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Terbutaline information


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
  • R03AC03 (WHO) R03CC03 (WHO)
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
IUPAC name
  • (RS)-5-[2-(tert-Butylamino)-1-hydroxyethyl]benzene-1,3-diol
CAS Number
  • 23031-25-6 ☒N
PubChem CID
  • 5403
IUPHAR/BPS
  • 560
DrugBank
  • DB00871 ☒N
ChemSpider
  • 5210 ☒N
UNII
  • N8ONU3L3PG
KEGG
  • D08570 ☒N
ChEBI
  • CHEBI:9449 ☒N
ChEMBL
  • ChEMBL1760 ☒N
CompTox Dashboard (EPA)
  • DTXSID7021310 Edit this at Wikidata
ECHA InfoCard100.041.244 Edit this at Wikidata
Chemical and physical data
FormulaC12H19NO3
Molar mass225.288 g·mol−1
3D model (JSmol)
  • Interactive image
ChiralityRacemic 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 ☒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.

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Terbutaline

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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...

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Autonomic drug

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|website= ignored (help) "Terbutaline". www.drugbank.ca. Retrieved 2019-04-01. "Common Side Effects of Terbutaline Sulfate (Terbutaline Sulfate) Drug Center"...

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ATC code R03

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R03AB02 Isoprenaline R03AB03 Orciprenaline R03AC02 Salbutamol R03AC03 Terbutaline R03AC04 Fenoterol R03AC05 Rimiterol R03AC06 Hexoprenaline R03AC07 Isoetarine...

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Bambuterol

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agonist (LABA) used in the treatment of asthma; it also is a prodrug of terbutaline. Commercially, the AstraZeneca pharmaceutical company produces and markets...

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Bronchospasm

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Beta2-adrenergic agonists are recommended for bronchospasm. Short acting (SABA) Terbutaline Salbutamol Levosalbutamol Long acting (LABA) Formoterol Salmeterol Others...

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Tocolytic

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CD014978.pub2. PMC 9364967. PMID 35947046. Why do doctors still use terbutaline to delay preterm labor despite its major health risks? Retrieved on October...

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Priapism

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those with recurrent ischemic priapism, diethylstilbestrol (DES) or terbutaline may be tried. Distal shunts, such as the Winter's,[clarification needed]...

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Yusuf Pathan

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October 2017, Pathan was charged with an anti-doping violation, having had Terbutaline detected in his urine sample following a domestic T20 match earlier in...

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List of medical inhalants

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Procaterol Racepinephrine (racemic epinephrine) Salbutamol Salmeterol Terbutaline Tiotropium Amyl nitrite Iloprost (Prostacyclin) Nitric oxide Beclomethasone...

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Bronchodilator

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Epinephrine (Asthmanefrin, Primatene Mist Replacement) Ephedrine (Bronkaid) Terbutaline Long-acting bronchodilators include Salmeterol (Serevent or Seretide)...

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Uterine hyperstimulation

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rupture, or placental abruption. It is usually treated by administering terbutaline. Mistoprostol is a drug treatment for peptic ulcers that can also cause...

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Phenylephrine

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Procaterol Reproterol Rimiterol Ritodrine Salbutamol Salmeterol Solabegron Terbutaline Tretoquinol Tulobuterol Vibegron Vilanterol Xamoterol XP21279 Zilpaterol...

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Cyclobenzaprine

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Procaterol Reproterol Rimiterol Ritodrine Salbutamol Salmeterol Solabegron Terbutaline Tretoquinol Tulobuterol Vibegron Vilanterol Xamoterol XP21279 Zilpaterol...

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LSD

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Chronic obstructive pulmonary disease

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short-acting β2 agonists are available, including salbutamol (albuterol) and terbutaline. They provide some relief of symptoms for four to six hours. A long-acting...

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Vaginal delivery

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persists, and uterine tachysystole continues, tocolytic remedies, such as terbutaline, may be used. Afterward, if beneficial and uterine tone has returned...

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WHO Model List of Essential Medicines

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fluticasone furoate/vilanterol, and mometasone/formoterol are alternatives Terbutaline is an alternative Aclidinium, glycopyrronium, and umeclidinium are alternatives...

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Adrenergic agonist

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dexmedetomidine. β1 selective: dobutamine. β2 selective: salbutamol/albuterol, terbutaline, salmeterol, formoterol, pirbuterol, clenbuterol. These are agents that...

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Olanzapine

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Procaterol Reproterol Rimiterol Ritodrine Salbutamol Salmeterol Solabegron Terbutaline Tretoquinol Tulobuterol Vibegron Vilanterol Xamoterol XP21279 Zilpaterol...

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Doxofylline

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Ping, Yi Suo, and Yili. It is also marketed as a combination drug with terbutaline as Doxoll-TL, Mucosma-T and Phylex-TR. It is also marketed as a combination...

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Promethazine

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Procaterol Reproterol Rimiterol Ritodrine Salbutamol Salmeterol Solabegron Terbutaline Tretoquinol Tulobuterol Vibegron Vilanterol Xamoterol XP21279 Zilpaterol...

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Tizanidine

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Procaterol Reproterol Rimiterol Ritodrine Salbutamol Salmeterol Solabegron Terbutaline Tretoquinol Tulobuterol Vibegron Vilanterol Xamoterol XP21279 Zilpaterol...

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Salbutamol

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Procaterol Reproterol Rimiterol Ritodrine Salbutamol Salmeterol Solabegron Terbutaline Tretoquinol Tulobuterol Vibegron Vilanterol Xamoterol XP21279 Zilpaterol...

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Chlorpromazine

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Procaterol Reproterol Rimiterol Ritodrine Salbutamol Salmeterol Solabegron Terbutaline Tretoquinol Tulobuterol Vibegron Vilanterol Xamoterol XP21279 Zilpaterol...

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