U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of ARBUTAMINE

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

HIDE SMILES / InChI

Molecular Formula C18H23NO4
Molecular Weight 317.3795
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P08588
Gene ID: 153.0
Gene Symbol: ADRB1
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
GENESA

Approved Use

Unknown

Launch Date

8.7402237E11
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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%)
Hypotension (9%)
Other AEs:
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%)
Arrhythmia (4%)
Hypotension (4%)
Dyspnea (4%)
Other AEs:
Arrhythmia (103 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim

Drug as victim

PubMed

PubMed

TitleDatePubMed
Characterization of the adrenergic activity of arbutamine, a novel agent for pharmacological stress testing.
1996 Mar
[Methodological aspects of performing exercise tests used in combination with perfusion scintigraphy of the myocardium].
2001
Identification of viable myocardium early after acute myocardial infarction using closed-loop arbutamine echocardiography: comparison with positron emission tomography.
2001 Dec
Pharmacological stress agents for evaluation of ischemic heart disease.
2001 Dec
Assessment of adenosine, arbutamine and dobutamine as pharmacological stress agents during (99m)Tc-tetrofosmin SPECT imaging: a randomized study.
2001 Dec
Arbutamine stimulation detects viable myocardium 4 weeks after coronary occlusion.
2001 Feb
Incremental prognostic value of RNA ejection fraction measurements during pharmacologic stress testing: a comparison with clinical and perfusion variables.
2001 Jun
Effect of ligand structure on the zinc-catalyzed Henry reaction. Asymmetric syntheses of (-)-denopamine and (-)-arbutamine.
2002 Aug 8
Arbutamine stress perfusion imaging in dogs with critical coronary artery stenoses: (99m)Tc-sestamibi versus (201)Tl.
2002 May
Pharmacologic interventions in nuclear radiology: indications, imaging protocols, and clinical results.
2002 May-Jun
Use of pharmaceuticals in noninvasive cardiovascular diagnosis.
2002 Sep-Oct
[Comparison of usefulness of dobutamine-atropine and dobutamine-adenosine stress echocardiography in detection of coronary artery disease].
2004 Apr
Myocardial perfusion scintigraphy: the evidence.
2004 Feb
Sonovue improves endocardial border detection and variability in assessing wall motion score and ejection fraction during stress echocardiography.
2004 Jan-Mar
Dobutamine stress echocardiography in healthy adult male rats.
2005 Oct 26
Asymmetric hydrogenation of alpha-primary and secondary amino ketones: efficient asymmetric syntheses of (-)-arbutamine and (-)-denopamine.
2007
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
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.
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:04:42 UTC 2023
Edited
by admin
on Wed Jul 05 23:04:42 UTC 2023
Record UNII
B07L15YAEV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ARBUTAMINE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
ARBUTAMINE [VANDF]
Common Name English
ARBUTAMINE [MI]
Common Name English
arbutamine [INN]
Common Name English
Arbutamine [WHO-DD]
Common Name English
1,2-BENZENEDIOL, 4-(1-HYDROXY-2-((4-(4-HYDROXYPHENYL)BUTYL)AMINO)ETHYL)-, (1R)
Common Name English
(R)-3,4-DIHYDROXY-.ALPHA.-(((4-(P-HYDROXYPHENYL)BUTYL)AMINO)METHYL)BENZYL ALCOHOL
Common Name English
Classification Tree Code System Code
WHO-ATC C01CA22
Created by admin on Wed Jul 05 23:04:42 UTC 2023 , Edited by admin on Wed Jul 05 23:04:42 UTC 2023
WHO-VATC QC01CA22
Created by admin on Wed Jul 05 23:04:42 UTC 2023 , Edited by admin on Wed Jul 05 23:04:42 UTC 2023
NCI_THESAURUS C48149
Created by admin on Wed Jul 05 23:04:42 UTC 2023 , Edited by admin on Wed Jul 05 23:04:42 UTC 2023
Code System Code Type Description
EVMPD
SUB05555MIG
Created by admin on Wed Jul 05 23:04:42 UTC 2023 , Edited by admin on Wed Jul 05 23:04:42 UTC 2023
PRIMARY
CAS
128470-16-6
Created by admin on Wed Jul 05 23:04:42 UTC 2023 , Edited by admin on Wed Jul 05 23:04:42 UTC 2023
PRIMARY
ChEMBL
CHEMBL1201251
Created by admin on Wed Jul 05 23:04:42 UTC 2023 , Edited by admin on Wed Jul 05 23:04:42 UTC 2023
PRIMARY
MESH
C076559
Created by admin on Wed Jul 05 23:04:42 UTC 2023 , Edited by admin on Wed Jul 05 23:04:42 UTC 2023
PRIMARY
CHEBI
50580
Created by admin on Wed Jul 05 23:04:42 UTC 2023 , Edited by admin on Wed Jul 05 23:04:42 UTC 2023
PRIMARY
EPA CompTox
DTXSID00155908
Created by admin on Wed Jul 05 23:04:42 UTC 2023 , Edited by admin on Wed Jul 05 23:04:42 UTC 2023
PRIMARY
DRUG CENTRAL
237
Created by admin on Wed Jul 05 23:04:42 UTC 2023 , Edited by admin on Wed Jul 05 23:04:42 UTC 2023
PRIMARY
RXCUI
61609
Created by admin on Wed Jul 05 23:04:42 UTC 2023 , Edited by admin on Wed Jul 05 23:04:42 UTC 2023
PRIMARY RxNorm
MERCK INDEX
M2032
Created by admin on Wed Jul 05 23:04:42 UTC 2023 , Edited by admin on Wed Jul 05 23:04:42 UTC 2023
PRIMARY Merck Index
FDA UNII
B07L15YAEV
Created by admin on Wed Jul 05 23:04:42 UTC 2023 , Edited by admin on Wed Jul 05 23:04:42 UTC 2023
PRIMARY
INN
6757
Created by admin on Wed Jul 05 23:04:42 UTC 2023 , Edited by admin on Wed Jul 05 23:04:42 UTC 2023
PRIMARY
DRUG BANK
DB01102
Created by admin on Wed Jul 05 23:04:42 UTC 2023 , Edited by admin on Wed Jul 05 23:04:42 UTC 2023
PRIMARY
PUBCHEM
60789
Created by admin on Wed Jul 05 23:04:42 UTC 2023 , Edited by admin on Wed Jul 05 23:04:42 UTC 2023
PRIMARY
WIKIPEDIA
ARBUTAMINE
Created by admin on Wed Jul 05 23:04:42 UTC 2023 , Edited by admin on Wed Jul 05 23:04:42 UTC 2023
PRIMARY
SMS_ID
100000087168
Created by admin on Wed Jul 05 23:04:42 UTC 2023 , Edited by admin on Wed Jul 05 23:04:42 UTC 2023
PRIMARY
NCI_THESAURUS
C65238
Created by admin on Wed Jul 05 23:04:42 UTC 2023 , Edited by admin on Wed Jul 05 23:04:42 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY