acebutolol hydrochloride

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acebutolol

WordNet

1. a complex consisting of an organic base in association with hydrogen chloride
2. an oral beta blocker (trade name Sectral) used in treating hypertension (同)Sectral

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/01/05 01:34:50」(JST)

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Acebutolol

Clinical data
Trade names	Sectral
AHFS/Drugs.com	Monograph
MedlinePlus	a687003
License data	US FDA: Acebutolol
Pregnancy category	AU: C US: B (No risk in non-human studies)
Routes of administration	oral, iv
ATC code	C07AB04 (WHO)
Legal status
Legal status	UK: POM (Prescription only) ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	40% (range 35 to 50%)
Metabolism	Hepatic
Biological half-life	3-4 hours (parent drug) 8-13 hours (active metabolite)
Excretion	Renal: 30% Biliary: 60%
Identifiers
IUPAC name (RS)-N-{3-acetyl-4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl}butanamide
CAS Number	37517-30-9 Y
PubChem (CID)	1978
IUPHAR/BPS	7107
DrugBank	DB01193 Y
ChemSpider	1901 Y
UNII	67P356D8GH Y
KEGG	D02338 Y
ChEBI	CHEBI:2379 Y
ChEMBL	CHEMBL642 Y
ECHA InfoCard	100.048.654
Chemical and physical data
Formula	C18H28N2O4
Molar mass	336.426 g/mol
3D model (Jmol)	Interactive image
Melting point	121 °C (250 °F)
SMILES O=C(Nc1ccc(OCC(O)CNC(C)C)c(c1)C(=O)C)CCC
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) Y Key:GOEMGAFJFRBGGG-UHFFFAOYSA-N Y
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Acebutolol (trade names Sectral, Prent) is a beta blocker for the treatment of hypertension and arrhythmias.

Pharmacology

Acebutolol is a cardioselective beta blocker with ISA (intrinsic sympathomimetic activity; see article on pindolol). It is therefore more suitable than non cardioselective beta blockers, if a patient with asthma or chronic obstructive pulmonary disease (COPD) needs treatment with a beta blocker. (For these reasons, it may be a beta-blocker of choice in inclusion in Polypill strategies). In doses lower than 800mg daily its constricting effects on the bronchial system and smooth muscle vessels are only 10% to 30% of those observed under propranolol treatment, but there is experimental evidence that the cardioselective properties diminish at doses of 800mg/day or more.

The drug has lipophilic properties, and therefore crosses the blood–brain barrier. Acebutolol has no negative impact on serum lipids (cholesterol and triglycerides). No HDL decrease has been observed. In this regard, it is unlike many other beta blockers which have this unfavourable property.

The drug works in hypertensive patients with high, normal, or low renin plasma concentrations, although acebutolol may be more efficient in patients with high or normal renin plasma concentrations. In clinically relevant concentrations, a membrane-stabilizing effect does not appear to play an important role.

Pharmacokinetics

Acebutolol is well absorbed from the GI tract, but undergoes substantial first-pass-metabolization, leading to a bioavailability of only 35% to 50%. Peak plasma levels of acebutolol are reached within 2 to 2.5 hours after oral dosing. Peak levels of the main active metabolite, diacetolol, are reached after 4 hours. Acebutolol has a half-life of 3 to 4 hours, and diacetolol a half-life of 8 to 13 hours.

Acebutolol undergoes extensive hepatic metabolization resulting in the desbutyl amine acetolol which is readily converted into diacetolol. Diacetolol is as active as acebutolol (equipotency) and appears to have the same pharmacologic profile. Geriatric patients tend to have higher peak plasma levels of both acebutolol and diacetolol and a slightly prolonged excretion. Excretion is substantially prolonged in patients with renal impairment, and so a dose reduction may be needed. Liver cirrhosis does not seem to alter the pharmacokinetic profile of the parent drug and metabolite.

Indications

• hypertension
• ventricular and atrial cardiac arrhythmia
• acute myocardial infarction in high-risk patients
• Smith-Magenis syndrome

Contraindications

• Stable or Unstable Angina (due to its partial agonist or ISA activity)

Contraindications and Precautions

Further information: Propranolol

Acebutolol may not be suitable in patients with Asthma bronchiale or COPD due to its bronchoconstricting (β2 antagonistic) effects.

Side effects

Further information: Propranolol

The development of anti-nuclear antibodies (ANA) has been found in 10 to 30% of patients under treatment with acebutolol. A systemic disease with arthralgic pain and myalgias has been observed in 1%. A lupus erythematosus-like syndrome with skin rash and multiforme organ involvement is even less frequent. The incidence of both ANA and symptomatic disease under acebutolol is higher than under Propranolol. Female patients are more likely to develop these symptoms than male patients. Some few cases of hepatotoxicity with increased liver enzymes (ALT, AST) have been seen. Altogether, 5 to 6% of all patients treated have to discontinue acebutolol due to intolerable side effects. When possible, the treatment should be discontinued gradually in order to avoid a withdrawal syndrome with increased frequency of angina and even precipitation of myocardial infarction.

External links

• AHFS Database

UpToDate Contents

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English Journal

• Exploring the Feasibility of Biowaiver Extension of BCS Class III Drugs with Site-Specific Absorption Using Gastrointestinal Simulation Technology.

• Sun L1, Sun J2, He Z3.
• European journal of drug metabolism and pharmacokinetics.Eur J Drug Metab Pharmacokinet.2017 Jun;42(3):471-487. doi: 10.1007/s13318-016-0361-2.
• PMID 27447171

• β1- and β2-adrenergic receptor stimulation differ in their effects on PGC-1α and atrogin-1/MAFbx gene expression in chick skeletal muscle.

• Shimamoto S1, Ijiri D2, Kawaguchi M3, Nakashima K4, Tada O5, Inoue H3, Ohtsuka A3.
• Comparative biochemistry and physiology. Part A, Molecular & integrative physiology.Comp Biochem Physiol A Mol Integr Physiol.2017 May 31. pii: S1095-6433(17)30120-4. doi: 10.1016/j.cbpa.2017.05.013. [Epub ahead of print]
• PMID 28578076

• Fast and sensitive analysis of beta blockers by ultra-high-performance liquid chromatography coupled with ultra-high-resolution TOF mass spectrometry.

• Tomková J1,2, Ondra P1,2, Kocianová E2,3, Václavík J2,3.
• Biomedical chromatography : BMC.Biomed Chromatogr.2016 Dec 7. doi: 10.1002/bmc.3911. [Epub ahead of print]
• PMID 27925253

Japanese Journal

• Spectrofluorimetric Determination of Drugs Containing Active Methylene Group Using N^1-Methyl Nicotinamide Chloride as a Fluorigenic Agent

• El Dawy Mohamed Abdelfattah,Mabrouk Mokhtar Mohamed,El Barbary Riad Ahmed
• Chemical & pharmaceutical bulletin 54(7), 1026-1029, 2006-07-01
• … The method was applied successfully to the determination of three life saving cardiovascular drugs, with narrow therapeutic indices: pentoxifylline (I), propafenone hydrochloride (II) and acebutolol hydrochloride (III), in laboratory-prepared mixtures, in commercial tablets and in plasma samples. …
• NAID 110004836428

• <Abstract of published report>Preparation of Controlled releasing Acrylic Polymer Microspheres of Acebutolol Hydrochloride and Those Powder Coated Microspheres with Sodium Alginate in a Polymeric Spherical Crystallization System.

• CUI FUDE,KAWASHIMA YOSHIAKI,TAKEUCHI HIROFUMI,NIWA TOSHIYUKI,HINO TOMOAKI
• 岐阜藥科大學紀要 46, 57, 1997-06-30
• NAID 110000053897

• Preparation of Controlled Releasing Acrylic Polymer Microspheres of Acebutolol Hydrochloride and Those Powder Coated Microspheres with Sodium Alginate in a Polymeric Spherical Crystallization System

• CUI Fude,KAWASHIMA Yoshiaki,TAKEUCHI Hirofumi,NIWA Toshiyuki,HINO Tomoaki
• Chemical & pharmaceutical bulletin 44(4), 837-842, 1996-04-15
• … Acrylic polymer (Eudragit-RS 100 or -RS PM) microspheres of acebutolol hydrochloride, a highly water soluble model drug, were prepared by the polymeric shpherical crystallization technique with a good slvent (acetone + ethanol), a bridging liquid (water) and a poor slvent (cyclohexane) system. …
• NAID 110003631978

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