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Identification
NameIsoprenaline
Accession NumberDB01064  (APRD00182)
Typesmall molecule
Groupsapproved
Description

Isopropyl analog of epinephrine; beta-sympathomimetic that acts on the heart, bronchi, skeletal muscle, alimentary tract, etc. It is used mainly as bronchodilator and heart stimulant. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
(±)-isoprenalineNot AvailableNot Available
(±)-isoproterenolNot AvailableNot Available
Isopropyl noradrenalineNot AvailableNot Available
IsoproterenolNot AvailableUSAN
N-isopropyl-β-dihydroxyphenyl-β-hydroxyethylamineNot AvailableNot Available
N-IsopropylnoradrenalineNot AvailableNot Available
N-IsopropylnorepinephrineNot AvailableNot Available
α-(isopropylaminomethyl)protocatechuyl alcoholNot AvailableNot Available
Salts
Name/CAS Structure Properties
Isoprenaline Hydrochloride
Thumb
  • InChI Key: IROWCYIEJAOFOW-UHFFFAOYNA-N
  • Monoisotopic Mass: 247.097521154
  • Average Mass: 247.719
DBSALT000429
Brand names
NameCompany
AeroloneNot Available
IsuprelNot Available
Medihaler-IsoNot Available
Proternol LNot Available
SaventrineNot Available
Brand mixturesNot Available
Categories
CAS number7683-59-2
WeightAverage: 211.2576
Monoisotopic: 211.120843415
Chemical FormulaC11H17NO3
InChI KeyInChIKey=JWZZKOKVBUJMES-UHFFFAOYSA-N
InChI
InChI=1S/C11H17NO3/c1-7(2)12-6-11(15)8-3-4-9(13)10(14)5-8/h3-5,7,11-15H,6H2,1-2H3
IUPAC Name
4-{1-hydroxy-2-[(propan-2-yl)amino]ethyl}benzene-1,2-diol
SMILES
CC(C)NCC(O)C1=CC(O)=C(O)C=C1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassPhenols and Derivatives
Direct parentCatecholamines and Derivatives
Alternative parentsSecondary Alcohols; Polyols; 1,2-Aminoalcohols; Enols; Dialkylamines; Polyamines
Substituents1,2-aminoalcohol; polyol; secondary alcohol; secondary aliphatic amine; polyamine; enol; secondary amine; amine; alcohol; organonitrogen compound
Classification descriptionThis compound belongs to the 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.
Pharmacology
IndicationFor the treatment of mild or transient episodes of heart block that do not require electric shock or pacemaker therapy also used in management of asthma and chronic bronchitis
PharmacodynamicsIsoproterenol is a relatively selective beta2-adrenergic bronchodilator. Isoproterenol is indicated for the relief of bronchospasm associated with chronic obstructive pulmonary disease. The pharmacologic effects of beta adrenergic agonist drugs, including Isoproterenol, are at least in part attributable to stimulation through beta adrenergic receptors of intracellular adenyl cyclase, the enzyme which catalyzes the conversion of adenosine triphosphate (ATP) to cyclic- 3',5'- adenosine monophosphate (c-AMP). Increased c-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.
Mechanism of actionThe pharmacologic effects of isoproterenol are at least in part 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationExcretion following inhalation administration is primarily renal and the major metabolite is the sulfate conjugate of isoproterenol.
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9936
Blood Brain Barrier - 0.9705
Caco-2 permeable - 0.6775
P-glycoprotein substrate Substrate 0.5776
P-glycoprotein inhibitor I Non-inhibitor 0.9039
P-glycoprotein inhibitor II Non-inhibitor 0.9709
Renal organic cation transporter Non-inhibitor 0.8983
CYP450 2C9 substrate Non-substrate 0.7778
CYP450 2D6 substrate Non-substrate 0.6679
CYP450 3A4 substrate Non-substrate 0.6939
CYP450 1A2 substrate Inhibitor 0.6221
CYP450 2C9 substrate Non-inhibitor 0.9558
CYP450 2D6 substrate Non-inhibitor 0.9231
CYP450 2C19 substrate Non-inhibitor 0.9484
CYP450 3A4 substrate Non-inhibitor 0.9556
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9318
Ames test Non AMES toxic 0.9133
Carcinogenicity Non-carcinogens 0.9182
Biodegradation Not ready biodegradable 0.8925
Rat acute toxicity 2.7434 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9576
hERG inhibition (predictor II) Non-inhibitor 0.8045
Pharmacoeconomics
Manufacturers
  • 3m pharmaceuticals inc
  • Alpharma us pharmaceuticals division
  • Sanofi aventis us llc
  • Abbott laboratories pharmaceutical products div
  • Abraxis pharmaceutical products
  • Baxter healthcare corp anesthesia and critical care
  • Hospira inc
  • International medication system
  • Eli lilly and co
  • Armour pharmaceutical co
  • Dey lp
  • Parke davis div warner lambert co
  • Fisons corp
Packagers
Dosage forms
FormRouteStrength
GelTopical
LiquidAuricular (otic)
LiquidTopical
LotionTopical
SolutionIntramuscular
SolutionTopical
SprayTopical
StickTopical
SwabTopical
Prices
Unit descriptionCostUnit
Isuprel 0.2 mg/ml ampul17.63USDml
Isoproterenol sulfate cryst2.86USDg
Isoproterenol 0.2 mg/ml amp0.73USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point170.5 °CPhysProp
logP1.4Not Available
Predicted Properties
PropertyValueSource
water solubility5.86e+00 g/lALOGPS
logP-0.27ALOGPS
logP0.24ChemAxon
logS-1.6ALOGPS
pKa (strongest acidic)9.81ChemAxon
pKa (strongest basic)8.96ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count4ChemAxon
polar surface area72.72ChemAxon
rotatable bond count4ChemAxon
refractivity58.4ChemAxon
polarizability23.04ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC07056
PubChem Compound3779
PubChem Substance46507323
ChemSpider3647
BindingDB25392
ChEBI64317
ChEMBLCHEMBL434
Therapeutic Targets DatabaseDNC000819
PharmGKBPA450121
IUPHAR536
Guide to Pharmacology536
Drug Product Database897639
RxListhttp://www.rxlist.com/cgi/generic3/isoproterenol.htm
Drugs.comhttp://www.drugs.com/cdi/isoproterenol.html
WikipediaIsoproterenol
ATC CodesC01CA02D08AX05
AHFS Codes
  • 84:04.92
  • 12:12.08.04
  • 52:92.00
  • 84:04.12
PDB EntriesNot Available
FDA labelshow(314 KB)
MSDSshow(73.3 KB)
Interactions
Drug Interactions
Drug
AcebutololAntagonism
AmitriptylineThe tricyclic antidepressant, amitriptyline, increases the sympathomimetic effect of isoproterenol.
AmoxapineThe tricyclic antidepressant, amoxapine, increases the sympathomimetic effect of isoproterenol.
AtenololAntagonism
BisoprololAntagonism
CarvedilolAntagonism
ClomipramineThe tricyclic antidepressant, clomipramine, increases the sympathomimetic effect of isoproterenol.
DesipramineThe tricyclic antidepressant, desipramine, increases the sympathomimetic effect of isoproterenol.
DoxepinThe tricyclic antidepressant, doxepin, increases the sympathomimetic effect of isoproterenol.
EntacaponeEntacapone increases the effect and toxicity of the sympathomimetic, isoproterenol.
EsmololAntagonism
ImipramineThe tricyclic antidepressant, imipramine, increases the sympathomimetic effect of isoproterenol.
IsocarboxazidIncreased arterial pressure
LabetalolAntagonism
LinezolidPossible increase of arterial pressure
MethyldopaIncreased arterial pressure
MetoprololAntagonism
MidodrineIncreased arterial pressure
MoclobemideMoclobemide increases the sympathomimetic effect of isoproterenol.
NadololAntagonism
NortriptylineThe tricyclic antidepressant, nortriptyline, increases the sympathomimetic effect of isoproterenol.
OxprenololAntagonism
PhenelzineIncreased arterial pressure
PindololAntagonism
PropranololAntagonism
RasagilineIncreased arterial pressure
ReserpineIncreased arterial pressure
TimololAntagonism
Food InteractionsNot Available

1. Beta-1 adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Beta-1 adrenergic receptor P08588 Details

References:

  1. Sato M, Gong H, Terracciano CM, Ranu H, Harding SE: Loss of beta-adrenoceptor response in myocytes overexpressing the Na+/Ca(2+)-exchanger. J Mol Cell Cardiol. 2004 Jan;36(1):43-8. Pubmed
  2. Jurgens CW, Rau KE, Knudson CA, King JD, Carr PA, Porter JE, Doze VA: Beta1 adrenergic receptor-mediated enhancement of hippocampal CA3 network activity. J Pharmacol Exp Ther. 2005 Aug;314(2):552-60. Epub 2005 May 20. Pubmed
  3. Kobayashi H, Narita Y, Nishida M, Kurose H: Beta-arrestin2 enhances beta2-adrenergic receptor-mediated nuclear translocation of ERK. Cell Signal. 2005 Oct;17(10):1248-53. Epub 2005 Feb 12. Pubmed
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  5. Ahlquist RP: Present state of alpha- and beta-adrenergic drugs I. The adrenergic receptor. Am Heart J. 1976 Nov;92(5):661-4. Pubmed

2. Beta-2 adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Beta-2 adrenergic receptor P07550 Details

References:

  1. Abraham G, Kottke C, Dhein S, Ungemach FR: Pharmacological and biochemical characterization of the beta-adrenergic signal transduction pathway in different segments of the respiratory tract. Biochem Pharmacol. 2003 Sep 15;66(6):1067-81. Pubmed
  2. Jones SM, Hiller FC, Jacobi SE, Foreman SK, Pittman LM, Cornett LE: Enhanced beta2-adrenergic receptor (beta2AR) signaling by adeno-associated viral (AAV)-mediated gene transfer. BMC Pharmacol. 2003 Dec 4;3:15. Pubmed
  3. Teixeira CE, Baracat JS, Zanesco A, Antunes E, De Nucci G: Atypical beta-adrenoceptor subtypes mediate relaxations of rabbit corpus cavernosum. J Pharmacol Exp Ther. 2004 May;309(2):587-93. Epub 2004 Jan 29. Pubmed
  4. Odley A, Hahn HS, Lynch RA, Marreez Y, Osinska H, Robbins J, Dorn GW 2nd: Regulation of cardiac contractility by Rab4-modulated beta2-adrenergic receptor recycling. Proc Natl Acad Sci U S A. 2004 May 4;101(18):7082-7. Epub 2004 Apr 22. Pubmed
  5. Uezono Y, Kaibara M, Murasaki O, Taniyama K: Involvement of G protein betagamma-subunits in diverse signaling induced by G(i/o)-coupled receptors: study using the Xenopus oocyte expression system. Am J Physiol Cell Physiol. 2004 Oct;287(4):C885-94. Epub 2004 May 19. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  7. Ahlquist RP: Present state of alpha- and beta-adrenergic drugs I. The adrenergic receptor. Am Heart J. 1976 Nov;92(5):661-4. Pubmed

3. Beta-3 adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Beta-3 adrenergic receptor P13945 Details

References:

  1. Ahlquist RP: Present state of alpha- and beta-adrenergic drugs I. The adrenergic receptor. Am Heart J. 1976 Nov;92(5):661-4. Pubmed
  2. Schiffelers SL, Blaak EE, Saris WH, van Baak MA: In vivo beta3-adrenergic stimulation of human thermogenesis and lipid use. Clin Pharmacol Ther. 2000 May;67(5):558-66. Pubmed

4. Mitogen-activated protein kinase 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Mitogen-activated protein kinase 1 P28482 Details

References:

  1. Vaniotis G, Del Duca D, Trieu P, Rohlicek CV, Hebert TE, Allen BG: Nuclear beta-adrenergic receptors modulate gene expression in adult rat heart. Cell Signal. 2010 Aug 21. Pubmed
  2. Oudit GY, Crackower MA, Eriksson U, Sarao R, Kozieradzki I, Sasaki T, Irie-Sasaki J, Gidrewicz D, Rybin VO, Wada T, Steinberg SF, Backx PH, Penninger JM: Phosphoinositide 3-kinase gamma-deficient mice are protected from isoproterenol-induced heart failure. Circulation. 2003 Oct 28;108(17):2147-52. Epub 2003 Sep 8. Pubmed
  3. Azzi M, Charest PG, Angers S, Rousseau G, Kohout T, Bouvier M, Pineyro G: Beta-arrestin-mediated activation of MAPK by inverse agonists reveals distinct active conformations for G protein-coupled receptors. Proc Natl Acad Sci U S A. 2003 Sep 30;100(20):11406-11. Epub 2003 Sep 17. Pubmed
  4. Adissu HA, Schuller HM: Antagonistic growth regulation of cell lines derived from human lung adenocarcinomas of Clara cell and aveolar type II cell lineage: Implications for chemoprevention. Int J Oncol. 2004 Jun;24(6):1467-72. Pubmed
  5. Dubey RK, Jackson EK, Gillespie DG, Zacharia LC, Imthurn B: Catecholamines block the antimitogenic effect of estradiol on human coronary artery smooth muscle cells. J Clin Endocrinol Metab. 2004 Aug;89(8):3922-31. Pubmed
  6. Yeh CK, Ghosh PM, Dang H, Liu Q, Lin AL, Zhang BX, Katz MS: beta-Adrenergic-responsive activation of extracellular signal-regulated protein kinases in salivary cells: role of epidermal growth factor receptor and cAMP. Am J Physiol Cell Physiol. 2005 Jun;288(6):C1357-66. Epub 2005 Feb 2. Pubmed

5. Phosphatidylinositol 3-kinase regulatory subunit alpha

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Phosphatidylinositol 3-kinase regulatory subunit alpha P27986 Details

References:

  1. Slomiany BL, Slomiany A: Salivary phospholipid secretion in response to beta-adrenergic stimulation is mediated by Src kinase-dependent epidermal growth factor receptor transactivation. Biochem Biophys Res Commun. 2004 May 21;318(1):247-52. Pubmed
  2. Slomiany BL, Slomiany A: Secretion of gastric mucus phospholipids in response to beta-adrenergic G protein-coupled receptor activation is mediated by SRC kinase-dependent epidermal growth factor receptor transactivation. J Physiol Pharmacol. 2004 Sep;55(3):627-38. Pubmed
  3. Slomiany BL, Slomiany A: Src-kinase-dependent epidermal growth factor receptor transactivation in salivary mucin secretion in response to beta-adrenergic G-protein-coupled receptor activation. Inflammopharmacology. 2004;12(3):233-45. Pubmed
  4. Machida K, Inoue H, Matsumoto K, Tsuda M, Fukuyama S, Koto H, Aizawa H, Kureishi Y, Hara N, Nakanishi Y: Activation of PI3K-Akt pathway mediates antiapoptotic effects of beta-adrenergic agonist in airway eosinophils. Am J Physiol Lung Cell Mol Physiol. 2005 May;288(5):L860-7. Epub 2004 Dec 23. Pubmed
  5. Slomiany BL, Slomiany A: Gastric mucin secretion in response to beta-adrenergic G protein-coupled receptor activation is mediated by SRC kinase-dependent epidermal growth factor receptor transactivation. J Physiol Pharmacol. 2005 Jun;56(2):247-58. Pubmed

6. Phosphatidylinositol 3-kinase regulatory subunit beta

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Phosphatidylinositol 3-kinase regulatory subunit beta O00459 Details

References:

  1. Slomiany BL, Slomiany A: Salivary phospholipid secretion in response to beta-adrenergic stimulation is mediated by Src kinase-dependent epidermal growth factor receptor transactivation. Biochem Biophys Res Commun. 2004 May 21;318(1):247-52. Pubmed
  2. Slomiany BL, Slomiany A: Secretion of gastric mucus phospholipids in response to beta-adrenergic G protein-coupled receptor activation is mediated by SRC kinase-dependent epidermal growth factor receptor transactivation. J Physiol Pharmacol. 2004 Sep;55(3):627-38. Pubmed
  3. Slomiany BL, Slomiany A: Src-kinase-dependent epidermal growth factor receptor transactivation in salivary mucin secretion in response to beta-adrenergic G-protein-coupled receptor activation. Inflammopharmacology. 2004;12(3):233-45. Pubmed
  4. Machida K, Inoue H, Matsumoto K, Tsuda M, Fukuyama S, Koto H, Aizawa H, Kureishi Y, Hara N, Nakanishi Y: Activation of PI3K-Akt pathway mediates antiapoptotic effects of beta-adrenergic agonist in airway eosinophils. Am J Physiol Lung Cell Mol Physiol. 2005 May;288(5):L860-7. Epub 2004 Dec 23. Pubmed
  5. Slomiany BL, Slomiany A: Gastric mucin secretion in response to beta-adrenergic G protein-coupled receptor activation is mediated by SRC kinase-dependent epidermal growth factor receptor transactivation. J Physiol Pharmacol. 2005 Jun;56(2):247-58. Pubmed

7. Phosphatidylinositol 3-kinase regulatory subunit gamma

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Phosphatidylinositol 3-kinase regulatory subunit gamma Q92569 Details

References:

  1. Slomiany BL, Slomiany A: Salivary phospholipid secretion in response to beta-adrenergic stimulation is mediated by Src kinase-dependent epidermal growth factor receptor transactivation. Biochem Biophys Res Commun. 2004 May 21;318(1):247-52. Pubmed
  2. Slomiany BL, Slomiany A: Secretion of gastric mucus phospholipids in response to beta-adrenergic G protein-coupled receptor activation is mediated by SRC kinase-dependent epidermal growth factor receptor transactivation. J Physiol Pharmacol. 2004 Sep;55(3):627-38. Pubmed
  3. Slomiany BL, Slomiany A: Src-kinase-dependent epidermal growth factor receptor transactivation in salivary mucin secretion in response to beta-adrenergic G-protein-coupled receptor activation. Inflammopharmacology. 2004;12(3):233-45. Pubmed
  4. Machida K, Inoue H, Matsumoto K, Tsuda M, Fukuyama S, Koto H, Aizawa H, Kureishi Y, Hara N, Nakanishi Y: Activation of PI3K-Akt pathway mediates antiapoptotic effects of beta-adrenergic agonist in airway eosinophils. Am J Physiol Lung Cell Mol Physiol. 2005 May;288(5):L860-7. Epub 2004 Dec 23. Pubmed
  5. Slomiany BL, Slomiany A: Gastric mucin secretion in response to beta-adrenergic G protein-coupled receptor activation is mediated by SRC kinase-dependent epidermal growth factor receptor transactivation. J Physiol Pharmacol. 2005 Jun;56(2):247-58. Pubmed

1. Cytochrome P450 1A1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 1A1 P04798 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

Comments
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:13