Terbutaline

Terbutaline
	Terbutaline (top),; and (R)-(−)-terbutaline (bottom)
Clinical data
AHFS/Drugs.com	Monograph
MedlinePlus	a682144
Pregnancy; category	AU: A; C;
Routes of; administration	Oral (tablets, oral solution), inhalational (DPI, nebulizer solution), SQ
ATC code	R03AC03 (WHO) R03CC03 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only);
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
	IUPAC name (RS)-5-[2-(tert-Butylamino)-1-hydroxyethyl]benzene-1,3-diol;
CAS Number	23031-25-6 ;
PubChem CID	5403;
IUPHAR/BPS	560;
DrugBank	DB00871 ;
ChemSpider	5210 ;
UNII	N8ONU3L3PG;
KEGG	D08570 ;
ChEBI	CHEBI:9449 ;
ChEMBL	ChEMBL1760 ;
CompTox Dashboard (EPA)	DTXSID7021310 ;
ECHA InfoCard	100.041.244
Chemical and physical data
Formula	C12H19NO3
Molar mass	225.288 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
	SMILES Oc1cc(cc(O)c1)C(O)CNC(C)(C)C;
	InChI 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 ; Key:XWTYSIMOBUGWOL-UHFFFAOYSA-N ;
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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]

^ 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.
^ "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 & 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.

[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.

[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.

[Fis2006-4] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 542. ISBN 9783527607495.

[WHO22nd-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.

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