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Arbutamine Hydrochloride

Synopsis, Chemistry

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Also known as: Genesa, Arbutamine hcl, Arbutamine hydrochloride [usan], 125251-66-3, K0nf2cpj7f, Gp-2-121-3

Molecular Formula

C₁₈H₂₄ClNO₄

Molecular Weight

353.8 g/mol

InChI Key

ATBUNPBAFFCFKY-FERBBOLQSA-N

FDA UNII

K0NF2CPJ7F

Arbutamine Hydrochloride is the hydrochloride salt form of arbutamine, 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

Arbutamine Hydrochloride

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;hydrochloride

2.1.2 InChI

InChI=1S/C18H23NO4.ClH/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;1H/t18-;/m0./s1

2.1.3 InChI Key

ATBUNPBAFFCFKY-FERBBOLQSA-N

2.1.4 Canonical SMILES

C1=CC(=CC=C1CCCCNCC(C2=CC(=C(C=C2)O)O)O)O.Cl

2.1.5 Isomeric SMILES

C1=CC(=CC=C1CCCCNC[C@@H](C2=CC(=C(C=C2)O)O)O)O.Cl

2.2 Other Identifiers

2.2.1 UNII

K0NF2CPJ7F

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Arbutamine

2. Arbutamine Hydrochloride, (r)-isomer

3. Genesa

2.3.2 Depositor-Supplied Synonyms

1. Genesa

2. Arbutamine Hcl

3. Arbutamine Hydrochloride [usan]

4. 125251-66-3

5. K0nf2cpj7f

6. Gp-2-121-3

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

8. Arbutamine (hydrochloride)

9. Arbutamine Hydrochloride (usan)

10. Unii-k0nf2cpj7f

11. Genesa (tn)

12. Schembl40757

13. Chembl1200385

14. Dtxsid40154718

15. Arbutamine Hydrochloride [mi]

16. Hy-16056a

17. 1,2-benzenediol, 4-(1-hydroxy-2-((4-(4-hydroxyphenyl)butyl)amino)ethyl)-, (r)-hydrochloride

18. Arbutamine Hydrochloride [mart.]

19. Arbutamine Hydrochloride [vandf]

20. Arbutamine Hydrochloride [who-dd]

21. 1,2-benzenediol, 4-(1-hydroxy-2-((4-(4-hydroxyphenyl)butyl)amino)ethyl)-, (r)-, Hydrochloride

22. Cs-0108214

23. Arbutamine Hydrochloride [orange Book]

24. D02976

25. Q27281787

26. 4-[(1r)-1-hydroxy-2-[4-(4-hydroxyphenyl)butylamino]ethyl]benzene-1,2-diol;hydrochloride

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

28. 1,2-benzenediol, 4-(1-hydroxy-2-((4-(4-hydroxyphenyl)butyl)amino)ethyl)-, (r) Hydrochloride

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₂₄ClNO₄
Molecular Weight	353.8 g/mol
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	8
Exact Mass	353.1393859 g/mol
Monoisotopic Mass	353.1393859 g/mol
Topological Polar Surface Area	93 Å²
Heavy Atom Count	24
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	2

4 Pharmacology and Biochemistry

4.1 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.)