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drug (trade name Isuprel) used to treat bronchial asthma and to stimulate the heart (同)Isuprel
a complex consisting of an organic base in association with hydrogen chloride

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/10/04 14:55:05」(JST)

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Isoprenaline (INN) or isoproterenol (USAN, trade names Medihaler-Iso and Isuprel) is a medication used for the treatment of bradycardia (slow heart rate), heart block, and rarely for asthma. It is a non-selective beta-adrenergic agonist and structurally similar to adrenaline.^[1]

Uses[edit]

Its primary use is for bradycardia or heart block. By activating β₁-receptors on the heart, it induces positive chronotropic, dromotropic, and inotropic effects.^[1]

It can be used as an inhaled aerosol to treat asthma, although this is currently a rare treatment.^[1] Although it activates all beta adrenergic receptors, it works in a similar fashion to the more selective β₂-adrenergic agonists e.g. salbutamol, by relaxing the airways to increase airflow.

It is also supplied in ampoules under the brand name Isuprel for injection and in sublingual pill form for treatment of asthma, chronic bronchitis and emphysema.

Used with caution, it can also be used to treat torsades de pointes by acquired defect, in conjunction with overdrive pacing and magnesium.

Pharmacology[edit]

Isoprenaline is a β₁- and β₂-adrenoreceptor agonist which was commonly used to treat asthma before the more widespread use of albuterol, which has more selective effects on the airways. Its route of administration is either intravenous, oral, intranasal, subcutaneous, or intramuscular, depending on use. The plasma half-life for isoprenaline is approximately two hours.

Isoprenaline's effects on the cardiovascular system (non-selective) relate to its actions on cardiac β₁ receptors and β₂ receptors on smooth muscle within the tunica media of arterioles. Isoprenaline has positive inotropic and chronotropic effects on the heart. β₂--adrenoceptor stimulation in arteriolar smooth muscle induces vasodilation. Its inotropic and chronotropic effects elevate systolic blood pressure, while its vasodilatory effects tend to lower diastolic blood pressure.

The adverse effects of isoprenaline are also related to the drug's cardiovascular effects. Isoprenaline can produce an elevated heart rate (tachycardia), which predisposes patients to cardiac dysrhythmias.

Warnings and contraindications[edit]

Isoprenaline should not be administered to patients with myocardial ischemia.

According to Code of Federal Regulations (CFR) Title 21 Section 201.305, use of isoprenaline has been regulated by mandating the inclusion of the following warning label: "Occasional patients have been reported to develop severe paradoxical airway resistance with repeated, excessive use of isoprenaline inhalation preparations. The cause of this refractory state is unknown. It is advisable that in such instances the use of this preparation be discontinued immediately and alternative therapy instituted, since in the reported cases the patients did not respond to other forms of therapy until the drug was withdrawn. Deaths have been reported following excessive use of isoprenaline inhalation preparations and the exact cause is unknown. Cardiac arrest was noted in several instances"

Chemistry[edit]

Isoprenaline is synthesized by an analogous scheme of making epinephrine. Interaction of ω-chloro-3,4-dihydroxyacetophenone (chloroacetylpyrocatechol) with isopropylamine gives ω-isopropylamino-3,4-dihydroxyacetophenone, reduction of the carbonyl group of which by hydrogen using a palladium on carbon catalyst gives isoprenaline.^[2]^[3]

Structure-activity relationship[edit]

The isopropyl amine group in isoprenaline makes it selective for β receptors. The free catechol hydroxy groups keeps it susceptible to enzymatic metabolism.^[4]

History[edit]

An epidemic of deaths within a group of individuals who were being treated for asthma was detected between 1963 and 1968 in England, Wales, Scotland, Ireland, Australia, and New Zealand. This was later found to be largely attributed to isoprenaline inhalers which were being used at 5 times the dose USA and Canada were using it at, subsequently, USA and Canada did not add to this epidemic.^[5] Shortly after realizing overdose of the drug was causing many deaths, the medication was withdrawn and the number of asthmatics dying quickly decreased.

References[edit]

^ ^a ^b ^c Shen, Howard (2008). Illustrated Pharmacology Memory Cards: PharMnemonics. Minireview. p. 5. ISBN 1-59541-101-1.
^ G. Schening, O. Thomae, US 723278 (1942)
^ G. Schening, O. Thomae, U.S. Patent 2,308,232 (1943)
^ Medicinal Chemistry of Adrenergics and Cholinergics
^ Pierce, Neil and Hensley, Michael J. (1998). "Epidemiologic Studies of Beta Agonists and Asthma Deaths". Epidemiologic Studies 20 (2).

UpToDate Contents

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1. 昇圧剤および強心剤の使用 use of vasopressors and inotropes
2. 洞不全症候群の診断および評価 diagnosis and evaluation of the sick sinus syndrome
3. 失神評価における立位チルト試験 upright tilt table testing in the evaluation of syncope
4. 後天性ＱＴ延長症候群 acquired long qt syndrome
5. 明らかな器質的心疾患のない患者の単形性心室頻脈 monomorphic ventricular tachycardia in the absence of apparent structural heart disease

English Journal

Role of PKCα-p(38)MAPK-G(i)α axis in peroxynitrite-mediated inhibition of β-adrenergic response in pulmonary artery smooth muscle cells.

Chakraborti S, Roy S, Chowdhury A, Mandal A, Chakraborti T.SourceDepartment of Biochemistry and Biophysics, University of Kalyani, Kalyani 741235, West Bengal, India. Electronic address: sajal_chakraborti@yahoo.com.
Cellular signalling.Cell Signal.2013 Feb;25(2):512-26. doi: 10.1016/j.cellsig.2012.11.011. Epub 2012 Nov 16.
In the context of cross-talk between transmembrane signaling pathways, we studied the loci within the β-adrenergic receptor/G protein/adenyl cyclase system at which PKC exerts regulatory effects of peroxynitrite (ONOO(-)) on isoproterenol stimulated adenyl cyclase activity in pulmonary artery smoot
PMID 23159577

The immunosuppressive agents rapamycin, cyclosporin A and tacrolimus increase lipolysis, inhibit lipid storage and alter expression of genes involved in lipid metabolism in human adipose tissue.

Pereira MJ, Palming J, Rizell M, Aureliano M, Carvalho E, Svensson MK, Eriksson JW.SourceThe Lundberg Laboratory for Diabetes Research, Department of Molecular and Clinical Medicine, The Sahlgrenska Academy at University of Gothenburg, 413 45 Gothenburg, Sweden; Centre for Marine Sciences (CCMar), DCBB/FCT, University of Algarve, 8005 139 Faro, Portugal; Center for Neuroscience and Cell Biology, University of Coimbra, 3000 Coimbra, Portugal. Electronic address: maria.pereira@gu.se.
Molecular and cellular endocrinology.Mol Cell Endocrinol.2013 Jan 30;365(2):260-9. doi: 10.1016/j.mce.2012.10.030. Epub 2012 Nov 15.
Cyclosporin A (CsA), tacrolimus and rapamycin are immunosuppressive agents (IAs) associated with insulin resistance and dyslipidemia, although their molecular effects on lipid metabolism in adipose tissue are unknown. We explored IAs effects on lipolysis, lipid storage and expression of genes involv
PMID 23160140

Ontogenic development of cardiomyocytes derived from transgene-free human induced pluripotent stem cells and its homology with human heart.

Sequiera GL, Mehta A, Ooi TH, Shim W.SourceResearch and Development Unit, National Heart Centre Singapore, Singapore.
Life sciences.Life Sci.2013 Jan 17;92(1):63-71. doi: 10.1016/j.lfs.2012.10.020. Epub 2012 Nov 7.
AIM: Reprogramming of somatic cells utilizing viral free methods provide a remarkable method to generate human induced pluripotent stem cells (hiPSCs) for regenerative medicine. In this study, we evaluate developmental ontogeny of cardiomyocytes following induced differentiation of hiPSCs.MAIN METHO
PMID 23142239

Japanese Journal

Inhibition of Phosphoinositide 3-Kinase Potentiates Relaxation of Porcine Coronary Arteries Induced by Nitroglycerin by Decreasing Phosphodiesterase Type 5 Activity

DOU Dou,GUO Yixuan,YING Lei,LIU Juan,XU Xiaojian,YU Xiaoxing,GAO Yuansheng
Circulation journal : official journal of the Japanese Circulation Society 76(1), 230-237, 2011-12-25
… Inhibition of PI3K with 2-(4-morpholinyl)-8-phenyl-1(4H)-benzopyran-4-one hydrochloride (LY294002) potentiated the relaxation of porcine coronary arteries to nitroglycerin and nitric oxide (NO), but not to 8-bromo-guanosine 3'5'-cyclic monophosphate, isoproterenol or (R)-(+)-trans-4-(1-Aminoethyl)-N-(4-Pyridyl)cyclohexanecarboxamide dihydrochloride monohydrate (Y27632). …
NAID 10030034860

A Case of Neurally Mediated Syncope Induced by Laughter Successfully Treated With Combination of Propranolol and Midodrine

Amaki Makoto,Kamide Kei,Takiuchi Shin,Niizuma Shinichiro,Horio Takeshi,Kawano Yuhei
International Heart Journal 48(1), 123-127, 2007
… His syncope was reproduced by head-up tilt testing with isoproterenol infusion and we concluded that his laughter-induced syncope was one type of neurally mediated syndrome (NMS). … Propranolol and midodrine hydrochloride, an alpha1-adrenergic stimulant, were effective at preventing his laughter-induced syncope. …
NAID 130000068832

徐脈を呈した二次性甲状腺機能低下症患者の麻酔経験

石井努,岩下成人,今宿康彦 [他]
麻酔 51(10), 1111-1113, 2002-10
NAID 40005477727

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★リンクテーブル★

リンク元	「イソプロテレノール」「isoproterenol sulfate」「isoprenaline sulfate」「dl-isoprenaline hydrochloride」「l-isoprenaline hydrochloride」
拡張検索	「dl-isoproterenol hydrochloride」
関連記事	「hydrochloride」「isoproterenol」

「イソプロテレノール」

Isoprenaline
Systematic (IUPAC) name
	(RS)-4-[1-hydroxy-2-(isopropylamino)ethyl]benzene-1,2-diol
Clinical data
AHFS/Drugs.com	International Drug Names
MedlinePlus	a601236
Pregnancy cat.	C
Legal status	℞ Prescription only
Routes	inhaled 80-120μg
Identifiers
CAS number	7683-59-2
ATC code	C01CA02 R03AB02; R03CB01
PubChem	CID 3779
IUPHAR ligand	536
DrugBank	DB01064
ChemSpider	3647
UNII	L628TT009W
KEGG	D08090
ChEMBL	CHEMBL434
Chemical data
Formula	C11H17NO3
Mol. mass	211.258 g/mol
	SMILES Oc1ccc(cc1O)C(O)CNC(C)C;
	InChI InChI=1S/C11H17NO3/c1-7(2)12-6-11(15)8-3-4-9(13)10(14)5-8/h3-5,7,11-15H,6H2,1-2H3 ; Key:JWZZKOKVBUJMES-UHFFFAOYSA-N ;
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