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Identification
NameArbutamine
Accession NumberDB01102  (APRD00802)
TypeSmall Molecule
GroupsApproved
DescriptionArbutamine, 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
Arbutamina
Arbutaminum
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
GenESANot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Arbutamine hydrochloride
ThumbNot applicableDBSALT001445
Categories
UNIIB07L15YAEV
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
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.
Structured Indications Not Available
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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Beta-1 adrenergic receptorProteinyes
agonist
HumanP08588 details
Beta-2 adrenergic receptorProteinunknown
agonist
HumanP07550 details
Beta-3 adrenergic receptorProteinunknown
agonist
HumanP13945 details
Related Articles
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
Interactions
Drug Interactions
DrugInteractionDrug group
7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINEThe risk or severity of adverse effects can be increased when 7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE is combined with Arbutamine.Experimental
AcebutololAcebutolol may decrease the bronchodilatory activities of Arbutamine.Approved
AlfuzosinAlfuzosin may decrease the vasoconstricting activities of Arbutamine.Approved, Investigational
AlprenololAlprenolol may decrease the bronchodilatory activities of Arbutamine.Approved, Withdrawn
AmineptineThe risk or severity of adverse effects can be increased when Amineptine is combined with Arbutamine.Illicit, Withdrawn
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Arbutamine.Approved
AtenololAtenolol may decrease the bronchodilatory activities of Arbutamine.Approved
AtomoxetineAtomoxetine may increase the tachycardic activities of Arbutamine.Approved
AtosibanThe risk or severity of adverse effects can be increased when Arbutamine is combined with Atosiban.Approved
BendroflumethiazideArbutamine may increase the hypokalemic activities of Bendroflumethiazide.Approved
BenmoxinThe risk or severity of adverse effects can be increased when Benmoxin is combined with Arbutamine.Withdrawn
Benzylpenicilloyl PolylysineArbutamine may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.Approved
BetahistineThe therapeutic efficacy of Arbutamine can be decreased when used in combination with Betahistine.Approved
BetaxololBetaxolol may decrease the bronchodilatory activities of Arbutamine.Approved
BisoprololBisoprolol may decrease the bronchodilatory activities of Arbutamine.Approved
BopindololBopindolol may decrease the bronchodilatory activities of Arbutamine.Approved
BromocriptineBromocriptine may increase the hypertensive activities of Arbutamine.Approved, Investigational
BucindololBucindolol may decrease the vasoconstricting activities of Arbutamine.Investigational
BumetanideArbutamine may increase the hypokalemic activities of Bumetanide.Approved
BupranololBupranolol may decrease the bronchodilatory activities of Arbutamine.Approved
CabergolineCabergoline may increase the hypertensive activities of Arbutamine.Approved
CaroxazoneThe risk or severity of adverse effects can be increased when Caroxazone is combined with Arbutamine.Withdrawn
CarteololCarteolol may decrease the bronchodilatory activities of Arbutamine.Approved
CarvedilolCarvedilol may decrease the vasoconstricting activities of Arbutamine.Approved, Investigational
CeliprololCeliprolol may decrease the bronchodilatory activities of Arbutamine.Approved, Investigational
ChlorothiazideArbutamine may increase the hypokalemic activities of Chlorothiazide.Approved, Vet Approved
ChlorthalidoneArbutamine may increase the hypokalemic activities of Chlorthalidone.Approved
ClomipramineThe risk or severity of adverse effects can be increased when Clomipramine is combined with Arbutamine.Approved, Vet Approved
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Arbutamine.Approved
DesipramineThe risk or severity of adverse effects can be increased when Desipramine is combined with Arbutamine.Approved
DesvenlafaxineDesvenlafaxine may increase the tachycardic activities of Arbutamine.Approved
DihydroergotamineDihydroergotamine may increase the hypertensive activities of Arbutamine.Approved
DosulepinThe risk or severity of adverse effects can be increased when Dosulepin is combined with Arbutamine.Approved
DoxazosinDoxazosin may decrease the vasoconstricting activities of Arbutamine.Approved
DoxepinThe risk or severity of adverse effects can be increased when Doxepin is combined with Arbutamine.Approved
DuloxetineDuloxetine may increase the tachycardic activities of Arbutamine.Approved
Ergoloid mesylateErgoloid mesylate may increase the hypertensive activities of Arbutamine.Approved
ErgonovineErgonovine may increase the hypertensive activities of Arbutamine.Approved
ErgotamineErgotamine may increase the hypertensive activities of Arbutamine.Approved
EsmirtazapineThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Arbutamine.Investigational
EsmololEsmolol may decrease the bronchodilatory activities of Arbutamine.Approved
Etacrynic acidArbutamine may increase the hypokalemic activities of Etacrynic acid.Approved
FurazolidoneThe risk or severity of adverse effects can be increased when Furazolidone is combined with Arbutamine.Approved, Vet Approved
FurosemideArbutamine may increase the hypokalemic activities of Furosemide.Approved, Vet Approved
HydracarbazineThe risk or severity of adverse effects can be increased when Hydracarbazine is combined with Arbutamine.Approved
HydrochlorothiazideArbutamine may increase the hypokalemic activities of Hydrochlorothiazide.Approved, Vet Approved
HydroflumethiazideArbutamine may increase the hypokalemic activities of Hydroflumethiazide.Approved
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Arbutamine.Approved
IndapamideArbutamine may increase the hypokalemic activities of Indapamide.Approved
IndoraminIndoramin may decrease the vasoconstricting activities of Arbutamine.Withdrawn
IproclozideThe risk or severity of adverse effects can be increased when Iproclozide is combined with Arbutamine.Withdrawn
IproniazidThe risk or severity of adverse effects can be increased when Iproniazid is combined with Arbutamine.Withdrawn
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Arbutamine.Approved
LabetalolLabetalol may decrease the vasoconstricting activities of Arbutamine.Approved
LevomilnacipranLevomilnacipran may increase the tachycardic activities of Arbutamine.Approved
MebanazineThe risk or severity of adverse effects can be increased when Mebanazine is combined with Arbutamine.Withdrawn
MethyclothiazideArbutamine may increase the hypokalemic activities of Methyclothiazide.Approved
Methylene blueThe risk or severity of adverse effects can be increased when Methylene blue is combined with Arbutamine.Investigational
MetolazoneArbutamine may increase the hypokalemic activities of Metolazone.Approved
MetoprololMetoprolol may decrease the bronchodilatory activities of Arbutamine.Approved, Investigational
MilnacipranMilnacipran may increase the tachycardic activities of Arbutamine.Approved
MinaprineThe risk or severity of adverse effects can be increased when Minaprine is combined with Arbutamine.Approved
MirtazapineThe risk or severity of adverse effects can be increased when Mirtazapine is combined with Arbutamine.Approved
MoclobemideThe risk or severity of adverse effects can be increased when Moclobemide is combined with Arbutamine.Approved
NadololNadolol may decrease the bronchodilatory activities of Arbutamine.Approved
NebivololNebivolol may decrease the bronchodilatory activities of Arbutamine.Approved, Investigational
NialamideThe risk or severity of adverse effects can be increased when Nialamide is combined with Arbutamine.Withdrawn
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Arbutamine.Approved
OctamoxinThe risk or severity of adverse effects can be increased when Octamoxin is combined with Arbutamine.Withdrawn
OpipramolThe risk or severity of adverse effects can be increased when Opipramol is combined with Arbutamine.Investigational
OxprenololOxprenolol may decrease the bronchodilatory activities of Arbutamine.Approved
PargylineThe risk or severity of adverse effects can be increased when Pargyline is combined with Arbutamine.Approved
PenbutololPenbutolol may decrease the bronchodilatory activities of Arbutamine.Approved, Investigational
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Arbutamine.Approved
PheniprazineThe risk or severity of adverse effects can be increased when Pheniprazine is combined with Arbutamine.Withdrawn
PhenoxypropazineThe risk or severity of adverse effects can be increased when Phenoxypropazine is combined with Arbutamine.Withdrawn
PindololPindolol may decrease the bronchodilatory activities of Arbutamine.Approved
PiretanideArbutamine may increase the hypokalemic activities of Piretanide.Experimental
PirlindoleThe risk or severity of adverse effects can be increased when Pirlindole is combined with Arbutamine.Approved
PivhydrazineThe risk or severity of adverse effects can be increased when Pivhydrazine is combined with Arbutamine.Withdrawn
PolythiazideArbutamine may increase the hypokalemic activities of Polythiazide.Approved
PrazosinPrazosin may decrease the vasoconstricting activities of Arbutamine.Approved
PropranololPropranolol may decrease the bronchodilatory activities of Arbutamine.Approved, Investigational
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Arbutamine.Approved
QuinethazoneArbutamine may increase the hypokalemic activities of Quinethazone.Approved
RasagilineThe risk or severity of adverse effects can be increased when Rasagiline is combined with Arbutamine.Approved
SafrazineThe risk or severity of adverse effects can be increased when Safrazine is combined with Arbutamine.Withdrawn
SelegilineThe risk or severity of adverse effects can be increased when Selegiline is combined with Arbutamine.Approved, Investigational, Vet Approved
SilodosinSilodosin may decrease the vasoconstricting activities of Arbutamine.Approved
SotalolSotalol may decrease the bronchodilatory activities of Arbutamine.Approved
SpironolactoneSpironolactone may decrease the vasoconstricting activities of Arbutamine.Approved
TamsulosinTamsulosin may decrease the vasoconstricting activities of Arbutamine.Approved, Investigational
TerazosinTerazosin may decrease the vasoconstricting activities of Arbutamine.Approved
TianeptineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Arbutamine.Approved
TimololTimolol may decrease the bronchodilatory activities of Arbutamine.Approved
ToloxatoneThe risk or severity of adverse effects can be increased when Toloxatone is combined with Arbutamine.Approved
TorasemideArbutamine may increase the hypokalemic activities of Torasemide.Approved
Trans-2-PhenylcyclopropylamineThe risk or severity of adverse effects can be increased when Trans-2-Phenylcyclopropylamine is combined with Arbutamine.Experimental
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Arbutamine.Approved
TrichlormethiazideArbutamine may increase the hypokalemic activities of Trichlormethiazide.Approved, Vet Approved
TrimazosinTrimazosin may decrease the vasoconstricting activities of Arbutamine.Experimental
TrimipramineThe risk or severity of adverse effects can be increased when Trimipramine is combined with Arbutamine.Approved
VenlafaxineVenlafaxine may increase the tachycardic activities of Arbutamine.Approved
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesC01CA22
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9464
Blood Brain Barrier-0.9026
Caco-2 permeable-0.7305
P-glycoprotein substrateSubstrate0.7596
P-glycoprotein inhibitor INon-inhibitor0.8011
P-glycoprotein inhibitor IINon-inhibitor0.5135
Renal organic cation transporterNon-inhibitor0.6511
CYP450 2C9 substrateNon-substrate0.8014
CYP450 2D6 substrateNon-substrate0.7951
CYP450 3A4 substrateNon-substrate0.5827
CYP450 1A2 substrateNon-inhibitor0.6669
CYP450 2C9 inhibitorNon-inhibitor0.9295
CYP450 2D6 inhibitorNon-inhibitor0.8282
CYP450 2C19 inhibitorNon-inhibitor0.9358
CYP450 3A4 inhibitorNon-inhibitor0.7648
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9401
Ames testNon AMES toxic0.7687
CarcinogenicityNon-carcinogens0.943
BiodegradationNot ready biodegradable0.5579
Rat acute toxicity1.9867 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.6306
hERG inhibition (predictor II)Inhibitor0.7594
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5234404 No1993-08-102010-08-10Us
US5395970 No1995-03-072012-03-07Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP2.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0842 mg/mLALOGPS
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 Area92.95 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity89.78 m3·mol-1ChemAxon
Polarizability35.54 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
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
  • Phenylbutylamine
  • 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 Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Receptor signaling protein activity
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. Mediates Ras activation through G(s)-alpha- and cAMP-mediated signaling.
Gene Name:
ADRB1
Uniprot ID:
P08588
Molecular Weight:
51322.1 Da
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:17139284 ]
  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:17016423 ]
  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:8723169 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
agonist
General Function:
Protein homodimerization activity
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:
46458.32 Da
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:8723169 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
agonist
General Function:
Protein homodimerization activity
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:
43518.615 Da
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:8723169 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23