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Record Information
Version3.6
Creation Date2012-09-06 15:16:51 UTC
Update Date2016-02-11 01:31:51 UTC
HMDB IDHMDB15197
Secondary Accession NumbersNone
Metabolite Identification
Common NameIsoproterenol
DescriptionIsoproterenol is only found in individuals that have used or taken this drug. It is an 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]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.
Structure
Thumb
Synonyms
ValueSource
(+-)-IsoprenalineChEBI
(+-)-IsoproterenolChEBI
1-(3,4-Dihydroxyphenyl)-2-(isopropylamino)ethanolChEBI
1-(3,4-Dihydroxyphenyl)-2-isopropylaminoethanolChEBI
3,4-Dihydroxy-alpha-[(isopropylamino)methyl]benzyl alcoholChEBI
alpha-(Isopropylaminomethyl)protocatechuyl alcoholChEBI
IsoprenalinaChEBI
IsoprenalinumChEBI
Isopropyl noradrenalineChEBI
IsoproterenolChEBI
N-Isopropyl-beta-dihydroxyphenyl-beta-hydroxyethylamineChEBI
N-IsopropylnoradrenalineChEBI
N-IsopropylnorepinephrineChEBI
Epinephrine isopropyl homologHMDB
IsoprenalinHMDB
IsopropydrinHMDB
IsopropyladrenalineHMDB
IsopropylarterenolHMDB
IsopropylnoradrenalineHMDB
IsopropylnorepinephrineHMDB
Isoproterenol chlorideHMDB
L-IsopropylnoradrenalineHMDB
L-IsoproterenolHMDB
Chemical FormulaC11H17NO3
Average Molecular Weight211.2576
Monoisotopic Molecular Weight211.120843415
IUPAC Name4-{1-hydroxy-2-[(propan-2-yl)amino]ethyl}benzene-1,2-diol
Traditional Nameisoproterenol
CAS Registry Number7683-59-2
SMILES
CC(C)NCC(O)C1=CC(O)=C(O)C=C1
InChI Identifier
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
InChI KeyInChIKey=JWZZKOKVBUJMES-UHFFFAOYSA-N
Chemical 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
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Adrenergic beta-Agonists
  • Bronchodilator Agents
  • Cardiotonic Agents
  • Sympathomimetic
  • Sympathomimetics
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point170.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.86e+00 g/LNot Available
LogP1.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility5.86 mg/mLALOGPS
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 Area72.72 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity58.4 m3·mol-1ChemAxon
Polarizability23.04 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Isoprenaline Action PathwaySMP00663Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01064
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01064
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01064
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3647
KEGG Compound IDC07056
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIsoproterenol
NuGOwiki LinkHMDB15197
Metagene LinkHMDB15197
METLIN IDNot Available
PubChem Compound3779
PDB IDNot Available
ChEBI ID64317
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in MAP kinase activity
Specific function:
Acts as a transcriptional repressor. Binds to a [GC]AAA[GC] consensus sequence. Repress the expression of interferon gamma-induced genes. Seems to bind to the promoter of CCL5, DMP1, IFIH1, IFITM1, IRF7, IRF9, LAMP3, OAS1, OAS2, OAS3 and STAT1. Transcriptional activity is independent of kinase activity
Gene Name:
MAPK1
Uniprot ID:
P28482
Molecular weight:
41389.3
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. 2011 Jan;23(1):89-98. Epub 2010 Aug 21. [20732414 ]
  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. [12963636 ]
  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. [13679574 ]
  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. [15138589 ]
  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. [15292328 ]
  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. [15689414 ]
General function:
Involved in monooxygenase activity
Specific function:
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.
Gene Name:
CYP1A1
Uniprot ID:
P04798
Molecular weight:
58164.815
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. [19934256 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
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
Gene Name:
ADRB1
Uniprot ID:
P08588
Molecular weight:
51322.1
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. [14734046 ]
  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. [15908512 ]
  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. [16038799 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
  5. Ahlquist RP: Present state of alpha- and beta-adrenergic drugs I. The adrenergic receptor. Am Heart J. 1976 Nov;92(5):661-4. [10722 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
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:
46458.3
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. [12963495 ]
  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. [14656380 ]
  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. [14752060 ]
  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. [15105445 ]
  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. [15151902 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
  7. Ahlquist RP: Present state of alpha- and beta-adrenergic drugs I. The adrenergic receptor. Am Heart J. 1976 Nov;92(5):661-4. [10722 ]
General function:
Involved in phosphoinositide 3-kinase regulator activity
Specific function:
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
Gene Name:
PIK3R1
Uniprot ID:
P27986
Molecular weight:
83597.7
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. [15110780 ]
  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. [15381832 ]
  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. [15527548 ]
  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. [15618457 ]
  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. [15985706 ]
General function:
Involved in phosphoinositide 3-kinase regulator activity
Specific function:
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
Gene Name:
PIK3R3
Uniprot ID:
Q92569
Molecular weight:
54462.1
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. [15110780 ]
  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. [15381832 ]
  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. [15527548 ]
  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. [15618457 ]
  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. [15985706 ]
General function:
Involved in phosphoinositide 3-kinase regulator activity
Specific function:
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
Gene Name:
PIK3R2
Uniprot ID:
O00459
Molecular weight:
81623.7
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. [15110780 ]
  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. [15381832 ]
  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. [15527548 ]
  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. [15618457 ]
  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. [15985706 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
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
Gene Name:
ADRB3
Uniprot ID:
P13945
Molecular weight:
43518.6
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. [10722 ]
  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. [10824635 ]