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convert into a sulfate
a salt or ester of sulphuric acid (同)sulphate
drug (trade name Isuprel) used to treat bronchial asthma and to stimulate the heart (同)Isuprel

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/11/13 01:45:45」(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. In humans, it is a non-selective beta-adrenergic agonist and TAAR1 agonist that is structurally similar to adrenaline.^[1]^[2]

Uses

Its primary use is for bradycardia or heart block. By activating β₁-receptors in the heart, it induces positive chronotropic, dromotropic, and inotropic effects.^[2]

It can be used as an inhaled aerosol to treat asthma, although this is currently a rare treatment.^[2] Although it activates all beta adrenergic receptors, it works in a similar fashion to 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 sulfate.

Pharmacology

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 agonist effects at TAAR1 provide it with a pharmacodynamic effects that resemble those of the endogenous trace amines, like tyramine,^[1] although its short half-life prevents it from producing persistent psychoactive effects from TAAR1 activation in the central nervous system. Its route of administration is either intravenous, oral, intranasal, subcutaneous, or intramuscular, depending on use. The plasma half-life for isoprenaline is approximately two minutes.

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 overall effect is to decrease mean arterial pressure due to the β₂ receptor's vasodilation.

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

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"

Structure-activity relationship

The isopropyl amine group in isoprenaline makes it selective for β receptors. The free catechol hydroxy groups keeps it susceptible to enzymatic metabolism.^[3]

History

Between 1963 and 1968 in England, Wales, Scotland, Ireland, Australia, and New Zealand there was an increase in deaths among people using isoprenaline to treat asthma. This was attributed to overdose: the inhalers produced in that area were dispensing five times the dosage dispensed by inhalers produced in the US and Canada, where the deaths were not observed.^[4]

References

^ ^a ^b Kleinau G, Pratzka J, Nürnberg D, Grüters A, Führer-Sakel D, Krude H, Köhrle J, Schöneberg T, Biebermann H (October 2011). "Differential modulation of Beta-adrenergic receptor signaling by trace amine-associated receptor 1 agonists". PLoS ONE 6 (10): e27073. doi:10.1371/journal.pone.0027073. PMC 3205048. PMID 22073124.
"Table 1: EC₅₀ values of different agonists at hTAAR1, hADRB1 and hADRB2."
^ ^a ^b ^c Shen, Howard (2008). Illustrated Pharmacology Memory Cards: PharMnemonics. Minireview. p. 5. ISBN 1-59541-101-1.
^ Medicinal Chemistry of Adrenergics and Cholinergics
^ Pierce, Neil and Hensley, Michael J. (1998). "Epidemiologic Studies of Beta Agonists and Asthma Deaths" (PDF). Epidemiologic Studies 20 (2).

UpToDate Contents

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English Journal

Protective effects of the standardized extract of Zingiber officinale on myocardium against isoproterenol-induced biochemical and histopathological alterations in rats.

Amran AZ1, Jantan I, Dianita R, Buang F.
Pharmaceutical biology.Pharm Biol.2015 Dec;53(12):1795-802. doi: 10.3109/13880209.2015.1008147. Epub 2015 Apr 14.
CONTEXT: Ginger [Zingiber officinale Roscoe. (Zingiberaceae)] has been universally used as a spice as well as for its health benefits.OBJECTIVE: The present study evaluates the protective effect of the standardized extract of ginger against isoproterenol (ISO)-induced myocardial infarction (MI) in r
PMID 25868620

Protective effect of a polysaccharide from Salvia miltiorrhiza on isoproterenol (ISO)-induced myocardial injury in rats.

Geng ZH1, Huang L1, Song MB1, Song YM2.
Carbohydrate polymers.Carbohydr Polym.2015 Nov 5;132:638-42. doi: 10.1016/j.carbpol.2015.06.086. Epub 2015 Jul 10.
In this study, we investigated the cardioprotective effect of one purified polysaccharide (SMP1) from Salvia miltiorrhiza on isoproterenol (ISO)-induced myocardial infarction (MI) in rats. ISO-treated rats showed severe myocardial damage and high lipid peroxidation level, as well as decreased endoge
PMID 26256391

Impaired mitochondrial energy supply coupled to increased H2O2 emission under energy/redox stress leads to myocardial dysfunction during Type I diabetes.

Tocchetti CG1, Stanley BA2, Sivakumaran V2, Bedja D3, O'Rourke B2, Paolocci N2, Cortassa S2, Aon MA4.
Clinical science (London, England : 1979).Clin Sci (Lond).2015 Oct 1;129(7):561-74. doi: 10.1042/CS20150204. Epub 2015 Jun 11.
In Type I diabetic (T1DM) patients, both peaks of hyperglycaemia and increased sympathetic tone probably contribute to impair systolic and diastolic function. However, how these stressors eventually alter cardiac function during T1DM is not fully understood. In the present study, we hypothesized th
PMID 26186741

Japanese Journal

Stereoselective sulfate conjugation of isoproterenol in humans : comparison of hepatic, intestinal, and platelet activity

PESOLA G. R.
Chirality 5, 602-609, 1993
NAID 30009033628

Increased Uncoupling of β-, β1-and β2-Adrenoceptor to Myocardial Contraction in Failing Human Myocardium : CLINICAL EVALUATION OF CARDIAC PERFORMANCE

TAKAHASHI MASAYUKI,SHICHIRI GENSHOU,AMANO MOTOYA,KANAMORI TOSHIYUKI,KINOSHITA MASAHIKO
Japanese circulation journal 56(7), 701-709, 1992-07-20
… β-AR mediated contraction,ΔVcfc by infusion of a β-AR agonist, isoproterenol, declined with the advancement of heart failure from 0.41 Circ/sec (NYHA I) to 0.31 (NYHA II), 0.22 (NYHA III) and 0.12 (NYHA IV). … Dobutamine, a β 1-AR full agonist, mediatedΔVcfc was 92-97% of that of isoproterenol. … On the other hand, terbutaline sulfate, a full agonist to β2-AR, increasedΔVcfc partially in comparison with isoproterenol; …
NAID 110002587537

Related Pictures

★リンクテーブル★

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

「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; category	C;
Legal status	℞ (Prescription only);
Routes of; administration	inhaled 80-120μg
Identifiers
CAS Registry Number	7683-59-2
ATC code	C01CA02 R03AB02; R03CB01
PubChem	CID: 3779
IUPHAR/BPS	536
DrugBank	DB01064
ChemSpider	3647
UNII	L628TT009W
KEGG	D08090
ChEMBL	CHEMBL434
Chemical data
Formula	C11H17NO3
Molecular 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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