Acebutolol
drug drugOn this page
Also known as C07AB04acebtutolol
Summary
Acebutolol (CHEMBL642) is an approved small-molecule β-adrenergic antagonist (ATC C07AB04) targeting ADRB1; indicated across 5 conditions including cardiovascular disorder and hemangioma.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: C07AB04
- Targets: 1 (ADRB1)
- Indications: 5 conditions
- Clinical trials: 3
- Chemistry: 336.4 Da · C18H28N2O4
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL642 |
| Name | Acebutolol |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | yes |
| PubChem CID | 1978 |
| ChEBI | CHEBI:2379 |
| ATC | C07AB04 |
| Molecular formula | C18H28N2O4 |
| Molecular weight | 336.4 |
| InChIKey | GOEMGAFJFRBGGG-UHFFFAOYSA-N |
SMILES: CCCC(=O)NC1=CC(=C(C=C1)OCC(CNC(C)C)O)C(=O)C
IUPAC name: N-[3-acetyl-4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]butanamide
ChEBI definition: An ether that is the 2-acetyl-4-(butanoylamino)phenyl ether of the primary hydroxy group of 3-(propan-2-ylamino)propane-1,2-diol.
Pharmacological roles (ChEBI): β-adrenergic antagonist, anti-arrhythmia drug, antihypertensive agent, sympathomimetic agent.
Also known as: Acebutolol, C07AB04, acebtutolol, acebutolol, ACEBUTOLOL
Parent form; salt/anhydrous children: CHEMBL1200813
Patent coverage: 5,251 distinct patent families (20,882 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 20,817 (100%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.
Targets
Targets
Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).
| Gene | Target | Action | pAffinity | Cancer dependency | UniProt |
|---|---|---|---|---|---|
| ADRB1 | β1-adrenoceptor | Antagonist | 6.5 | 0% | P08588 |
Broader ChEMBL bioactivity targets: 4 (assay-derived). Sample: Beta-2 adrenergic receptor, Beta-1 adrenergic receptor, 5-hydroxytryptamine receptor 1A, Solute carrier family 22 member 1.
Bioactivity
ChEMBL activities: 4 potent at pChembl ≥ 5 of 6 total. Top 100 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| ADRB1 | 6.38 | Ki | 422 | nM | CHEMBL_ACT_7631720 |
| ADRB1 | 6.14 | IC50 | 731 | nM | CHEMBL_ACT_7631719 |
| ADRB1 | 6 | AC50 | 1000 | nM | CHEMBL_ACT_25121428 |
| P19327 | 5 | Ki | 10000 | nM | CHEMBL_ACT_843819 |
Target pathways
Aggregated over 1 target gene(s): ADRB1.
Top Reactome pathways
8 total, by targets touching each:
| Pathway | Targets | Genes |
|---|---|---|
| Signal Transduction | 1 | ADRB1 |
| Signaling by GPCR | 1 | ADRB1 |
| Class A/1 (Rhodopsin-like receptors) | 1 | ADRB1 |
| Amine ligand-binding receptors | 1 | ADRB1 |
| GPCR downstream signalling | 1 | ADRB1 |
| Adrenoceptors | 1 | ADRB1 |
| G alpha (s) signalling events | 1 | ADRB1 |
| GPCR ligand binding | 1 | ADRB1 |
Dominant GO biological processes
| GO term | Targets |
|---|---|
| positive regulation of heart rate by epinephrine-norepinephrine | 1 |
| positive regulation of the force of heart contraction by epinephrine-norepinephrine | 1 |
| diet induced thermogenesis | 1 |
| norepinephrine-epinephrine-mediated vasodilation involved in regulation of systemic arterial blood pressure | 1 |
| adenylate cyclase-activating G protein-coupled receptor signaling pathway | 1 |
| response to cold | 1 |
| positive regulation of cardiac muscle cell apoptotic process | 1 |
| heat generation | 1 |
| negative regulation of multicellular organism growth | 1 |
| fear response | 1 |
| positive regulation of MAPK cascade | 1 |
| regulation of circadian sleep/wake cycle, sleep | 1 |
| brown fat cell differentiation | 1 |
| adenylate cyclase-activating adrenergic receptor signaling pathway | 1 |
| positive regulation of cold-induced thermogenesis | 1 |
Indications & clinical
Indications
1 approved indication. FDA phase 4, plus an anticancer drug’s labelled cancer uses (which ChEMBL often logs at phase 3).
| Indication | Phase | MONDO | EFO |
|---|---|---|---|
| cardiovascular disorder | 4 | MONDO:0004995 | EFO:0000319 |
4 diseases in clinical trials (phase 1–3, investigational — not approved indications). Highest ChEMBL trial phase per disease; a non-cancer approved use is occasionally logged at phase 3 here.
| Disease (in trials) | Phase | MONDO | EFO |
|---|---|---|---|
| hemangioma | 3 | MONDO:0006500 | EFO:1000635 |
| hypertensive disorder | 2 | MONDO:0005044 | EFO:0000537 |
| heart disorder | 2 | MONDO:0005267 | EFO:0003777 |
| vascular disorder | 2 | MONDO:0005385 | EFO:0004264 |
Clinical trials
Total trials: 3.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE4 | 1 |
| PHASE3 | 1 |
| PHASE2 | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT01514019 | PHASE4 | COMPLETED | An Open-label, Single-dose, Two-treatment, Randomized, Cross-over Study to Investigate the Effects of the SLCO2B1 c.1457C>T Polymorphism and Apple Juice on the Pharmacokinetics and Pharmacodynamics of Acebutolol in Healthy Korean and Japanese Volunteers |
| NCT01743885 | PHASE3 | TERMINATED | Efficacy and Safety of Propranolol Versus Acebutolol on the Proliferative Phase of Infantile Hemangioma |
| NCT00000522 | PHASE2 | COMPLETED | Treatment of Mild Hypertension Study (TOMHS) |
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
PharmGKB dosing guidelines (2) — CPIC / DPWG genotype-guided dosing for this drug (drug × pharmacogene):
| Guideline | Source | Gene(s) | Dosing | Recommendation |
|---|---|---|---|---|
| Annotation of CPIC Guideline for acebutolol, betaxolol, bisoprolol, ca | CPIC | CYP2D6 | ||
| Annotation of CPIC Guideline for acebutolol, atenolol, betaxolol, biso | CPIC | ADRA2C;ADRB1;GRK4;GRK5 |
PharmGKB also curates 0 clinical and 1 variant annotation(s) for this drug (gene-keyed; see PharmGKB).
Related molecules
Related molecules
Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.
179 molecules share ≥1 primary target. Top 100 by shared-target count:
| Molecule | Source | Status | Shared targets |
|---|---|---|---|
| OLODATEROL | ChEMBL + PubChem | Phase 4 (approved) | ADRB1 |
| TAMSULOSIN | ChEMBL + PubChem | Phase 4 (approved) | ADRB1 |
| ALBUTEROL | ChEMBL | Phase 4 (approved) | ADRB1 |
| AMIODARONE | ChEMBL | Phase 4 (approved) | ADRB1 |
| AMITRIPTYLINE | ChEMBL | Phase 4 (approved) | ADRB1 |
| ARFORMOTEROL | ChEMBL | Phase 4 (approved) | ADRB1 |
| ARIPIPRAZOLE | ChEMBL | Phase 4 (approved) | ADRB1 |
| ASTEMIZOLE | ChEMBL | Phase 4 (approved) | ADRB1 |
| ATENOLOL | ChEMBL | Phase 4 (approved) | ADRB1 |
| AZELASTINE | ChEMBL | Phase 4 (approved) | ADRB1 |
| BENFLUOREX | ChEMBL | Phase 4 (approved) | ADRB1 |
| BENPERIDOL | ChEMBL | Phase 4 (approved) | ADRB1 |
| BENZBROMARONE | ChEMBL | Phase 4 (approved) | ADRB1 |
| BEPRIDIL | ChEMBL | Phase 4 (approved) | ADRB1 |
| BETAXOLOL | ChEMBL | Phase 4 (approved) | ADRB1 |
| BISOPROLOL | ChEMBL | Phase 4 (approved) | ADRB1 |
| BREXPIPRAZOLE | ChEMBL | Phase 4 (approved) | ADRB1 |
| BROMOCRIPTINE | ChEMBL | Phase 4 (approved) | ADRB1 |
| CANDESARTAN CILEXETIL | ChEMBL | Phase 4 (approved) | ADRB1 |
| CARIPRAZINE | ChEMBL | Phase 4 (approved) | ADRB1 |
| CARTEOLOL | ChEMBL | Phase 4 (approved) | ADRB1 |
| CARVEDILOL | ChEMBL | Phase 4 (approved) | ADRB1 |
| CELIPROLOL | ChEMBL | Phase 4 (approved) | ADRB1 |
| CHLORHEXIDINE | ChEMBL | Phase 4 (approved) | ADRB1 |
| CHLORPROTHIXENE | ChEMBL | Phase 4 (approved) | ADRB1 |
| CINACALCET | ChEMBL | Phase 4 (approved) | ADRB1 |
| CLEMASTINE | ChEMBL | Phase 4 (approved) | ADRB1 |
| CLOMIPRAMINE | ChEMBL | Phase 4 (approved) | ADRB1 |
| CLOTRIMAZOLE | ChEMBL | Phase 4 (approved) | ADRB1 |
| CODEINE | ChEMBL | Phase 4 (approved) | ADRB1 |
| DARIFENACIN | ChEMBL | Phase 4 (approved) | ADRB1 |
| DAUNORUBICIN | ChEMBL | Phase 4 (approved) | ADRB1 |
| DECITABINE | ChEMBL | Phase 4 (approved) | ADRB1 |
| DIETHYLSTILBESTROL | ChEMBL | Phase 4 (approved) | ADRB1 |
| DOBUTAMINE | ChEMBL | Phase 4 (approved) | ADRB1 |
| DOMPERIDONE | ChEMBL | Phase 4 (approved) | ADRB1 |
| DULOXETINE | ChEMBL | Phase 4 (approved) | ADRB1 |
| EBASTINE | ChEMBL | Phase 4 (approved) | ADRB1 |
| ECONAZOLE | ChEMBL | Phase 4 (approved) | ADRB1 |
| EFAVIRENZ | ChEMBL | Phase 4 (approved) | ADRB1 |
| EPALRESTAT | ChEMBL | Phase 4 (approved) | ADRB1 |
| EPINEPHRINE | ChEMBL | Phase 4 (approved) | ADRB1 |
| ERGOTAMINE | ChEMBL | Phase 4 (approved) | ADRB1 |
| ESMOLOL | ChEMBL | Phase 4 (approved) | ADRB1 |
| FENOTEROL | ChEMBL | Phase 4 (approved) | ADRB1 |
| FLUSPIRILENE | ChEMBL | Phase 4 (approved) | ADRB1 |
| FORMOTEROL | ChEMBL | Phase 4 (approved) | ADRB1 |
| INDACATEROL | ChEMBL | Phase 4 (approved) | ADRB1 |
| INDOCYANINE GREEN ACID FORM | ChEMBL | Phase 4 (approved) | ADRB1 |
| ISOCONAZOLE | ChEMBL | Phase 4 (approved) | ADRB1 |
| ISOPROTERENOL | ChEMBL | Phase 4 (approved) | ADRB1 |
| LABETALOL | ChEMBL | Phase 4 (approved) | ADRB1 |
| LASOFOXIFENE | ChEMBL | Phase 4 (approved) | ADRB1 |
| LEVOBUNOLOL | ChEMBL | Phase 4 (approved) | ADRB1 |
| LORCASERIN | ChEMBL | Phase 4 (approved) | ADRB1 |
| METARAMINOL | ChEMBL | Phase 4 (approved) | ADRB1 |
| METHYLERGONOVINE | ChEMBL | Phase 4 (approved) | ADRB1 |
| METOPROLOL | ChEMBL | Phase 4 (approved) | ADRB1 |
| MICONAZOLE | ChEMBL | Phase 4 (approved) | ADRB1 |
| MONTELUKAST | ChEMBL | Phase 4 (approved) | ADRB1 |
| NADOLOL | ChEMBL | Phase 4 (approved) | ADRB1 |
| NAFTOPIDIL | ChEMBL | Phase 4 (approved) | ADRB1 |
| NEBIVOLOL | ChEMBL | Phase 4 (approved) | ADRB1 |
| NITAZOXANIDE | ChEMBL | Phase 4 (approved) | ADRB1 |
| NOREPINEPHRINE | ChEMBL | Phase 4 (approved) | ADRB1 |
| NORTRIPTYLINE | ChEMBL | Phase 4 (approved) | ADRB1 |
| NOSCAPINE | ChEMBL | Phase 4 (approved) | ADRB1 |
| OXPRENOLOL | ChEMBL | Phase 4 (approved) | ADRB1 |
| OXYPERTINE | ChEMBL | Phase 4 (approved) | ADRB1 |
| PHENYLEPHRINE | ChEMBL | Phase 4 (approved) | ADRB1 |
| PIMOZIDE | ChEMBL | Phase 4 (approved) | ADRB1 |
| PINDOLOL | ChEMBL | Phase 4 (approved) | ADRB1 |
| PRACTOLOL | ChEMBL | Phase 4 (approved) | ADRB1 |
| PRENYLAMINE | ChEMBL | Phase 4 (approved) | ADRB1 |
| PRIMAQUINE | ChEMBL | Phase 4 (approved) | ADRB1 |
| PROCHLORPERAZINE | ChEMBL | Phase 4 (approved) | ADRB1 |
| PROPAFENONE | ChEMBL | Phase 4 (approved) | ADRB1 |
| PROPRANOLOL | ChEMBL | Phase 4 (approved) | ADRB1 |
| PYRVINIUM | ChEMBL | Phase 4 (approved) | ADRB1 |
| RANOLAZINE | ChEMBL | Phase 4 (approved) | ADRB1 |
| RIFAMPIN | ChEMBL | Phase 4 (approved) | ADRB1 |
| RIFAXIMIN | ChEMBL | Phase 4 (approved) | ADRB1 |
| RITODRINE | ChEMBL | Phase 4 (approved) | ADRB1 |
| RUCAPARIB | ChEMBL | Phase 4 (approved) | ADRB1 |
| SALMETEROL | ChEMBL | Phase 4 (approved) | ADRB1 |
| SERTINDOLE | ChEMBL | Phase 4 (approved) | ADRB1 |
| SERTRALINE | ChEMBL | Phase 4 (approved) | ADRB1 |
| SORAFENIB | ChEMBL | Phase 4 (approved) | ADRB1 |
| SOTALOL | ChEMBL | Phase 4 (approved) | ADRB1 |
| SUNITINIB | ChEMBL | Phase 4 (approved) | ADRB1 |
| TAMOXIFEN | ChEMBL | Phase 4 (approved) | ADRB1 |
| TEGASEROD | ChEMBL | Phase 4 (approved) | ADRB1 |
| THIORIDAZINE | ChEMBL | Phase 4 (approved) | ADRB1 |
| TIMOLOL | ChEMBL | Phase 4 (approved) | ADRB1 |
| TIOCONAZOLE | ChEMBL | Phase 4 (approved) | ADRB1 |
| TROGLITAZONE | ChEMBL | Phase 4 (approved) | ADRB1 |
| VALDECOXIB | ChEMBL | Phase 4 (approved) | ADRB1 |
| VILANTEROL | ChEMBL | Phase 4 (approved) | ADRB1 |
| AROTINOLOL | ChEMBL | Phase 3 | ADRB1 |
| AZELNIDIPINE | ChEMBL | Phase 3 | ADRB1 |
Related Atlas pages
- Genes: ADRB1
- Indicated for: cardiovascular disorder
- In clinical trials for: hemangioma, hypertensive disorder, heart disorder, vascular disorder
- Drugs: Olodaterol, Tamsulosin, Albuterol, Amiodarone, Amitriptyline, Arformoterol, Aripiprazole, Astemizole, Atenolol, Azelastine, Benfluorex, Benperidol, Benzbromarone, Bepridil, Betaxolol, Bisoprolol, Brexpiprazole, Bromocriptine, Candesartan Cilexetil, Cariprazine, Carteolol, Carvedilol, Celiprolol, Chlorhexidine, Chlorprothixene, Cinacalcet, Clemastine, Clomipramine, Clotrimazole, Codeine, Darifenacin, Daunorubicin, Decitabine, Diethylstilbestrol, Dobutamine, Domperidone, Duloxetine, Ebastine, Econazole, Efavirenz, Epalrestat, Epinephrine, Ergotamine, Esmolol, Fenoterol, Fluspirilene, Formoterol, Indacaterol, Indocyanine Green Acid Form, Isoconazole, Isoproterenol, Labetalol, Lasofoxifene, Levobunolol, Lorcaserin, Metaraminol, Methylergonovine, Metoprolol, Montelukast, Nadolol, Naftopidil, Nebivolol, Nitazoxanide, Norepinephrine, Nortriptyline, Noscapine, Oxprenolol, Oxypertine, Phenylephrine, Pimozide, Pindolol, Practolol, Prenylamine, Primaquine, Prochlorperazine, Propafenone, Propranolol, Pyrvinium, Ranolazine, Rifampin, Rifaximin, Ritodrine, Rucaparib, Salmeterol, Sertindole, Sertraline, Sorafenib, Sotalol, Sunitinib, Tamoxifen, Tegaserod, Thioridazine, Timolol, Tioconazole, Troglitazone, Valdecoxib, Vilanterol, Arotinolol, Azelnidipine