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targets (3)
for drugs
Identification
Name Arbutamine
Accession Number DB01102 (APRD00802)
Type small molecule
Groups approved
Description

Arbutamine, administered through a closed-loop, computer-controlled drug-delivery system, is indicated to elicit acute cardiovascular responses, similar to those produced by exercise, in order to aid in diagnosing the presence or absence of coronary artery disease in patients who cannot exercise adequately .
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names
Name Company
GenESA
Brand mixtures Not Available
Categories
  • Adrenergic beta-Agonists
  • Cardiotonic Agents
CAS number 128470-16-6
Weight Average: 317.3795
Monoisotopic: 317.162708229
Chemical Formula C18H23NO4
InChI Key InChIKey=IIRWWTKISYTTBL-SFHVURJKSA-N
InChI
InChI=1S/C18H23NO4/c20-15-7-4-13(5-8-15)3-1-2-10-19-12-18(23)14-6-9-16(21)17(22)11-14/h4-9,11,18-23H,1-3,10,12H2/t18-/m0/s1
Plain Text
IUPAC Name
4-[(1R)-1-hydroxy-2-{[4-(4-hydroxyphenyl)butyl]amino}ethyl]benzene-1,2-diol
SMILES
O[C@@H](CNCCCCC1=CC=C(O)C=C1)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 Used to elicit acute cardiovascular responses (cardiac stumulant), similar to those produced by exercise, in order to aid in diagnosing the presence or absence of coronary artery disease (CAD) in patients who cannot exercise adequately.
Pharmacodynamics Not Available
Mechanism of action Arbutamine is a synthetic catecholamine with positive chronotropic and inotropic properties. The chronotropic (increase in heart rate) and inotropic (increase in force of contraction) effects of arbutamine serve to mimic exercise by increasing cardiac work (producing stress) and provoke myocardial ischemia in patients with compromised coronary arteries. The increase in heart rate caused by arbutamine is thought to limit regional subendocardial perfusion, thereby limiting tissue oxygenation. In functional assays, arbutamine is more selective for beta-adrenergic receptors than for alpha-adrenergic receptors. The beta-agonist activity of arbutamine provides cardiac stress by increasing heart rate, cardiac contractility, and systolic blood pressure. The degree of hypotension that occurs for a given chronotropic activity is less with arbutamine than, for example, with isoproterenol because alpha receptor activity is retained.
Absorption Not Available
Volume of distribution Not Available
Protein binding 58%
Metabolism
Primarily metabolized to methoxyarbutamine. Another possible metabolite is ketoarbutamine. The metabolites of arbutamine appear to have less pharmacological activity and a longer half-life and than the parental drug.

Important The metabolism module of DrugBank is currently in beta. Questions or suggestions? Please contact us.

Substrate Enzymes Product
Arbutamine
    		Ketoarbutamine Details
    Arbutamine
      		Methoxyarbutamine Details
      Route of elimination Not Available
      Half life Elimination half-life is approximately 8 minutes.
      Clearance Not Available
      Toxicity Not Available
      Affected organisms
      • Humans and other mammals
      Pathways Not Available
      Pharmacoeconomics
      Manufacturers
      • Gensia automedics inc
      Packagers Not Available
      Dosage forms Not Available
      Prices Not Available
      Patents
      Country Patent Number Approved Expires (estimated)
      United States 5395970 1995-03-07 2012-03-07
      United States 5234404 1993-08-10 2010-08-10
      Properties
      State solid
      Experimental Properties
      Property Value Source
      logP 2.9 Not Available
      Predicted Properties
      Property Value Source
      water solubility 8.42e-02 g/l ALOGPS
      logP 2.08 ALOGPS
      logP 2 ChemAxon
      logS -3.6 ALOGPS
      pKa (strongest acidic) 8.97 ChemAxon
      pKa (strongest basic) 9.76 ChemAxon
      physiological charge 1 ChemAxon
      hydrogen acceptor count 5 ChemAxon
      hydrogen donor count 5 ChemAxon
      polar surface area 92.95 ChemAxon
      rotatable bond count 8 ChemAxon
      refractivity 89.78 ChemAxon
      polarizability 35.54 ChemAxon
      References
      Synthesis Reference Not Available
      General Reference Not Available
      External Links
      Resource Link
      PubChem Compound 60789 Link_out
      PubChem Substance 46509010 Link_out
      ChemSpider 54785 Link_out
      ChEBI 50580 Link_out
      ChEMBL 50580 Link_out
      Therapeutic Targets Database DAP000936 Link_out
      PharmGKB PA164747979 Link_out
      ATC Codes
      • C01CA22
      AHFS Codes Not Available
      PDB Entries Not Available
      FDA label Not Available
      MSDS Not Available
      Interactions
      Drug Interactions Not Available
      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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
      2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
      3. Abou-Mohamed G, Nagarajan R, Ibrahim TM, Caldwell RW: Characterization of the adrenergic activity of arbutamine, a novel agent for pharmacological stress testing. Cardiovasc Drugs Ther. 1996 Mar;10(1):39-47. Pubmed

      2. Beta-2 adrenergic receptor

      Pharmacological action: unknown
      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. Abou-Mohamed G, Nagarajan R, Ibrahim TM, Caldwell RW: Characterization of the adrenergic activity of arbutamine, a novel agent for pharmacological stress testing. Cardiovasc Drugs Ther. 1996 Mar;10(1):39-47. Pubmed

      3. Beta-3 adrenergic receptor

      Pharmacological action: unknown
      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. Abou-Mohamed G, Nagarajan R, Ibrahim TM, Caldwell RW: Characterization of the adrenergic activity of arbutamine, a novel agent for pharmacological stress testing. Cardiovasc Drugs Ther. 1996 Mar;10(1):39-47. Pubmed
      Comments
      Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19