ; 26751529 ; 29224139 ; 46508094 ; 47440015 ; 47515108 ; 47588789 ; 47810535 ; 47810536 ; 48034873 ; 48334245 ; 49698375 ; 49890627 ; 50100339 ; 50104104 ; 50104105 ; 53778170 ; 57322593 ; 57566695 ; 57641351 ; 74971764 ; 85089205 ; 85171908 ; 85231207 ; 85787918 ; 85788320
ChEBI ID
CHEBI:8863
CAS Number
1744-22-5
TTD Drug ID
D0H0KB
Formula
C8H5F3N2OS
Canonical SMILES
C1=CC2=C(C=C1OC(F)(F)F)SC(=N2)N
InChI
1S/C8H5F3N2OS/c9-8(10,11)14-4-1-2-5-6(3-4)15-7(12)13-5/h1-3H,(H2,12,13)
InChIKey
FTALBRSUTCGOEG-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
2-Amino-6-OH-benzothiazole DM015007
33462
Unclear - Unclear 1 [6]
4-OH-riluzole DM016369
85752610
Oxidation - Aromatic hydroxylation 1 [6]
5-OH-riluzole DM015959
19063893
Oxidation - Aromatic hydroxylation 1 [6]
7-OH-riluzole DM016370
85752611
Oxidation - Aromatic hydroxylation 1 [6]
N-OH-riluzole DM015543
9859774
Oxidation - N-oxidation 1 [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009539 Riluzole 4-OH-riluzole Oxidation - Aromatic hydroxylation CYP1A1 [6]
MR009540 Riluzole 5-OH-riluzole Oxidation - Aromatic hydroxylation CYP1A1 [6]
MR009541 Riluzole 7-OH-riluzole Oxidation - Aromatic hydroxylation CYP1A1 [6]
MR009542 Riluzole N-OH-riluzole Oxidation - N-oxidation CYP1A1 ... [6]
MR009543 Riluzole 2-Amino-6-OH-benzothiazole Unclear - Unclear CYP1A1 [6]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[2]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[3]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[4]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1355 Akkermansia muciniphila Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1357 Alistipes indistinctus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1362 Bacteroides caccae Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1366 Bacteroides eggerthii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1376 Bacteroides ovatus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1379 Bacteroides stercoris Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1391 Bifidobacterium ruminatum Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1404 Clostridium sporogenes Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1420 Erysipelatoclostridium ramosum Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1435 Lactobacillus reuteri Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1445 Parabacteroides distasonis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1449 Prevotella copri Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1456 Roseburia intestinalis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1467 Subdoligranulum variabile Not Available Not Available [5]
⏷ Show the Full List of 26  DME(s)
References
1 Riluzole was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
3 Association between CYP1A2 activity and riluzole clearance in patients with amyotrophic lateral sclerosis. Br J Clin Pharmacol. 2005 Mar;59(3):310-3.
4 Involvement of human CYP1A isoenzymes in the metabolism and drug interactions of riluzole in vitro. J Pharmacol Exp Ther. 1997 Sep;282(3):1465-72.
5 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
6 Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218.

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