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Identification
NameIsoetarine
Accession NumberDB00221  (APRD00750)
TypeSmall Molecule
GroupsApproved
DescriptionIsoetarine 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 Identifiers
  • WIN-3046
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
BronkometerNot Available
BronkosolNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Isoetarine hydrochloride
2576-92-3
Thumb
  • InChI Key: MUFDLGGSOCHQOC-HTKOBJQYSA-N
  • Monoisotopic Mass: 275.1288213
  • Average Mass: 275.77
DBSALT000349
Isoetharine mesylate
7279-75-6
Thumb
  • InChI Key: SOYAGMVKMXZVNZ-HTKOBJQYSA-N
  • Monoisotopic Mass: 335.140258703
  • Average Mass: 335.42
DBSALT000886
Categories
UNIIYV0SN3276Q
CAS number79490-84-9
WeightAverage: 239.3107
Monoisotopic: 239.152143543
Chemical FormulaC13H21NO3
InChI KeyInChIKey=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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as catecholamines and derivatives. These are compounds containing 4-(2-Aminoethyl)pyrocatechol [4-(2-aminoethyl)benzene-1,2-diol] or a derivative thereof formed by substitution.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenols and derivatives
Direct ParentCatecholamines and derivatives
Alternative Parents
Substituents
  • Catecholamine
  • Aralkylamine
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of asthma, wheezing, and chronic asthmatic bronchitis.
PharmacodynamicsIsoetharine 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 actionThe 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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySigns of overdose include tachycardia, palpitations, nausea, headache, and epinephrine-like side effects.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
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 formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
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
ATC CodesR03AC07R03CC06
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (6.51 KB)
Interactions
Drug Interactions
Drug
7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINEThe risk or severity of adverse effects can be increased when 7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE is combined with Isoetarine.
AcebutololAcebutolol may decrease the bronchodilatory activities of Isoetarine.
AlprenololAlprenolol may decrease the bronchodilatory activities of Isoetarine.
AmineptineThe risk or severity of adverse effects can be increased when Amineptine is combined with Isoetarine.
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Isoetarine.
AtenololAtenolol may decrease the bronchodilatory activities of Isoetarine.
AtomoxetineAtomoxetine may increase the tachycardic activities of Isoetarine.
AtosibanThe risk or severity of adverse effects can be increased when Isoetarine is combined with Atosiban.
BendroflumethiazideIsoetarine may increase the hypokalemic activities of Bendroflumethiazide.
BenmoxinThe risk or severity of adverse effects can be increased when Benmoxin is combined with Isoetarine.
BetahistineThe therapeutic efficacy of Isoetarine can be decreased when used in combination with Betahistine.
BetaxololBetaxolol may decrease the bronchodilatory activities of Isoetarine.
BisoprololBisoprolol may decrease the bronchodilatory activities of Isoetarine.
BopindololBopindolol may decrease the bronchodilatory activities of Isoetarine.
BumetanideIsoetarine may increase the hypokalemic activities of Bumetanide.
BupranololBupranolol may decrease the bronchodilatory activities of Isoetarine.
CaroxazoneThe risk or severity of adverse effects can be increased when Caroxazone is combined with Isoetarine.
CarteololCarteolol may decrease the bronchodilatory activities of Isoetarine.
CeliprololCeliprolol may decrease the bronchodilatory activities of Isoetarine.
ChlorothiazideIsoetarine may increase the hypokalemic activities of Chlorothiazide.
ChlorthalidoneIsoetarine may increase the hypokalemic activities of Chlorthalidone.
ClomipramineThe risk or severity of adverse effects can be increased when Clomipramine is combined with Isoetarine.
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Isoetarine.
DesipramineThe risk or severity of adverse effects can be increased when Desipramine is combined with Isoetarine.
DosulepinThe risk or severity of adverse effects can be increased when Dosulepin is combined with Isoetarine.
DoxepinThe risk or severity of adverse effects can be increased when Doxepin is combined with Isoetarine.
EsmirtazapineThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Isoetarine.
EsmololEsmolol may decrease the bronchodilatory activities of Isoetarine.
Etacrynic acidIsoetarine may increase the hypokalemic activities of Etacrynic acid.
FurazolidoneThe risk or severity of adverse effects can be increased when Furazolidone is combined with Isoetarine.
FurosemideIsoetarine may increase the hypokalemic activities of Furosemide.
HydracarbazineThe risk or severity of adverse effects can be increased when Hydracarbazine is combined with Isoetarine.
HydrochlorothiazideIsoetarine may increase the hypokalemic activities of Hydrochlorothiazide.
HydroflumethiazideIsoetarine may increase the hypokalemic activities of Hydroflumethiazide.
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Isoetarine.
IndapamideIsoetarine may increase the hypokalemic activities of Indapamide.
IproclozideThe risk or severity of adverse effects can be increased when Iproclozide is combined with Isoetarine.
IproniazidThe risk or severity of adverse effects can be increased when Iproniazid is combined with Isoetarine.
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Isoetarine.
MebanazineThe risk or severity of adverse effects can be increased when Mebanazine is combined with Isoetarine.
MethyclothiazideIsoetarine may increase the hypokalemic activities of Methyclothiazide.
Methylene blueThe risk or severity of adverse effects can be increased when Methylene blue is combined with Isoetarine.
MetolazoneIsoetarine may increase the hypokalemic activities of Metolazone.
MetoprololMetoprolol may decrease the bronchodilatory activities of Isoetarine.
MinaprineThe risk or severity of adverse effects can be increased when Minaprine is combined with Isoetarine.
MirtazapineThe risk or severity of adverse effects can be increased when Mirtazapine is combined with Isoetarine.
MoclobemideThe risk or severity of adverse effects can be increased when Moclobemide is combined with Isoetarine.
NadololNadolol may decrease the bronchodilatory activities of Isoetarine.
NebivololNebivolol may decrease the bronchodilatory activities of Isoetarine.
NialamideThe risk or severity of adverse effects can be increased when Nialamide is combined with Isoetarine.
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Isoetarine.
OctamoxinThe risk or severity of adverse effects can be increased when Octamoxin is combined with Isoetarine.
OxprenololOxprenolol may decrease the bronchodilatory activities of Isoetarine.
PargylineThe risk or severity of adverse effects can be increased when Pargyline is combined with Isoetarine.
PenbutololPenbutolol may decrease the bronchodilatory activities of Isoetarine.
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Isoetarine.
PheniprazineThe risk or severity of adverse effects can be increased when Pheniprazine is combined with Isoetarine.
PhenoxypropazineThe risk or severity of adverse effects can be increased when Phenoxypropazine is combined with Isoetarine.
PindololPindolol may decrease the bronchodilatory activities of Isoetarine.
PiretanideIsoetarine may increase the hypokalemic activities of Piretanide.
PirlindoleThe risk or severity of adverse effects can be increased when Pirlindole is combined with Isoetarine.
PivhydrazineThe risk or severity of adverse effects can be increased when Pivhydrazine is combined with Isoetarine.
PolythiazideIsoetarine may increase the hypokalemic activities of Polythiazide.
PropranololPropranolol may decrease the bronchodilatory activities of Isoetarine.
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Isoetarine.
QuinethazoneIsoetarine may increase the hypokalemic activities of Quinethazone.
RasagilineThe risk or severity of adverse effects can be increased when Rasagiline is combined with Isoetarine.
SafrazineThe risk or severity of adverse effects can be increased when Safrazine is combined with Isoetarine.
SelegilineThe risk or severity of adverse effects can be increased when Selegiline is combined with Isoetarine.
SotalolSotalol may decrease the bronchodilatory activities of Isoetarine.
TianeptineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Isoetarine.
TimololTimolol may decrease the bronchodilatory activities of Isoetarine.
ToloxatoneThe risk or severity of adverse effects can be increased when Toloxatone is combined with Isoetarine.
TorasemideIsoetarine may increase the hypokalemic activities of Torasemide.
Trans-2-PhenylcyclopropylamineThe risk or severity of adverse effects can be increased when Trans-2-Phenylcyclopropylamine is combined with Isoetarine.
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Isoetarine.
TrichlormethiazideIsoetarine may increase the hypokalemic activities of Trichlormethiazide.
TrimipramineThe risk or severity of adverse effects can be increased when Trimipramine is combined with Isoetarine.
Food InteractionsNot Available

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 equal affinity. Mediates Ras activation through G(s)-alpha- and cAMP-mediated signaling.
Gene Name:
ADRB1
Uniprot ID:
P08588
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 30-fold greater affinity than it does norepinephrine.
Gene Name:
ADRB2
Uniprot ID:
P07550
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 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23