|Trade names||Bricanyl, Marex, others|
|Drug class||β2 adrenergic receptor agonist|
|Main uses||Asthma, COPD, preterm labor|
|Side effects||Anxiety, shakiness, fast heart rate, nausea|
|bY MOUTH (tablets, solution), inhalational (DPI, nebulizer solution), SQ|
|Metabolism||GI tract (oral), liver; CYP450: unknown|
|Elimination half-life||11-16 hours|
|Excretion||urine 90% (60% unchanged), bile/faeces|
|Chemical and physical data|
|Molar mass||225.288 g·mol−1|
|3D model (JSmol)|
|(what is this?)|
Terbutaline, sold under the brand names Bricanyl among others, is a medication used for symptoms of asthma or COPD and to temporally delay delivery in preterm labor. The delay in deliver is used to allow time for steroids to speed lung development in the baby or moving a women to a location with more resources. It is generally take by mouth, inhaled, or injected under the skin.
Common side effects include anxiety, shakiness, fast heart rate, and nausea. Other side effects may include high blood sugar, low potassium, heart arrhythmia, and insufficient blood flow to the heart. It should not be used to prevent preterm labor or delay labor more than 48–72 hours. It is a β2 adrenergic receptor agonist.
Terbutaline was patented in 1966 and came into medical use in 1970. It is available as a generic medication. In the United Kingdom 100 tablets of 5 mg costs the NHS about 15 pounds. This amount in the United States costs about 135 USD as of 2021.
As an asthma treatment, the inhaled form of terbutaline, starts working within 15 minutes and can last up to 6 hours. It is also sold as an injectable solution, an oral tablet, and as a syrup (in combination with guaifenesin).
Terbutaline is a pregnancy category C medication and is prescribed to stop contractions. After successful intravenous tocolysis, little evidence exists that oral terbutaline is effective. Terbutaline as a treatment for premature labor is an off-label use not approved by the US FDA, who have warned that oral terbutaline is not effective and can cause severe heart problems or death, and while injectable terbutaline can be used for premature labor in emergency situations in a hospital setting, it should only be usedfor short periods of time.
For asthma it may be used at a dose of 2.5 to 5 mg by mouth up to three times per day; 0.25 to 0.5 mg by injection up to four times per day; or 0.5 mg by inhalation up to four times per day.
- Adult — tachycardia, anxiety, nervousness, tremors, headache, hyperglycemia, hypokalemia, hypotension and, rarely, pulmonary edema.
- Fetal — tachycardia and hypoglycemia.
The tertiary butyl group in terbutaline makes it more selective for β2 receptors. Since there is no hydroxy group on position 4 of the benzene ring, the molecule is less susceptible to metabolism by the enzyme catechol-O-methyl transferase.
Terbutaline is synthesized by brominating 3,5-dibenzyloxyacetophenone into 3,5-dibenzyloxybromoacetophenone, which is reacted with N-benzyl-N-tert-butylamine, giving a ketone intermediate. Reduction of this product with H₂ over Pd/C leads to terbutaline.
|Enantiomers of terbutaline|
Society and culture
As with all β2-adrenergic receptor agonists, terbutaline is on the World Anti-Doping Agency's list of prohibited drugs, except when administered by inhalation and a Therapeutic Use Exemption (TUE) has been obtained in advance.
Brand names include Bronclyn, Brethine, Bricanyl, Brethaire, Marex, and Terbulin.
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- Draco Lunds Farmacevtiska Aktiebolag, GB 1199630 (1967)
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