For research use only. Not for therapeutic Use.
Acebutolol is a synthetic butyranilide derivative with hypotensive and antiarrhythmic activity. This drug is a cardioselective beta-1 adrenergic antagonist with little effect on the bronchial receptors. Having stabilizing and quinidine-like effects on cardiac rhythm, as well as weak inherent sympathomimetic action, Acebutolol is used in ventricular arrhythmias. (
| Catalog Number | I001075 |
| CAS Number | 37517-30-9 |
| Synonyms | Acebutolol; Acetobutolol; Neptal; Prent; Sectral; Dl-Acebutolol.;N-[3-acetyl-4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]butanamide |
| Molecular Formula | C18H28N2O4 |
| Purity | ≥95% |
| Target | Neuronal Signaling |
| Solubility | Soluble in DMSO, not in water |
| Storage | 0 - 4°Cfor short term (days to weeks), or -20 °C for long term (months). |
| IUPAC Name | N-[3-acetyl-4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]butanamide |
| 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 |
| SMILES | CCCC(=O)NC1=CC(=C(C=C1)OCC(CNC(C)C)O)C(=O)C |
| Reference | </br>1:Synthesis and In Vitro Pharmacological Evaluation of 5-(Alkoxymethyl)-2-(3-alkylamino-2-hydroxypropoxy)phenylethanones Related to Acebutolol and Celiprolol. Bruchatá K, Némethy A, Čižmáriková R, Račanská E, Habala L.Arch Pharm (Weinheim). 2016 Sep;349(9):733-40. doi: 10.1002/ardp.201600136. Epub 2016 Jul 15. PMID: 27417385 </br>2:Aqueous chlorination of acebutolol: kinetics, transformation by-products, and mechanism. Khalit WN, Tay KS.Environ Sci Pollut Res Int. 2016 Feb;23(3):2521-9. doi: 10.1007/s11356-015-5470-y. Epub 2015 Oct 1. PMID: 26423291 </br>3:A proposed mechanism for the adverse effects of acebutolol: CES2 and CYP2C19-mediated metabolism and antinuclear antibody production. Muta K, Fukami T, Nakajima M.Biochem Pharmacol. 2015 Dec 15;98(4):659-70. doi: 10.1016/j.bcp.2015.09.016. Epub 2015 Sep 25. PMID: 26408002 </br>4:Biocatalytic Approach for the Synthesis of Enantiopure Acebutolol as a β₁-Selective Blocker. Banoth L, Thakur NS, Bhaumik J, Banerjee UC.Chirality. 2015 Jun;27(6):382-91. doi: 10.1002/chir.22444. Epub 2015 May 15. PMID: 25977108 </br>5:Identification of Radiodegradation Products of Acebutolol and Alprenolol by HPLC/MS/MS. Ogrodowczyk M, Dettlaff K, Kachlicki P, Marciniec B.J AOAC Int. 2015 Jan-Feb;98(1):46-50. doi: 10.5740/jaoacint.14-096. PMID: 25857877 </br>6:Radioiodinated acebutolol as a new highly selective radiotracer for myocardial perfusion imaging. Swidan MM, Sakr TM, Motaleb MA, El-Bary AA, El-Kolaly MT.J Labelled Comp Radiopharm. 2014 Aug;57(10):593-9. doi: 10.1002/jlcr.3223. Epub 2014 Sep 5. PMID: 25196119 </br>7:Interactions of beta-blockers with model lipid membranes: molecular view of the interaction of acebutolol, oxprenolol, and propranolol with phosphatidylcholine vesicles by time-dependent fluorescence shift and molecular dynamics simulations. Först G, Cwiklik L, Jurkiewicz P, Schubert R, Hof M.Eur J Pharm Biopharm. 2014 Aug;87(3):559-69. doi: 10.1016/j.ejpb.2014.03.013. Epub 2014 Mar 28. PMID: 24681296 </br>8:Acebutolol and alprenolol metabolism predictions: comparative study of electrochemical and cytochrome P450-catalyzed reactions using liquid chromatography coupled to high-resolution mass spectrometry. Bussy U, Delaforge M, El-Bekkali C, Ferchaud-Roucher V, Krempf M, Tea I, Galland N, Jacquemin D, Boujtita M.Anal Bioanal Chem. 2013 Jul;405(18):6077-85. doi: 10.1007/s00216-013-7050-7. Epub 2013 May 23. PMID: 23700103 </br>9:Voltammetry coupled to mass spectrometry in the presence of isotope 18O labeled water for the prediction of oxidative transformation pathways of activated aromatic ethers: acebutolol. Bussy U, Tea I, Ferchaud-Roucher V, Krempf M, Silvestre V, Galland N, Jacquemin D, Andresen-Bergström M, Jurva U, Boujtita M.Anal Chim Acta. 2013 Jan 31;762:39-46. doi: 10.1016/j.aca.2012.12.002. Epub 2012 Dec 10. PMID: 23327943 </br>10:Biophysical characterization of the drug-membrane interactions: the case of propranolol and acebutolol. Pereira-Leite C, Carneiro C, Soares JX, Afonso C, Nunes C, Lúcio M, Reis S.Eur J Pharm Biopharm. 2013 May;84(1):183-91. doi: 10.1016/j.ejpb.2012.12.005. Epub 2013 Jan 2. PMID: 23291047 |
