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

General Information of Drug (ID: DR0241)
Drug Name
Bufuralol
Synonyms
Bufuralol; Bufuralol [BAN:INN]; Bufuralol [INN:BAN]; Bufuralolum; Bufuralolum [INN-Latin]; Ro 3-4787; dl-Bufuralol; (RS)-alpha-(tert-Butylamino)methyl)-7-ethyl-12-benzofuranmethanol; 1-(7-Ethylbenzofuran-2-yl)-2-tert-butylamino-1-hydroxyethane; 2-(tert-butylamino)-1-(7-ethyl-1-benzofuran-2-yl)ethanol; 2-(tert-butylamino)-1-(7-ethylbenzofuran-2-yl)ethanol; 54340-62-4; AC1L2GPJ; AC1Q777C; CHEBI:34593; CHEMBL296035; EINECS 259-112-5; GTPL9834; SCHEMBL78552; alpha-((tert-Butylamino)methyl)-7-ethyl-2-benzofuranmethanol
Indication Cardiac arrhythmia [ICD11: BC65] Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 261.36 Topological Polar Surface Area 45.4
Heavy Atom Count 19 Rotatable Bond Count 5
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
71733
ChEBI ID
CHEBI:34593
CAS Number
54340-62-4
Formula
C16H23NO2
Canonical SMILES
CCC1=CC=CC2=C1OC(=C2)C(CNC(C)(C)C)O
InChI
1S/C16H23NO2/c1-5-11-7-6-8-12-9-14(19-15(11)12)13(18)10-17-16(2,3)4/h6-9,13,17-18H,5,10H2,1-4H3
InChIKey
SSEBTPPFLLCUMN-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
1'-Hydroxybufuralol DM006960
162836
Oxidation - Hydrolyzationn 1 [5]
1'2'-Ethenylbufuralol DM006963 N. A. Unclear 1 [6]
4-hydroxybufuralol DM006961
173807
Oxidation - Hydrolyzationn 1 [2]
6-hydroxybufuralol DM006962
101674387
Oxidation - Hydrolyzationn 1 [2]
Unclear DM009999 N. A. Unclear 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007577 Bufuralol 1'-Hydroxybufuralol Oxidation - Hydrolyzationn CYP2D6 [5]
MR007578 Bufuralol 4-hydroxybufuralol Oxidation - Hydrolyzationn CYP1A2 [2]
MR007579 Bufuralol 6-hydroxybufuralol Oxidation - Hydrolyzationn CYP1A2 [2]
MR007580 Bufuralol Unclear Unclear CYP2C19 [4]
MR007581 Bufuralol 1'2'-Ethenylbufuralol Unclear Unclear [6]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[4]
References
1 Pharmacodynamic and pharmacokinetic studies on bufuralol in man. Br J Clin Pharmacol. 1986 Nov;22(5):527-34.
2 Bufuralol hydroxylation by cytochrome P450 2D6 and 1A2 enzymes in human liver microsomes
3 Cytochrome b5 is a major determinant of human cytochrome P450 CYP2D6 and CYP3A4 activity in vivo. Mol Pharmacol. 2015 Apr;87(4):733-9.
4 The role of CYP2C19 in the metabolism of (+/-) bufuralol, the prototypic substrate of CYP2D6
5 In Vitro Interaction of AB-FUBINACA with Human Cytochrome P450, UDP-Glucuronosyltransferase Enzymes and Drug Transporters
6 S73 | METXBIODB | Metabolite:Bufuralol

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