LEVISOPRENALINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C11H17NO3
Molecular Weight	211.2576
Optical Activity	( - )
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)NC[C@H](O)C1=CC=C(O)C(O)=C1

InChI

InChIKey=JWZZKOKVBUJMES-NSHDSACASA-N

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/t11-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/30846304 | https://www.ncbi.nlm.nih.gov/pubmed/30135280 | https://www.ncbi.nlm.nih.gov/pubmed/10452785

Levisoprenaline (l-isoproterenol) is beta1- and beta2-adrenoreceptor agonist. In Japan, continuous inhalation of levisoprenaline is a recommended treatment for pediatric patients with acute severe exacerbation. Compared with salbutamol, l-isoproterenol reduced modified pulmonary index score more rapidly. But in most countries do not recommend continuous inhalation of l-isoproterenol to treat pediatric patients with acute severe exacerbation of asthma due to worsening asthma control. Levisoprenaline was used to cause experimental chronic heart failure in rats.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Beta-1 adrenergic receptor 158 Target ID: CHEMBL213 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7562902	Agonist 2678		2.2 nM [EC50]
Beta-2 adrenergic receptor 203 Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7562902	Agonist 2678		3.0 nM [EC50]

PubMed

Title	Date	PubMed
Method for non-invasively recording electrocardiograms in conscious mice.	2001	11476671
beta-Adrenoceptor blocking activities of nipradilol and its optical isomers in pig coronary artery.	2001 Apr	11251639
The hyperpolarization-activated current If in ventricular myocytes of non-transgenic and beta2-adrenoceptor overexpressing mice.	2001 Aug	11534852
Autoantibodies against the beta1 adrenoceptor from patients with dilated cardiomyopathy prolong action potential duration and enhance contractility in isolated cardiomyocytes.	2001 Aug	11448139
Identification and characterisation of beta-adrenoceptors on intact equine peripheral blood lymphocytes with the radioligand (-)-[125I]-iodocyanopindolol.	2001 Sep	11558744
Mouse beta 3a- and beta 3b-adrenoceptors expressed in Chinese hamster ovary cells display identical pharmacology but utilize distinct signalling pathways.	2002 Apr	11959793
Comparison of the affinity of beta-blockers for two states of the beta 1-adrenoceptor in ferret ventricular myocardium.	2002 Jan	11815381
Similarities and differences in the coupling of human beta1- and beta2-adrenoceptors to Gs(alpha) splice variants.	2002 Jul 1	12106601
(-)-Isoproterenol modulation of maxi-K(+) channel in nonpigmented ciliary epithelial cells through a G-protein gated pathway.	2002 Mar	12221524
Inotropic responses to human gene 2 (B29) relaxin in a rat model of myocardial infarction (MI): effect of pertussis toxin.	2002 Nov	12381685
Sarcolemmal beta-adrenoceptors determined in rat ventricular heart biopsies with (-)-[3H]CGP-12177.	2002 Oct	12530466
Regulation of equine lymphocyte beta-adrenoceptors under the influence of clenbuterol and dexamethasone.	2002 Sep	12357998
Cardiostimulant and cardiodepressant effects through overexpressed human beta2-adrenoceptors in murine heart: regional differences and functional role of beta1-adrenoceptors.	2003 Apr	12690430
Characterization of beta 3-adrenoceptor-mediated relaxation in rat abdominal aorta smooth muscle.	2003 Dec 15	14660028
Enhanced beta2-adrenergic receptor (beta2AR) signaling by adeno-associated viral (AAV)-mediated gene transfer.	2003 Dec 4	14656380
(-)-CGP 12177 increases contractile force and hastens relaxation of human myocardial preparations through a propranolol-resistant state of the beta 1-adrenoceptor.	2003 Jan	12616336
Enzyme-linked immunosorbent assay development for the beta-adrenergic agonist zilpaterol.	2004 Apr 21	15080615
Agonist binding and activation of the rat beta(1)-adrenergic receptor: role of Trp(134(3.28)), Ser(190(4.57)) and Tyr(356(7.43)).	2004 Aug 15	15276075
Pacemaker channels in mouse thalamocortical neurones are regulated by distinct pathways of cAMP synthesis.	2004 Jan 1	14678496
Molecular characterization of pharmacological properties and selectivity of SWR-0315NA for beta3-adrenoceptors.	2004 May	15133253
Binding of (-)-[3H]-CGP12177 at two sites in recombinant human beta 1-adrenoceptors and interaction with beta-blockers.	2004 May	15060759
Markedly reduced effects of (-)-isoprenaline but not of (-)-CGP12177 and unchanged affinity of beta-blockers at Gly389-beta1-adrenoceptors compared to Arg389-beta1-adrenoceptors.	2004 May	15037517
Expression of functional beta2-adrenergic receptors in the lung epithelial cell lines 16HBE14o(-), Calu-3 and A549.	2004 May 3	15110997
Possible role of dexamethasone in sensitizing the beta-2-adrenergic receptor system in vivo in calves during concomitant treatment with clenbuterol.	2004 Nov	15452369
Functional serotonin 5-HT4 receptors in porcine and human ventricular myocardium with increased 5-HT4 mRNA in heart failure.	2004 Sep	15365689
Aspartate138 is required for the high-affinity ligand binding site but not for the low-affinity binding site of the beta1-adrenoceptor.	2004 Sep	15322738
Effects of immunoglobulin G from patients with dilated cardiomyopathy on rat cardiomyocytes.	2005 Jun	15910408
Development of a monoclonal antibody-based enzyme-linked immuosorbent assay for the beta-adrenergic agonist zilpaterol.	2005 May 4	15853359
Role of NO in the systemic hemodynamic response to beta2-adrenoceptor stimulation.	2006 Aug	17369929
Pharmacological evaluation of plasma membrane beta-adrenoceptors in rat hearts using the tissue segment binding method.	2006 Aug 1	16725159
Caveolin-1 knockout alters beta-adrenoceptors function in mouse small intestine.	2006 Dec	16782699
Multiple signalling pathways involved in beta2-adrenoceptor-mediated glucose uptake in rat skeletal muscle cells.	2006 Feb	16415914
Interaction between autoantibodies against the beta1-adrenoceptor and isoprenaline in enhancing L-type Ca2+ current in rat ventricular myocytes.	2006 Oct	16889792
Neonatal murine heart slices. A robust model to study ventricular isometric contractions.	2007	17982265
The function of alpha- and beta-adrenoceptors of the saphenous artery in caveolin-1 knockout and wild-type mice.	2007 Feb	17179950
In vitro and in vivo pharmacological characterization of ethyl-4-[trans-4-[((2S)-2-hydroxy-3-[4-hydroxy-3[(methylsulfonyl)amino]-phenoxy]propyl) amino]cyclohexyl]benzoate hydrochloride (SAR150640), a new potent and selective human beta3-adrenoceptor agonist for the treatment of preterm labor.	2007 Jun	17351104
Is the beta3-adrenoceptor (ADRB3) a potential target for uterorelaxant drugs?	2007 Jun 1	17570158
Ligand-directed signaling at the beta3-adrenoceptor produced by 3-(2-Ethylphenoxy)-1-[(1,S)-1,2,3,4-tetrahydronapth-1-ylamino]-2S-2-propanol oxalate (SR59230A) relative to receptor agonists.	2007 Nov	17717109
Distinct interactions of human beta1- and beta2-adrenoceptors with isoproterenol, epinephrine, norepinephrine, and dopamine.	2008 Dec	18772317
Phosphodiesterases PDE3 and PDE4 jointly control the inotropic effects but not chronotropic effects of (-)-CGP12177 despite PDE4-evoked sinoatrial bradycardia in rat atrium.	2009 Apr	19005642
Mutagenesis of important amino acid reveals unconventional homologous internalization of beta(1)-adrenergic receptor.	2009 Aug 12	19580817
Catecholamines relax detrusor through beta 2-adrenoceptors in mouse and beta 3-adrenoceptors in man.	2009 Jan	18820136
Analysis of full and partial agonists binding to beta2-adrenergic receptor suggests a role of transmembrane helix V in agonist-specific conformational changes.	2009 Jul-Aug	19353579
Phosphodiesterases do not limit beta1-adrenoceptor-mediated sinoatrial tachycardia: evidence with PDE3 and PDE4 in rabbits and PDE1-5 in rats.	2009 Nov	19693491
Cigarette smoke and lipopolysaccharide induce a proliferative airway smooth muscle phenotype.	2010 Apr 29	20429916
High concentrations of dexmedetomidine inhibit compound action potentials in frog sciatic nerves without alpha(2) adrenoceptor activation.	2010 Aug	20649570
Beta1-adrenergic receptor activation decreases ANP release via cAMP-Ca2+ signaling in perfused beating rabbit atria.	2010 Aug 14	20609369
Receptor-mediated enhancement of beta adrenergic drug activity by ascorbate in vitro and in vivo.	2010 Dec 13	21179213
The laminin β1-competing peptide YIGSR induces a hypercontractile, hypoproliferative airway smooth muscle phenotype in an animal model of allergic asthma.	2010 Dec 3	21129174
Beta1-adrenoceptor polymorphism predicts flecainide action in patients with atrial fibrillation.	2010 Jul 2	20625396

Sample Use Guides

In Vivo Use Guide

10 μg/kg/h for 12 hours

Route of Administration: Respiratory

Name

Type

Language

LEVISOPRENALINE

Official Name

English

ISOPRENALINE, (R)-

Common Name

English

levisoprenaline [INN]

Common Name

English

ISOPROTERENOL L-FORM [MI]

Common Name

English

ISOPROTERENOL, L-

Common Name

English

(-)-(R)-.ALPHA.-(ISOPROPYLAMINOMETHYL)PROTOCATECHUYL ALCOHOL

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C319