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
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
MRTD (Maximum Recommended Therapeutic Daily Dose) 46.09 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
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
Sedation complication 333.14 22.83 77 4779 3568 46677638
Cognitive disorder 312.33 22.83 124 4732 36759 46644447
Orthostatic hypotension 299.67 22.83 108 4748 24550 46656656
Sedation 280.82 22.83 101 4755 22809 46658397
Creatinine renal clearance decreased 270.11 22.83 74 4782 6846 46674360
Blood calcium decreased 214.35 22.83 75 4781 15598 46665608
Balance disorder 205.46 22.83 110 4746 64411 46616795
Hypotension 195.84 22.83 174 4682 232415 46448791
Depressed level of consciousness 150.98 22.83 81 4775 47488 46633718
Mobility decreased 135.29 22.83 82 4774 60512 46620694
Fall 127.35 22.83 163 4693 328934 46352272
Constipation 112.95 22.83 113 4743 173984 46507222
Toxicity to various agents 106.46 22.83 120 4736 211646 46469560
Diabetes mellitus inadequate control 67.06 22.83 31 4825 13183 46668023
Hypocoagulable state 63.97 22.83 16 4840 1031 46680175
Bradycardia 60.16 22.83 52 4804 66246 46614960
Cardiogenic shock 57.83 22.83 30 4826 16354 46664852
Multiple drug therapy 56.05 22.83 14 4842 897 46680309
Cor pulmonale acute 39.90 22.83 9 4847 371 46680835
Coma 36.05 22.83 37 4819 58312 46622894
Blood pressure inadequately controlled 34.35 22.83 14 4842 4392 46676814
Hyponatraemia 30.98 22.83 45 4811 101287 46579919
Cerebral haematoma 30.87 22.83 12 4844 3327 46677879
Cardiorenal syndrome 30.64 22.83 8 4848 612 46680594
Prothrombin time shortened 30.20 22.83 10 4846 1749 46679457
Drug reaction with eosinophilia and systemic symptoms 28.45 22.83 24 4832 29524 46651682
Haemodynamic instability 26.83 22.83 14 4842 7711 46673495
Sinus rhythm 26.05 22.83 7 4849 598 46680608
Exercise tolerance decreased 24.03 22.83 11 4845 4566 46676640

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
Pancreatic carcinoma metastatic 64.10 21.78 19 2228 3228 29947003
Linear IgA disease 38.83 21.78 11 2236 1591 29948640
Pulmonary fibrosis 37.67 21.78 20 2227 15870 29934361
Pancreatitis acute 33.58 21.78 22 2225 25673 29924558
Interstitial lung disease 33.39 21.78 31 2216 60166 29890065
Cerebral haematoma 31.18 21.78 12 2235 4502 29945729
Tendonitis 24.52 21.78 12 2235 8024 29942207
Ureteric stenosis 23.40 21.78 7 2240 1224 29949007
Cholestasis 22.43 21.78 17 2230 24933 29925298
Lymphocele 22.22 21.78 7 2240 1453 29948778
Eosinophilia 21.94 21.78 16 2231 22144 29928087
Subdural haematoma 21.79 21.78 15 2232 18957 29931274

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
FDA MoA N0000000161 Adrenergic beta-Antagonists
FDA EPC N0000175556 beta-Adrenergic Blocker
MeSH PA D018663 Adrenergic Agents
MeSH PA D018674 Adrenergic Antagonists
MeSH PA D058671 Adrenergic beta-1 Receptor Antagonists
MeSH PA D000319 Adrenergic beta-Antagonists
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
MeSH PA D013566 Sympathomimetics
CHEBI has role CHEBI:35524 sympathomimetic
CHEBI has role CHEBI:35530 beta-adrenoceptor antagonists
CHEBI has role CHEBI:35674 antihypertensive
CHEBI has role CHEBI:38070 antiarrhythmic agent

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
67P356D8GH UNII
4018063 VUID
N0000179521 NUI
D00597 KEGG_DRUG
34381-68-5 SECONDARY_CAS_RN
C0000946 UMLSCUI
CHEBI:2379 CHEBI
CHEMBL642 ChEMBL_ID
CHEMBL1200813 ChEMBL_ID
1978 PUBCHEM_CID
DB01193 DRUGBANK_ID
D000070 MESH_DESCRIPTOR_UI
3295 INN_ID
7107 IUPHAR_LIGAND_ID
142130 RXNORM
4118 MMSL
64 MMSL
d00128 MMSL
001858 NDDF
004742 NDDF
3597005 SNOMEDCT_US
372815001 SNOMEDCT_US
68088000 SNOMEDCT_US
4018063 VANDF
4019592 VANDF

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Acebutolol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-1200 CAPSULE 200 mg ORAL ANDA 24 sections
Acebutolol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-1400 CAPSULE 400 mg ORAL ANDA 24 sections
Acebutolol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10135-630 CAPSULE 200 mg ORAL ANDA 21 sections
Acebutolol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10135-631 CAPSULE 400 mg ORAL ANDA 21 sections
Acebutolol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50268-050 CAPSULE 200 mg ORAL ANDA 13 sections
Acebutolol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 53746-669 CAPSULE 200 mg ORAL ANDA 14 sections
Acebutolol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 53746-670 CAPSULE 400 mg ORAL ANDA 14 sections
Acebutolol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 54868-4216 CAPSULE 400 mg ORAL ANDA 14 sections
Acebutolol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 54868-5520 CAPSULE 200 mg ORAL ANDA 14 sections
Acebutolol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 65162-669 CAPSULE 200 mg ORAL ANDA 14 sections
Acebutolol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 65162-670 CAPSULE 400 mg ORAL ANDA 14 sections
SECTRAL HUMAN PRESCRIPTION DRUG LABEL 1 67857-700 CAPSULE 200 mg ORAL NDA 26 sections
SECTRAL HUMAN PRESCRIPTION DRUG LABEL 1 67857-701 CAPSULE 400 mg ORAL NDA 26 sections