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Identification
Name Isoproterenol
Accession Number DB01064 (APRD00182)
Type small molecule
Groups approved
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Epinephrine Isopropyl Homolog
Isoprenalin
Isoprenaline
Isopropydrin
Isopropyladrenaline
Isopropylarterenol
Isopropylnoradrenaline
Isopropylnorepinephrine
Isoproterenol Chloride
Isoproterenol HCl
L-Isopropylnoradrenaline
L-Isoproterenol
N-Isopropylnoradrenaline
N-Isopropylnorepinephrine
First Prev Next Last
Salts Not Available
Brand names
Name Company
Aerolone
Aleudrin
Aleudrine
Aludrin
Aludrine
Asiprenol
Asmalar
Assiprenol
Bellasthman
Bronkephrine
Euspiran
Isadrine
Isonorene
Isonorin
Isorenin
Isuprel
Isuprel Mistometer
Isupren
Medihaler-Iso
Neo-Epinine
Neodrenal
Norisodrine
Norisodrine Aerotrol
Novodrin
Proternol
Respifral
Saventrine
Vapo-Iso
First Prev Next Last
Brand mixtures Not Available
Categories
  • Sympathomimetics
  • Bronchodilator Agents
  • Adrenergic beta-Agonists
  • Cardiotonic Agents
  • Sympathomimetic
CAS number 7683-59-2
Weight Average: 211.2576
Monoisotopic: 211.120843415
Chemical Formula C11H17NO3
InChI Key InChIKey=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
Plain Text
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Catecholamines and Derivatives
Substructures
  • Hydroxy Compounds
  • Phenols and Derivatives
  • Catecholamines and Derivatives
  • Benzyl Alcohols and Derivatives
  • Aliphatic and Aryl Amines
  • Benzene and Derivatives
  • Amino Alcohols
  • Catechols
  • Phenethylamines
  • Aromatic compounds
  • Alcohols and Polyols
  • Phenyl Esters
Pharmacology
Indication For 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
Pharmacodynamics Isoproterenol 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 action The 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.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism Not Available
Route of elimination Excretion following inhalation administration is primarily renal and the major metabolite is the sulfate conjugate of isoproterenol.
Half life Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
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
Form Route Strength
Gel Topical
Liquid Auricular (otic)
Liquid Topical
Lotion Topical
Solution Intramuscular
Solution Topical
Spray Topical
Stick Topical
Swab Topical
Prices
Unit description Cost Unit
Isuprel 0.2 mg/ml ampul 17.63 USD ml
Isoproterenol sulfate cryst 2.86 USD g
Isoproterenol 0.2 mg/ml amp 0.73 USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 170.5 °C PhysProp
logP 1.4 Not Available
Predicted Properties
Property Value Source
water solubility 5.86e+00 g/l ALOGPS
logP -0.27 ALOGPS
logP 0.24 ChemAxon
logS -1.6 ALOGPS
pKa (strongest acidic) 9.81 ChemAxon
pKa (strongest basic) 8.96 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 4 ChemAxon
hydrogen donor count 4 ChemAxon
polar surface area 72.72 ChemAxon
rotatable bond count 4 ChemAxon
refractivity 58.4 ChemAxon
polarizability 23.04 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C07056 Link_out
PubChem Compound 3779 Link_out
PubChem Substance 46507323 Link_out
ChemSpider 3647 Link_out
BindingDB 25392 Link_out
ChEBI 6046 Link_out
ChEMBL 6046 Link_out
Therapeutic Targets Database DNC000819 Link_out
PharmGKB PA450121 Link_out
IUPHAR 536 Link_out
Guide to Pharmacology 536 Link_out
Drug Product Database 897639 Link_out
RxList http://www.rxlist.com/cgi/generic3/isoproterenol.htm Link_out
Drugs.com http://www.drugs.com/cdi/isoproterenol.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Isoproterenol Link_out
ATC Codes
  • C01CA02
  • D08AX05
AHFS Codes
  • 84:04.92
  • 12:12.08.04
  • 52:92.00
  • 84:04.12
PDB Entries Not Available
FDA label show (314 KB)
MSDS show (73.3 KB)
Interactions
Drug Interactions
Drug Interaction
Acebutolol Antagonism
Amitriptyline The tricyclic antidepressant, amitriptyline, increases the sympathomimetic effect of isoproterenol.
Amoxapine The tricyclic antidepressant, amoxapine, increases the sympathomimetic effect of isoproterenol.
Atenolol Antagonism
Bisoprolol Antagonism
Carvedilol Antagonism
Clomipramine The tricyclic antidepressant, clomipramine, increases the sympathomimetic effect of isoproterenol.
Desipramine The tricyclic antidepressant, desipramine, increases the sympathomimetic effect of isoproterenol.
Doxepin The tricyclic antidepressant, doxepin, increases the sympathomimetic effect of isoproterenol.
Entacapone Entacapone increases the effect and toxicity of the sympathomimetic, isoproterenol.
Esmolol Antagonism
Imipramine The tricyclic antidepressant, imipramine, increases the sympathomimetic effect of isoproterenol.
Isocarboxazid Increased arterial pressure
Labetalol Antagonism
Linezolid Possible increase of arterial pressure
Methyldopa Increased arterial pressure
Metoprolol Antagonism
Midodrine Increased arterial pressure
Moclobemide Moclobemide increases the sympathomimetic effect of isoproterenol.
Nadolol Antagonism
Nortriptyline The tricyclic antidepressant, nortriptyline, increases the sympathomimetic effect of isoproterenol.
Oxprenolol Antagonism
Phenelzine Increased arterial pressure
Pindolol Antagonism
Propranolol Antagonism
Rasagiline Increased arterial pressure
Reserpine Increased arterial pressure
Timolol Antagonism
Food Interactions Not Available
Targets

1. Beta-1 adrenergic receptor

Pharmacological action: yes
Actions: agonist

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

Organism class: human
UniProt ID: P08588 Link_out
Gene: ADRB1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: yes
Actions: agonist

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

Organism class: human
UniProt ID: P07550 Link_out
Gene: ADRB2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: yes
Actions: agonist

Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. Beta-3 is involved in the regulation of lipolysis and thermogenesis

Organism class: human
UniProt ID: P13945 Link_out
Gene: ADRB3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: unknown
Actions: inducer

Involved in both the initiation and regulation of meiosis, mitosis, and postmitotic functions in differentiated cells by phosphorylating a number of transcription factors such as ELK1. Phosphorylates EIF4EBP1; required for initiation of translation. Phosphorylates microtubule-associated protein 2 (MAP2). Phosphorylates SPZ1

Organism class: human
UniProt ID: P28482 Link_out
Gene: MAPK1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: unknown
Actions: agonist

Binds to activated (phosphorylated) protein-Tyr kinases, through its SH2 domain, and acts as an adapter, mediating the association of the p110 catalytic unit to the plasma membrane. Necessary for the insulin-stimulated increase in glucose uptake and glycogen synthesis in insulin-sensitive tissues

Organism class: human
UniProt ID: P27986 Link_out
Gene: PIK3R1 Link_out
Protein Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: unknown
Actions: agonist

Binds to activated (phosphorylated) protein-tyrosine kinases, through its SH2 domain, and acts as an adapter, mediating the association of the p110 catalytic unit to the plasma membrane

Organism class: human
UniProt ID: O00459 Link_out
Gene: PIK3R2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: unknown
Actions: agonist

Binds to activated (phosphorylated) protein-tyrosine kinases through its SH2 domain and regulates their kinase activity. During insulin stimulation, it also binds to IRS-1

Organism class: human
UniProt ID: Q92569 Link_out
Gene: PIK3R3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Enzymes

1. Cytochrome P450 1A1

Actions: inhibitor

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics

UniProt ID: P04798 Link_out
Gene: CYP1A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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 February 08, 2013 16:19