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

General Information of Drug (ID: DR1249)
Drug Name
Penbutolol
Synonyms
Penbutolol [INN:BAN]; Penbutololum; Penbutololum [INN-Latin]; S(-)-Penbutolol; l-Penbutolol; Betapressin; Levatol; Levopenbutol; PENBUTOLOL SULFATE; penbutolol; (-)-Penbutolol; (2S)-1-(tert-butylamino)-3-(2-cyclopentylphenoxy)propan-2-ol; 1-(tert-Butylamino)-3-(o-cyclopentylphenoxy)propan-2-ol; 2-Propanol, 1-(2-cyclopentylphenoxy)-3-((1,1-dimethylethyl)amino)-; 38363-40-5; 78W62V43DY; BRN 4484348; C18H29NO2; CCRIS 2855; CHEBI:7954; EINECS 253-074-3; HOE 893; HOE 893d; Hoe-893d; UNII-78W62V43DY
Indication Essential hypertension [ICD11: BA00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 291.4 Topological Polar Surface Area 41.5
Heavy Atom Count 21 Rotatable Bond Count 7
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
37464
PubChem SID
9620 ; 8175027 ; 15902888 ; 34678763 ; 46504929 ; 47291267 ; 47589134 ; 48416387 ; 50022970 ; 50064728 ; 57312048 ; 77621769 ; 96024764 ; 103293389 ; 103400617 ; 104326642 ; 117556859 ; 124954107 ; 128421871 ; 134223256 ; 134338213 ; 134999314 ; 135049302 ; 137001394 ; 142047536 ; 160964648 ; 175266991 ; 178103837 ; 179150414 ; 223440604 ; 226426442
ChEBI ID
CHEBI:7954
CAS Number
36507-48-9
TTD Drug ID
D0W8SB
Formula
C18H29NO2
Canonical SMILES
CC(C)(C)NCC(COC1=CC=CC=C1C2CCCC2)O
InChI
1S/C18H29NO2/c1-18(2,3)19-12-15(20)13-21-17-11-7-6-10-16(17)14-8-4-5-9-14/h6-7,10-11,14-15,19-20H,4-5,8-9,12-13H2,1-3H3/t15-/m0/s1
InChIKey
KQXKVJAGOJTNJS-HNNXBMFYSA-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
4-hydroxypenbutolol DM001186
133713
Oxidation - Hydroxylation 1 [4]
Penbutolol glucuronide DM001187
13933749
Conjugation - Glucuronidation 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002869 Penbutolol 4-hydroxypenbutolol Oxidation - Hydroxylation Unclear [4]
MR002870 Penbutolol Penbutolol glucuronide Conjugation - Glucuronidation Unclear [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1431 Holdemanella biformis Not Available Not Available [3]
References
1 Penbutolol was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Application of substrate depletion assay to evaluation of CYP isoforms responsible for stereoselective metabolism of carvedilol. Drug Metab Pharmacokinet. 2016 Dec;31(6):425-432.
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
4 Pharmacokinetics of penbutolol and its metabolites in renal insufficiency Eur J Clin Pharmacol. 1985;29(2):215-9. doi: 10.1007/BF00547425.

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