3395. Dobutamine

Nomenclature

CAS number: 34368-04-2
4-[2-[[3-(4-Hydroxyphenyl)-1-methylpropyl]amino]ethyl]-1,2-benzenediol; (±)-4-[2-[[3-(p-hydroxyphenyl)-1-methylpropyl]amino]ethyl]pyrocatechol; 3,4-dihydroxy-N-[3-(4-hydroxyphenyl)-1-methylpropyl]-β-phenylethylamine; Compound 81929.
C18H23NO3; mol wt 301.38.
C 71.73%, H 7.69%, N 4.65%, O 15.93%.

Description and references

Synthetic catecholamine with β1-, α1-, and β2-adrenergic agonist activity. Increases myocardial contractility, atrioventricular conduction, and heart rate. Structurally related to dopamine, q.v. Prepn: R. R. Tuttle, J. Mills, DE 2317710; eidem, US 3987200 (1973, 1976 to Lilly). Pharmacology: R. Weber, R. R. Tuttle in Pharmacological and Biochemical Properties of Drug Substances vol. 1, M. E. Goldberg, Ed. (Am. Pharm. Assoc., Washington, DC, 1977) pp 109-124; E. H. Sonnenblick et al., N. Engl. J. Med. 300, 17 (1979). Comprehensive description: R. H. Bishara, H. B. Long, Anal. Profiles Drug Subs. 8, 139-158 (1979). Review of diagnostic use in stress echocardiography: M. L. Geleijnse et al., J. Am. Coll. Cardiol. 30, 595-606 (1997); in myocardial perfusion imaging: A. Elhendy et al., J. Nucl. Med. 43, 1634-1646 (2002); in cardiovascular magnetic resonance: S. Mandapaka, W. G. Hundley, J. Magn. Reson. Imaging 24, 499-512 (2006).

Chemical structure

Derivative

Hydrochloride.

Nomenclature

CAS number: 49745-95-1
Dobuject (Pisa); Dobutrex (Lilly).
C18H23NO3.HCl; mol wt 337.84.
C 63.99%, H 7.16%, N 4.15%, O 14.21%, Cl 10.49%.

Properties

Crystals, mp 184-186°. uv max (methanol): 281, 223 nm (ε 4768, 14400). pKa 9.45. Rapidly oxidized at pH 11-13. Sparingly sol in water, methanol; sol in ethanol, pyridine. LD50 i.v. in mice: ≈73 mg/kg (Weber, Tuttle).

Therapeutic Category

Cardiotonic; diagnostic aid (cardiac stress testing).

Therapeutic Category (Veterinary)

Cardiotonic.

Keywords

Cardiotonic; Diagnostic Aid; β-Adrenergic Agonist