Identification
- Generic Name
- Isoetharine
- DrugBank Accession Number
- DB00221
- Background
Isoetharine is a selective adrenergic beta-2 agonist used as fast acting bronchodilator for emphysema, bronchitis and asthma.
- Type
- Small Molecule
- Groups
- Approved
- Structure
- Weight
- Average: 239.3107
Monoisotopic: 239.152143543 - Chemical Formula
- C13H21NO3
- Synonyms
- Isoetarina
- Isoetarinum
- Isoetharine
- External IDs
- WIN-3046
Pharmacology
- Indication
For the treatment of asthma, wheezing, and chronic asthmatic bronchitis.
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- 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.
Target Actions Organism ABeta-1 adrenergic receptor agonistHumans UBeta-2 adrenergic receptor agonistHumans - 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
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Signs of overdose include tachycardia, palpitations, nausea, headache, and epinephrine-like side effects.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcebutolol The therapeutic efficacy of Isoetharine can be decreased when used in combination with Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when Isoetharine is combined with Aceclofenac. Acemetacin The risk or severity of hypertension can be increased when Isoetharine is combined with Acemetacin. Acetylsalicylic acid The risk or severity of hypertension can be increased when Isoetharine is combined with Acetylsalicylic acid. Aclidinium The risk or severity of Tachycardia can be increased when Isoetharine is combined with Aclidinium. Adenosine The risk or severity of Tachycardia can be increased when Isoetharine is combined with Adenosine. Alclofenac The risk or severity of hypertension can be increased when Isoetharine is combined with Alclofenac. Alfentanil The risk or severity of hypertension can be increased when Isoetharine is combined with Alfentanil. Alfuzosin The therapeutic efficacy of Isoetharine can be decreased when used in combination with Alfuzosin. Aliskiren Isoetharine may decrease the antihypertensive activities of Aliskiren. Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Isoetharine hydrochloride 51V8U784H3 2576-92-3 MUFDLGGSOCHQOC-UHFFFAOYSA-N Isoetharine mesylate DV74WJ5PJB 7279-75-6 SOYAGMVKMXZVNZ-UHFFFAOYSA-N - International/Other Brands
- Bronkometer / Bronkosol
Categories
- Drug Categories
- Adrenergic Agents
- Adrenergic Agonists
- Adrenergic beta-2 Receptor Agonists
- Adrenergic beta-Agonists
- Agents producing tachycardia
- Agents that produce hypertension
- Alcohols
- Amines
- Amino Alcohols
- Anti-Asthmatic Agents
- Autonomic Agents
- Bronchodilator Agents
- Neurotransmitter Agents
- Peripheral Nervous System Agents
- Respiratory System Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as catechols. These are compounds containing a 1,2-benzenediol moiety.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Phenols
- Sub Class
- Benzenediols
- Direct Parent
- Catechols
- Alternative Parents
- Aralkylamines / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Secondary alcohols / 1,2-aminoalcohols / Dialkylamines / Organopnictogen compounds / Hydrocarbon derivatives / Aromatic alcohols
- Substituents
- 1,2-aminoalcohol / 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Alcohol / Amine / Aralkylamine / Aromatic alcohol / Aromatic homomonocyclic compound / Catechol / Hydrocarbon derivative
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- catecholamine (CHEBI:6005)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- YV0SN3276Q
- CAS number
- 79490-84-9
- InChI Key
- 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
- 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
References
- General References
- 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. [Article]
- External Links
- Human Metabolome Database
- HMDB0014366
- KEGG Drug
- D04625
- KEGG Compound
- C07053
- PubChem Compound
- 3762
- PubChem Substance
- 46505384
- ChemSpider
- 3630
- BindingDB
- 52083
- 6023
- ChEBI
- 6005
- ChEMBL
- CHEMBL1201213
- Therapeutic Targets Database
- DAP000935
- PharmGKB
- PA450103
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Isoetarine
- MSDS
- Download (6.51 KB)
Clinical Trials
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
- Nephron Pharmaceuticals Corp.
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility Appreciable Not Available logP 2.2 Not Available - Predicted Properties
Property Value Source Water Solubility 3.18 mg/mL ALOGPS logP 0.63 ALOGPS logP 1.05 Chemaxon logS -1.9 ALOGPS pKa (Strongest Acidic) 10.01 Chemaxon pKa (Strongest Basic) 9.01 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 72.72 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 67.34 m3·mol-1 Chemaxon Polarizability 26.39 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9956 Blood Brain Barrier - 0.9488 Caco-2 permeable - 0.5564 P-glycoprotein substrate Substrate 0.5499 P-glycoprotein inhibitor I Non-inhibitor 0.882 P-glycoprotein inhibitor II Non-inhibitor 0.962 Renal organic cation transporter Non-inhibitor 0.9379 CYP450 2C9 substrate Non-substrate 0.8052 CYP450 2D6 substrate Non-substrate 0.5843 CYP450 3A4 substrate Non-substrate 0.5841 CYP450 1A2 substrate Non-inhibitor 0.7285 CYP450 2C9 inhibitor Non-inhibitor 0.8126 CYP450 2D6 inhibitor Non-inhibitor 0.7513 CYP450 2C19 inhibitor Non-inhibitor 0.8375 CYP450 3A4 inhibitor Non-inhibitor 0.8819 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7781 Ames test Non AMES toxic 0.7703 Carcinogenicity Non-carcinogens 0.8754 Biodegradation Not ready biodegradable 0.9363 Rat acute toxicity 2.4960 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9676 hERG inhibition (predictor II) Non-inhibitor 0.7683
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets

- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Receptor signaling protein activity
- Specific Function
- 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 e...
- Gene Name
- ADRB1
- Uniprot ID
- P08588
- Uniprot Name
- Beta-1 adrenergic receptor
- Molecular Weight
- 51322.1 Da
References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Protein homodimerization activity
- Specific Function
- Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately ...
- Gene Name
- ADRB2
- Uniprot ID
- P07550
- Uniprot Name
- Beta-2 adrenergic receptor
- Molecular Weight
- 46458.32 Da
References
- Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP: ChEMBL: a large-scale bioactivity database for drug discovery. Nucleic Acids Res. 2012 Jan;40(Database issue):D1100-7. doi: 10.1093/nar/gkr777. Epub 2011 Sep 23. [Article]
- Sneader, Walter (1996). Drug Prototypes and Their Exploitation. John Wiley & Sons. [ISBN:0471948470]
Drug created at June 13, 2005 13:24 / Updated at January 03, 2023 04:25