Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C18H23NO4 |
Molecular Weight | 317.3795 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@@H](CNCCCCC1=CC=C(O)C=C1)C2=CC=C(O)C(O)=C2
InChI
InChIKey=IIRWWTKISYTTBL-SFHVURJKSA-N
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
Arbutamine was indicated to elicit acute cardiovascular responses in order to aid in diagnosing the presence or absence of coronary artery disease in patients who cannot exercise adequately. Arbutamine is a synthetic catecholamine with positive chronotropic and inotropic properties. The chronotropic (increase in heart rate [HR]) 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. 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 HR, cardiac contractility, and systolic blood pressure.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P08588 Gene ID: 153.0 Gene Symbol: ADRB1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/8723169 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Diagnostic | GENESA Approved UseUnknown Launch Date8.7402237E11 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
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5 min |
10 μg/kg single, intravenous dose: 10 μg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
ARBUTAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
42% |
10 μg/kg single, intravenous dose: 10 μg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
ARBUTAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
4.62 mg/kg single, oral (mean) Recommended Dose: 4.62 mg/kg Route: oral Route: single Dose: 4.62 mg/kg Sources: |
healthy, 20-70 n = 53 Health Status: healthy Condition: diagnostic test Age Group: 20-70 Sex: M+F Population Size: 53 Sources: |
Disc. AE: Arrhythmia, Hypotension... Other AEs: Arrhythmia... AEs leading to discontinuation/dose reduction: Arrhythmia (2%) Other AEs:Hypotension (9%) Arrhythmia (29 patients) Sources: |
3.58 mg/kg single, oral (mean) Recommended Dose: 3.58 mg/kg Route: oral Route: single Dose: 3.58 mg/kg Sources: |
healthy, 37 - 79 years n = 134 Health Status: healthy Condition: diagnostic test Age Group: 37 - 79 years Sex: M+F Population Size: 134 Sources: |
Disc. AE: Angina, Arrhythmia... Other AEs: Arrhythmia... AEs leading to discontinuation/dose reduction: Angina (21%) Other AEs:Arrhythmia (4%) Hypotension (4%) Dyspnea (4%) Arrhythmia (103 patients) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Arrhythmia | 2% Disc. AE |
4.62 mg/kg single, oral (mean) Recommended Dose: 4.62 mg/kg Route: oral Route: single Dose: 4.62 mg/kg Sources: |
healthy, 20-70 n = 53 Health Status: healthy Condition: diagnostic test Age Group: 20-70 Sex: M+F Population Size: 53 Sources: |
Arrhythmia | 29 patients | 4.62 mg/kg single, oral (mean) Recommended Dose: 4.62 mg/kg Route: oral Route: single Dose: 4.62 mg/kg Sources: |
healthy, 20-70 n = 53 Health Status: healthy Condition: diagnostic test Age Group: 20-70 Sex: M+F Population Size: 53 Sources: |
Hypotension | 9% Disc. AE |
4.62 mg/kg single, oral (mean) Recommended Dose: 4.62 mg/kg Route: oral Route: single Dose: 4.62 mg/kg Sources: |
healthy, 20-70 n = 53 Health Status: healthy Condition: diagnostic test Age Group: 20-70 Sex: M+F Population Size: 53 Sources: |
Arrhythmia | 103 patients | 3.58 mg/kg single, oral (mean) Recommended Dose: 3.58 mg/kg Route: oral Route: single Dose: 3.58 mg/kg Sources: |
healthy, 37 - 79 years n = 134 Health Status: healthy Condition: diagnostic test Age Group: 37 - 79 years Sex: M+F Population Size: 134 Sources: |
Angina | 21% Disc. AE |
3.58 mg/kg single, oral (mean) Recommended Dose: 3.58 mg/kg Route: oral Route: single Dose: 3.58 mg/kg Sources: |
healthy, 37 - 79 years n = 134 Health Status: healthy Condition: diagnostic test Age Group: 37 - 79 years Sex: M+F Population Size: 134 Sources: |
Arrhythmia | 4% Disc. AE |
3.58 mg/kg single, oral (mean) Recommended Dose: 3.58 mg/kg Route: oral Route: single Dose: 3.58 mg/kg Sources: |
healthy, 37 - 79 years n = 134 Health Status: healthy Condition: diagnostic test Age Group: 37 - 79 years Sex: M+F Population Size: 134 Sources: |
Dyspnea | 4% Disc. AE |
3.58 mg/kg single, oral (mean) Recommended Dose: 3.58 mg/kg Route: oral Route: single Dose: 3.58 mg/kg Sources: |
healthy, 37 - 79 years n = 134 Health Status: healthy Condition: diagnostic test Age Group: 37 - 79 years Sex: M+F Population Size: 134 Sources: |
Hypotension | 4% Disc. AE |
3.58 mg/kg single, oral (mean) Recommended Dose: 3.58 mg/kg Route: oral Route: single Dose: 3.58 mg/kg Sources: |
healthy, 37 - 79 years n = 134 Health Status: healthy Condition: diagnostic test Age Group: 37 - 79 years Sex: M+F Population Size: 134 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Characterization of the adrenergic activity of arbutamine, a novel agent for pharmacological stress testing. | 1996 Mar |
|
Assessment of adenosine, arbutamine and dobutamine as pharmacological stress agents during (99m)Tc-tetrofosmin SPECT imaging: a randomized study. | 2001 Dec |
|
Pharmacologic interventions in nuclear radiology: indications, imaging protocols, and clinical results. | 2002 May-Jun |
|
[Comparison of usefulness of dobutamine-atropine and dobutamine-adenosine stress echocardiography in detection of coronary artery disease]. | 2004 Apr |
|
Feasibility, safety and tolerability of accelerated dobutamine stress echocardiography. | 2007 Nov 21 |
Sample Use Guides
Intravenous infusion, up to a maximum of 10 mcg per kg of body weight as administered by the drug delivery device
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8723169
It was characterized the interactions of arbutamine with different adrenergic receptor subtypes in vitro. In the electrically stimulated left atria of rats, arbutamine increased contractile force. The pD2 values (- log of the dose that produces 50% of the maximal responses) for arbutamine and isoproterenol were 8.45 +/- 0.15 and 8.55 +/- 0.02, respectively. Both arbutamine and isoproterenol increased the rate of spontaneously beating rat right atria with pD2 values of 9.0 +/- 0.19 and 8.82 +/- 0.18, respectively. The affinity constants (KA) of arbutamine and isoproterenol for cardiac beta1-adrenergic receptors, as determined by competition binding assays, were found to be 7.32 and 6.04, respectively. In guinea pig trachea, arbutamine and isoproterenol produced a concentration-dependent relaxation that was blocked by propranolol. Their pD2 values were 7.9 +/- 0.1 and 8.2 +/- 0.1, respectively. Arbutamine contracted isolated rat aortic rings with a maximal increase of 38.1 +/- 6.7% that of 10 microM of norepinephrine. In rat white adipocytes, arbutamine, isoproterenol, and BRL-37344 stimulated glycerol release, with the order of potency being BRL-37344 > arbutamine > isoproterenol. In hamster brown adipocytes, the order was arbutamine > isoproterenol > BRL-37344. Moreover, arbutamine stimulated beta3-adrenergic receptors in guinea pig ileum. Arbutamine does not stimulate alpha-adrenergic receptors at concentrations that were high enough to maximally activate the beta-adrenergic receptors.
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Classification Tree | Code System | Code | ||
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WHO-ATC |
C01CA22
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WHO-VATC |
QC01CA22
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NCI_THESAURUS |
C48149
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SUB05555MIG
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128470-16-6
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CHEMBL1201251
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C076559
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50580
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DTXSID00155908
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237
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61609
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m2032
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B07L15YAEV
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6757
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DB01102
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60789
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ARBUTAMINE
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100000087168
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C65238
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)