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2D Structure
Also known as: 128470-16-6, Arbutaminum, Arbutamina, B07l15yaev, Chebi:50580, 4-[(1r)-1-hydroxy-2-[4-(4-hydroxyphenyl)butylamino]ethyl]benzene-1,2-diol
Molecular Formula
C18H23NO4
Molecular Weight
317.4  g/mol
InChI Key
IIRWWTKISYTTBL-SFHVURJKSA-N
FDA UNII
B07L15YAEV

Arbutamine is a synthetic catecholamine with positive chronotropic and inotropic properties, used in echocardiography and diagnostic coronary angiography. Arbutamine binds to and activates beta-1 adrenergic receptors in the myocardium, thereby increasing heart rate and increasing force of myocardial contraction. By exerting a chronotropic and inotropic effect, arbutamine mimics the cardiac stress caused by exercise that may prevent adequate tissue perfusion and oxygenation, and may provoke myocardial ischemia in patients with coronary artery disease.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-[(1R)-1-hydroxy-2-[4-(4-hydroxyphenyl)butylamino]ethyl]benzene-1,2-diol
2.1.2 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
2.1.3 InChI Key
IIRWWTKISYTTBL-SFHVURJKSA-N
2.1.4 Canonical SMILES
C1=CC(=CC=C1CCCCNCC(C2=CC(=C(C=C2)O)O)O)O
2.1.5 Isomeric SMILES
C1=CC(=CC=C1CCCCNC[C@@H](C2=CC(=C(C=C2)O)O)O)O
2.2 Other Identifiers
2.2.1 UNII
B07L15YAEV
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Arbutamine Hydrochloride

2. Arbutamine Hydrochloride, (r)-isomer

3. Genesa

2.3.2 Depositor-Supplied Synonyms

1. 128470-16-6

2. Arbutaminum

3. Arbutamina

4. B07l15yaev

5. Chebi:50580

6. 4-[(1r)-1-hydroxy-2-[4-(4-hydroxyphenyl)butylamino]ethyl]benzene-1,2-diol

7. 1,2-benzenediol, 4-[(1r)-1-hydroxy-2-[[4-(4-hydroxyphenyl)butyl]amino]ethyl]-

8. 4-[(1r)-1-hydroxy-2-{[4-(4-hydroxyphenyl)butyl]amino}ethyl]benzene-1,2-diol

9. Arbutamine [inn:ban]

10. Arbutaminum [inn-latin]

11. Arbutamina [inn-spanish]

12. Unii-b07l15yaev

13. Arbutamine [mi]

14. Arbutamine [inn]

15. Arbutamine [vandf]

16. Arbutamine [who-dd]

17. Schembl521645

18. Chembl1201251

19. Dtxsid00155908

20. Db01102

21. Hy-16056

22. Cs-0006131

23. Q4784959

24. (r)-3,4-dihydroxy-.alpha.-(((4-(p-hydroxyphenyl)butyl)amino)methyl)benzyl Alcohol

25. 1,2-benzenediol, 4-(1-hydroxy-2-((4-(4-hydroxyphenyl)butyl)amino)ethyl)-, (1r)

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 317.4 g/mol
Molecular Formula C18H23NO4
XLogP30.9
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count5
Rotatable Bond Count8
Exact Mass317.16270821 g/mol
Monoisotopic Mass317.16270821 g/mol
Topological Polar Surface Area93 Ų
Heavy Atom Count23
Formal Charge0
Complexity320
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug 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.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Adrenergic beta-Agonists

Drugs that selectively bind to and activate beta-adrenergic receptors. (See all compounds classified as Adrenergic beta-Agonists.)


Cardiotonic Agents

Agents that have a strengthening effect on the heart or that can increase cardiac output. They may be CARDIAC GLYCOSIDES; SYMPATHOMIMETICS; or other drugs. They are used after MYOCARDIAL INFARCT; CARDIAC SURGICAL PROCEDURES; in SHOCK; or in congestive heart failure (HEART FAILURE). (See all compounds classified as Cardiotonic Agents.)


5.2 ATC Code

C - Cardiovascular system

C01 - Cardiac therapy

C01C - Cardiac stimulants excl. cardiac glycosides

C01CA - Adrenergic and dopaminergic agents

C01CA22 - Arbutamine


5.3 Metabolism/Metabolites

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.


5.4 Biological Half-Life

Elimination half-life is approximately 8 minutes.


5.5 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.