QuickView for Terbutaline (compound)

Summary
General Info

PubChem

PubChem Compound 31620

Name:	Terbutaline
PubChem Compound ID:	31620
Description:	A selective beta-2 adrenergic agonist used as a bronchodilator and tocolytic.
Molecular formula:	C₂₄H₄₀N₂O₁₀S
Molecular weight:	548.648 g/mol
Synonyms:	Terbutaline sulfate [USAN:JAN]; 98225-49-1; 1-(3,5-Dihydroxyphenyl)-2-tert-butylaminoethanol sulphate; Bricanyl; BENZYL ALCOHOL, alpha-((tert-BUTYLAMINO)METHYL)-3,5-DIHYDROXY-, SULFATE (2:1); Terbutaline sulfate; 1,3-Benzenediol, 5-(2-((1,1-dimethylethyl)amino)-1-hydroxyethyl)-, sulfate (2:1) (salt); 23031-25-6; (+-)-alpha-((tert-Butylamino)methyl)-3,5-dihydroxybenzyl alcohol sulfate (2:1) (salt); KWD 2019. show more » Terbutaline sulfate [USAN:JAN]; 98225-49-1; 1-(3,5-Dihydroxyphenyl)-2-tert-butylaminoethanol sulphate; Bricanyl; BENZYL ALCOHOL, alpha-((tert-BUTYLAMINO)METHYL)-3,5-DIHYDROXY-, SULFATE (2:1); Terbutaline sulfate; 1,3-Benzenediol, 5-(2-((1,1-dimethylethyl)amino)-1-hydroxyethyl)-, sulfate (2:1) (salt); 23031-25-6; (+-)-alpha-((tert-Butylamino)methyl)-3,5-dihydroxybenzyl alcohol sulfate (2:1) (salt); KWD 2019; Brethine; 23031-32-5; EINECS 245-386-3; Terbutaline sulphate; Brethaire show less «

DrugBank

Identification

Name:	Terbutaline
Name (isomeric):	DB00871
Drug Type:	small molecule
Description:	A selective beta-2 adrenergic agonist used as a bronchodilator and tocolytic.
Synonyms:	Terbutalina [Dcit]; Terbutaline Sulfate; Terbutalin; Terbutalino [INN-Spanish]; Terbutalinum [INN-Latin]
Brand:	Bricaril, Bricyn, Brican, Brethine, Bricar, Bricanyl, Brethaire
Category:	Sympathomimetic, Tocolytic Agents, Adrenergic beta-Agonists, Sympathomimetics, Bronchodilator Agents
CAS number:	23031-25-6

Pharmacology

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 stimulatin... show more » 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. show less «
Mechanism of Action:	The pharmacologic effects of terbutaline are at least in part attributable to stimulation through beta-adrenergic receptors of intracellular adenyl cyclase, the enzyme that catalyzes the conversion of adenosine triphosphate (ATP) to cyclic- 3',5'- adenosine monophosphate (c-AMP). Increased c-AMP levels are associated with relaxation of bronchial sm... show more » The pharmacologic effects of terbutaline are at least in part attributable to stimulation through beta-adrenergic receptors of intracellular adenyl cyclase, the enzyme that catalyzes the conversion of adenosine triphosphate (ATP) to cyclic- 3',5'- adenosine monophosphate (c-AMP). Increased c-AMP levels are associated with relaxation of bronchial smooth muscle and inhibition of release of mediators of immediate hypersensitivity from cells, especially from mast cells. show less «
Absorption:	Approximately 30-50% if administered orally and well absorbed subcutaneously.
Route of 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
Half Life:	5.5-5.9 hours
Clearance:	311 +/- 112 mL/min
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

Interactions

Drug interaction:

Phenelzine	Increased arterial pressure
Alseroxylon	Increased arterial pressure
Reserpine	Increased arterial pressure
Bevantolol	Antagonism
Clomipramine	The tricyclic antidepressant, clomipramine, increases the sympathomimetic effect of terbutaline.

Targets

Beta-2 adrenergic receptor

Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine

UniProt ID:

P07550

Gene:

ADRB2

Actions:

agonist

References:

Schafers RF, Piest U, von Birgelen C, Jakubetz J, Daul AE, Philipp T, Brodde OE: Disodium cromoglycate does not prevent terbutaline-induced desensitization of beta 2-adrenoceptor-mediated cardiovascular in vivo functions in human volunteers. J Cardiovasc Pharmacol. 1999 May;33(5):822-7.
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Ramer-Quinn DS, Swanson MA, Lee WT, Sanders VM: Cytokine production by naive and primary effector CD4+ T cells exposed to norepinephrine. Brain Behav Immun. 2000 Dec;14(4):239-55.
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Zetterlund A, Hjemdahl P, Larsson K: beta2-Adrenoceptor desensitization in human alveolar macrophages induced by inhaled terbutaline in vivo is not counteracted by budesonide. Clin Sci (Lond). 2001 Apr;100(4):451-7.
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Nakamura A, Johns EJ, Imaizumi A, Yanagawa Y, Kohsaka T: Activation of beta(2)-adrenoceptor prevents shiga toxin 2-induced TNF-alpha gene transcription. J Am Soc Nephrol. 2001 Nov;12(11):2288-99.
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Chong LK, Suvarna K, Chess-Williams R, Peachell PT: Desensitization of beta2-adrenoceptor-mediated responses by short-acting beta2-adrenoceptor agonists in human lung mast cells. Br J Pharmacol. 2003 Feb;138(3):512-20.
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Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5.
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Riether C, Kavelaars A, Wirth T, Pacheco-Lopez G, Doenlen R, Willemen H, Heijnen CJ, Schedlowski M, Engler H: Stimulation of beta(2)-adrenergic receptors inhibits calcineurin activity in CD4(+) T cells via PKA-AKAP interaction. Brain Behav Immun. 2010 Jul 30.
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Cooperberg BA, Breckenridge SM, Arbelaez AM, Cryer PE: Terbutaline and the prevention of nocturnal hypoglycemia in type 1 diabetes. Diabetes Care. 2008 Dec;31(12):2271-2. Epub 2008 Sep 9.
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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.
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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.
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Enzymes

Cholinesterase