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Identification
Name Isoetharine
Accession Number DB00221 (APRD00750)
Type small molecule
Groups approved
Description

Isoetharine is a selective adrenergic beta-2 agonist used as fast acting bronchodilator for emphysema, bronchitis and asthma. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Isoetarina [INN-Spanish]
  • Isoetarinum [INN-Latin]
  • Isoetharine Hcl
  • Isoetharine mesylate
Synonyms
Isoetarina [INN-Spanish]
Isoetarinum [INN-Latin]
Isoetharine Hcl
Isoetharine mesylate
Salts Not Available
Brand names
Name Company
Beta-2
Bronkometer
Bronkosol
Dey-Lute Isoetharine
Dilabron
Etyprenaline
Isoetarin
Isoetarine
Isoetharine HCl S/F
Neoisuprel
Brand mixtures Not Available
Categories
  • Bronchodilator Agents
  • Adrenergic beta-Agonists
CAS number 530-08-5
Weight Average: 239.3107
Monoisotopic: 239.152143543
Chemical Formula C13H21NO3
InChI Key InChIKey=HUYWAWARQUIQLE-UHFFFAOYSA-N
InChI
InChI=1S/C13H21NO3/c1-4-10(14-8(2)3)13(17)9-5-6-11(15)12(16)7-9/h5-8,10,13-17H,4H2,1-3H3
Plain Text
IUPAC Name
4-{1-hydroxy-2-[(propan-2-yl)amino]butyl}benzene-1,2-diol
SMILES
CCC(NC(C)C)C(O)C1=CC(O)=C(O)C=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Catecholamines and Derivatives
Substructures
  • Hydroxy Compounds
  • Phenols and Derivatives
  • Catecholamines and Derivatives
  • Benzyl Alcohols and Derivatives
  • Aliphatic and Aryl Amines
  • Benzene and Derivatives
  • Amino Alcohols
  • Catechols
  • Phenethylamines
  • Aromatic compounds
  • Alcohols and Polyols
  • Phenyl Esters
  • Amphetamines
Pharmacology
Indication For the treatment of asthma, wheezing, and chronic asthmatic bronchitis.
Pharmacodynamics Isoetharine is a relatively selective beta2-adrenergic bronchodilator. Isoetharine is indicated for the relief of bronchospasm associated with chronic obstructive pulmonary disease. Adrenergic bronchodilators are breathed in through the mouth to open up the bronchial tubes (air passages) of the lungs.
Mechanism of action The pharmacologic effects of isoetharine are 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.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism Not Available
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Signs of overdose include tachycardia, palpitations, nausea, headache, and epinephrine-like side effects.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Nephron corp
  • Sanofi aventis us llc
  • Alpharma us pharmaceuticals division
  • Astrazeneca lp
  • Baxter healthcare corp
  • Dey lp
  • International medication systems ltd
  • Parke davis pharmaceutical research div warner lambert co
  • Roxane laboratories inc
Packagers
Dosage forms
Form Route Strength
Solution Respiratory (inhalation)
Prices Not Available
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties
Property Value Source
water solubility Appreciable PhysProp
logP 2.2 PhysProp
Predicted Properties
Property Value Source
water solubility 3.18e+00 g/l ALOGPS
logP 0.63 ALOGPS
logP 1.05 ChemAxon Molconvert
logS -1.9 ALOGPS
pKa 12.64 ChemAxon Molconvert
hydrogen acceptor count 4 ChemAxon Molconvert
hydrogen donor count 4 ChemAxon Molconvert
polar surface area 72.72 ChemAxon Molconvert
rotatable bond count 5 ChemAxon Molconvert
refractivity 67.34 ChemAxon Molconvert
polarizability 26.39 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  1. Emerman CL, Cydulka RK, Effron D, Lukens TW, Gershman H, Boehm SP: A randomized, controlled comparison of isoetharine and albuterol in the treatment of acute asthma. Ann Emerg Med. 1991 Oct;20(10):1090-3. Pubmed
External Links
Resource Link
KEGG Drug D04625 Link_out
KEGG Compound C07053 Link_out
PubChem Compound 3762 Link_out
PubChem Substance 46505384 Link_out
ChemSpider 3630 Link_out
Therapeutic Targets Database DAP000935 Link_out
PharmGKB PA450103 Link_out
Drugs.com http://www.drugs.com/mtm/isoetharine-inhalation.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Isoetharine Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS show (6.51 KB)
Interactions
Drug Interactions
Drug Interaction
Entacapone Entacapone increases the effect and toxicity of the sympathomimetic, isoetharine.
Food Interactions Not Available
Targets

1. Beta-1 adrenergic receptor

Pharmacological action: yes
Actions: agonist

Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity

Organism class: human
UniProt ID: P08588 Link_out
Gene: ADRB1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Rodrigues LL, Oliveira MC, Pelegrini-da-Silva A, de Arruda Veiga MC, Parada CA, Tambeli CH: Peripheral sympathetic component of the temporomandibular joint inflammatory pain in rats. J Pain. 2006 Dec;7(12):929-36. Pubmed
  2. Horinouchi T, Morishima S, Tanaka T, Suzuki F, Tanaka Y, Koike K, Miwa S, Muramatsu I: Different changes of plasma membrane beta-adrenoceptors in rat heart after chronic administration of propranolol, atenolol and bevantolol. Life Sci. 2007 Jul 12;81(5):399-404. Epub 2007 Jun 16. Pubmed
  3. Terra SG, McGorray SP, Wu R, McNamara DM, Cavallari LH, Walker JR, Wallace MR, Johnson BD, Bairey Merz CN, Sopko G, Pepine CJ, Johnson JA: Association between beta-adrenergic receptor polymorphisms and their G-protein-coupled receptors with body mass index and obesity in women: a report from the NHLBI-sponsored WISE study. Int J Obes (Lond). 2005 Jul;29(7):746-54. Pubmed
  4. Burniston JG, Tan LB, Goldspink DF: Relative myotoxic and haemodynamic effects of the beta-agonists fenoterol and clenbuterol measured in conscious unrestrained rats. Exp Physiol. 2006 Nov;91(6):1041-9. Epub 2006 Sep 14. Pubmed
  5. Muszkat M: Interethnic differences in drug response: the contribution of genetic variability in beta adrenergic receptor and cytochrome P4502C9. Clin Pharmacol Ther. 2007 Aug;82(2):215-8. Epub 2007 Feb 28. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 14, 2012 11:40