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

General Information of Drug (ID: DR1730)
Drug Name
Zileuton
Synonyms
Zileutonum; Zileutonum [INN-Latin]; Zyflo (TN); Zyflo CR; Leutrol; ZILEUTON; (+-)-1-(1-Benzo(b)thien-2-ylethyl)-1-hydroxyurea; 1-(1-(Benzo[b]thiophen-2-yl)ethyl)-1-hydroxyurea; 1-[1-(1-benzothien-2-yl)ethyl]-1-hydroxyurea; 1-[1-(1-benzothiophen-2-yl)ethyl]-1-hydroxyurea; 111406-87-2; A 64077; A-64077; ABBOTT-64077; Abbott 64077; C11H12N2O2S; CHEBI:10112; CHEMBL93; N-(1-Benzo(b)thien-2-ylethyl)-N-hydroxyurea; N-[1-(benzo[b]thiophen-2-yl)ethyl]-N-hydroxyurea; Urea, N-(1-benzo[b]thien-2-ylethyl)-N-hydroxy-; Zyflo
Indication Asthma [ICD11: CA23] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 236.29 Topological Polar Surface Area 94.8
Heavy Atom Count 16 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
60490
PubChem SID
6596772 ; 7847480 ; 7980907 ; 8186886 ; 11467118 ; 11528751 ; 12014274 ; 14718475 ; 14749468 ; 26719885 ; 29215400 ; 43117882 ; 46386751 ; 46506394 ; 48416711 ; 48428761 ; 49681668 ; 53787380 ; 57314021 ; 78313368 ; 92307976 ; 92308490 ; 92308868 ; 92712341 ; 99437271 ; 103172204 ; 103857276 ; 103915089 ; 104320888 ; 104828550 ; 118048365 ; 118055406 ; 124658902 ; 124757252 ; 124801354 ; 124892201 ; 124892202 ; 125164056 ; 125333651 ; 126592904 ; 126625644 ; 126635297 ; 126682817 ; 128657786 ; 134337882 ; 135016842 ; 135565945 ; 135692156 ; 137171648 ; 140137208
ChEBI ID
ChEBI:10112
CAS Number
111406-87-2
TTD Drug ID
D09JUG
Formula
C11H12N2O2S
Canonical SMILES
CC(C1=CC2=CC=CC=C2S1)N(C(=O)N)O
InChI
1S/C11H12N2O2S/c1-7(13(15)11(12)14)10-6-8-4-2-3-5-9(8)16-10/h2-7,15H,1H3,(H2,12,14)
InChIKey
MWLSOWXNZPKENC-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
Dehydroxyzyleuton DM005344
10104880
Reduction - N-dehydroxylation 1 [4] , [2]
Hydroxyzileuton DM005347
131750722
Oxidation - Hydrolyzationn 1 [4] , [2]
Zileuton O-glucuronide metabolite DM005349
71752997
Conjugation - N-hydroxy glucuronidation 1 [4] , [2]
Zileuton sulfoxide DM005348
71752998
Oxidation - Sulfoxidation 1 [4] , [2]
Dehydroxyzileuton sulfoxide metabolite DM005345
154699738
Oxidation - Sulfoxidation 2 [4] , [2]
OH-dehydroxyzileuton DM005346 N. A. Oxidation - Hydrolyzationn 2 [4] , [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013296 Zileuton Dehydroxyzyleuton Reduction - N-dehydroxylation Unclear [4], [2]
MR013299 Zileuton Hydroxyzileuton Oxidation - Hydrolyzationn CYP2C9 ... [4], [2]
MR013300 Zileuton Zileuton sulfoxide Oxidation - Sulfoxidation CYP3A4 [4], [2]
MR013301 Zileuton Zileuton O-glucuronide metabolite Conjugation - N-hydroxy glucuronidation UGT1A9 [4], [2]
MR013297 Dehydroxyzyleuton Dehydroxyzileuton sulfoxide metabolite Oxidation - Sulfoxidation CYP3A4 [4], [2]
MR013298 Dehydroxyzyleuton OH-dehydroxyzileuton Oxidation - Hydrolyzationn CYP2C9 ... [4], [2]
⏷ 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 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Prostaglandin G/H synthase 1 (COX-1) DME0091 Homo sapiens
PGH1_HUMAN
1.14.99.1
[4]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[4]
References
1 Zileuton was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218.
3 Identification of the human liver cytochrome P450 enzymes involved in the metabolism of zileuton (ABT-077) and its N-dehydroxylated metabolite, Abbott-66193. Drug Metab Dispos. 1995 Oct;23(10):1163-74.
4 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.

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