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

General Information of Drug (ID: DR1460)
Drug Name
Salmeterol xinafoate
Synonyms
Salmetedur; Salmeterol (xinafoate); Salmeterol 1-hydroxy-2-naphthoate; Salmeterol xinafonate; Serevent Inhaler and Disks; Serevent diskus; Salmeterol; Salmeterolum; Salmeterolum [Latin]; Serevent; (+-)-4-Hydroxy-alpha'-(((6-(4-phenylbutoxy)hexyl)amino)methyl)-m-xylene-alpha,alpha'-diol; (+-)-4-Hydroxy-alpha1-(((6-(4-phenylbutoxy)hexyl)amino)methyl)-1,3-benzenedimethanol; 136112-01-1; 2-(hydroxymethyl)-4-(1-hydroxy-2-{[6-(4-phenylbutoxy)hexyl]amino}ethyl)phenol; 2-(hydroxymethyl)-4-[1-hydroxy-2-[6-(4-phenylbutoxy)hexylamino]ethyl]phenol; 89365-50-4; Aeromax; Astmerole; CHEBI:64064; CPD000466295; GIIZNNXWQWCKIB-UHFFFAOYSA-N; GR 33343X; HSDB 7315; SALMATEROL; Ultrabeta; salmeterol xinafoate; 4-(1-Hydroxy-2-((6-(4-phenylbutoxy)hexyl)amino)ethyl)-2-(hydroxymethyl)phenol 1-hydroxy-2-naphthoate; 94749-08-3; Arial; Asmerole; Beglan; Betamican; DSSTox_CID_25798; DSSTox_GSID_45798; DSSTox_RID_81137; Dilamax; GR 33343 G; GR 33343X xinafoate; Inaspir; MFCD00897708; NCGC00094372-03
Indication Asthma [ICD11: CA23] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 603.7 Topological Polar Surface Area 140
Heavy Atom Count 44 Rotatable Bond Count 17
Hydrogen Bond Donor Count 6 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
56801
ChEBI ID
CHEBI:9012
CAS Number
94749-08-3
TTD Drug ID
D0L5YV
Formula
C36H45NO7
Canonical SMILES
C1=CC=C(C=C1)CCCCOCCCCCCNCC(C2=CC(=C(C=C2)O)CO)O.C1=CC=C2C(=C1)C=CC(=C2O)C(=O)O
InChI
1S/C25H37NO4.C11H8O3/c27-20-23-18-22(13-14-24(23)28)25(29)19-26-15-7-1-2-8-16-30-17-9-6-12-21-10-4-3-5-11-21;12-10-8-4-2-1-3-7(8)5-6-9(10)11(13)14/h3-5,10-11,13-14,18,25-29H,1-2,6-9,12,15-17,19-20H2;1-6,12H,(H,13,14)
InChIKey
XTZNCVSCVHTPAI-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
Alpha-hydroxysalmeterol DM001279
197627
Oxidation - Hydroxylation 1 [4] , [5] , [6]
Salmeterol O-dealkylated metabolite DM001280 N. A. Oxidation - O-Dealkylation 1 [7]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002221 Salmeterol xinafoate Alpha-hydroxysalmeterol Oxidation - Hydroxylation CYP3A4 ... [4], [5], [6]
MR002222 Salmeterol xinafoate Salmeterol O-dealkylated metabolite Oxidation - O-Dealkylation Unclear [7]
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]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[3]
References
1 Salmeterol Xinafoate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Clinical pharmacokinetics of salmeterol. Clin Pharmacokinet. 2002;41(1):19-30.
3 Drug Interactions Flockhart Table
4 Determination of salmeterol, -hydroxysalmeterol and fluticasone propionate in human urine and plasma for doping control using UHPLC-QTOF-MS. Biomed Chromatogr. 2021 Aug;35(8):e5114. doi: 10.1002/bmc.5114.
5 Pharmacokinetics of salmeterol and its main metabolite -hydroxysalmeterol after acute and chronic dry powder inhalation in exercising endurance-trained men: Implications for doping control. Drug Test Anal. 2021 Apr;13(4):747-761. doi: 10.1002/dta.2978.
6 The salmeterol anomaly and the need for a urine threshold. Drug Test Anal. 2022 Jun;14(6):997-1003. doi: 10.1002/dta.2810.
7 Disposition of salmeterol xinafoate in laboratory animals and humans Drug Metab Dispos. 1993 Nov-Dec;21(6):1022-8.

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