acebutolol Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
beta-adrenoreceptor antagonists 40 37517-30-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • IL-17803A
  • acebutolol HCl
  • acebutolol
  • acebutolol hydrochloride
  • (RS)-Acebutolol
  • (+/-)-Acebutolol
  • dl-Acebutolol
A cardioselective beta-1 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.
  • Molecular weight: 336.43
  • Formula: C18H28N2O4
  • CLOGP: 1.71
  • LIPINSKI: 0
  • HAC: 6
  • HDO: 3
  • TPSA: 87.66
  • ALOGS: -3.29
  • ROTB: 10

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.40 g O
0.40 g P

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 46.09 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 10 % Benet LZ, Broccatelli F, Oprea TI
BA (Bioavailability) 37 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 1.70 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 10 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.74 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 3.50 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Dec. 28, 1984 FDA PROMIUS PHARMA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Toxicity to various agents 143.46 94.90 38 150 32716 2325181
Hypotension 129.30 94.90 35 153 32401 2325496
Cognitive disorder 115.67 94.90 23 165 5358 2352539
Orthostatic hypotension 110.11 94.90 20 168 2859 2355038
Fall 103.29 94.90 32 156 47067 2310830
Bradycardia 101.51 94.90 23 165 9958 2347939

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event

Pharmacologic Action:

SourceCodeDescription
ATC C07AB04 CARDIOVASCULAR SYSTEM
BETA BLOCKING AGENTS
BETA BLOCKING AGENTS
Beta blocking agents, selective
ATC C07BB04 CARDIOVASCULAR SYSTEM
BETA BLOCKING AGENTS
BETA BLOCKING AGENTS AND THIAZIDES
Beta blocking agents, selective, and thiazides
MeSH PA D018663 Adrenergic Agents
MeSH PA D018674 Adrenergic Antagonists
MeSH PA D058671 Adrenergic beta-1 Receptor Antagonists
MeSH PA D000319 Adrenergic beta-Antagonists
CHEBI has role CHEBI:35530 beta-adrenergic antagonist
CHEBI has role CHEBI:38070 anti-arrhythmia drug
CHEBI has role CHEBI:35674 antihypertensive agent
CHEBI has role CHEBI:35524 sympathomimetic agent
MeSH PA D000889 Anti-Arrhythmia Agents
MeSH PA D000959 Antihypertensive Agents
MeSH PA D002317 Cardiovascular Agents
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018373 Peripheral Nervous System Agents
FDA EPC N0000175556 beta-Adrenergic Blocker
MeSH PA D013566 Sympathomimetics

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Ventricular premature beats indication 17338001
Hypertensive disorder indication 38341003 DOID:10763
Anxiety off-label use 48694002
Thyrotoxicosis off-label use 90739004 DOID:7997
Angina pectoris off-label use 194828000
Mitral valve prolapse off-label use 409712001
Myocardial Reinfarction Prevention off-label use
Psoriasis contraindication 9014002 DOID:8893
Complete atrioventricular block contraindication 27885002
Depressive disorder contraindication 35489007
Sick sinus syndrome contraindication 36083008 DOID:13884
Anaphylaxis contraindication 39579001
Sinus bradycardia contraindication 49710005
Diabetes mellitus contraindication 73211009 DOID:9351
Pulmonary emphysema contraindication 87433001
Cardiogenic shock contraindication 89138009
Kidney disease contraindication 90708001 DOID:557
Myasthenia gravis contraindication 91637004 DOID:437
Partial atrioventricular block contraindication 195039008
Decompensated cardiac failure contraindication 195111005
Asthma contraindication 195967001 DOID:2841
Disease of liver contraindication 235856003 DOID:409
Raynaud's phenomenon contraindication 266261006
Pregnancy, function contraindication 289908002
Pheochromocytoma contraindication 302835009
Severe chronic obstructive pulmonary disease contraindication 313299006
Peripheral arterial occlusive disease contraindication 399957001
Peripheral vascular disease contraindication 400047006
Acute exacerbation of asthma contraindication 708038006

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.19 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Beta-1 adrenergic receptor GPCR ANTAGONIST Ki 7.30 WOMBAT-PK CHEMBL
Beta-2 adrenergic receptor GPCR Ki 6.40 WOMBAT-PK
5-hydroxytryptamine receptor 1A GPCR Ki 5 CHEMBL

External reference:

IDSource
D000070 MESH_DESCRIPTOR_UI
4018063 VUID
N0000179521 NUI
C0543447 UMLSCUI
D00597 KEGG_DRUG
67P356D8GH UNII
3295 INN_ID
68088000 SNOMEDCT_US
372815001 SNOMEDCT_US
4019592 VANDF
004742 NDDF
149 RXNORM
d00128 MMSL
34381-68-5 SECONDARY_CAS_RN
CHEMBL642 ChEMBL_ID
CHEMBL1200813 ChEMBL_ID
DB01193 DRUGBANK_ID
CHEBI:2379 CHEBI
7107 IUPHAR_LIGAND_ID
1978 PUBCHEM_CID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Acebutolol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-1200 CAPSULE 200 mg ORAL ANDA 11 sections
Acebutolol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-1400 CAPSULE 400 mg ORAL ANDA 11 sections
Acebutolol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10135-630 CAPSULE 200 mg ORAL ANDA 12 sections
Acebutolol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10135-631 CAPSULE 400 mg ORAL ANDA 12 sections
Acebutolol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50268-050 CAPSULE 200 mg ORAL ANDA 11 sections
Acebutolol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 53746-669 CAPSULE 200 mg ORAL ANDA 11 sections
Acebutolol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 53746-670 CAPSULE 400 mg ORAL ANDA 11 sections
Acebutolol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 54868-4216 CAPSULE 400 mg ORAL ANDA 12 sections
Acebutolol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 54868-5520 CAPSULE 200 mg ORAL ANDA 12 sections
Acebutolol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 65162-669 CAPSULE 200 mg ORAL ANDA 11 sections
Acebutolol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 65162-670 CAPSULE 400 mg ORAL ANDA 11 sections
SECTRAL HUMAN PRESCRIPTION DRUG LABEL 1 67857-700 CAPSULE 200 mg ORAL NDA 19 sections
SECTRAL HUMAN PRESCRIPTION DRUG LABEL 1 67857-701 CAPSULE 400 mg ORAL NDA 19 sections