Terbutaline
Clinical data | |
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AHFS/Drugs.com | Monograph |
MedlinePlus | a682144 |
Pregnancy category |
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ATC code | |
Legal status | |
Legal status | |
Pharmacokinetic data | |
Protein binding | 25% |
Metabolism | GI tract (oral), liver; CYP450: unknown |
Elimination half-life | 11–16 hours |
Excretion | urine 90% (60% unchanged), bile/faeces |
Identifiers | |
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JSmol) | |
Chirality | Racemic mixture |
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Terbutaline, sold under the brand names Bricanyl and Marex among others, is a
It was patented in 1966 and came into medical use in 1970.[4] It is on the World Health Organization's List of Essential Medicines.[5]
Medical uses
Terbutaline is used as a fast-acting
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.[7] 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 used for short periods of time.[8]
Side effects
- Adult — tachycardia, anxiety, nervousness, tremors, headache, hyperglycemia, hypokalemia, hypotension and, rarely, pulmonary edema.[9]
- Fetal — tachycardia and hypoglycemia.[10]
Pharmacology
The tertiary butyl group in terbutaline makes it more selective for
Chemistry
Terbutaline is synthesized by brominating 3,5-dibenzyloxy
Stereochemistry
Terbutaline contains a stereocenter and consists of two enantiomers. This is a
Enantiomers of terbutaline | |
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(R)-Terbutaline |
(S)-Terbutaline |
Society and culture
Athletics
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
Brand names include Bronclyn, Brethine, Bricanyl, Brethaire, Marex, and Terbulin.
References
- ^ WHO. "Antenatal administration of corticosteroids for women at risk of preterm birth". WHO. Archived from the original on July 24, 2009. Retrieved 2013-03-25.
- ^ "Most Popular E-mail Newsletter". USA Today. 18 February 2011.[permanent dead link]
- ^ "FDA warns against certain uses of asthma drug terbutaline for preterm labor". Food and Drug Administration. Archived from the original on 2015-09-21. Retrieved 2015-09-13.
- ISBN 9783527607495.
- hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
- S2CID 20258298.
- PMID 12423870. Archived from the originalon 2011-07-20.
- ^ "FDA Drug Safety Communication: New warnings against use of terbutaline to treat preterm labor". Center for Drug Evaluation and Research. FDA. 17 February 2011. Retrieved 11 May 2021.
- ISBN 978-1-59541-101-3.
- ^ "Terbutaline: Drug information". Original Source: UpToDate. Archived from the original on 2013-06-28. Retrieved 2021-11-25 – via 5 Minute Consult.
- ^ Mehta A (1992). Melloni B, Germouty J (eds.). "Medicinal Chemistry of the Peripheral Nervous System–Adrenergics and Cholinergics their Biosynthesis, Metabolism, and Structure Activity Relationships". PharmaXChange. pp. 503–507. Archived from the original on 2010-11-04.
- ^ GB 1199630, "Phenylethanolamine Derivatives Effective in the Treatment of Bronchospastic Conditions", issued 1967, assigned to Draco Lunds Farmacevtiska Aktiebolag
- ^ BE 704932, "1-3,5-dihydroxyphenyl-2-alkylaminoethanols", issued 1968, assigned to Draco Lunds Farmacevtiska Aktiebolag
- ^ US 3937838, Svensson LA, Wetterlin ID, "Orally Active Bronchospasmolytic Compounds and Their Preparation", issued 1976
- ISBN 978-3-642-63389-8.