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

General Information of Drug (ID: DR5252)
Drug Name
Bambuterol
Prodrug Info Bambuterol is the prodrug of Bambuterol metabolite M1
Synonyms
Bambec; Bambuterolum; Oxeol; Bambuterolum [Latin]; Terbutaline bisdimethylcarbamate; Bambec (TN); Bambuterol (INN); Bambuterol [BAN:INN]; KWD-2183; Oxeol (TN); Terbutaline bis(dimethylcarbamate); [3-[2-(tert-butylamino)-1-hydroxyethyl]-5-(dimethylcarbamoyloxy)phenyl] N,N-dimethylcarbamate; (+-)-5-(2-(tert-Butylamino)-1-hydroxyethyl)-m-phenylene bis(dimethylcarbamate); 5-(2-(tert-butylamino)-1-hydroxyethyl)-3-phenylene bis(dimethylcarbamate); 5-[2-(tert-butylamino)-1-hydroxyethyl]benzene-1,3-diyl bis(dimethylcarbamate)
Indication Asthma [ICD11: CA23] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 367.4 Topological Polar Surface Area 91.3
Heavy Atom Count 26 Rotatable Bond Count 8
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
54766
ChEBI ID
CHEBI:553827
CAS Number
81732-65-2
TTD Drug ID
D07XYV
Formula
C18H29N3O5
Canonical SMILES
CC(C)(C)NCC(C1=CC(=CC(=C1)OC(=O)N(C)C)OC(=O)N(C)C)O
InChI
InChI=1S/C18H29N3O5/c1-18(2,3)19-11-15(22)12-8-13(25-16(23)20(4)5)10-14(9-12)26-17(24)21(6)7/h8-10,15,19,22H,11H2,1-7H3
InChIKey
ANZXOIAKUNOVQU-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
Bambuterol metabolite M1 DM014880
5403
Hydrolysis - Hydrolysis 1 [7]
Bambuterol metabolite M12 DM016937 N. A. Multi-steps Reaction - Demethylation; GluA conjugation 1 [7]
Bambuterol metabolite M3 DM015176
133750
Hydrolysis - Hydrolysis 1 [7]
Bambuterol metabolite M7 DM016927 N. A. Oxidation - Demethylation 1 [7]
Bambuterol metabolite M9 DM016932 N. A. Oxidation - Oxidation 1 [7]
Bambuterol metabolite IV DM016934 N. A. Oxidation - Demethylation 2 [8]
Bambuterol metabolite M1 DM014880
5403
Hydrolysis - Hydrolysis 2 [7]
Bambuterol metabolite M2 DM016931 N. A. Oxidation - Demethylation 2 [7]
Bambuterol metabolite M6 DM016933 N. A. Hydrolysis - Hydrolysis 2 [7]
Bambuterol metabolite M8 DM016928 N. A. Oxidation - Oxidation 2 [7]
Bambuterol metabolite M8 DM016928 N. A. Oxidation - Demethylation 2 [7]
Bambuterol metabolite M1 DM014880
5403
Hydrolysis - Hydrolysis 3 [7]
Bambuterol metabolite M10 DM016930 N. A. Conjugation - GluA conjugation 3 [7]
Bambuterol metabolite M11 DM016936 N. A. Conjugation - GluA conjugation 3 [7]
Bambuterol metabolite M4 DM016929 N. A. Hydrolysis - Hydrolysis 3 [7]
Bambuterol metabolite M4 DM016929 N. A. Oxidation - Oxidation 3 [7]
Bambuterol metabolite M4 DM016929 N. A. Oxidation - Demethylation 3 [7]
Bambuterol metabolite M5 DM016415
91810535
Conjugation - Sulphation conjugation 3 [7]
Bambuterol metabolite V DM016935 N. A. Unclear - Unclear 3 [7]
Bambuterol metabolite M1 DM014880
5403
Hydrolysis - Hydrolysis 4 [7]
Bambuterol metabolite M1 DM014880
5403
Unclear - Unclear 4 [7]
Bambuterol metabolite M10 DM016930 N. A. Conjugation - GluA conjugation 4 [7]
Bambuterol metabolite M5 DM016415
91810535
Conjugation - Sulphation conjugation 4 [7]
Bambuterol metabolite M10 DM016930 N. A. Conjugation - GluA conjugation 5 [7]
Bambuterol metabolite M5 DM016415
91810535
Conjugation - Sulphation conjugation 5 [7]
⏷ Show the Full List of 25  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007762 Bambuterol Bambuterol metabolite M7 Oxidation - Demethylation Unclear [7]
MR007768 Bambuterol Bambuterol metabolite M3 Hydrolysis - Hydrolysis Unclear [7]
MR007771 Bambuterol Bambuterol metabolite M9 Oxidation - Oxidation Unclear [7]
MR007782 Bambuterol Bambuterol metabolite M1 Hydrolysis - Hydrolysis CHE1 [7]
MR007783 Bambuterol Bambuterol metabolite M12 Multi-steps Reaction - Demethylation; GluA conjugation Unclear [7]
MR007769 Bambuterol metabolite M3 Bambuterol metabolite M2 Oxidation - Demethylation Unclear [7]
MR007779 Bambuterol metabolite M3 Bambuterol metabolite M1 Hydrolysis - Hydrolysis Unclear [7]
MR007763 Bambuterol metabolite M7 Bambuterol metabolite M8 Oxidation - Oxidation Unclear [7]
MR007772 Bambuterol metabolite M9 Bambuterol metabolite M6 Hydrolysis - Hydrolysis Unclear [7]
MR007774 Bambuterol metabolite M9 Bambuterol metabolite IV Oxidation - Demethylation Unclear [8]
MR007777 Bambuterol metabolite M9 Bambuterol metabolite M8 Oxidation - Demethylation Unclear [7]
MR007775 Bambuterol metabolite IV Bambuterol metabolite V Unclear - Unclear Unclear [7]
MR014133 Bambuterol metabolite M1 Bambuterol metabolite M5 Conjugation - Sulphation conjugation Unclear [7]
MR014134 Bambuterol metabolite M1 Bambuterol metabolite M10 Conjugation - GluA conjugation Unclear [7]
MR007770 Bambuterol metabolite M2 Bambuterol metabolite M4 Oxidation - Oxidation Unclear [7]
MR007780 Bambuterol metabolite M2 Bambuterol metabolite M11 Conjugation - GluA conjugation Unclear [7]
MR007781 Bambuterol metabolite M2 Bambuterol metabolite M1 Hydrolysis - Hydrolysis Unclear [7]
MR007773 Bambuterol metabolite M6 Bambuterol metabolite M4 Oxidation - Demethylation Unclear [7]
MR007778 Bambuterol metabolite M6 Bambuterol metabolite M1 Hydrolysis - Hydrolysis Unclear [7]
MR007764 Bambuterol metabolite M8 Bambuterol metabolite M4 Hydrolysis - Hydrolysis Unclear [7]
MR014131 Bambuterol metabolite M1 Bambuterol metabolite M10 Conjugation - GluA conjugation Unclear [7]
MR014132 Bambuterol metabolite M1 Bambuterol metabolite M5 Conjugation - Sulphation conjugation Unclear [7]
MR007765 Bambuterol metabolite M4 Bambuterol metabolite M1 Hydrolysis - Hydrolysis Unclear [7]
MR007776 Bambuterol metabolite V Bambuterol metabolite M1 Unclear - Unclear Unclear [7]
MR007766 Bambuterol metabolite M1 Bambuterol metabolite M5 Conjugation - Sulphation conjugation Unclear [7]
MR007767 Bambuterol metabolite M1 Bambuterol metabolite M10 Conjugation - GluA conjugation Unclear [7]
⏷ Show the Full List of 26 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Arylsulfatase A (ARSA) DME0193 Homo sapiens
ARSA_HUMAN
3.1.6.8
[2]
Beta-glucuronidase (GUSB) DME0106 Homo sapiens
BGLR_HUMAN
3.2.1.31
[3]
Butyrylcholine esterase (BCHE) DME0069 Homo sapiens
CHLE_HUMAN
3.1.1.8
[4]
Butyrylcholine esterase (BCHE) DME0069 Homo sapiens
CHLE_HUMAN
3.1.1.8
[5]
Butyrylcholine esterase (BCHE) DME0069 Homo sapiens
CHLE_HUMAN
3.1.1.8
[6]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[5]
⏷ Show the Full List of 6  DME(s)
References
1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6601).
2 Metabolism of terbutaline in man and dog
3 The metabolism of terbutaline in man
4 DrugBank(Pharmacology-Metabolism):Bambuterol
5 Pharmacokinetics of bambuterol in subjects homozygous for the atypical gene for plasma cholinesterase
6 The emerging role of human esterases
7 In vivo metabolism study of (R)-bambuterol in humans using ultra high performance liquid chromatography with tandem mass spectrometry
8 Bambuterol: uptake and metabolism in guinea pig isolated lungs

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