Terbutaline

For the UK-based company, see Marex Spectron.
Terbutaline
Terbutaline (top),
and (R)-(−)-terbutaline (bottom)
Clinical data
AHFS/Drugs.comMonograph
MedlinePlusa682144
Pregnancy
category
  • AU: A
  • C
Routes of
administration		Oral (tablets, oral solution), inhalational (DPI, nebulizer solution), SQ
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
Pharmacokinetic data
Protein binding25%
MetabolismGI tract (oral), liver; CYP450: unknown
Elimination half-life11–16 hours
Excretionurine 90% (60% unchanged), bile/faeces
Identifiers
  • (RS)-5-[2-(tert-Butylamino)-1-hydroxyethyl]benzene-1,3-diol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.041.244 Edit this at Wikidata
Chemical and physical data
FormulaC12H19NO3
Molar mass225.288 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • Oc1cc(cc(O)c1)C(O)CNC(C)(C)C
  • 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 ☒N
  • Key:XWTYSIMOBUGWOL-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

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]

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]

  1. ^ 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.
  2. ^ "Most Popular E-mail Newsletter". USA Today. 18 February 2011.[permanent dead link‍]
  3. ^ "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.
  4. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 542. ISBN 9783527607495.
  5. ^ 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.