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

General Information of Drug (ID: DR1684)
Drug Name
Vilanterol
Synonyms
Vilanterol; Vilanterol (USAN); Vilanterol [USAN:INN]; Vilanterol base; ZINC3991624; vilanterolum; 028LZY775B; 4-((1R)-2-((6-(2-((2,6-dichlorophenyl)methoxy)ethoxy)hexyl)amino)-1-hydroxyethyl)-2-(hydroxymethyl)phenol; 4-[(1R)-2-[(6-{2-[(2,6-dichlorophenyl)methoxy]ethoxy}hexyl)amino]-1-hydroxyethyl]-2-(hydroxymethyl)phenol; DAFYYTQWSAWIGS-DEOSSOPVSA-N; SCHEMBL142630; 503068-34-6; BCP25897; CHEBI:75037; CHEMBL1198857; DTXSID80198318; EX-A2177; GTPL7353; GW 642444; GW 642444X; GW-642444x; GW642444x; MFCD18782703; UNII-028LZY775B
Indication Asthma [ICD11: CA23] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 486.4 Topological Polar Surface Area 91.2
Heavy Atom Count 32 Rotatable Bond Count 16
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
10184665
PubChem SID
15180153 ; 22579535 ; 40274235 ; 80028218 ; 124490436 ; 135291438 ; 137063375 ; 160677153 ; 163365084 ; 163835568 ; 175268108 ; 178103925 ; 210275079 ; 210280717 ; 223936788 ; 226509475 ; 242700176 ; 250184675 ; 251963097 ; 252224058
ChEBI ID
ChEBI:75037
CAS Number
503068-34-6
TTD Drug ID
D0L0GM
Formula
C24H33Cl2NO5
Canonical SMILES
C1=CC(=C(C(=C1)Cl)COCCOCCCCCCNCC(C2=CC(=C(C=C2)O)CO)O)Cl
InChI
1S/C24H33Cl2NO5/c25-21-6-5-7-22(26)20(21)17-32-13-12-31-11-4-2-1-3-10-27-15-24(30)18-8-9-23(29)19(14-18)16-28/h5-9,14,24,27-30H,1-4,10-13,15-17H2/t24-/m0/s1
InChIKey
DAFYYTQWSAWIGS-DEOSSOPVSA-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
Vilanterol metabolite M16 DM005264
156596409
Oxidation - Oxidationn 1 [3]
Vilanterol metabolite M20 DM005266
73425539
Oxidation - N-dealkylation 1 [3]
Vilanterol metabolite M26 DM005265
156596396
Oxidation - C-dealkylation 1 [3]
Vilanterol metabolite M29 DM005262
46832227
Oxidation - O-dealkylation 1 [3]
Vilanterol metabolite M30 DM005260
101649722
Oxidation - O-dealkylation 1 [3]
Vilanterol metabolite M33 DM005263
146675120
Oxidation - O-dealkylation 1 [3]
Vilanterol metabolite M1 DM005261
156028111
Conjugation - Glucuronidation 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013228 Vilanterol Vilanterol metabolite M30 Oxidation - O-dealkylation Unclear [3]
MR013230 Vilanterol Vilanterol metabolite M29 Oxidation - O-dealkylation Unclear [3]
MR013231 Vilanterol Vilanterol metabolite M33 Oxidation - O-dealkylation Unclear [3]
MR013232 Vilanterol Vilanterol metabolite M16 Oxidation - Oxidationn Unclear [3]
MR013233 Vilanterol Vilanterol metabolite M26 Oxidation - C-dealkylation Unclear [3]
MR013234 Vilanterol Vilanterol metabolite M20 Oxidation - N-dealkylation Unclear [3]
MR013229 Vilanterol metabolite M30 Vilanterol metabolite M1 Conjugation - Glucuronidation Unclear [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 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
References
1 Vilanterol was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 The effect of ketoconazole on the pharmacokinetics and pharmacodynamics of inhaled fluticasone furoate and vilanterol trifenatate in healthy subjects. Br J Clin Pharmacol. 2013 Jun;75(6):1478-87.
3 Metabolism and disposition of vilanterol, a long-acting (2)-adrenoceptor agonist for inhalation use in humans

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