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 hydrochloride51V8U784H32576-92-3MUFDLGGSOCHQOC-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.

Structured Indications
Not Available
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
DrugInteractionDrug group
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.Experimental
AcebutololAcebutolol may decrease the bronchodilatory activities of Isoetarine.Approved
AlfuzosinAlfuzosin may decrease the vasoconstricting activities of Isoetarine.Approved, Investigational
AlprenololAlprenolol may decrease the bronchodilatory activities of Isoetarine.Approved, Withdrawn
AmineptineThe risk or severity of adverse effects can be increased when Amineptine is combined with Isoetarine.Illicit, Withdrawn
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Isoetarine.Approved
AmoxapineThe risk or severity of adverse effects can be increased when Amoxapine is combined with Isoetarine.Approved
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Isoetarine.Approved, Illicit
AtenololAtenolol may decrease the bronchodilatory activities of Isoetarine.Approved
AtomoxetineAtomoxetine may increase the tachycardic activities of Isoetarine.Approved
AtosibanThe risk or severity of adverse effects can be increased when Isoetarine is combined with Atosiban.Approved, Investigational
BendroflumethiazideIsoetarine may increase the hypokalemic activities of Bendroflumethiazide.Approved
BenmoxinThe risk or severity of adverse effects can be increased when Benmoxin is combined with Isoetarine.Withdrawn
Benzylpenicilloyl PolylysineIsoetarine may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.Approved
BetahistineThe therapeutic efficacy of Isoetarine can be decreased when used in combination with Betahistine.Approved
BetaxololBetaxolol may decrease the bronchodilatory activities of Isoetarine.Approved
BisoprololBisoprolol may decrease the bronchodilatory activities of Isoetarine.Approved
BopindololBopindolol may decrease the bronchodilatory activities of Isoetarine.Approved
BrofaromineThe risk or severity of adverse effects can be increased when Brofaromine is combined with Isoetarine.Experimental
BromocriptineBromocriptine may increase the hypertensive activities of Isoetarine.Approved, Investigational
BucindololBucindolol may decrease the vasoconstricting activities of Isoetarine.Investigational
BumetanideIsoetarine may increase the hypokalemic activities of Bumetanide.Approved
BunazosinBunazosin may decrease the vasoconstricting activities of Isoetarine.Investigational
BupranololBupranolol may decrease the bronchodilatory activities of Isoetarine.Approved
CabergolineCabergoline may increase the hypertensive activities of Isoetarine.Approved
CaroxazoneThe risk or severity of adverse effects can be increased when Caroxazone is combined with Isoetarine.Withdrawn
CarteololCarteolol may decrease the bronchodilatory activities of Isoetarine.Approved
CarvedilolCarvedilol may decrease the vasoconstricting activities of Isoetarine.Approved, Investigational
CeliprololCeliprolol may decrease the bronchodilatory activities of Isoetarine.Approved, Investigational
ChlorothiazideIsoetarine may increase the hypokalemic activities of Chlorothiazide.Approved, Vet Approved
ChlorthalidoneIsoetarine may increase the hypokalemic activities of Chlorthalidone.Approved
ClomipramineThe risk or severity of adverse effects can be increased when Clomipramine is combined with Isoetarine.Approved, Vet Approved
CloranololCloranolol may decrease the bronchodilatory activities of Isoetarine.Experimental
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Isoetarine.Approved
CyclopenthiazideIsoetarine may increase the hypokalemic activities of Cyclopenthiazide.Experimental
DesipramineThe risk or severity of adverse effects can be increased when Desipramine is combined with Isoetarine.Approved
DesvenlafaxineDesvenlafaxine may increase the tachycardic activities of Isoetarine.Approved
DibenzepinThe risk or severity of adverse effects can be increased when Dibenzepin is combined with Isoetarine.Experimental
DihydroergotamineDihydroergotamine may increase the hypertensive activities of Isoetarine.Approved
DosulepinThe risk or severity of adverse effects can be increased when Dosulepin is combined with Isoetarine.Approved
DoxazosinDoxazosin may decrease the vasoconstricting activities of Isoetarine.Approved
DoxepinThe risk or severity of adverse effects can be increased when Doxepin is combined with Isoetarine.Approved
DuloxetineDuloxetine may increase the tachycardic activities of Isoetarine.Approved
Ergoloid mesylateErgoloid mesylate may increase the hypertensive activities of Isoetarine.Approved
ErgonovineErgonovine may increase the hypertensive activities of Isoetarine.Approved
ErgotamineErgotamine may increase the hypertensive activities of Isoetarine.Approved
EsmirtazapineThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Isoetarine.Investigational
EsmololEsmolol may decrease the bronchodilatory activities of Isoetarine.Approved
Etacrynic acidIsoetarine may increase the hypokalemic activities of Etacrynic acid.Approved
FurazolidoneThe risk or severity of adverse effects can be increased when Furazolidone is combined with Isoetarine.Approved, Investigational, Vet Approved
FurosemideIsoetarine may increase the hypokalemic activities of Furosemide.Approved, Vet Approved
HarmalineThe risk or severity of adverse effects can be increased when Harmaline is combined with Isoetarine.Experimental
HydracarbazineThe risk or severity of adverse effects can be increased when Hydracarbazine is combined with Isoetarine.Experimental
HydrochlorothiazideIsoetarine may increase the hypokalemic activities of Hydrochlorothiazide.Approved, Vet Approved
HydroflumethiazideIsoetarine may increase the hypokalemic activities of Hydroflumethiazide.Approved, Investigational
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Isoetarine.Approved
IndapamideIsoetarine may increase the hypokalemic activities of Indapamide.Approved
IndoraminIndoramin may decrease the vasoconstricting activities of Isoetarine.Withdrawn
IprindoleThe risk or severity of adverse effects can be increased when Iprindole is combined with Isoetarine.Experimental
IproclozideThe risk or severity of adverse effects can be increased when Iproclozide is combined with Isoetarine.Withdrawn
IproniazidThe risk or severity of adverse effects can be increased when Iproniazid is combined with Isoetarine.Withdrawn
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Isoetarine.Approved
LabetalolLabetalol may decrease the vasoconstricting activities of Isoetarine.Approved
LevomilnacipranLevomilnacipran may increase the tachycardic activities of Isoetarine.Approved
LofepramineThe risk or severity of adverse effects can be increased when Lofepramine is combined with Isoetarine.Experimental
MebanazineThe risk or severity of adverse effects can be increased when Mebanazine is combined with Isoetarine.Withdrawn
MepindololMepindolol may decrease the bronchodilatory activities of Isoetarine.Experimental
MethyclothiazideIsoetarine may increase the hypokalemic activities of Methyclothiazide.Approved
Methylene blueThe risk or severity of adverse effects can be increased when Methylene blue is combined with Isoetarine.Approved, Investigational
MethylergometrineMethylergometrine may increase the hypertensive activities of Isoetarine.Approved
MetolazoneIsoetarine may increase the hypokalemic activities of Metolazone.Approved
MetoprololMetoprolol may decrease the bronchodilatory activities of Isoetarine.Approved, Investigational
MilnacipranMilnacipran may increase the tachycardic activities of Isoetarine.Approved
MinaprineThe risk or severity of adverse effects can be increased when Minaprine is combined with Isoetarine.Approved
MirtazapineThe risk or severity of adverse effects can be increased when Mirtazapine is combined with Isoetarine.Approved
MoclobemideThe risk or severity of adverse effects can be increased when Moclobemide is combined with Isoetarine.Approved
NebivololNebivolol may decrease the bronchodilatory activities of Isoetarine.Approved, Investigational
NialamideThe risk or severity of adverse effects can be increased when Nialamide is combined with Isoetarine.Withdrawn
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Isoetarine.Approved
OctamoxinThe risk or severity of adverse effects can be increased when Octamoxin is combined with Isoetarine.Withdrawn
OpipramolThe risk or severity of adverse effects can be increased when Opipramol is combined with Isoetarine.Investigational
OxprenololOxprenolol may decrease the bronchodilatory activities of Isoetarine.Approved
PargylineThe risk or severity of adverse effects can be increased when Pargyline is combined with Isoetarine.Approved
PenbutololPenbutolol may decrease the bronchodilatory activities of Isoetarine.Approved, Investigational
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Isoetarine.Approved
PheniprazineThe risk or severity of adverse effects can be increased when Pheniprazine is combined with Isoetarine.Withdrawn
PhenoxypropazineThe risk or severity of adverse effects can be increased when Phenoxypropazine is combined with Isoetarine.Withdrawn
PiretanideIsoetarine may increase the hypokalemic activities of Piretanide.Experimental
PirlindoleThe risk or severity of adverse effects can be increased when Pirlindole is combined with Isoetarine.Approved
PivhydrazineThe risk or severity of adverse effects can be increased when Pivhydrazine is combined with Isoetarine.Withdrawn
PolythiazideIsoetarine may increase the hypokalemic activities of Polythiazide.Approved
PrazosinPrazosin may decrease the vasoconstricting activities of Isoetarine.Approved
ProcarbazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Isoetarine.Approved
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Isoetarine.Approved
QuinethazoneIsoetarine may increase the hypokalemic activities of Quinethazone.Approved
RasagilineThe risk or severity of adverse effects can be increased when Rasagiline is combined with Isoetarine.Approved
SafrazineThe risk or severity of adverse effects can be increased when Safrazine is combined with Isoetarine.Withdrawn
SelegilineThe risk or severity of adverse effects can be increased when Selegiline is combined with Isoetarine.Approved, Investigational, Vet Approved
SilodosinSilodosin may decrease the vasoconstricting activities of Isoetarine.Approved
SotalolSotalol may decrease the bronchodilatory activities of Isoetarine.Approved
SpironolactoneSpironolactone may decrease the vasoconstricting activities of Isoetarine.Approved
TamsulosinTamsulosin may decrease the vasoconstricting activities of Isoetarine.Approved, Investigational
TerazosinTerazosin may decrease the vasoconstricting activities of Isoetarine.Approved
TertatololTertatolol may decrease the bronchodilatory activities of Isoetarine.Experimental
TianeptineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Isoetarine.Approved, Investigational
ToloxatoneThe risk or severity of adverse effects can be increased when Toloxatone is combined with Isoetarine.Approved
TorasemideIsoetarine may increase the hypokalemic activities of Torasemide.Approved
Trans-2-PhenylcyclopropylamineThe risk or severity of adverse effects can be increased when Trans-2-Phenylcyclopropylamine is combined with Isoetarine.Experimental
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Isoetarine.Approved
TrichlormethiazideIsoetarine may increase the hypokalemic activities of Trichlormethiazide.Approved, Vet Approved
TrimazosinTrimazosin may decrease the vasoconstricting activities of Isoetarine.Experimental
TrimipramineThe risk or severity of adverse effects can be increased when Trimipramine is combined with Isoetarine.Approved
UrapidilUrapidil may decrease the vasoconstricting activities of Isoetarine.Investigational
VemurafenibThe risk or severity of QTc prolongation can be increased when Vemurafenib is combined with Isoetarine.Approved
VenlafaxineVenlafaxine may increase the tachycardic activities of Isoetarine.Approved
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
HMDB14366
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
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 December 01, 2017 17:17