Details of the Drug

General Information of Drug (ID: DM0TI4U)

Drug Name
Acebutolol
Synonyms
Acebrutololum; Acebutololo; Acebutololum; Acetobutolol; Neptal; Prent; Sectral; Acebutolol HCL; RP 21823; Acebrutololum [INN-Latin]; Acebutololum [INN-Latin]; Acetobutolol [INN-Spanish]; Dl-Acebutolol; M & B 17803A; Prent (TN); Sectral (TN); Acebutolol (USAN/INN); Acebutolol [USAN:INN:BAN]; M&B-17803 A; N-(3-Acetyl-4-[2-hydroxy-3-(isopropylamino)propoxy]phenyl)butanamide; N-[3-acetyl-4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]phenyl]butanamide; N-[3-acetyl-4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]butanamide; N-{3-acetyl-4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl}butanamide; (+-)-3'-Acetyl-4'-(2-hydroxy-3-(isopropylamino)propoxy)butyranilide; (+-)-Acebutolol; (+-)-N-(3-Acetyl-4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)phenyl)butanamide; 1-(2-Acetyl-4-n-butyramidophenoxy)-2-hydroxy-3-isopropylaminopropane; 3'-(Acetyl-4'-(2-hydroxy-3-(isopropylamino)propoxy)butyranilide; 3'-Acetyl-4'-(2-hydroxy-3-(isopropylamino)propoxy)butyranilide; 3'-Acetyl-4'-(2-hydroxy-3-isopropylaminopropoxy)butyranilid; 5'-Butyramido-2'-(2-hydroxy-3-isopropylaminopropoxy)acetophenone
Indication
Disease Entry ICD 11 Status REF
Hypertension BA00-BA04 Approved [1]
Malignant essential hypertension BA00 Approved [2]
Therapeutic Class
Antihypertensive Agents
Affected Organisms
Humans and other mammals
ATC Code
C07AB04: Acebutolol
C07AB: Beta blocking agents, selective
C07A: BETA BLOCKING AGENTS
C07: BETA BLOCKING AGENTS
C: CARDIOVASCULAR SYSTEM
C07AB04: Acebutolol
C07AB: Beta blocking agents, selective
C07A: BETA BLOCKING AGENTS
C07: BETA BLOCKING AGENTS
C: CARDIOVASCULAR SYSTEM
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 336.4
Logarithm of the Partition Coefficient (xlogp) 1.7
Rotatable Bond Count (rotbonds) 10
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 5
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [3]
Bioavailability
The bioavailability of drug is 40% []
Clearance
The drug present in the plasma can be removed from the body at the rate of 10 mL/min/kg [4]
Elimination
10% of drug is excreted from urine in the unchanged form [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 3 - 4 hours [4]
Metabolism
The drug is metabolized via the hepatic []
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 46.0916 micromolar/kg/day [5]
Unbound Fraction
The unbound fraction of drug in plasma is 0.74% [4]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 1.7 L/kg [4]
Chemical Identifiers
Formula
C18H28N2O4
IUPAC Name
N-[3-acetyl-4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]butanamide
Canonical SMILES
CCCC(=O)NC1=CC(=C(C=C1)OCC(CNC(C)C)O)C(=O)C
InChI
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
Cross-matching ID
PubChem CID
1978
ChEBI ID
CHEMBL642
CAS Number
37517-30-9
UNII
67P356D8GH
DrugBank ID
DB01193
TTD ID
D0HD9K
VARIDT ID
DR00627
INTEDE ID
DR0032
ACDINA ID
D00008
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Adrenergic receptor beta-1 (ADRB1) TTR6W5O ADRB1_HUMAN Antagonist [6]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Organic cation transporter 1 (SLC22A1) DTT79CX S22A1_HUMAN Substrate [7]
Organic anion transporting polypeptide 1A2 (SLCO1A2) DTE2B1D SO1A2_HUMAN Substrate [8]
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [9]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2D6 (CYP2D6)
Main DME 		DECB0K3 CP2D6_HUMAN Substrate [10]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Protein c-Fos (FOS) OTJBUVWS FOS_HUMAN Gene/Protein Processing [11]
Renin (REN) OT52GZR2 RENI_HUMAN Gene/Protein Processing [12]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Acebutolol
DDI Drug Name DDI Drug ID Severity Mechanism Disease REF
Levamlodipine DM92S6N Moderate Increased risk of cardiac depression by the combination of Acebutolol and Levamlodipine. Hypertension [BA00-BA04] [13]
Coadministration of a Drug Treating the Disease Different from Acebutolol (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Bepridil DM0RKS4 Moderate Increased risk of cardiac depression by the combination of Acebutolol and Bepridil. Angina pectoris [BA40] [13]
Aminophylline DML2NIB Major Antagonize the effect of Acebutolol when combined with Aminophylline. Asthma [CA23] [14]
Cariprazine DMJYDVK Moderate Additive hypotensive effects by the combination of Acebutolol and Cariprazine. Bipolar disorder [6A60] [15]
Atracurium DM42HXN Moderate Additive cardiorespiratory depression effects by the combination of Acebutolol and Atracurium. Corneal disease [9A76-9A78] [16]
Mivacurium DM473VD Moderate Additive neuromuscular blocking effects by the combination of Acebutolol and Mivacurium. Corneal disease [9A76-9A78] [16]
Pancuronium DMB0VY8 Moderate Additive neuromuscular blocking effects by the combination of Acebutolol and Pancuronium. Corneal disease [9A76-9A78] [16]
Tubocurarine DMBZIVP Moderate Additive neuromuscular blocking effects by the combination of Acebutolol and Tubocurarine. Corneal disease [9A76-9A78] [16]
Oxtriphylline DMLHSE3 Major Antagonize the effect of Acebutolol when combined with Oxtriphylline. Cough [MD12] [14]
Pasireotide DMHM7JS Moderate Increased risk of bradycardia by the combination of Acebutolol and Pasireotide. Cushing syndrome [5A70] [17]
OPC-34712 DMHG57U Moderate Additive hypotensive effects by the combination of Acebutolol and OPC-34712. Depression [6A70-6A7Z] [15]
Mepenzolate DM8YU2F Moderate Antagonize the effect of Acebutolol when combined with Mepenzolate. Digestive system disease [DE2Z] [18]
Stiripentol DMMSDOY Moderate Decreased metabolism of Acebutolol caused by Stiripentol mediated inhibition of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [19]
Belladonna DM2RBWK Moderate Antagonize the effect of Acebutolol when combined with Belladonna. Infectious gastroenteritis/colitis [1A40] [18]
Amobarbital DM0GQ8N Moderate Increased metabolism of Acebutolol caused by Amobarbital mediated induction of CYP450 enzyme. Insomnia [7A00-7A0Z] [20]
ITI-007 DMUQ1DO Moderate Additive hypotensive effects by the combination of Acebutolol and ITI-007. Insomnia [7A00-7A0Z] [15]
Glycerol phenylbutyrate DMDGRQO Moderate Decreased metabolism of Acebutolol caused by Glycerol phenylbutyrate mediated inhibition of CYP450 enzyme. Liver disease [DB90-DB9Z] [18]
Lanthanum carbonate DMMJQSH Moderate Decreased absorption of Acebutolol due to formation of complexes caused by Lanthanum carbonate. Mineral absorption/transport disorder [5C64] [17]
Siponimod DM2R86O Major Increased risk of bradycardia by the combination of Acebutolol and Siponimod. Multiple sclerosis [8A40] [21]
Fingolimod DM5JVAN Major Increased risk of atrioventricular block by the combination of Acebutolol and Fingolimod. Multiple sclerosis [8A40] [22]
Ozanimod DMT6AM2 Moderate Increased risk of bradycardia by the combination of Acebutolol and Ozanimod. Multiple sclerosis [8A40] [23]
Polythiazide DMCH80F Moderate Increased risk of hypertriglyceridemia by the combination of Acebutolol and Polythiazide. Oedema [MG29] [24]
Methylscopolamine DM5VWOB Moderate Antagonize the effect of Acebutolol when combined with Methylscopolamine. Peptic ulcer [DA61] [18]
Silodosin DMJSBT6 Moderate Additive hypotensive effects by the combination of Acebutolol and Silodosin. Prostate hyperplasia [GA90] [25]
Levomepromazine DMIKFEL Moderate Additive hypotensive effects by the combination of Acebutolol and Levomepromazine. Psychotic disorder [6A20-6A25] [15]
Quetiapine DM1N62C Moderate Additive hypotensive effects by the combination of Acebutolol and Quetiapine. Schizophrenia [6A20] [15]
Aripiprazole DM3NUMH Moderate Additive hypotensive effects by the combination of Acebutolol and Aripiprazole. Schizophrenia [6A20] [15]
Iloperidone DM6AUFY Moderate Additive hypotensive effects by the combination of Acebutolol and Iloperidone. Schizophrenia [6A20] [15]
Paliperidone DM7NPJS Moderate Additive hypotensive effects by the combination of Acebutolol and Paliperidone. Schizophrenia [6A20] [15]
Molindone DMAH70G Moderate Additive hypotensive effects by the combination of Acebutolol and Molindone. Schizophrenia [6A20] [15]
Thiothixene DMDINC4 Moderate Additive hypotensive effects by the combination of Acebutolol and Thiothixene. Schizophrenia [6A20] [15]
Amisulpride DMSJVAM Moderate Increased risk of ventricular arrhythmias by the combination of Acebutolol and Amisulpride. Schizophrenia [6A20] [18]
Asenapine DMSQZE2 Moderate Additive hypotensive effects by the combination of Acebutolol and Asenapine. Schizophrenia [6A20] [15]
Pipecuronium DM5F84A Moderate Additive neuromuscular blocking effects by the combination of Acebutolol and Pipecuronium. Tonus and reflex abnormality [MB47] [16]
Vecuronium DMP0UK2 Moderate Additive neuromuscular blocking effects by the combination of Acebutolol and Vecuronium. Tonus and reflex abnormality [MB47] [16]
Trimeprazine DMEMV9D Moderate Additive hypotensive effects by the combination of Acebutolol and Trimeprazine. Vasomotor/allergic rhinitis [CA08] [26]
⏷ Show the Full List of 35 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Allura red AC dye E00338 33258 Colorant
D&C red no. 22 E00206 11048 Colorant
D&C red no. 28 E00491 6097185 Colorant
FD&C blue no. 1 E00263 19700 Colorant
FD&C blue no. 2 E00446 2723854 Colorant
Quinoline yellow WS E00309 24671 Colorant
Sodium lauryl sulfate E00464 3423265 Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Stearic acid E00079 5281 Emulsifying agent; Solubilizing agent; Viscosity-controlling agent; lubricant
Sunset yellow FCF E00255 17730 Colorant
Ferrosoferric oxide E00231 14789 Colorant
Gelatin E00630 Not Available Other agent
Povidone E00667 Not Available Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Propylene glycol E00040 1030 Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Titanium dioxide E00322 26042 Coating agent; Colorant; Opacifying agent
Pregelatinized starch E00674 Not Available Binding agent; Diluent; Disintegrant
⏷ Show the Full List of 15 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Acebutolol 200 mg capsule 200 mg Oral Capsule Oral
Acebutolol 400 mg capsule 400 mg Oral Capsule Oral
Acebutolol Hydrochloride eq 200mg base capsule eq 200mg base Capsule Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 Acebutolol FDA Label
3 BDDCS applied to over 900 drugs
4 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
6 Prediction and experimental validation of acute toxicity of beta-blockers in Ceriodaphnia dubia. Environ Toxicol Chem. 2005 Oct;24(10):2470-6.
7 Implications of genetic polymorphisms in drug transporters for pharmacotherapy. Cancer Lett. 2006 Mar 8;234(1):4-33.
8 Fruit juice inhibition of uptake transport: a new type of food-drug interaction. Br J Clin Pharmacol. 2010 Nov;70(5):645-55.
9 Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
10 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.
11 Selection of drugs to test the specificity of the Tg.AC assay by screening for induction of the gadd153 promoter in vitro. Toxicol Sci. 2003 Aug;74(2):260-70. doi: 10.1093/toxsci/kfg113. Epub 2003 May 2.
12 Addition of acebutolol to diuretics in hypertension. Clin Pharmacol Ther. 1981 Dec;30(6):739-44. doi: 10.1038/clpt.1981.232.
13 Anastassiades CJ "Nifedipine and beta-blocker drugs." Br Med J 281 (1980): 1251-2. [PMID: 6107167]
14 Conrad KA, Nyman DW "Effects of metoprolol and propranolol on theophylline elimination." Clin Pharmacol Ther 28 (1980): 463-7. [PMID: 7408406]
15 Aronowitz JS, Chakos MH, Safferman AZ, Lieberman JA "Syncope associated with the combination of clozapine and enalapril." J Clin Psychopharmacol 14 (1994): 429-30. [PMID: 7884028]
16 Chapple DJ, Clark JS, Hughes R "Interaction between atracurium and drugs used in anaesthesia." Br J Anaesth 55 Suppl 1 (1983): s17-22. [PMID: 6688011]
17 Canadian Pharmacists Association.
18 Cerner Multum, Inc. "UK Summary of Product Characteristics.".
19 EMEA. European Medicines Agency "EPARs. European Union Public Assessment Reports.".
20 Branch RA, Herman RJ "Enzyme induction and beta-adrenergic receptor blocking drugs." Br J Clin Pharmacol 17 (1984): s77-84. [PMID: 6146342]
21 Cerner Multum, Inc. "Australian Product Information.".
22 Product Information. Gilenya (fingolimod). Novartis Pharmaceuticals, East Hanover, NJ.
23 Product Information. Zeposia (ozanimod). Celgene Corporation, Summit, NJ.
24 Dean S, Kendall MJ, Potter S, Thompson MH, Jackson DA "Nadolol in combination with indapamide and xipamide in resistant hypertensives." Eur J Clin Pharmacol 28 (1985): 29-33. [PMID: 3987783]
25 Chrysant SG "Experience with terazosin administered in combination with other antihypertensive agents." Am J Med 80 (1986): 55-61. [PMID: 2872808]
26 Product Information. Clozaril (clozapine). Novartis Pharmaceuticals, East Hanover, NJ.