Acebutolol (CED0006848)

Record Information
Version1.0
Creation Date2016-05-25 18:25:52 UTC
Update Date2026-08-20 01:19:40 UTC
Accession NumberCHEM022258
Identification
Common NameAcebutolol
ClassSmall Molecule
Description
Acebutolol is an organic compound with the chemical formula C18H28N2O4 and an average molecular weight of 336.43 g/mol. Acebutolol belongs to the carbonyl compounds, a subclass of organooxygen compounds within the organic compounds. In terms of protein targets, the compound acts as a partial agonist of the Beta-1 adrenergic receptor (ADRB1) and the Beta-2 adrenergic receptor (ADRB2). The compound is associated with 13 recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it is utilized as a beta blocking agent. Other recorded sources include drinking water and water supply, specifically drinking water, and food, food processing, and cookware, where it is used in food preservation. It is also found in building and construction materials such as tents or canopies. Additionally, it is released from household cleaning and consumer products, including tobacco smoke filters, perfumes within detergents and soaps, and non electric simulated smoking devices. Further sources are linked to electrical and electronic equipment, including electrodes, hybrid capacitors, antennas, conductors or conductive bodies characterised by the conductive materials, and electrically stimulated smoking devices. The recorded exposure route for this compound is oral.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
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 hydrochlorideHMDB
NovoAcebutololHMDB
Bayer brand OF acebutolol hydrochlorideHMDB
Heumann brand OF acebutolol hydrochlorideHMDB
Italfarmaco brand OF acebutolol hydrochlorideHMDB
m And b 17803 aHMDB
Novo acebutololHMDB
PrentHMDB
SectralHMDB
Specia brand OF acebutolol hydrochlorideHMDB
Acebutolol gepepharm brandHMDB
Apo acebutololHMDB
Apo-acebutololHMDB
Apotex brand OF acebutolol hydrochlorideHMDB
Gepepharm brand OF acebutololHMDB
Heumann, acebutololHMDB
m And b-17803 aHMDB
m And b17803 aHMDB
MonitanHMDB
Novopharm brand OF acebutolol hydrochlorideHMDB
Proctor and gamble brand OF acebutolol hydrochlorideHMDB
Rhône poulenc rorer brand OF acebutolol hydrochlorideHMDB
Acebutolol heumannHMDB
Acébutolol ratiopharmHMDB
Acébutolol-ratiopharmHMDB
AcébutololratiopharmHMDB
ApoAcebutololHMDB
Hydrochloride, acebutololHMDB
Lafon-ratiopharm brand OF acebutolol hydrochlorideHMDB
m And b 17803aHMDB
NeptalHMDB
Novo-acebutololHMDB
Rhodiapharm brand OF acebutolol hydrochlorideHMDB
RhotralHMDB
Rhône-poulenc rorer brand OF acebutolol hydrochlorideHMDB
Wyeth brand OF acebutolol hydrochlorideHMDB
Chemical FormulaC18H28N2O4
Average Molecular Mass336.426 g/mol
Monoisotopic Mass336.205 g/mol
CAS Registry Number37517-30-9
IUPAC NameN-(3-acetyl-4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)butanamide
Traditional Nameacebutolol
SMILESCCCC(=O)NC1=CC(C(C)=O)=C(OCC(O)CNC(C)C)C=C1
InChI IdentifierInChI=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
Description Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl 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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00di-9252000000-7827544ebe33c12ef3bbNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-006x-4927000000-729380ab7bcc06a189bfNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-015a-0940000000-cd2be0ebcdc412c13c1dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0291000000-d2c79f57907dfecd3ab6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0920000000-7ee5e8843c0d3c66cea4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-007k-0900000000-86cb0a76fcc4e9480bedNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0900000000-d4a06670b3e12a3f0d4dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0009000000-72f0325748e2bf5430c4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0900000000-b9cf35fe287fe7fa1e58Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014r-0595000000-5ed3946399d12d6cbe7eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-015a-0940000000-d6b151173b7e6e7831deNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0009000000-bc4eec9d529011d6a177Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0009000000-6d0d67c3acd18ae44924Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014r-2095000000-a0c01f6fa89d23cb8b78Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00xr-6190000000-4fd1c0b6ff7eba1b576fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00dl-9110000000-5127458f77fd32591066Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0079-3179000000-b67d7480f1ca6f97c175Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-2490000000-15d368948cd4505e7114Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-4920000000-d65e636290545a9b04c5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0019000000-80019c4cccdbe0d63d65Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00xr-9311000000-855c3de48116392e6d1dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0abc-9000000000-40e5b46c1b5f9852aafeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kr-0696000000-2aa0e3161d69561d76c6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f6t-0920000000-98a8831324919178688eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-2910000000-06dafa94cb8131dd5bdaNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2044.0Log mg/kg[1100:3600]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
115Drinking waterDrinking water & water supplyNot Available
293Beta blocking agentsHealthcare, pharmaceuticals & veterinary productsNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
Pathways
4 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structure5-hydroxytryptamine receptor 1AP19327Rattus norvegicusPredicted (SEA)21.6421
Beta-1 adrenergic receptor structureClick to view 3D structureBeta-1 adrenergic receptorP08588HumansPredicted (SEA)3.03612
Click to view 3D structureBeta-2 adrenergic receptorQ8K4Z4Cavia porcellusPredicted (SEA)4.43741
Click to view 3D structureBeta-1 adrenergic receptorB0FL73Cavia porcellusPredicted (SEA)3.26967
Beta-2 adrenergic receptor structureClick to view 3D structureBeta-2 adrenergic receptorP07550HumansPredicted (SEA)13.935
Click to view 3D structureBeta-1 adrenergic receptorP18090Rattus norvegicusPredicted (SEA)2.64687
Sigma non-opioid intracellular receptor 1 structureClick to view 3D structureSigma non-opioid intracellular receptor 1Q99720HumansPredicted (SEA)62.8243
Beta-3 adrenergic receptor structureClick to view 3D structureBeta-3 adrenergic receptorP13945HumansPredicted (SEA)9.26406
5-hydroxytryptamine receptor 1A structureClick to view 3D structure5-hydroxytryptamine receptor 1AP08908HumansPredicted (SEA)113.348
Click to view 3D structureBeta-2 adrenergic receptorP18762Mus musculusPredicted (SEA)0.233548
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)110.468
Click to view 3D structure5-hydroxytryptamine receptor 1BP28564Rattus norvegicusPredicted (SEA)26.5466
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)78.1606
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)115.84
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)166.675
5-hydroxytryptamine receptor 6 structureClick to view 3D structure5-hydroxytryptamine receptor 6P50406HumansPredicted (SEA)82.4423
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)104.084
Click to view 3D structureBeta-2 adrenergic receptorP54833Canis lupus familiarisPredicted (SEA)1.71268
Click to view 3D structureBeta-2 adrenergic receptorQ28044Bos taurusPredicted (SEA)2.64687
5-hydroxytryptamine receptor 1B structureClick to view 3D structure5-hydroxytryptamine receptor 1BP28222HumansPredicted (SEA)76.8372
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)590.953
Click to view 3D structureDNA (cytosine-5)-methyltransferase 1P13864Mus musculusPredicted (SEA)2.33548
Click to view 3D structureSigma intracellular receptor 2Q5BJF2HumansPredicted (SEA)149.393
Potassium voltage-gated channel subfamily B member 1 structureClick to view 3D structurePotassium voltage-gated channel subfamily B member 1Q14721HumansPredicted (SEA)1.63483
Click to view 3D structureBeta-1 adrenergic receptorP34971Mus musculusPredicted (SEA)8.95266
Concentrations
Not Available
External Links
DrugBank IDDB01193
HMDB IDHMDB0015324
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAcebutolol
Chemspider ID1901
ChEBI ID2379
PubChem Compound ID1978
Kegg Compound IDC06803
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1378852