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(O)=C(O)C=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

Molecular Formula	C11H17NO3
Molecular Weight	211.2576
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 163 Target ID: CHEMBL213 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7562902	Agonist 2752		2.2 nM [EC50]
Beta-2 adrenergic receptor 209 Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7562902	Agonist 2752		3.0 nM [EC50]

PubMed

Title	Date	PubMed
Receptor-mediated enhancement of beta adrenergic drug activity by ascorbate in vitro and in vivo.	2010-12-13	21179213
The laminin β1-competing peptide YIGSR induces a hypercontractile, hypoproliferative airway smooth muscle phenotype in an animal model of allergic asthma.	2010-12-03	21129174
Beta1-adrenergic receptor activation decreases ANP release via cAMP-Ca2+ signaling in perfused beating rabbit atria.	2010-08-14	20609369
High concentrations of dexmedetomidine inhibit compound action potentials in frog sciatic nerves without alpha(2) adrenoceptor activation.	2010-08	20649570
Beta1-adrenoceptor polymorphism predicts flecainide action in patients with atrial fibrillation.	2010-07-02	20625396
Cigarette smoke and lipopolysaccharide induce a proliferative airway smooth muscle phenotype.	2010-04-29	20429916
Phosphodiesterases do not limit beta1-adrenoceptor-mediated sinoatrial tachycardia: evidence with PDE3 and PDE4 in rabbits and PDE1-5 in rats.	2009-11	19693491
Mutagenesis of important amino acid reveals unconventional homologous internalization of beta(1)-adrenergic receptor.	2009-08-12	19580817
Analysis of full and partial agonists binding to beta2-adrenergic receptor suggests a role of transmembrane helix V in agonist-specific conformational changes.	2009-04-09	19353579
Phosphodiesterases PDE3 and PDE4 jointly control the inotropic effects but not chronotropic effects of (-)-CGP12177 despite PDE4-evoked sinoatrial bradycardia in rat atrium.	2009-04	19005642
Catecholamines relax detrusor through beta 2-adrenoceptors in mouse and beta 3-adrenoceptors in man.	2009-01	18820136
Distinct interactions of human beta1- and beta2-adrenoceptors with isoproterenol, epinephrine, norepinephrine, and dopamine.	2008-12	18772317
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.	2007-11	17717109
Is the beta3-adrenoceptor (ADRB3) a potential target for uterorelaxant drugs?	2007-06-01	17570158
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.	2007-06	17351104
The function of alpha- and beta-adrenoceptors of the saphenous artery in caveolin-1 knockout and wild-type mice.	2007-02	17179950
Neonatal murine heart slices. A robust model to study ventricular isometric contractions.	2007	17982265
Caveolin-1 knockout alters beta-adrenoceptors function in mouse small intestine.	2006-12	16782699
Interaction between autoantibodies against the beta1-adrenoceptor and isoprenaline in enhancing L-type Ca2+ current in rat ventricular myocytes.	2006-10	16889792
Pharmacological evaluation of plasma membrane beta-adrenoceptors in rat hearts using the tissue segment binding method.	2006-08-01	16725159
Role of NO in the systemic hemodynamic response to beta2-adrenoceptor stimulation.	2006-08	17369929
Multiple signalling pathways involved in beta2-adrenoceptor-mediated glucose uptake in rat skeletal muscle cells.	2006-02	16415914
Effects of immunoglobulin G from patients with dilated cardiomyopathy on rat cardiomyocytes.	2005-06	15910408
Development of a monoclonal antibody-based enzyme-linked immuosorbent assay for the beta-adrenergic agonist zilpaterol.	2005-05-04	15853359
Possible role of dexamethasone in sensitizing the beta-2-adrenergic receptor system in vivo in calves during concomitant treatment with clenbuterol.	2004-11	15452369
Functional serotonin 5-HT4 receptors in porcine and human ventricular myocardium with increased 5-HT4 mRNA in heart failure.	2004-09	15365689
Aspartate138 is required for the high-affinity ligand binding site but not for the low-affinity binding site of the beta1-adrenoceptor.	2004-09	15322738
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)).	2004-08-15	15276075
Expression of functional beta2-adrenergic receptors in the lung epithelial cell lines 16HBE14o(-), Calu-3 and A549.	2004-05-03	15110997
Molecular characterization of pharmacological properties and selectivity of SWR-0315NA for beta3-adrenoceptors.	2004-05	15133253
Binding of (-)-[3H]-CGP12177 at two sites in recombinant human beta 1-adrenoceptors and interaction with beta-blockers.	2004-05	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.	2004-05	15037517
Enzyme-linked immunosorbent assay development for the beta-adrenergic agonist zilpaterol.	2004-04-21	15080615
Pacemaker channels in mouse thalamocortical neurones are regulated by distinct pathways of cAMP synthesis.	2004-01-01	14678496
Characterization of beta 3-adrenoceptor-mediated relaxation in rat abdominal aorta smooth muscle.	2003-12-15	14660028
Enhanced beta2-adrenergic receptor (beta2AR) signaling by adeno-associated viral (AAV)-mediated gene transfer.	2003-12-04	14656380
Cardiostimulant and cardiodepressant effects through overexpressed human beta2-adrenoceptors in murine heart: regional differences and functional role of beta1-adrenoceptors.	2003-04	12690430
(-)-CGP 12177 increases contractile force and hastens relaxation of human myocardial preparations through a propranolol-resistant state of the beta 1-adrenoceptor.	2003-01	12616336
Inotropic responses to human gene 2 (B29) relaxin in a rat model of myocardial infarction (MI): effect of pertussis toxin.	2002-11	12381685
Sarcolemmal beta-adrenoceptors determined in rat ventricular heart biopsies with (-)-[3H]CGP-12177.	2002-10	12530466
Regulation of equine lymphocyte beta-adrenoceptors under the influence of clenbuterol and dexamethasone.	2002-09	12357998
Similarities and differences in the coupling of human beta1- and beta2-adrenoceptors to Gs(alpha) splice variants.	2002-07-01	12106601
Mouse beta 3a- and beta 3b-adrenoceptors expressed in Chinese hamster ovary cells display identical pharmacology but utilize distinct signalling pathways.	2002-04	11959793
(-)-Isoproterenol modulation of maxi-K(+) channel in nonpigmented ciliary epithelial cells through a G-protein gated pathway.	2002-03	12221524
Comparison of the affinity of beta-blockers for two states of the beta 1-adrenoceptor in ferret ventricular myocardium.	2002-01	11815381
Identification and characterisation of beta-adrenoceptors on intact equine peripheral blood lymphocytes with the radioligand (-)-[125I]-iodocyanopindolol.	2001-09	11558744
The hyperpolarization-activated current If in ventricular myocytes of non-transgenic and beta2-adrenoceptor overexpressing mice.	2001-08	11534852
Autoantibodies against the beta1 adrenoceptor from patients with dilated cardiomyopathy prolong action potential duration and enhance contractility in isolated cardiomyocytes.	2001-08	11448139
beta-Adrenoceptor blocking activities of nipradilol and its optical isomers in pig coronary artery.	2001-04	11251639
Method for non-invasively recording electrocardiograms in conscious mice.	2001	11476671

Sample Use Guides

In Vivo Use Guide

10 μg/kg/h for 12 hours

Route of Administration: Respiratory

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:13:02 GMT 2025` Edited by `admin` on `Mon Mar 31 18:13:02 GMT 2025`
Record UNII	588N0603CT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LEVISOPRENALINE

Official Name

English

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

Preferred Name

English

ISOPRENALINE, (R)-

Common Name

English

levisoprenaline [INN]

Common Name

English

ISOPROTERENOL L-FORM [MI]

Common Name

English

ISOPROTERENOL, L-

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C319