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ACTIVE PHARMA INGREDIENTS

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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

Genesa

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 Formula	C₁₈H₂₃NO₄
Molecular Weight	317.4 g/mol
XLogP3	0.9
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	8
Exact Mass	317.16270821 g/mol
Monoisotopic Mass	317.16270821 g/mol
Topological Polar Surface Area	93 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	320
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.

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