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

General Information of Drug (ID: DR1111)
Drug Name
Montelukast sodium
Synonyms
Montelukast (sodium); Montelukast sodium [USAN]; Montelukast sodium salt; Montelukast [INN:BAN]; Singular; montelukast; (R-(E))-1-(((1-(3-(2-(7-Chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropaneacetic acid; 1-((((1R)-1-(3-((1E)-2-(7-Chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropaneacetic acid; 158966-92-8; CHEBI:50730; CHEMBL787; UNII-MHM278SD3E; MHM278SD3E; U1O3J18SFL; 151767-02-1; CHEBI:6993; CPD000469188; Cyclopropaneacetic acid, 1-[[[(1R)-1-[3-[(1E)-2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]methyl]-, sodium salt (1:1); DSSTox_CID_26450; DSSTox_GSID_46450; DSSTox_RID_81624; UNII-U1O3J18SFL; MK 476; MK-0476; MK-476; MONTELUKAST Na; MONTELUKAST SODIUM; Montair
Indication Asthma [ICD11: CA23] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 608.2 Topological Polar Surface Area 98.6
Heavy Atom Count 42 Rotatable Bond Count 12
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
23663996
ChEBI ID
CHEBI:6993
CAS Number
151767-02-1
TTD Drug ID
D00QET
Formula
C35H35ClNNaO3S
Canonical SMILES
CC(C)(C1=CC=CC=C1CCC(C2=CC=CC(=C2)C=CC3=NC4=C(C=CC(=C4)Cl)C=C3)SCC5(CC5)CC(=O)[O-])O.[Na+]
InChI
1S/C35H36ClNO3S.Na/c1-34(2,40)30-9-4-3-7-25(30)13-17-32(41-23-35(18-19-35)22-33(38)39)27-8-5-6-24(20-27)10-15-29-16-12-26-11-14-28(36)21-31(26)37-29;/h3-12,14-16,20-21,32,40H,13,17-19,22-23H2,1-2H3,(H,38,39);/q;+1/p-1/b15-10+;/t32-;/m1./s1
InChIKey
LBFBRXGCXUHRJY-HKHDRNBDSA-M
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
21-Hydroxymontelukast DM004473
11801753
Oxidation - Aliphatic hydroxylation 1 [2]
21-Hydroxymontelukast DM004473
11801753
Oxidation - Hydrolyzationn 1 [2] , [4]
25-OH Montelukast DM004479
71587626
Unclear 1 [4]
Montelukast 1, 2-Diol DM004467
9960377
Oxidation - Methyl-hydroxylation 1 [2]
Montelukast 1, 2-Diol DM004467
9960377
Oxidation - Aliphatic hydroxylation 1 [2]
Montelukast ether glucuronide DM004480 N. A. Unclear 1 [4]
Montelukast metabolite M1 DM004469
11061671
Conjugation - O-glucuronidation 1 [2] , [4]
Montelukast metabolite M2a/b DM004470
15297728
Oxidation - S-oxidation 1 [2] , [4]
Montelukast metabolite M2a/b DM004470
15297728
Unclear 1 [2]
Montelukast metabolite M5a DM004472
10841306
Oxidation - Aliphatic hydroxylation 1 [2]
Montelukast metabolite M5a DM004472
10841306
Oxidation - Hydrolyzationn 1 [2] , [4]
Montelukast metabolite M5b DM004473
10841306
Oxidation - Aliphatic hydroxylation 1 [2]
Montelukast metabolite M5b DM004473
10841306
Oxidation - Hydrolyzationn 1 [2] , [4]
Montelukast dicarboxylic acid DM004468
9873776
Unclear 2 [4]
⏷ Show the Full List of 14  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004796 Montelukast sodium Montelukast 1, 2-Diol Oxidation - Aliphatic hydroxylation CYP2C9 [2]
MR004798 Montelukast sodium Montelukast metabolite M1 Conjugation - O-glucuronidation UGT1A3 [2], [4]
MR004799 Montelukast sodium Montelukast metabolite M2a/b Unclear CYP3A4 ... [2]
MR004800 Montelukast sodium Montelukast metabolite M5a Oxidation - Hydrolyzationn CYP3A4 ... [2], [4]
MR004801 Montelukast sodium Montelukast metabolite M5b Oxidation - Hydrolyzationn CYP3A4 ... [2], [4]
MR004802 Montelukast sodium 25-OH Montelukast Unclear CYP2C8 ... [4]
MR004803 Montelukast sodium Montelukast ether glucuronide Unclear UGT1A3 [4]
MR004797 Montelukast 1, 2-Diol Montelukast dicarboxylic acid Unclear CYP2C8 [4]
⏷ Show the Full List of 8 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2A6 (CYP2A6) DME0005 Homo sapiens
CP2A6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[2] , [4]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[4]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[4]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[2] , [4]
⏷ Show the Full List of 8  DME(s)
References
1 Montelukast Sodium was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 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.
3 Determinants of cytochrome P450 2C8 substrate binding: structures of complexes with montelukast, troglitazone, felodipine, and 9-cis-retinoic acid. J Biol Chem. 2008 Jun 20;283(25):17227-37.
4 In vitro metabolism of montelukast by cytochrome P450s and UDP-glucuronosyltransferases. Drug Metab Dispos. 2015 Dec;43(12):1905-16.

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