You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2017-10-23 19:06:29 UTC
HMDB IDHMDB0015324
Secondary Accession Numbers
  • HMDB15324
Metabolite Identification
Common NameAcebutolol
DescriptionAcebutolol is only found in individuals that have used or taken this drug. It is a cardioselective beta-adrenergic antagonist with little effect on the bronchial receptors. The drug has stabilizing and quinidine-like effects on cardiac rhythm as well as weak inherent sympathomimetic action. [PubChem]Acebutolol is a selective β1-receptor antagonist. Activation of β1-receptors by epinephrine increases the heart rate and the blood pressure, and the heart consumes more oxygen. Acebutolol blocks these receptors, lowering the heart rate and blood pressure. This drug then has the reverse effect of epinephrine. In addition, beta blockers prevent the release of renin, which is a hormone produced by the kidneys which leads to constriction of blood vessels.
Structure
Thumb
Synonyms
ValueSource
(+-)-AcebutololChEBI
3'-Acetyl-4'-(2-hydroxy-3-(isopropylamino)propoxy)butyranilideChEBI
5'-butyramido-2'-(2-Hydroxy-3-isopropylaminopropoxy)acetophenoneChEBI
AcebutololumChEBI
AcetobutololChEBI
N-(3-Acetyl-4-[2-hydroxy-3-(isopropylamino)propoxy]phenyl)butanamideChEBI
N-[3-Acetyl-4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]phenyl]butanamideChEBI
Acebutolol HCLHMDB
Acebutolol hydrochlorideHMDB
AcebutololoHMDB
DL-AcebutololHMDB
Lafon ratiopharm brand OF acebutolol hydrochlorideMeSH
NovoAcebutololMeSH
Bayer brand OF acebutolol hydrochlorideMeSH
Heumann brand OF acebutolol hydrochlorideMeSH
italfarmaco Brand OF acebutolol hydrochlorideMeSH
m And b 17803 aMeSH
novo AcebutololMeSH
PrentMeSH
SectralMeSH
Specia brand OF acebutolol hydrochlorideMeSH
Acebutolol gepepharm brandMeSH
apo AcebutololMeSH
apo-AcebutololMeSH
Apotex brand OF acebutolol hydrochlorideMeSH
Gepepharm brand OF acebutololMeSH
Heumann, acebutololMeSH
m And b-17803 aMeSH
m And b17803 aMeSH
MonitanMeSH
Novopharm brand OF acebutolol hydrochlorideMeSH
Proctor and gamble brand OF acebutolol hydrochlorideMeSH
Rhône poulenc rorer brand OF acebutolol hydrochlorideMeSH
Acebutolol heumannMeSH
Acébutolol ratiopharmMeSH
Acébutolol-ratiopharmMeSH
AcébutololratiopharmMeSH
ApoAcebutololMeSH
Hydrochloride, acebutololMeSH
Lafon-ratiopharm brand OF acebutolol hydrochlorideMeSH
m And b 17803aMeSH
NeptalMeSH
novo-AcebutololMeSH
Rhodiapharm brand OF acebutolol hydrochlorideMeSH
RhotralMeSH
Rhône-poulenc rorer brand OF acebutolol hydrochlorideMeSH
Wyeth brand OF acebutolol hydrochlorideMeSH
Chemical FormulaC18H28N2O4
Average Molecular Weight336.4259
Monoisotopic Molecular Weight336.204907394
IUPAC NameN-(3-acetyl-4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)butanamide
Traditional Nameacebutolol
CAS Registry Number37517-30-9
SMILES
CCCC(=O)NC1=CC(C(C)=O)=C(OCC(O)CNC(C)C)C=C1
InChI Identifier
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)
InChI KeyGOEMGAFJFRBGGG-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Acetophenone
  • Benzoyl
  • Phenol ether
  • Aryl alkyl ketone
  • Phenoxy compound
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidic acid
  • Carboximidic acid derivative
  • Secondary aliphatic amine
  • Ether
  • Secondary amine
  • Organic oxide
  • Alcohol
  • Hydrocarbon derivative
  • Amine
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

    Cardiovascular drug:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point119 - 123 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.17 g/LNot Available
LogP1.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.17 g/LALOGPS
logP1.43ALOGPS
logP1.53ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)13.91ChemAxon
pKa (Strongest Basic)9.57ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area87.66 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity94.87 m³·mol⁻¹ChemAxon
Polarizability38.51 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9252000000-7827544ebe33c12ef3bbView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-4927000000-729380ab7bcc06a189bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-2095000000-a0c01f6fa89d23cb8b78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00xr-6190000000-4fd1c0b6ff7eba1b576fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-9110000000-5127458f77fd32591066View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0079-3179000000-b67d7480f1ca6f97c175View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-2490000000-15d368948cd4505e7114View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-4920000000-d65e636290545a9b04c5View in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Acebutolol PathwayPw000364Pw000364 greyscalePw000364 simpleNot Available
Displaying 1 entry
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01193 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01193 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01193
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID1901
KEGG Compound IDC06803
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcebutolol
METLIN IDNot Available
PubChem Compound1978
PDB IDNot Available
ChEBI ID2379
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity
Gene Name:
ADRB1
Uniprot ID:
P08588
Molecular weight:
51322.1
References
  1. van den Meiracker AH, Man in 't Veld AJ, Fischberg DJ, Molinoff PB, van Eck HJ, Boomsma F, Derkx FH, Schalekamp MA: Acute and long-term effects of acebutolol on systemic and renal hemodynamics, body fluid volumes, catecholamines, active renin, aldosterone, and lymphocyte beta-adrenoceptor density. J Cardiovasc Pharmacol. 1988 Apr;11(4):413-23. [PubMed:2453744 ]
  2. Abrahamsson T: Characterization of the beta 1-adrenoceptor stimulatory effects of the partial beta 1-agonists acebutolol, xamoterol, H142/08 and H201/70. Eur J Pharmacol. 1989 May 2;164(1):121-8. [PubMed:2568935 ]
  3. Fraysse B, Garric J: Prediction and experimental validation of acute toxicity of beta-blockers in Ceriodaphnia dubia. Environ Toxicol Chem. 2005 Oct;24(10):2470-6. [PubMed:16268148 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine
Gene Name:
ADRB2
Uniprot ID:
P07550
Molecular weight:
46458.3
References
  1. Fraysse B, Garric J: Prediction and experimental validation of acute toxicity of beta-blockers in Ceriodaphnia dubia. Environ Toxicol Chem. 2005 Oct;24(10):2470-6. [PubMed:16268148 ]
  2. Varma DR, Shen H, Deng XF, Peri KG, Chemtob S, Mulay S: Inverse agonist activities of beta-adrenoceptor antagonists in rat myocardium. Br J Pharmacol. 1999 Jun;127(4):895-902. [PubMed:10433496 ]
  3. Lima JJ: Relationship between beta adrenoceptor occupancy and receptor down-regulation induced by beta antagonists with intrinsic sympathomimetic activity. J Recept Signal Transduct Res. 1996 Sep-Nov;16(5-6):357-72. [PubMed:8968966 ]

Transporters

General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
References
  1. Troutman MD, Thakker DR: Novel experimental parameters to quantify the modulation of absorptive and secretory transport of compounds by P-glycoprotein in cell culture models of intestinal epithelium. Pharm Res. 2003 Aug;20(8):1210-24. [PubMed:12948019 ]
  2. Terao T, Hisanaga E, Sai Y, Tamai I, Tsuji A: Active secretion of drugs from the small intestinal epithelium in rats by P-glycoprotein functioning as an absorption barrier. J Pharm Pharmacol. 1996 Oct;48(10):1083-9. [PubMed:8953513 ]
General function:
Involved in ion transmembrane transporter activity
Specific function:
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase
Gene Name:
SLC22A1
Uniprot ID:
O15245
Molecular weight:
61187.4
References
  1. Zhang L, Schaner ME, Giacomini KM: Functional characterization of an organic cation transporter (hOCT1) in a transiently transfected human cell line (HeLa). J Pharmacol Exp Ther. 1998 Jul;286(1):354-61. [PubMed:9655880 ]