Basic information
- CAS
114-45-4- Standard SMILES
CC(C)NCC(O)c1ccc(O)c(O)c1- InChIKey
JWZZKOKVBUJMES-UHFFFAOYSA-N- Molecular formula
- C11H17NO3
- Average molar mass
- 211.26 g/mol
- Monoisotopic mass
- 211.1208434
Overview
Isoprenaline is a secondary amino compound that is noradrenaline in which one of the hydrogens attached to the nitrogen is replaced by an isopropyl group. A sympathomimetic acting almost exclusively on beta-adrenergic receptors, it is used (mainly as the hydrochloride salt) as a bronghodilator and heart stimulant for the management of a variety of cardiac disorders. It has a role as a beta-adrenergic agonist, a bronchodilator agent, a sympathomimetic agent and a cardiotonic drug. It is a member of catechols, a secondary alcohol and a secondary amino compound.
Names & identifiers
- Preferred name
- Isoproterenol
- IUPAC
- 4-[1-hydroxy-2-(propan-2-ylamino)ethyl]benzene-1,2-diol
- English name
- Isoproterenol
- Molecular formula
- C11H17NO3
- Molecular weight
- 211.26
Names & synonyms
isoproterenolIsoprenaline7683-59-2IsopropydrinAludrineNovodrinAsiprenolAssiprenolBellasthmanIsoprenalinRespifralAsmalar
Show more names
4-(1-hydroxy-2-(isopropylaMino)ethyl)benzene-1,2-diolA 21isoprelAludrinNSC 9975LomuprenAleudrine
NeodrenalProternolneo-EpinineIsonorinIsoreninSaventrineIsopropylarterenolN-Isopropylnoradrenaline
Database identifiers
- CAS
114-45-4、7683-59-2- PubChem CID
- 3779
- DTXSID
DTXSID4023175- ChEMBL
CHEMBL434- ChEBI
CHEBI:64317- UNII
- L628TT009W
- EC Number
- 204-049-0、231-687-7
- Nikkaji
- J28.477G
Properties
Computed structural properties
- XLogP
- -0.6
- Topological polar surface area
- 72.7 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 187
Experimental & physicochemical properties
LogP
1.4
-0.61
Solubility5.86e+00 g/L
Human DrugsPharmaceuticals
Melting Point170.5 °C
Physical DescriptionSolid
Dissociation Constants8.65
Collision Cross Section
151.0 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID6025486]
147.87 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
149.4 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
150 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated]
Physicochemical properties
- Melting point
- 170.5 °C · 170.5°C
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Regulatory InformationIsoprenaline: Does not have an individual approval but may be used under an appropriate group standard
Toxicology
Adverse EffectsAdverse effects of isoproterenol may involve multiple organ systems, as mentioned below.
Toxicity Summary
Signs and Symptoms of Overdose
The pharmacologic effects of isoproterenol are at least in part attributable to stimulation through beta-adrenergic receptors of intracellular adenyl cyclase, the enzyme that catalyzes the conversion of adenosine triphosphate (ATP) to cyclic AMP. Increased cyclic AMP levels are associated with relaxation of bronchial smooth muscle and inhibition of release of mediators of immediate hypersensitivity from cells, especially from mast cells.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury
Benchmark Dataset for the Liver Toxicity Knowledge Base (LTKB)
isoproterenol
Alupent®
Adrenergics
Not Applicable
no-DILI-concern
Chemistry & industry
Pharmacology
ATC Code
C01CA02
C - Cardiovascular system
R - Respiratory system
R - Respiratory system
QR - Respiratory system
QC - Cardiovascular system
Protein BindingIsoprenaline is 68.8 ± 1.2% protein bound in plasma, mainly to serum albumin.
Pharmacodynamics
Isoprenaline is a non-selective beta adrenergic receptor agonist used in a number of indications for the heart, as well as bronchospasm in anesthesia. Isoprenaline has a short duration of action as it is rapidly cleared, and a wide therapeutic index. Patients should be counselled regarding the risks of isoprenaline in the treatment of cardiogenic shock following myocardial infarction, paradoxical worsening of heart block, or precipitation of Adams-Stokes attacks.
Mechanism of Action
Isoprenaline is a non-selective beta adrenergic receptor agonist. Agonism of beta-1 and beta-2 adrenergic receptors causes the alpha subunit of G-protein coupled receptors to exchange GMP for GTP, activating them, and allowing the alpha subunit to dissociate from the beta and gamma subunits. Dissociation of the alpha subunit activates adenylate cyclase, converting ATP to cyclic AMP. Cyclic AMP activates protein kinase A (PKA), which phosphorylates cardiac L-type calcium channels such as Ca<sub>v</sub>1.2. These channels depolarize cells by inward active transport of calcium ions. Agonism of beta-1 adrenergic receptors lead to increased strength of contractility, conduction of nerve impulses, speed of relaxation, and rate in the heart. Agonism of beta-2 adrenergic receptors leads to glycogenolysis in the liver, glucagon release from the pancreas, and activation of the renin-angiotensin-aldosterone system. In the alveoli, agonism of beta-2 adrenergic receptors, activates similar pathways to the heart, however the end result is regulation of sodium channels, the cystic fibrosis transmembrane conductance regulator (CFTR), and sodium potassium ATPase. PKA phosphorylates scaffolding proteins and sodium channels, increasing the number of sodium channels on the apical side of alveolar cells and increasing active transport of sodium ions into cells. Agonism of beta-2 adrenergic receptors can also increase chloride ion transport across CFTR. Together, these actions lead to passive transport of water out of the alveoli, and the clearance of alveolar fluid.
Related reactions
5 records
Compound notes
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