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Terbutaline

Catalog No. DB00871 Name DrugBank
CAS Number 23031-25-6 Website http://www.ualberta.ca/
M. F. C12H19NO3 Telephone (780) 492-3111
M. W. 225.28416 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 749

SYNONYMS

IUPAC name
5-[2-(tert-butylamino)-1-hydroxyethyl]benzene-1,3-diol
IUPAC Traditional name
terbutaline
Brand Name
Brethine
Bricyn
Bricaril
Brethaire
Brican
Bricanyl
Bricar
Synonyms
Terbutalino [INN-Spanish]
Terbutalin
Terbutalina [Dcit]
Terbutaline Sulfate
Terbutalinum [INN-Latin]

DATABASE IDS

CAS Number 23031-25-6
PubChem SID 46506887
PubChem CID 5403

PROPERTIES

Hydrophobicity(logP) 1.4
Solubility 213 mg/mL

DETAILS

Description (English)
Item Information
Drug Groups approved
Description A selective beta-2 adrenergic agonist used as a bronchodilator and tocolytic. [PubChem]
Indication For the prevention and reversal of bronchospasm in patients 12 years of age and older with reversible, obstructive airway disease, as well as symptomatic management of reversible bronchospasm associated with bronchitis and emphysema. Also used acute IV and sub-Q therapy in selected women to inhibit uterine contractions in preterm labor (tocolysis) and prolong gestation when beneficial.
Pharmacology Terbutaline is a relatively selective beta2-adrenergic bronchodilator that has little or no effect on alpha-adrenergic receptors. The drug has exerts a preferential effect on beta2-adrenergic receptors but stimulates beta-adrenergic receptors less selectively than relatively selective beta2-agonists. Terbutaline appears to have a greater stimulating effect on beta-receptors of the bronchial, vascular, and uterine smooth muscles (beta2 receptors) than on the beta-receptors of the heart (beta1 receptors). This drug relaxes smooth muscle and inhibits uterine contractions, but may also cause some cardiostimulatory effects and CNS stimulation.
Toxicity Terbutaline Sulfate: Oral LD50(rat) = 8.7 g/kg; Oral LD50(mouse) = 205 mg/kg; Oral LD50(dog) = 1.5 g/kg; IP LD50(rat)= 220 mg/kg ; IP LD50(mouse) = 130 mg/kg; Oral LD50(rabbit) = >8 g/kg; IV LD50(mouse) = 36 mg/kg; IV LD50(dog) = 116 mg/kg; IV LD50(rabbit) = 110 mg/kg
Affected Organisms
Humans and other mammals
Absorption Approximately 30-50% if administered orally and well absorbed subcutaneously.
Half Life 5.5-5.9 hours
Elimination About 90% of the drug was excreted in the urine at 96 hours after subcutaneous administration, with about 60% of this being unchanged drug. It appears that the sulfate conjugate is a major metabolite of terbutaline and urinary excretion is the primary route of elimination
Clearance * 311 +/- 112 mL/min
References
Rhodes MC, Seidler FJ, Abdel-Rahman A, Tate CA, Nyska A, Rincavage HL, Slotkin TA: Terbutaline is a developmental neurotoxicant: effects on neuroproteins and morphology in cerebellum, hippocampus, and somatosensory cortex. J Pharmacol Exp Ther. 2004 Feb;308(2):529-37. Epub 2003 Nov 10. [Pubmed]
Hochhaus G, Mollmann H: Pharmacokinetic/pharmacodynamic characteristics of the beta-2-agonists terbutaline, salbutamol and fenoterol. Int J Clin Pharmacol Ther Toxicol. 1992 Sep;30(9):342-62. [Pubmed]
Haahtela T, Jarvinen M, Kava T, Kiviranta K, Koskinen S, Lehtonen K, Nikander K, Persson T, Reinikainen K, Selroos O, et al.: Comparison of a beta 2-agonist, terbutaline, with an inhaled corticosteroid, budesonide, in newly detected asthma. N Engl J Med. 1991 Aug 8;325(6):388-92. [Pubmed]
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REFERENCES

  • Rhodes MC, Seidler FJ, Abdel-Rahman A, Tate CA, Nyska A, Rincavage HL, Slotkin TA: Terbutaline is a developmental neurotoxicant: effects on neuroproteins and morphology in cerebellum, hippocampus, and somatosensory cortex. J Pharmacol Exp Ther. 2004 Feb;308(2):529-37. Epub 2003 Nov 10. Pubmed
  • Hochhaus G, Mollmann H: Pharmacokinetic/pharmacodynamic characteristics of the beta-2-agonists terbutaline, salbutamol and fenoterol. Int J Clin Pharmacol Ther Toxicol. 1992 Sep;30(9):342-62. Pubmed
  • Haahtela T, Jarvinen M, Kava T, Kiviranta K, Koskinen S, Lehtonen K, Nikander K, Persson T, Reinikainen K, Selroos O, et al.: Comparison of a beta 2-agonist, terbutaline, with an inhaled corticosteroid, budesonide, in newly detected asthma. N Engl J Med. 1991 Aug 8;325(6):388-92. Pubmed