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Tox | Related Drugs | BioActivity |

Stem definition	Drug id	CAS RN
beta-adrenoreceptor antagonists	40	37517-30-9

Description:

Molecule	Description
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

Molecule

Description

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:

Dose	Unit	Route
0.40	g	O
0.40	g	P

ADMET properties:

Property	Value	Reference
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 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	40 %	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

Predicted pharmacokinetic/toxicological properties (PK-AZ):

Property	Description	Value	Unit	Confidence	Similarity
azlogd74	LogD at pH 7.4	0.057		High	1
caco2-efflux	Caco-2 efflux ratio (BA/AB)	16.827		High	1
caco2-intrinsic-papp	Caco-2 intrinsic apparent permeability	0.908	10^-6 cm/s	High	1
dh-clint	Dog hepatocyte intrinsic clearance	1.535	uL/min/10^6 cells	High	1
dppb	Dog plasma protein binding (% unbound)	79.890	%	High	1
fcs-ppb	Fetal calf serum protein binding (% unbound)	77.130	%	High	1
herg	hERG pIC50	4.277	pIC50	High	1
hh-clint	Human hepatocyte intrinsic clearance	1.047	uL/min/10^6 cells	High	1
hlm-clint	Human liver microsomal intrinsic clearance	2.999	uL/min/mg protein	High	1
hppb	Human plasma protein binding (% unbound)	83.270	%	High	1
kinase-safety-class	ACVR2A,ACVR2B,AKT2,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK4,CDK5,CDK9,DDR1,DYRK1B,EGFR,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,GSK3B,IKBKB,ITK,JAK1,JAK2,JAK3,MAP2K6,MAP3K21,MAP3K7,MAPK7,MAPK8,MAPK9,MAPKAPK2,MET,MTOR,NTRK2,PDK2,PDK4,PDPK1,PIK3CB,PIM2,PLK1,PRKCD,PRKDC,SIK2,SIK3,STK33,SYK,TEK,TTK,ZAP70	51
kinase-selectivity-class	PDK4	1
mdck-mdr1-efflux	MDCK-MDR1 efflux ratio	4.603		High	1
mh-clint	Mouse hepatocyte intrinsic clearance	6.653		High	1
mppb	Mouse plasma protein binding (% unbound)	72.320		High	1
nih-mdck-mdr1-efflux	NIH MDCK-MDR1 efflux ratio	7.228		High	1
pfas-class	PFAS structural alert (1 = True, 0 = False)	0
pppb	Pig plasma protein binding (% unbound)	87.720	%	High	1
rh-clint	Rat hepatocyte intrinsic clearance	2.118	uL/min/10^6 cells	High	1
rh-fuinc	Rat hepatocyte fraction unbound in incubation	86.180	%	High	1
rppb	Rat plasma protein binding (% unbound)	76.640	%	High	1
solubility-dd	Solubility at pH 7.4 in DMSO	931.108	uM	High	1

Approvals:

Date	Agency	Company	Orphan
Dec. 28, 1984	FDA	PROMIUS PHARMA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Orthostatic hypotension	1512.02	36.68	431	10188	41396	90576432
Creatinine renal clearance decreased	1491.37	36.68	362	10257	18537	90599291
Cognitive disorder	1487.94	36.68	478	10141	68929	90548899
Sedation complication	1483.63	36.68	353	10266	16591	90601237
Sedation	1360.51	36.68	410	10209	47761	90570067
Blood calcium decreased	1318.52	36.68	361	10258	29821	90588007
Balance disorder	1177.43	36.68	437	10182	96643	90521185
Depressed level of consciousness	1016.93	36.68	364	10255	72420	90545408
Hypotension	788.42	36.68	482	10137	324915	90292913
Constipation	729.31	36.68	435	10184	279960	90337868
Mobility decreased	688.37	36.68	403	10216	250331	90367497
Toxicity to various agents	647.03	36.68	407	10212	287439	90330389
Fall	632.15	36.68	489	10130	481321	90136507
Multiple drug therapy	333.90	36.68	90	10529	6919	90610909
Creatinine renal clearance increased	184.20	36.68	48	10571	3233	90614595
Renal function test abnormal	167.48	36.68	53	10566	7138	90610690
Pain	162.70	36.68	358	10261	995983	89621845
Blood pressure inadequately controlled	162.23	36.68	50	10569	6174	90611654
Diabetes mellitus inadequate control	151.02	36.68	63	10556	18621	90599207
Exercise tolerance decreased	144.68	36.68	48	10571	7503	90610325
Endometriosis	108.94	36.68	37	10582	6211	90611617
Drug specific antibody	77.57	36.68	23	10596	2489	90615339
Fatigue	60.57	36.68	30	10589	1153993	89463835
Headache	59.77	36.68	14	10605	862732	89755096
Depressed mood	58.71	36.68	48	10571	50174	90567654
Hypocoagulable state	55.36	36.68	16	10603	1583	90616245
Treatment noncompliance	53.37	36.68	46	10573	51681	90566147
Drug abuse	50.47	36.68	55	10564	82292	90535536
Nausea	46.99	36.68	37	10582	1110279	89507549
Cardiogenic shock	45.71	36.68	31	10588	24437	90593391
Medication error	44.16	36.68	52	10567	84600	90533228
Alopecia	43.45	36.68	4	10615	495067	90122761
Pneumonia	42.87	36.68	11	10608	638048	89979780
Drug specific antibody present	42.55	36.68	18	10601	5496	90612332
Joint swelling	41.77	36.68	5	10614	503295	90114533
Oesophageal food impaction	41.13	36.68	9	10610	285	90617543
Bradycardia	39.64	36.68	49	10570	83798	90534030
Overdose	39.19	36.68	68	10551	157641	90460187
Hypersensitivity	39.03	36.68	4	10615	454673	90163155
Diarrhoea	38.81	36.68	32	10587	939158	89678670
Oesophageal achalasia	38.59	36.68	10	10609	658	90617170
Rash	38.31	36.68	23	10596	796077	89821751
Morbid thoughts	37.38	36.68	10	10609	744	90617084
Cor pulmonale acute	37.38	36.68	9	10610	438	90617390
Chronic kidney disease	36.98	36.68	37	10582	50154	90567674

FDA Adverse Event Reporting System (Male)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Pancreatic carcinoma metastatic	68.54	21.67	19	2568	3147	42615601
Linear IgA disease	56.67	21.67	15	2572	2088	42616660
Interstitial lung disease	50.13	21.67	40	2547	78422	42540326
Eosinophilia	37.77	21.67	24	2563	32875	42585873
Bradycardia	37.17	21.67	35	2552	85449	42533299
Eyelid oedema	30.94	21.67	12	2575	5683	42613065
Pancreatitis acute	30.10	21.67	21	2566	33543	42585205
Ischaemic stroke	30.04	21.67	18	2569	22215	42596533
Cerebral haematoma	27.59	21.67	11	2576	5599	42613149
Dermatitis exfoliative generalised	27.19	21.67	11	2576	5813	42612935
Pulmonary fibrosis	27.02	21.67	18	2569	26663	42592085
Sudden death	26.53	21.67	15	2572	16614	42602134
Blood growth hormone increased	24.25	21.67	6	2581	638	42618110
Asthma-chronic obstructive pulmonary disease overlap syndrome	23.23	21.67	7	2580	1552	42617196
Thrombocytopenia	22.66	21.67	41	2546	190238	42428510
Agranulocytosis	22.54	21.67	17	2570	30595	42588153
Subdural haematoma	21.97	21.67	15	2572	23123	42595625
Bronchial hyperreactivity	21.76	21.67	7	2580	1922	42616826

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Sedation complication	1471.27	26.91	363	12820	19492	110556624
Creatinine renal clearance decreased	1467.17	26.91	369	12814	21446	110554670
Cognitive disorder	1411.66	26.91	489	12694	87022	110489094
Orthostatic hypotension	1323.73	26.91	435	12748	65814	110510302
Blood calcium decreased	1294.53	26.91	371	12812	35474	110540642
Sedation	1210.99	26.91	412	12771	69271	110506845
Balance disorder	1108.16	26.91	442	12741	116118	110459998
Depressed level of consciousness	899.94	26.91	377	12806	111901	110464215
Mobility decreased	722.62	26.91	411	12772	237011	110339105
Hypotension	667.80	26.91	527	12656	523322	110052794
Constipation	647.42	26.91	445	12738	357341	110218775
Fall	580.21	26.91	516	12667	602966	109973150
Toxicity to various agents	477.05	26.91	419	12764	480136	110095980
Multiple drug therapy	334.06	26.91	93	13090	7921	110568195
Pain	193.39	26.91	379	12804	954576	109621540
Creatinine renal clearance increased	183.33	26.91	49	13134	3576	110572540
Renal function test abnormal	155.19	26.91	53	13130	8893	110567223
Blood pressure inadequately controlled	151.32	26.91	50	13133	7583	110568533
Diabetes mellitus inadequate control	127.69	26.91	65	13118	29710	110546406
Exercise tolerance decreased	121.89	26.91	48	13135	12019	110564097
Endometriosis	117.35	26.91	36	13147	4298	110571818
Drug specific antibody	70.28	26.91	22	13161	2806	110573310
Bradycardia	60.11	26.91	83	13100	155434	110420682
Pancreatic carcinoma metastatic	54.43	26.91	20	13163	4144	110571972
Fatigue	52.59	26.91	41	13142	1215917	109360199
Pneumonia	51.71	26.91	20	13163	876694	109699422
Headache	50.62	26.91	21	13162	882356	109693760
Depressed mood	50.05	26.91	48	13135	60761	110515355
Hypocoagulable state	47.33	26.91	16	13167	2599	110573517
Cerebral haematoma	41.20	26.91	21	13162	9611	110566505
Nausea	40.47	26.91	53	13130	1235637	109340479
Dermatitis exfoliative generalised	38.62	26.91	21	13162	10951	110565165
Bladder disorder	38.33	26.91	21	13162	11116	110565000
Treatment noncompliance	37.70	26.91	45	13138	72945	110503171
Medication error	35.93	26.91	53	13130	105313	110470803
Linear IgA disease	35.87	26.91	15	13168	4374	110571742
Morbid thoughts	35.25	26.91	10	13173	909	110575207
Oesophageal food impaction	35.09	26.91	9	13174	558	110575558
Drug specific antibody present	34.95	26.91	18	13165	8416	110567700
Hypersensitivity	34.28	26.91	4	13179	403994	110172122
Oesophageal achalasia	34.21	26.91	10	13173	1011	110575105
Death	33.52	26.91	21	13162	698848	109877268
Cor pulmonale acute	32.48	26.91	9	13174	751	110575365
Amnesia	31.67	26.91	50	13133	105358	110470758
Diarrhoea	31.36	26.91	55	13128	1139450	109436666
Overdose	31.28	26.91	79	13104	233715	110342401
Vomiting	30.86	26.91	38	13145	910637	109665479
Drug hypersensitivity	29.06	26.91	9	13174	454081	110122035
Cardiogenic shock	29.03	26.91	35	13148	57303	110518813
Rash	28.08	26.91	34	13149	820930	109755186
Alopecia	27.72	26.91	5	13178	364748	110211368

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
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
CHEBI has role	CHEBI:35524	sympathomimetic agent
CHEBI has role	CHEBI:35530	β-adrenergic antagonist
CHEBI has role	CHEBI:35554	cardiovascular drug
CHEBI has role	CHEBI:35610	antineoplastic agent
CHEBI has role	CHEBI:35674	antihypertensive agent
CHEBI has role	CHEBI:38070	anti-arrhythmia drug
MeSH PA	D000319	Adrenergic beta-Antagonists
MeSH PA	D000889	Anti-Arrhythmia Agents
MeSH PA	D000959	Antihypertensive Agents
MeSH PA	D002317	Cardiovascular Agents
MeSH PA	D013566	Sympathomimetics
MeSH PA	D018377	Neurotransmitter Agents
MeSH PA	D018663	Adrenergic Agents
MeSH PA	D018674	Adrenergic Antagonists
MeSH PA	D058671	Adrenergic beta-1 Receptor Antagonists

Related Drugs by ATC class:

C07AB Beta blocking agents, selective 13 drugs

atenolol betaxolol bevantolol bisoprolol celiprolol epanolol esatenolol esmolol landiolol metoprolol nebivolol practolol show all 13 →

C07BB Beta blocking agents, selective, and thiazides 5 drugs

atenolol bevantolol bisoprolol metoprolol nebivolol

Drug Use | Suggest Off label Use Form| |View source of the data|

Disease	Relation	SNOMED_ID	DOID
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

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	9.19	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Beta-1 adrenergic receptor	GPCR	P08588	ADRB1_HUMAN	ANTAGONIST	Ki	7.30	WOMBAT-PK	CHEMBL
Beta-2 adrenergic receptor	GPCR	P07550	ADRB2_HUMAN		Ki	6.40	WOMBAT-PK
5-hydroxytryptamine receptor 1A	GPCR		5HT1A_RAT		Ki	5	CHEMBL

External reference:

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

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
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	42291-010	CAPSULE	200 mg	ORAL	ANDA	14 sections
Acebutolol Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	50268-050	CAPSULE	200 mg	ORAL	ANDA	13 sections
Acebutolol Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	51407-666	CAPSULE	200 mg	ORAL	ANDA	23 sections
Acebutolol Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	51407-667	CAPSULE	400 mg	ORAL	ANDA	23 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	62559-255	CAPSULE	200 mg	ORAL	ANDA	23 sections
Acebutolol Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	62559-255	CAPSULE	200 mg	ORAL	ANDA	23 sections
Acebutolol Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	62559-256	CAPSULE	400 mg	ORAL	ANDA	23 sections
Acebutolol Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	62559-256	CAPSULE	400 mg	ORAL	ANDA	23 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

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acebutolol 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Description:

Drug dosage:

ADMET properties:

Predicted pharmacokinetic/toxicological properties (PK-AZ):

Approvals:

FDA Adverse Event Reporting System (Female)

FDA Adverse Event Reporting System (Male)

FDA Adverse Event Reporting System (Geriatric)

FDA Adverse Event Reporting System (Pediatric)

Pharmacologic Action:

Related Drugs by ATC class:

Drug Use | Suggest Off label Use Form| |View source of the data|

🐶 Veterinary Drug Use

🐶 Veterinary products

Acid dissociation constants calculated using MoKa v3.0.0

Orange Book patent data (new drug applications)

Orange Book exclusivity data (new drug applications)

Bioactivity Summary:

External reference:

Pharmaceutical products: