You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameArbutamine
Accession NumberDB01102  (APRD00802)
Typesmall molecule
Groupsapproved
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
Synonyms
SynonymLanguageCode
ArbutaminaNot AvailableNot Available
ArbutaminumNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
GenESANot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number128470-16-6
WeightAverage: 317.3795
Monoisotopic: 317.162708229
Chemical FormulaC18H23NO4
InChI KeyIIRWWTKISYTTBL-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
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
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
IndicationUsed 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.
PharmacodynamicsNot Available
Mechanism of actionArbutamine 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein binding58%
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.

SubstrateEnzymesProduct
Arbutamine
Not Available
KetoarbutamineDetails
Arbutamine
Not Available
MethoxyarbutamineDetails
Route of eliminationNot Available
Half lifeElimination half-life is approximately 8 minutes.
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Arbutamine Action PathwayDrug actionSMP00664
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9464
Blood Brain Barrier - 0.9026
Caco-2 permeable - 0.7305
P-glycoprotein substrate Substrate 0.7596
P-glycoprotein inhibitor I Non-inhibitor 0.8011
P-glycoprotein inhibitor II Non-inhibitor 0.5135
Renal organic cation transporter Non-inhibitor 0.6511
CYP450 2C9 substrate Non-substrate 0.8014
CYP450 2D6 substrate Non-substrate 0.7951
CYP450 3A4 substrate Non-substrate 0.5827
CYP450 1A2 substrate Non-inhibitor 0.6669
CYP450 2C9 substrate Non-inhibitor 0.9295
CYP450 2D6 substrate Non-inhibitor 0.8282
CYP450 2C19 substrate Non-inhibitor 0.9358
CYP450 3A4 substrate Non-inhibitor 0.7648
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9401
Ames test Non AMES toxic 0.7687
Carcinogenicity Non-carcinogens 0.943
Biodegradation Not ready biodegradable 0.5579
Rat acute toxicity 1.9867 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Strong inhibitor 0.6306
hERG inhibition (predictor II) Inhibitor 0.7594
Pharmacoeconomics
Manufacturers
  • Gensia automedics inc
PackagersNot Available
Dosage formsNot Available
PricesNot Available
Patents
CountryPatent NumberApprovedExpires (estimated)
United States53959701995-03-072012-03-07
United States52344041993-08-102010-08-10
Properties
Statesolid
Experimental Properties
PropertyValueSource
logP2.9Not Available
Predicted Properties
PropertyValueSource
water solubility8.42e-02 g/lALOGPS
logP2.08ALOGPS
logP2ChemAxon
logS-3.6ALOGPS
pKa (strongest acidic)8.97ChemAxon
pKa (strongest basic)9.76ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count5ChemAxon
hydrogen donor count5ChemAxon
polar surface area92.95ChemAxon
rotatable bond count8ChemAxon
refractivity89.78ChemAxon
polarizability35.54ChemAxon
number of rings2ChemAxon
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
PubChem Compound60789
PubChem Substance46509010
ChemSpider54785
ChEBI50580
ChEMBL
Therapeutic Targets DatabaseDAP000936
PharmGKBPA164747979
ATC CodesC01CA22
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

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. 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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Beta-2 adrenergic receptor P07550 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Beta-3 adrenergic receptor P13945 Details

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
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:13