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Identification
Name Terbutaline
Accession Number DB00871 (APRD00589)
Type small molecule
Groups approved
Description

A selective beta-2 adrenergic agonist used as a bronchodilator and tocolytic. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Terbutalin
  • Terbutalina [Dcit]
  • Terbutaline Sulfate
  • Terbutalino [INN-Spanish]
  • Terbutalinum [INN-Latin]
Brand names
  • Brethaire
  • Brethine
  • Brican
  • Bricanyl
  • Bricar
  • Bricaril
  • Bricyn
Brand name mixtures Not Available
Categories
  • Sympathomimetics
  • Bronchodilator Agents
  • Adrenergic beta-Agonists
  • Tocolytic Agents
  • Sympathomimetic
CAS number 23031-25-6
Weight Average: 225.2842
Monoisotopic: 225.136493479
Chemical Formula C12H19NO3
InChI Key InChIKey=XWTYSIMOBUGWOL-UHFFFAOYSA-N
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
Plain Text
IUPAC Name
5-[2-(tert-butylamino)-1-hydroxyethyl]benzene-1,3-diol
SMILES
CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Benzyl Alcohols and Derivatives
  • Phenols and Derivatives
  • Phenethylamines
  • Resorcinols
Substructures
  • Hydroxy Compounds
  • Benzyl Alcohols and Derivatives
  • Aliphatic and Aryl Amines
  • Phenols and Derivatives
  • Benzene and Derivatives
  • Amino Alcohols
  • Phenethylamines
  • Aromatic compounds
  • Alcohols and Polyols
  • Phenyl Esters
  • Resorcinols
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.
Pharmacodynamics 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.
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 smooth muscle and inhibition of release of mediators of immediate hypersensitivity from cells, especially from mast cells.
Absorption Approximately 30-50% if administered orally and well absorbed subcutaneously.
Volume of distribution Not Available
Protein binding Not Available
Metabolism
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
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Novartis pharmaceuticals corp
  • Sanofi aventis us llc
  • Aaipharma llc
  • Akorn inc
  • App pharmaceuticals llc
  • Bedford laboratories div ben venue laboratories inc
  • Hikma farmaceutica (portugal) sa
  • Teva parenteral medicines inc
  • Impax laboratories inc
  • Lannett holdings inc
Packagers
Dosage forms
Form Route Strength
Aerosol, metered Respiratory (inhalation)
Prices
Unit description Cost Unit
Terbutaline sulfate powder 38.4 USD g
Terbutaline Sulfate 1 mg/ml vial 12.99 USD vial
Terbutaline sulf 1 mg/ml vial 4.8 USD ml
Brethine 5 mg tablet 0.83 USD tablet
Terbutaline sulfate 5 mg tablet 0.63 USD tablet
Brethine 2.5 mg tablet 0.57 USD tablet
Terbutaline sulfate 2.5 mg tablet 0.47 USD tablet
Bricanyl Turbuhaler 0.5 mg/dose Metered Inhalation Powder 0.08 USD dose
Patents Not Available
Properties
State solid
Melting point 119-122 oC
Experimental Properties
Property Value Source
water solubility 213 mg/mL PhysProp
logP 1.4 PhysProp
Caco2 permeability -6.38 [ADME Research, USCD] BiGG
Predicted Properties
Property Value Source
water solubility 5.84e+00 g/l ALOGPS
logP 0.55 ALOGPS
logP 0.34 ChemAxon Molconvert
logS -1.59 ALOGPS
pKa 10.64 ChemAxon Molconvert
hydrogen acceptor count 4 ChemAxon Molconvert
hydrogen donor count 4 ChemAxon Molconvert
polar surface area 72.72 ChemAxon Molconvert
rotatable bond count 4 ChemAxon Molconvert
refractivity 63.04 ChemAxon Molconvert
polarizability 24.82 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  1. 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
  2. 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
  3. 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
External Links
Resource Link
KEGG Compound C07129 Link_out
PubChem Compound 5403 Link_out
PubChem Substance 46506887 Link_out
ChemSpider 5210 Link_out
BindingDB 25770 Link_out
Therapeutic Targets Database DAP000246 Link_out
PharmGKB PA451616 Link_out
Drug Product Database 786616 Link_out
RxList http://www.rxlist.com/cgi/generic3/terbutaline.htm Link_out
Drugs.com http://www.drugs.com/cdi/terbutaline.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Terbutaline Link_out
ATC Codes
  • R03AC03
  • R03CC03
AHFS Codes
  • 12:12.08.12
PDB Entries Not Available
FDA label Not Available
MSDS show (73.1 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Beta-2 adrenergic receptor

Pharmacological action: yes
Actions: agonist

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

Organism class: human
UniProt ID: P07550 Link_out
Gene: ADRB2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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. Pubmed
  2. 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. Pubmed
  3. 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. Pubmed
  4. 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. Pubmed
  5. 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. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  7. 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. Pubmed
  8. 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. Pubmed
  9. 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
  10. 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
Enzymes

1. Cholinesterase

Actions: inhibitor

An acylcholine + H(2)O = choline + a carboxylate

UniProt ID: P06276 Link_out
Gene: BCHE Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Kovarik Z, Simeon-Rudolf V: Interaction of human butyrylcholinesterase variants with bambuterol and terbutaline. J Enzyme Inhib Med Chem. 2004 Apr;19(2):113-7. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on August 12, 2011 08:46

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.