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

General Information of Drug (ID: DR0032)
Drug Name
Acebutolol
Synonyms
(+-)-Acebutolol; 3'-Acetyl-4'-(2-hydroxy-3-(isopropylamino)propoxy)butyranilide; 37517-30-9; 5'-Butyramido-2'-(2-hydroxy-3-isopropylaminopropoxy)acetophenone; Acebrutololum [INN-Latin]; Acebutolol [USAN:INN:BAN]; Acebutololo; Acebutololum; Acebutololum [INN-Latin]; BRN 2162244; CCRIS 9214; CHEBI:2379; EINECS 253-539-0; N-(3-Acetyl-4-(2-hydroxy-3-(isopropylamino)propoxy)phenyl)butyramide; Prent; acebutolol; Acetobutolol; Acetobutolol [INN-Spanish]; Neptal; RP 21823; Sectral; dl-Acebutolol
Indication Essential hypertension [ICD11: BA00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 336.4 Topological Polar Surface Area 87.7
Heavy Atom Count 24 Rotatable Bond Count 10
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
1978
PubChem SID
9022 ; 5199954 ; 7849397 ; 7978630 ; 8148212 ; 8151358 ; 10520758 ; 11335787 ; 11361026 ; 11363385 ; 11365947 ; 11368509 ; 11371586 ; 11374422 ; 11376671 ; 11461998 ; 11466097 ; 11467217 ; 11485235 ; 11485914 ; 11489156 ; 11490389 ; 11492617 ; 11494305 ; 15075320 ; 29221166 ; 46509113 ; 47216767 ; 47216768 ; 47291119 ; 47365171 ; 47365172 ; 47440234 ; 47810742 ; 49698901 ; 49895324 ; 50427938 ; 56413043 ; 57321077 ; 85209697 ; 85787903 ; 99222788 ; 103189011 ; 104299258 ; 124883487 ; 126443068 ; 126679412 ; 127982055 ; 134337777 ; 134999047
ChEBI ID
ChEBI:2379
CAS Number
37517-30-9
TTD Drug ID
D0HD9K
Formula
C18H28N2O4
Canonical SMILES
CCCC(=O)NC1=CC(=C(C=C1)OCC(CNC(C)C)O)C(=O)C
InChI
1S/C18H28N2O4/c1-5-6-18(23)20-14-7-8-17(16(9-14)13(4)21)24-11-15(22)10-19-12(2)3/h7-9,12,15,19,22H,5-6,10-11H2,1-4H3,(H,20,23)
InChIKey
GOEMGAFJFRBGGG-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
Acetolol DM000601
155703
Hydrolysis - Hydrolysis 1 [2] , [5]
Diacetolol DM000602
50894
Conjugation - Acetylation 2 [5]
N-hydroxy acetolol DM000603 N. A. Oxidation - Hydroxylation 2 [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003123 Acebutolol Acetolol Hydrolysis - Hydrolysis CES2 [2], [5]
MR003124 Acebutolol N-hydroxy acetolol Oxidation - Hydroxylation CYP2C19 [6]
MR003122 Acetolol Diacetolol Conjugation - Acetylation NAT2 [5]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Carboxylesterase 2 (CES2) DME0057 Homo sapiens
EST2_HUMAN
3.1.1.1
[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
[3]
N-acetyltransferase 2 (NAT2) DME0051 Homo sapiens
ARY2_HUMAN
2.3.1.5
[4]
References
1 Acebutolol was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 It is our problem too ASDC J Dent Child. 1979 May-Jun;46(3):184.
3 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.
4 The etiology of osteosarcoma. A review of current considerations Clin Orthop Relat Res. 1975 Sep;(111):14-22. doi: 10.1097/00003086-197509000-00003.
5 Evaluation of drug-drug interactions via inhibition of hydrolases by orlistat, an anti-obesity drug. Drug Metab Dispos. 2023 May 3:DMD-AR-2023-001266. doi: 10.1124/dmd.123.001266.
6 U. S. FDA Label - Acebutolol

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