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

General Information of Drug (ID: DR1723)
Drug Name
Zafirlukast
Synonyms
Zafirlukast (Accolate); Aeronix; Olmoran; Vanticon; XZ629S5L50; zafirlukast; 107753-78-6; Accolate; Accoleit; C31H33N3O6S; CHEBI:10100; CHEMBL603; CPD000466316; Cyclopentyl (3-(2-methoxy-4-((o-tolylsulfonyl)carbamoyl)benzyl)-1-methyl-1H-indol-5-yl)carbamate; Cyclopentyl 3-(2-methoxy-4-((o-tolylsulfonyl)carbamoyl)benzyl)-1-methylindole-5-carbamate; DSSTox_CID_3746; DSSTox_GSID_23746; DSSTox_RID_77181; ICI 204,219; ICI 204219; ICI-204219; MFCD00864775; NCGC00164547-01; NCGC00164547-06; UNII-XZ629S5L50
Indication Asthma [ICD11: CA23] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 575.7 Topological Polar Surface Area 124
Heavy Atom Count 41 Rotatable Bond Count 9
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
5717
PubChem SID
9415 ; 5366114 ; 7847477 ; 7980903 ; 8148198 ; 8153502 ; 11528636 ; 12014035 ; 14788829 ; 26719823 ; 26757966 ; 29224754 ; 46386595 ; 46506874 ; 48416705 ; 49681658 ; 53788583 ; 57322909 ; 75347132 ; 81041165 ; 81092894 ; 85209709 ; 92308342 ; 92308866 ; 93166425 ; 103183576 ; 103922131 ; 104219525 ; 104253269 ; 104310052 ; 117890551 ; 124659012 ; 124757391 ; 124893156 ; 124893157 ; 124893158 ; 124893159 ; 125164195 ; 125335352 ; 126616863 ; 126658431 ; 126665183 ; 127318333 ; 127318334 ; 127318335 ; 127318336 ; 127318337 ; 127318338 ; 127318339 ; 127318340
ChEBI ID
ChEBI:10100
CAS Number
107753-78-6
TTD Drug ID
D05DVP
Formula
C31H33N3O6S
Canonical SMILES
CC1=CC=CC=C1S(=O)(=O)NC(=O)C2=CC(=C(C=C2)CC3=CN(C4=C3C=C(C=C4)NC(=O)OC5CCCC5)C)OC
InChI
1S/C31H33N3O6S/c1-20-8-4-7-11-29(20)41(37,38)33-30(35)22-13-12-21(28(17-22)39-3)16-23-19-34(2)27-15-14-24(18-26(23)27)32-31(36)40-25-9-5-6-10-25/h4,7-8,11-15,17-19,25H,5-6,9-10,16H2,1-3H3,(H,32,36)(H,33,35)
InChIKey
YEEZWCHGZNKEEK-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
Zafirlukast metabolite M1 DM005326
11454035
Hydrolysis - Hydrolysis 1 [5] , [6]
Zafirlukast metabolite M5 DM005330
71549171
Unclear 1 [5] , [6]
Zafirlukast metabolite M6 DM020013 N. A. Unclear 1 [5] , [6]
Zafirlukast metabolite M2 DM005327
71549040
Unclear 2 [5] , [6]
Zafirlukast metabolite M7 DM020014 N. A. Unclear 2 [5] , [6]
Zafirlukast metabolite M8 DM005331
44461163
Unclear 2 [5] , [6]
Zafirlukast metabolite M3 DM005329
71549172
Unclear 3 [5] , [6]
Zafirlukast metabolite M4 DM005328
71549170
Oxidation - Methyl-hydroxylation 3 [5] , [6]
Zafirlukast metabolite M7 DM020014 N. A. Unclear 3 [5] , [6]
Zafirlukast metabolite M3 DM005329
71549172
Unclear 4 [5] , [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013278 Zafirlukast Zafirlukast metabolite M1 Hydrolysis - Hydrolysis Unclear [5], [6]
MR013282 Zafirlukast Zafirlukast metabolite M5 Unclear CYP2C9 ... [5], [6]
MR013286 Zafirlukast Zafirlukast metabolite M6 Unclear CYP2C9 ... [5], [6]
MR013279 Zafirlukast metabolite M1 Zafirlukast metabolite M2 Unclear NAT1 ... [5], [6]
MR013283 Zafirlukast metabolite M5 Zafirlukast metabolite M8 Unclear Unclear [5], [6]
MR013287 Zafirlukast metabolite M6 Zafirlukast metabolite M7 Unclear Unclear [5], [6]
MR013280 Zafirlukast metabolite M2 Zafirlukast metabolite M4 Oxidation - Methyl-hydroxylation Unclear [5], [6]
MR013284 Zafirlukast metabolite M8 Zafirlukast metabolite M3 Unclear Unclear [5], [6]
MR013285 Zafirlukast metabolite M8 Zafirlukast metabolite M7 Unclear Unclear [5], [6]
MR013281 Zafirlukast metabolite M4 Zafirlukast metabolite M3 Unclear Unclear [5], [6]
⏷ Show the Full List of 10 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_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]
N-acetyltransferase 1 (NAT1) DME0050 Homo sapiens
ARY1_HUMAN
2.3.1.5
[5] , [6]
N-acetyltransferase 2 (NAT2) DME0051 Homo sapiens
ARY2_HUMAN
2.3.1.5
[5] , [6]
Prostaglandin G/H synthase 1 (COX-1) DME0091 Homo sapiens
PGH1_HUMAN
1.14.99.1
[5]
⏷ Show the Full List of 6  DME(s)
References
1 Zafirlukast was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Pioglitazone is metabolised by CYP2C8 and CYP3A4 in vitro: potential for interactions with CYP2C8 inhibitors. Basic Clin Pharmacol Toxicol. 2006 Jul;99(1):44-51.
3 Potential of pranlukast and zafirlukast in the inhibition of human liver cytochrome P450 enzymes. Xenobiotica. 2004 May;34(5):429-38.
4 Fluconazole but not the CYP3A4 inhibitor, itraconazole, increases zafirlukast plasma concentrations. Eur J Clin Pharmacol. 2012 May;68(5):681-8.
5 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.
6 Metabolism and excretion of zafirlukast in dogs, rats, and mice

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