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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 of LEVISOPRENALINE

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

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

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

Targets

Primary TargetPharmacologyConditionPotency
2.2 nM [EC50]
3.0 nM [EC50]
PubMed

PubMed

TitleDatePubMed
Method for non-invasively recording electrocardiograms in conscious mice.
2001
beta-Adrenoceptor blocking activities of nipradilol and its optical isomers in pig coronary artery.
2001 Apr
The hyperpolarization-activated current If in ventricular myocytes of non-transgenic and beta2-adrenoceptor overexpressing mice.
2001 Aug
Autoantibodies against the beta1 adrenoceptor from patients with dilated cardiomyopathy prolong action potential duration and enhance contractility in isolated cardiomyocytes.
2001 Aug
Methanol solvent may cause increased apparent metabolic instability in in vitro assays.
2001 Feb
beta(1)-Adrenoceptors compensate for beta(3)-adrenoceptors in ileum from beta(3)-adrenoceptor knock-out mice.
2001 Jan
Identification and characterisation of beta-adrenoceptors on intact equine peripheral blood lymphocytes with the radioligand (-)-[125I]-iodocyanopindolol.
2001 Sep
Mouse beta 3a- and beta 3b-adrenoceptors expressed in Chinese hamster ovary cells display identical pharmacology but utilize distinct signalling pathways.
2002 Apr
Comparison of the affinity of beta-blockers for two states of the beta 1-adrenoceptor in ferret ventricular myocardium.
2002 Jan
Similarities and differences in the coupling of human beta1- and beta2-adrenoceptors to Gs(alpha) splice variants.
2002 Jul 1
(-)-Isoproterenol modulation of maxi-K(+) channel in nonpigmented ciliary epithelial cells through a G-protein gated pathway.
2002 Mar
Inotropic responses to human gene 2 (B29) relaxin in a rat model of myocardial infarction (MI): effect of pertussis toxin.
2002 Nov
Sarcolemmal beta-adrenoceptors determined in rat ventricular heart biopsies with (-)-[3H]CGP-12177.
2002 Oct
Regulation of equine lymphocyte beta-adrenoceptors under the influence of clenbuterol and dexamethasone.
2002 Sep
Cardiostimulant and cardiodepressant effects through overexpressed human beta2-adrenoceptors in murine heart: regional differences and functional role of beta1-adrenoceptors.
2003 Apr
Characterization of beta 3-adrenoceptor-mediated relaxation in rat abdominal aorta smooth muscle.
2003 Dec 15
Enhanced beta2-adrenergic receptor (beta2AR) signaling by adeno-associated viral (AAV)-mediated gene transfer.
2003 Dec 4
(-)-CGP 12177 increases contractile force and hastens relaxation of human myocardial preparations through a propranolol-resistant state of the beta 1-adrenoceptor.
2003 Jan
Enzyme-linked immunosorbent assay development for the beta-adrenergic agonist zilpaterol.
2004 Apr 21
Pacemaker channels in mouse thalamocortical neurones are regulated by distinct pathways of cAMP synthesis.
2004 Jan 1
Molecular characterization of pharmacological properties and selectivity of SWR-0315NA for beta3-adrenoceptors.
2004 May
Binding of (-)-[3H]-CGP12177 at two sites in recombinant human beta 1-adrenoceptors and interaction with beta-blockers.
2004 May
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
Expression of functional beta2-adrenergic receptors in the lung epithelial cell lines 16HBE14o(-), Calu-3 and A549.
2004 May 3
Possible role of dexamethasone in sensitizing the beta-2-adrenergic receptor system in vivo in calves during concomitant treatment with clenbuterol.
2004 Nov
Functional serotonin 5-HT4 receptors in porcine and human ventricular myocardium with increased 5-HT4 mRNA in heart failure.
2004 Sep
Effects of immunoglobulin G from patients with dilated cardiomyopathy on rat cardiomyocytes.
2005 Jun
Development of a monoclonal antibody-based enzyme-linked immuosorbent assay for the beta-adrenergic agonist zilpaterol.
2005 May 4
Role of NO in the systemic hemodynamic response to beta2-adrenoceptor stimulation.
2006 Aug
Multiple signalling pathways involved in beta2-adrenoceptor-mediated glucose uptake in rat skeletal muscle cells.
2006 Feb
Interaction between autoantibodies against the beta1-adrenoceptor and isoprenaline in enhancing L-type Ca2+ current in rat ventricular myocytes.
2006 Oct
Neonatal murine heart slices. A robust model to study ventricular isometric contractions.
2007
The function of alpha- and beta-adrenoceptors of the saphenous artery in caveolin-1 knockout and wild-type mice.
2007 Feb
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
Is the beta3-adrenoceptor (ADRB3) a potential target for uterorelaxant drugs?
2007 Jun 1
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
Distinct interactions of human beta1- and beta2-adrenoceptors with isoproterenol, epinephrine, norepinephrine, and dopamine.
2008 Dec
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
Mutagenesis of important amino acid reveals unconventional homologous internalization of beta(1)-adrenergic receptor.
2009 Aug 12
Catecholamines relax detrusor through beta 2-adrenoceptors in mouse and beta 3-adrenoceptors in man.
2009 Jan
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
Phosphodiesterases do not limit beta1-adrenoceptor-mediated sinoatrial tachycardia: evidence with PDE3 and PDE4 in rabbits and PDE1-5 in rats.
2009 Nov
Cigarette smoke and lipopolysaccharide induce a proliferative airway smooth muscle phenotype.
2010 Apr 29
High concentrations of dexmedetomidine inhibit compound action potentials in frog sciatic nerves without alpha(2) adrenoceptor activation.
2010 Aug
Beta1-adrenergic receptor activation decreases ANP release via cAMP-Ca2+ signaling in perfused beating rabbit atria.
2010 Aug 14
Receptor-mediated enhancement of beta adrenergic drug activity by ascorbate in vitro and in vivo.
2010 Dec 13
The laminin β1-competing peptide YIGSR induces a hypercontractile, hypoproliferative airway smooth muscle phenotype in an animal model of allergic asthma.
2010 Dec 3
Beta1-adrenoceptor polymorphism predicts flecainide action in patients with atrial fibrillation.
2010 Jul 2

Sample Use Guides

10 μg/kg/h for 12 hours
Route of Administration: Respiratory
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:54:49 GMT 2023
Edited
by admin
on Fri Dec 15 15:54:49 GMT 2023
Record UNII
588N0603CT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEVISOPRENALINE
INN  
INN  
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
Created by admin on Fri Dec 15 15:54:49 GMT 2023 , Edited by admin on Fri Dec 15 15:54:49 GMT 2023
NCI_THESAURUS C48149
Created by admin on Fri Dec 15 15:54:49 GMT 2023 , Edited by admin on Fri Dec 15 15:54:49 GMT 2023
Code System Code Type Description
EVMPD
SUB08460MIG
Created by admin on Fri Dec 15 15:54:49 GMT 2023 , Edited by admin on Fri Dec 15 15:54:49 GMT 2023
PRIMARY
CAS
51-31-0
Created by admin on Fri Dec 15 15:54:49 GMT 2023 , Edited by admin on Fri Dec 15 15:54:49 GMT 2023
PRIMARY
SMS_ID
100000082804
Created by admin on Fri Dec 15 15:54:49 GMT 2023 , Edited by admin on Fri Dec 15 15:54:49 GMT 2023
PRIMARY
NCI_THESAURUS
C74197
Created by admin on Fri Dec 15 15:54:49 GMT 2023 , Edited by admin on Fri Dec 15 15:54:49 GMT 2023
PRIMARY
INN
864
Created by admin on Fri Dec 15 15:54:49 GMT 2023 , Edited by admin on Fri Dec 15 15:54:49 GMT 2023
PRIMARY
DRUG CENTRAL
2388
Created by admin on Fri Dec 15 15:54:49 GMT 2023 , Edited by admin on Fri Dec 15 15:54:49 GMT 2023
PRIMARY
PUBCHEM
443372
Created by admin on Fri Dec 15 15:54:49 GMT 2023 , Edited by admin on Fri Dec 15 15:54:49 GMT 2023
PRIMARY
CHEBI
6257
Created by admin on Fri Dec 15 15:54:49 GMT 2023 , Edited by admin on Fri Dec 15 15:54:49 GMT 2023
PRIMARY
FDA UNII
588N0603CT
Created by admin on Fri Dec 15 15:54:49 GMT 2023 , Edited by admin on Fri Dec 15 15:54:49 GMT 2023
PRIMARY
ChEMBL
CHEMBL460574
Created by admin on Fri Dec 15 15:54:49 GMT 2023 , Edited by admin on Fri Dec 15 15:54:49 GMT 2023
PRIMARY
EPA CompTox
DTXSID2043878
Created by admin on Fri Dec 15 15:54:49 GMT 2023 , Edited by admin on Fri Dec 15 15:54:49 GMT 2023
PRIMARY
MERCK INDEX
m6533
Created by admin on Fri Dec 15 15:54:49 GMT 2023 , Edited by admin on Fri Dec 15 15:54:49 GMT 2023
PRIMARY Merck Index
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