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]
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Therapeutic Class

Antihypertensive Agents

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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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]

Adverse Drug Reaction (ADR)

ADR Term	Variation	Related DOT	DOT ID	REF
Adverse drug reaction	Not Available	CYP2D6	OTZJC802	[6]
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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: CHEBI:2379
CAS Number: 37517-30-9
DrugBank ID: DB01193
TTD ID: D0HD9K
VARIDT ID: DR00627
INTEDE ID: DR0032
ACDINA ID: D00008

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	[7]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Organic cation transporter 1 (SLC22A1)	DTT79CX	S22A1_HUMAN	Substrate	[8]
Organic anion transporting polypeptide 1A2 (SLCO1A2)	DTE2B1D	SO1A2_HUMAN	Substrate	[9]
P-glycoprotein 1 (ABCB1)	DTUGYRD	MDR1_HUMAN	Substrate	[10]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 2D6 (CYP2D6)_{Main DME}	DECB0K3	CP2D6_HUMAN	Substrate	[11]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Cytochrome P450 2D6 (CYP2D6)	OTZJC802	CP2D6_HUMAN	Drug Response	[6]
Protein c-Fos (FOS)	OTJBUVWS	FOS_HUMAN	Gene/Protein Processing	[12]
Renin (REN)	OT52GZR2	RENI_HUMAN	Gene/Protein Processing	[13]

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Molecular Interaction Atlas (MIA)

MIA Detail

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]	[14]
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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]	[14]
Aminophylline	DML2NIB	Major	Antagonize the effect of Acebutolol when combined with Aminophylline.	Asthma [CA23]	[15]
Cariprazine	DMJYDVK	Moderate	Additive hypotensive effects by the combination of Acebutolol and Cariprazine.	Bipolar disorder [6A60]	[16]
Atracurium	DM42HXN	Moderate	Additive cardiorespiratory depression effects by the combination of Acebutolol and Atracurium.	Corneal disease [9A76-9A78]	[17]
Mivacurium	DM473VD	Moderate	Additive neuromuscular blocking effects by the combination of Acebutolol and Mivacurium.	Corneal disease [9A76-9A78]	[17]
Pancuronium	DMB0VY8	Moderate	Additive neuromuscular blocking effects by the combination of Acebutolol and Pancuronium.	Corneal disease [9A76-9A78]	[17]
Tubocurarine	DMBZIVP	Moderate	Additive neuromuscular blocking effects by the combination of Acebutolol and Tubocurarine.	Corneal disease [9A76-9A78]	[17]
Oxtriphylline	DMLHSE3	Major	Antagonize the effect of Acebutolol when combined with Oxtriphylline.	Cough [MD12]	[15]
Pasireotide	DMHM7JS	Moderate	Increased risk of bradycardia by the combination of Acebutolol and Pasireotide.	Cushing syndrome [5A70]	[18]
OPC-34712	DMHG57U	Moderate	Additive hypotensive effects by the combination of Acebutolol and OPC-34712.	Depression [6A70-6A7Z]	[16]
Mepenzolate	DM8YU2F	Moderate	Antagonize the effect of Acebutolol when combined with Mepenzolate.	Digestive system disease [DE2Z]	[19]
Stiripentol	DMMSDOY	Moderate	Decreased metabolism of Acebutolol caused by Stiripentol mediated inhibition of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[20]
Belladonna	DM2RBWK	Moderate	Antagonize the effect of Acebutolol when combined with Belladonna.	Infectious gastroenteritis/colitis [1A40]	[19]
Amobarbital	DM0GQ8N	Moderate	Increased metabolism of Acebutolol caused by Amobarbital mediated induction of CYP450 enzyme.	Insomnia [7A00-7A0Z]	[21]
ITI-007	DMUQ1DO	Moderate	Additive hypotensive effects by the combination of Acebutolol and ITI-007.	Insomnia [7A00-7A0Z]	[16]
Glycerol phenylbutyrate	DMDGRQO	Moderate	Decreased metabolism of Acebutolol caused by Glycerol phenylbutyrate mediated inhibition of CYP450 enzyme.	Liver disease [DB90-DB9Z]	[19]
Lanthanum carbonate	DMMJQSH	Moderate	Decreased absorption of Acebutolol due to formation of complexes caused by Lanthanum carbonate.	Mineral absorption/transport disorder [5C64]	[18]
Siponimod	DM2R86O	Major	Increased risk of bradycardia by the combination of Acebutolol and Siponimod.	Multiple sclerosis [8A40]	[22]
Fingolimod	DM5JVAN	Major	Increased risk of atrioventricular block by the combination of Acebutolol and Fingolimod.	Multiple sclerosis [8A40]	[23]
Ozanimod	DMT6AM2	Moderate	Increased risk of bradycardia by the combination of Acebutolol and Ozanimod.	Multiple sclerosis [8A40]	[24]
Polythiazide	DMCH80F	Moderate	Increased risk of hypertriglyceridemia by the combination of Acebutolol and Polythiazide.	Oedema [MG29]	[25]
Methylscopolamine	DM5VWOB	Moderate	Antagonize the effect of Acebutolol when combined with Methylscopolamine.	Peptic ulcer [DA61]	[19]
Silodosin	DMJSBT6	Moderate	Additive hypotensive effects by the combination of Acebutolol and Silodosin.	Prostate hyperplasia [GA90]	[26]
Levomepromazine	DMIKFEL	Moderate	Additive hypotensive effects by the combination of Acebutolol and Levomepromazine.	Psychotic disorder [6A20-6A25]	[16]
Quetiapine	DM1N62C	Moderate	Additive hypotensive effects by the combination of Acebutolol and Quetiapine.	Schizophrenia [6A20]	[16]
Aripiprazole	DM3NUMH	Moderate	Additive hypotensive effects by the combination of Acebutolol and Aripiprazole.	Schizophrenia [6A20]	[16]
Iloperidone	DM6AUFY	Moderate	Additive hypotensive effects by the combination of Acebutolol and Iloperidone.	Schizophrenia [6A20]	[16]
Paliperidone	DM7NPJS	Moderate	Additive hypotensive effects by the combination of Acebutolol and Paliperidone.	Schizophrenia [6A20]	[16]
Molindone	DMAH70G	Moderate	Additive hypotensive effects by the combination of Acebutolol and Molindone.	Schizophrenia [6A20]	[16]
Thiothixene	DMDINC4	Moderate	Additive hypotensive effects by the combination of Acebutolol and Thiothixene.	Schizophrenia [6A20]	[16]
Amisulpride	DMSJVAM	Moderate	Increased risk of ventricular arrhythmias by the combination of Acebutolol and Amisulpride.	Schizophrenia [6A20]	[19]
Asenapine	DMSQZE2	Moderate	Additive hypotensive effects by the combination of Acebutolol and Asenapine.	Schizophrenia [6A20]	[16]
Pipecuronium	DM5F84A	Moderate	Additive neuromuscular blocking effects by the combination of Acebutolol and Pipecuronium.	Tonus and reflex abnormality [MB47]	[17]
Vecuronium	DMP0UK2	Moderate	Additive neuromuscular blocking effects by the combination of Acebutolol and Vecuronium.	Tonus and reflex abnormality [MB47]	[17]
Trimeprazine	DMEMV9D	Moderate	Additive hypotensive effects by the combination of Acebutolol and Trimeprazine.	Vasomotor/allergic rhinitis [CA08]	[27]
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⏷ 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
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⏷ 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	ADReCS-Target: target profiles for aiding drug safety research and application. Nucleic Acids Res. 2018 Jan 4;46(D1):D911-D917. doi: 10.1093/nar/gkx899.
7	Prediction and experimental validation of acute toxicity of beta-blockers in Ceriodaphnia dubia. Environ Toxicol Chem. 2005 Oct;24(10):2470-6.
8	Implications of genetic polymorphisms in drug transporters for pharmacotherapy. Cancer Lett. 2006 Mar 8;234(1):4-33.
9	Fruit juice inhibition of uptake transport: a new type of food-drug interaction. Br J Clin Pharmacol. 2010 Nov;70(5):645-55.
10	Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
11	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.
12	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.
13	Addition of acebutolol to diuretics in hypertension. Clin Pharmacol Ther. 1981 Dec;30(6):739-44. doi: 10.1038/clpt.1981.232.
14	Anastassiades CJ "Nifedipine and beta-blocker drugs." Br Med J 281 (1980): 1251-2. [PMID: 6107167]
15	Conrad KA, Nyman DW "Effects of metoprolol and propranolol on theophylline elimination." Clin Pharmacol Ther 28 (1980): 463-7. [PMID: 7408406]
16	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]
17	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]
18	Canadian Pharmacists Association.
19	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
20	EMEA. European Medicines Agency "EPARs. European Union Public Assessment Reports.".
21	Branch RA, Herman RJ "Enzyme induction and beta-adrenergic receptor blocking drugs." Br J Clin Pharmacol 17 (1984): s77-84. [PMID: 6146342]
22	Cerner Multum, Inc. "Australian Product Information.".
23	Product Information. Gilenya (fingolimod). Novartis Pharmaceuticals, East Hanover, NJ.
24	Product Information. Zeposia (ozanimod). Celgene Corporation, Summit, NJ.
25	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]
26	Chrysant SG "Experience with terazosin administered in combination with other antihypertensive agents." Am J Med 80 (1986): 55-61. [PMID: 2872808]
27	Product Information. Clozaril (clozapine). Novartis Pharmaceuticals, East Hanover, NJ.