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Details

Stereochemistry ABSOLUTE
Molecular Formula C11H17NO3.ClH
Molecular Weight 247.719
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVISOPRENALINE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=IROWCYIEJAOFOW-MERQFXBCSA-N
InChI=1S/C11H17NO3.ClH/c1-7(2)12-6-11(15)8-3-4-9(13)10(14)5-8;/h3-5,7,11-15H,6H2,1-2H3;1H/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

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Sample Use Guides

10 μg/kg/h for 12 hours
Route of Administration: Respiratory
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:27:25 GMT 2025
Edited
by admin
on Mon Mar 31 21:27:25 GMT 2025
Record UNII
6X46C92UF9
Record Status Validated (UNII)
Record Version
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Name Type Language
L-ISOPRENALINE HYDROCHLORIDE
JAN  
Preferred Name English
LEVISOPRENALINE HYDROCHLORIDE
Common Name English
1,2-BENZENEDIOL, 4-(1-HYDROXY-2-((1-METHYLETHYL)AMINO)ETHYL)-, HYDROCHLORIDE, (R)-
Common Name English
1,2-BENZENEDIOL, 4-((1R)-1-HYDROXY-2-((1-METHYLETHYL)AMINO)ETHYL)-, HYDROCHLORIDE (1:1)
Systematic Name English
BENZYL ALCOHOL, 3,4-DIHYDROXY-.ALPHA.-((ISOPROPYLAMINO)METHYL)-, HYDROCHLORIDE, (-)-
Systematic Name English
(-)-ISOPROPYL ARTERENOL HYDROCHLORIDE
Common Name English
N-ISOPROPYLNORADRENALINE HYDROCHLORIDE
Common Name English
L-ISOPRENALINE HYDROCHLORIDE [JAN]
Common Name English
(R)-ISOPROTERENOL HYDROCHLORIDE
Common Name English
L-ISOPROTERENOL HYDROCHLORIDE
Common Name English
(R)-ISOPRENALINE HYDROCHLORIDE
Common Name English
ISOPROTERENOL L-FORM HYDROCHLORIDE [MI]
Common Name English
L-ISOPRENALINE CHLORIDE
Common Name English
(-)-ISOPROTERENOL HYDROCHLORIDE
Common Name English
(-)-ISOPRENALINE HYDROCHLORIDE
Common Name English
Code System Code Type Description
PUBCHEM
656783
Created by admin on Mon Mar 31 21:27:25 GMT 2025 , Edited by admin on Mon Mar 31 21:27:25 GMT 2025
PRIMARY
SMS_ID
100000138934
Created by admin on Mon Mar 31 21:27:25 GMT 2025 , Edited by admin on Mon Mar 31 21:27:25 GMT 2025
PRIMARY
MERCK INDEX
m6533
Created by admin on Mon Mar 31 21:27:25 GMT 2025 , Edited by admin on Mon Mar 31 21:27:25 GMT 2025
PRIMARY Merck Index
CAS
5984-95-2
Created by admin on Mon Mar 31 21:27:25 GMT 2025 , Edited by admin on Mon Mar 31 21:27:25 GMT 2025
PRIMARY
ChEMBL
CHEMBL434
Created by admin on Mon Mar 31 21:27:25 GMT 2025 , Edited by admin on Mon Mar 31 21:27:25 GMT 2025
PRIMARY
EVMPD
SUB79394
Created by admin on Mon Mar 31 21:27:25 GMT 2025 , Edited by admin on Mon Mar 31 21:27:25 GMT 2025
PRIMARY
EPA CompTox
DTXSID4037243
Created by admin on Mon Mar 31 21:27:25 GMT 2025 , Edited by admin on Mon Mar 31 21:27:25 GMT 2025
PRIMARY
FDA UNII
6X46C92UF9
Created by admin on Mon Mar 31 21:27:25 GMT 2025 , Edited by admin on Mon Mar 31 21:27:25 GMT 2025
PRIMARY
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