Identification

Name
Isoetarine
Accession Number
DB00221  (APRD00750)
Type
Small Molecule
Groups
Approved
Description

Isoetarine is a selective adrenergic beta-2 agonist used as fast acting bronchodilator for emphysema, bronchitis and asthma. [PubChem]

Structure
Thumb
Synonyms
  • Isoetarina
  • Isoetarinum
  • Isoetharine
External IDs
WIN-3046
Product Ingredients
IngredientUNIICASInChI Key
Isoetarine hydrochloride37SR0CHR8L2576-92-3MUFDLGGSOCHQOC-HTKOBJQYSA-N
Isoetharine mesylateDV74WJ5PJB7279-75-6SOYAGMVKMXZVNZ-HTKOBJQYSA-N
International/Other Brands
Bronkometer / Bronkosol
Categories
UNII
YV0SN3276Q
CAS number
79490-84-9
Weight
Average: 239.3107
Monoisotopic: 239.152143543
Chemical Formula
C13H21NO3
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

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.

TargetActionsOrganism
ABeta-1 adrenergic receptor
agonist
Human
UBeta-2 adrenergic receptor
agonist
Human
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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AbediterolThe risk or severity of adverse effects can be increased when Isoetarine is combined with Abediterol.
AcebutololThe therapeutic efficacy of Isoetarine can be decreased when used in combination with Acebutolol.
AcepromazineThe therapeutic efficacy of Isoetarine can be decreased when used in combination with Acepromazine.
AldosteroneThe risk or severity of hypokalemia can be increased when Aldosterone is combined with Isoetarine.
AlfuzosinThe therapeutic efficacy of Isoetarine can be decreased when used in combination with Alfuzosin.
AlprenololAlprenolol may decrease the bronchodilatory activities of Isoetarine.
AmineptineThe risk or severity of hypertension can be increased when Amineptine is combined with Isoetarine.
AmitriptylineThe therapeutic efficacy of Isoetarine can be decreased when used in combination with Amitriptyline.
AmitriptylinoxideThe risk or severity of hypertension can be increased when Amitriptylinoxide is combined with Isoetarine.
AmoxapineThe therapeutic efficacy of Isoetarine can be decreased when used in combination with Amoxapine.
Food Interactions
Not Available

References

General References
  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:1928879]
External Links
Human Metabolome Database
HMDB0014366
KEGG Drug
D04625
KEGG Compound
C07053
PubChem Compound
3762
PubChem Substance
46505384
ChemSpider
3630
BindingDB
52083
ChEBI
6005
ChEMBL
CHEMBL1201213
Therapeutic Targets Database
DAP000935
PharmGKB
PA450103
Drugs.com
Drugs.com Drug Page
Wikipedia
Isoetharine
ATC Codes
R03AC07 — IsoetarineR03CC06 — Isoetarine
MSDS
Download (6.51 KB)

Clinical Trials

Clinical Trials
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
  • Nephron Pharmaceuticals Corp.
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilityAppreciableNot Available
logP2.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.18 mg/mLALOGPS
logP0.63ALOGPS
logP1.05ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)10.01ChemAxon
pKa (Strongest Basic)9.01ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area72.72 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity67.34 m3·mol-1ChemAxon
Polarizability26.39 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9956
Blood Brain Barrier-0.9488
Caco-2 permeable-0.5564
P-glycoprotein substrateSubstrate0.5499
P-glycoprotein inhibitor INon-inhibitor0.882
P-glycoprotein inhibitor IINon-inhibitor0.962
Renal organic cation transporterNon-inhibitor0.9379
CYP450 2C9 substrateNon-substrate0.8052
CYP450 2D6 substrateNon-substrate0.5843
CYP450 3A4 substrateNon-substrate0.5841
CYP450 1A2 substrateNon-inhibitor0.7285
CYP450 2C9 inhibitorNon-inhibitor0.8126
CYP450 2D6 inhibitorNon-inhibitor0.7513
CYP450 2C19 inhibitorNon-inhibitor0.8375
CYP450 3A4 inhibitorNon-inhibitor0.8819
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7781
Ames testNon AMES toxic0.7703
CarcinogenicityNon-carcinogens0.8754
BiodegradationNot ready biodegradable0.9363
Rat acute toxicity2.4960 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9676
hERG inhibition (predictor II)Non-inhibitor0.7683
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Catechol / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Aralkylamine / Monocyclic benzene moiety / 1,2-aminoalcohol / Secondary alcohol / Secondary amine / Secondary aliphatic amine / Aromatic alcohol
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
catecholamine (CHEBI:6005)

Targets

Kind
Protein
Organism
Human
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
  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:17157779]
  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:17628611]
  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:15917856]
  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:16973691]
  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:17329986]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:21948594]
  2. Sneader, Walter (1996). Drug Prototypes and Their Exploitation. John Wiley & Sons. [ISBN:0471948470]

Drug created on June 13, 2005 07:24 / Updated on October 01, 2018 16:30