Dobutamine

• IUPAC: (RS ) -4 - {2 - [ 3 - (4 - hydroxyphenyl ) -1 - methylpropylamino ] ethyl} catechol
• Latin: Dobutaminum

• 34368-04-2 ( dobutamine )
• 49745-95-1 ( · dobutamine hydrochloride)

C01CA07

White crystalline powder ( dobutamine · hydrochloride)

Sympathomimetic

• 301.38 g · mol -1 ( dobutamine )
• 337.84 g.mol -1 ( · dobutamine hydrochloride)

184-186 ° C ( dobutamine · hydrochloride)

9.45 (HCl)

Slightly soluble in water, soluble in methanol, sparingly soluble in ethanol ( HCl)

Attention

73 mg · kg -1 ( LD50, mouse, i.v. hydrochloride)

Template: Infobox chemical / molecular formula search available

Dobutamine is a drug which is used as an emergency drug in acute heart failure or cardiogenic shock. It can be administered intravenously. In Germany, Austria and Switzerland it is marketed by various manufacturers as a generic product, in Austria under the name Inotop.

Operation

Dobutamine has no stimulatory effect on dopamine receptors, but acts as an agonist at α1 -, β1 - and β2 - adrenergic receptors, the β1 - stimulation of the heart is a key priority, as the alpha-1 and beta-2 effects cancel each other ( = apparent beta -1 selectivity) ( dobutamine is a mixture of enantiomers: the ( ) enantiomer activates β1 - and β2 - receptors and the (- ) enantiomer is responsible for the effect on the α1 receptor. ) All the above. result, the major effects of dobutamine, namely an increase in the contractility of the heart muscle cells ( positive inotropy ), and usually only slightly pronounced acceleration of the heart rate (positive chronotropy ). Thus, there is an increase of stroke volume ( SV ) and cardiac output (CO ) with consecutive improvement of blood flow to vital organs ( brain, kidney, etc.).

Areas of application

Acute heart failure, cardiogenic shock, intraoperative use in cardiac surgery.

In addition, dobutamine is used in the Belastungsechokardiografie to stress on the heart medication.

Contraindications and warnings

Due to the agonistic effect on β2 - receptors and the associated peripheral vasodilation Dobutamine should not be used in volume depletion, since this may lead to additional reduction in cardiac filling pressures. Other contraindications are cardiac tamponade and hypertrophic obstructive cardiomyopathy.

Side effects

Common adverse effects resulting from the beta - mimetic effects: tachycardia, tachyarrhythmias, extrasystoles, and angina pectoris.

Chemistry

Stereochemistry

Dobutamine is a synthetic catecholamine with a chiral stereocenter. The two stereoisomers have different pharmacological properties (see above, Section of action). Therapeutically is the racemate, the 1:1 mixture of the (S ) - and the (R ) isomer, is used as hydrochloride.