Terbutaline, sold under the brand names Bricanyl and Marex among others, is a β2 adrenergic receptor agonist, used as a "reliever" inhaler in the management of asthma symptoms and as a tocolytic (anti-contraction medication) to delay preterm labor for up to 48 hours. This time can then be used to administer steroid injections to the mother which help fetal lung maturity and reduce complications of prematurity.[1] It should not be used to prevent preterm labor or delay labor more than 48–72 hours. In February 2011, the Food and Drug Administration began requiring a black box warning on the drug's label. Pregnant women should not be given injections of the drug terbutaline for the prevention of preterm labor or for long-term (beyond 48–72 hours) management of preterm labor, and should not be given oral terbutaline for any type of prevention or treatment of preterm labor "due to the potential for serious maternal heart problems and death."[2][3]
Terbutaline
Terbutaline (top), and (R)-(−)-terbutaline (bottom)
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]
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.[11]
Chemistryedit
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.[12][13][14]
Stereochemistryedit
Terbutaline contains a stereocenter and consists of two enantiomers. This is a racemate, ie a 1: 1 mixture of (R) - and the (S) - form:[15]
Enantiomers of terbutaline
(R)-Terbutaline
(S)-Terbutaline
Society and cultureedit
Athleticsedit
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 namesedit
Brand names include Bronclyn, Brethine, Bricanyl, Brethaire, Marex, and Terbulin.
Referencesedit
^WHO. . 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]
^Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 542. ISBN9783527607495.
^World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
^Mohamed Ismail NA, Ibrahim M, Mohd Naim N, Mahdy ZA, Jamil MA, Mohd Razi ZR (September 2008). "Nifedipine versus terbutaline for tocolysis in external cephalic version". International Journal of Gynaecology and Obstetrics. 102 (3): 263–266. doi:10.1016/j.ijgo.2008.04.010. PMID 18554601. S2CID 20258298.
^Goldenberg RL (November 2002). . Obstetrics and Gynecology. 100 (5 Pt 1): 1020–1037. doi:10.1016/S0029-7844(02)02212-3. PMID 12423870. Archived from the original on 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.
^Shen H (2008). Illustrated Pharmacology Memory Cards: PharMnemonics. Minireview. p. 7. ISBN978-1-59541-101-3.
^"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.). . 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
^US 3937838, Svensson LA, Wetterlin ID, "Orally Active Bronchospasmolytic Compounds and Their Preparation", issued 1976
^Hager H, von Bruchhausen F, Dannhard G, Ebel S, Frahm AW, Hackenthal E, Holzgrabe U, eds. (2014). Hagers Handbuch der Pharmazeutischen Praxis Band 9: Stoffe P-Z. Vol. 5. Berlin: Springer Verlag. p. 804. ISBN978-3-642-63389-8.
January 01, 1970
terbutaline, based, company, marex, spectron, sold, under, brand, names, bricanyl, marex, among, others, adrenergic, receptor, agonist, used, reliever, inhaler, management, asthma, symptoms, tocolytic, anti, contraction, medication, delay, preterm, labor, hour. For the UK based company see Marex Spectron Terbutaline sold under the brand names Bricanyl and Marex among others is a b2 adrenergic receptor agonist used as a reliever inhaler in the management of asthma symptoms and as a tocolytic anti contraction medication to delay preterm labor for up to 48 hours This time can then be used to administer steroid injections to the mother which help fetal lung maturity and reduce complications of prematurity 1 It should not be used to prevent preterm labor or delay labor more than 48 72 hours In February 2011 the Food and Drug Administration began requiring a black box warning on the drug s label Pregnant women should not be given injections of the drug terbutaline for the prevention of preterm labor or for long term beyond 48 72 hours management of preterm labor and should not be given oral terbutaline for any type of prevention or treatment of preterm labor due to the potential for serious maternal heart problems and death 2 3 TerbutalineTerbutaline top and R terbutaline bottom Clinical dataAHFS Drugs comMonographMedlinePlusa682144PregnancycategoryAU A CRoutes ofadministrationOral tablets oral solution inhalational DPI nebulizer solution SQATC codeR03AC03 WHO R03CC03 WHO Legal statusLegal statusAU S4 Prescription only UK POM Prescription only Pharmacokinetic dataProtein binding25 MetabolismGI tract oral liver CYP450 unknownElimination half life11 16 hoursExcretionurine 90 60 unchanged bile faecesIdentifiersIUPAC name RS 5 2 tert Butylamino 1 hydroxyethyl benzene 1 3 diolCAS Number23031 25 6 NPubChem CID5403IUPHAR BPS560DrugBankDB00871 NChemSpider5210 NUNIIN8ONU3L3PGKEGGD08570 NChEBICHEBI 9449 NChEMBLChEMBL1760 NCompTox Dashboard EPA DTXSID7021310ECHA InfoCard100 041 244Chemical and physical dataFormulaC 12H 19N O 3Molar mass225 288 g mol 13D model JSmol Interactive imageChiralityRacemic mixtureSMILES Oc1cc cc O c1 C O CNC C C CInChI InChI 1S C12H19NO3 c1 12 2 3 13 7 11 16 8 4 9 14 6 10 15 5 8 h4 6 11 13 16H 7H2 1 3H3 NKey XWTYSIMOBUGWOL UHFFFAOYSA N N N Y what is this verify 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 Contents 1 Medical uses 2 Side effects 3 Pharmacology 4 Chemistry 4 1 Stereochemistry 5 Society and culture 5 1 Athletics 5 2 Brand names 6 ReferencesMedical uses editTerbutaline is used as a fast acting bronchodilator often used as a short term asthma treatment and as a tocolytic 6 to delay premature labor 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 editAdult tachycardia anxiety nervousness tremors headache hyperglycemia hypokalemia hypotension and rarely pulmonary edema 9 Fetal tachycardia and hypoglycemia 10 Pharmacology editThe tertiary butyl group in terbutaline makes it more selective for b2 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 11 Chemistry editTerbutaline 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 H over Pd C leads to terbutaline 12 13 14 nbsp Stereochemistry edit Terbutaline contains a stereocenter and consists of two enantiomers This is a racemate ie a 1 1 mixture of R and the S form 15 Enantiomers of terbutaline nbsp R Terbutaline nbsp S TerbutalineSociety and culture editAthletics edit As with all b2 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 edit Brand names include Bronclyn Brethine Bricanyl Brethaire Marex and Terbulin References edit 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 Fischer J Ganellin CR 2006 Analogue based Drug Discovery John Wiley amp Sons p 542 ISBN 9783527607495 World Health Organization 2021 World Health Organization model list of essential medicines 22nd list 2021 Geneva World Health Organization hdl 10665 345533 WHO MHP HPS EML 2021 02 Mohamed Ismail NA Ibrahim M Mohd Naim N Mahdy ZA Jamil MA Mohd Razi ZR September 2008 Nifedipine versus terbutaline for tocolysis in external cephalic version International Journal of Gynaecology and Obstetrics 102 3 263 266 doi 10 1016 j ijgo 2008 04 010 PMID 18554601 S2CID 20258298 Goldenberg RL November 2002 The management of preterm labor Obstetrics and Gynecology 100 5 Pt 1 1020 1037 doi 10 1016 S0029 7844 02 02212 3 PMID 12423870 Archived from the original on 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 Shen H 2008 Illustrated Pharmacology Memory Cards PharMnemonics Minireview p 7 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 Hager H von Bruchhausen F Dannhard G Ebel S Frahm AW Hackenthal E Holzgrabe U eds 2014 Hagers Handbuch der Pharmazeutischen Praxis Band 9 Stoffe P Z Vol 5 Berlin Springer Verlag p 804 ISBN 978 3 642 63389 8 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