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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyTerbutaline
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
Structure for Terbutaline (DB00871)
- Synonyms
- Terbutalin
- Terbutalina
- Terbutaline
- Terbutaline (sulfate de)
- Terbutalini sulfas
- Terbutalinsulfat
- Terbutalinum
- External IDs
- KWD 2019
- Product Ingredients
Ingredient UNII CAS InChI Key Terbutaline Sulfate 576PU70Y8E 23031-32-5 MUPQZWGSBCWCAV-UHFFFAOYSA-N - Product Images
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Bricanyl Tab 2.5 mg Tablet 2.5 mg Oral Astra Zeneca 1978-12-31 2000-07-20 Canada 
Bricanyl Tab 5 mg Tablet 5 mg Oral Astra Zeneca 1975-12-31 2001-07-23 Canada Bricanyl Turbuhaler Powder, metered 0.5 mg Respiratory (inhalation) Astra Zeneca 1990-12-31 Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Terbutaline Sulfate Injection 1 mg/1mL Subcutaneous Teva Parenteral Medicines, Inc. 2004-07-20 2011-12-31 US 
Terbutaline Sulfate Tablet 2.5 mg/1 Oral Lannett Company, Inc. 2005-03-25 Not applicable US Terbutaline Sulfate Injection, solution 1 mg/1mL Subcutaneous Athenex Pharmaceutical Division, Llc. 2017-02-22 Not applicable US Terbutaline Sulfate Tablet 2.5 mg/1 Oral Marlex Pharmaceuticals Inc 2014-10-01 Not applicable US Terbutaline Sulfate Tablet 5 mg/1 Oral PD-Rx Pharmaceuticals, Inc. 2001-06-26 2018-08-20 US Terbutaline Sulfate Tablet 5 mg/1 Oral PD-Rx Pharmaceuticals, Inc. 2005-03-25 Not applicable US 
Terbutaline Sulfate Injection 1 mg/1mL Subcutaneous Bedford Pharmaceuticals 2004-04-28 2011-12-31 US Terbutaline Sulfate Tablet 2.5 mg/1 Oral Impax Generics 2001-06-26 Not applicable US Terbutaline Sulfate Tablet 5 mg/1 Oral Av Kare, Inc. 2001-06-26 2015-12-09 US Terbutaline Sulfate Tablet 5 mg/1 Oral Rebel Distributors 2005-03-25 Not applicable US - International/Other Brands
- Brethaire (Novartis) / Brethine / Bricanyl (AstraZeneca) / Bricardyl (Johnson) / Bricasma (AstraZeneca) / Bricasol (AstraZeneca) / Dracanyl (AstraZeneca) / Terbasmin (AstraZeneca)
- Categories
- Adrenergic Agents
- Adrenergic Agonists
- Adrenergic beta-2 Receptor Agonists
- Adrenergic beta-Agonists
- Adrenergics for Systemic Use
- Adrenergics, Inhalants
- Agents producing tachycardia
- Agents that produce hypertension
- Agents to Treat Airway Disease
- Alcohols
- Amines
- Amino Alcohols
- Anti-Asthmatic Agents
- Autonomic Agents
- Bronchodilator Agents
- Cholinesterase Inhibitors
- Drugs for Obstructive Airway Diseases
- Ethanolamines
- Neurotransmitter Agents
- Peripheral Nervous System Agents
- Potential QTc-Prolonging Agents
- QTc Prolonging Agents
- Reproductive Control Agents
- Respiratory System Agents
- Selective Beta 2-adrenergic Agonists
- Sympathomimetics
- Tocolytic Agents
- UNII
- N8ONU3L3PG
- CAS number
- 23031-25-6
- Weight
- Average: 225.2842
Monoisotopic: 225.136493479 - Chemical Formula
- C12H19NO3
- InChI Key
- 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
- IUPAC Name
- 5-[2-(tert-butylamino)-1-hydroxyethyl]benzene-1,3-diol
- SMILES
- CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1
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.
- Associated Conditions
- 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.
Target Actions Organism ABeta-2 adrenergic receptor agonistHumans UBeta-3 adrenergic receptor agonistHumans UBeta-1 adrenergic receptor antagonistHumans - Absorption
Approximately 30-50% if administered orally and well absorbed subcutaneously.
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
- Not Available
- 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
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid The risk or severity of hypertension can be increased when Terbutaline is combined with 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid. 1-benzylimidazole The risk or severity of hypertension can be increased when Terbutaline is combined with 1-benzylimidazole. 2,5-Dimethoxy-4-ethylamphetamine The risk or severity of adverse effects can be increased when Terbutaline is combined with 2,5-Dimethoxy-4-ethylamphetamine. 2,5-Dimethoxy-4-ethylthioamphetamine The risk or severity of adverse effects can be increased when Terbutaline is combined with 2,5-Dimethoxy-4-ethylthioamphetamine. 3-isobutyl-1-methyl-7H-xanthine The risk or severity of adverse effects can be increased when Terbutaline is combined with 3-isobutyl-1-methyl-7H-xanthine. 3,4-Methylenedioxyamphetamine The risk or severity of adverse effects can be increased when Terbutaline is combined with 3,4-Methylenedioxyamphetamine. 4-Bromo-2,5-dimethoxyamphetamine The risk or severity of adverse effects can be increased when Terbutaline is combined with 4-Bromo-2,5-dimethoxyamphetamine. 4-Methoxyamphetamine The risk or severity of hypertension can be increased when Terbutaline is combined with 4-Methoxyamphetamine. 5-methoxy-N,N-dimethyltryptamine The risk or severity of hypertension can be increased when Terbutaline is combined with 5-methoxy-N,N-dimethyltryptamine. 6-O-benzylguanine The risk or severity of adverse effects can be increased when Terbutaline is combined with 6-O-benzylguanine. - Food Interactions
- Not Available
References
- Synthesis Reference
Alison B. Lukacsko, Joseph J. Piala, "Effect of a combination of a terbutaline, diphenhydramine and ranitidine composition on gastrointestinal injury produced by nonsteroidal anti-inflammatory compositions." U.S. Patent US5260333, issued December, 1983.
US5260333- General 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:14610225]
- 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:1358833]
- 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:2062329]
- External Links
- Human Metabolome Database
- HMDB0015009
- KEGG Compound
- C07129
- PubChem Compound
- 5403
- PubChem Substance
- 46506887
- ChemSpider
- 5210
- BindingDB
- 25770
- ChEBI
- 9449
- ChEMBL
- CHEMBL1760
- Therapeutic Targets Database
- DAP000246
- PharmGKB
- PA451616
- IUPHAR
- 560
- Guide to Pharmacology
- GtP Drug Page
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Terbutaline
- ATC Codes
- R03CC53 — Terbutaline, combinations
- R03CC — Selective beta-2-adrenoreceptor agonists
- R03C — ADRENERGICS FOR SYSTEMIC USE
- R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
- R — RESPIRATORY SYSTEM
- R03CC — Selective beta-2-adrenoreceptor agonists
- R03C — ADRENERGICS FOR SYSTEMIC USE
- R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
- R — RESPIRATORY SYSTEM
- AHFS Codes
- 12:12.08.12 — Selective Beta 2-adrenergic Agonists
- MSDS
- Download (73.1 KB)
Clinical Trials
- Clinical Trials
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
- Akorn Inc.
- Amerisource Health Services Corp.
- APP Pharmaceuticals
- AstraZeneca Inc.
- Bedford Labs
- Ben Venue Laboratories Inc.
- Cardinal Health
- Dept Health Central Pharmacy
- Dispensing Solutions
- Gallipot
- Global Pharmaceuticals
- Hikma Pharmaceuticals
- Lannett Co. Inc.
- Mckesson Corp.
- Murfreesboro Pharmaceutical Nursing Supply
- Novartis AG
- Nucare Pharmaceuticals Inc.
- Pharmaceutical Utilization Management Program VA Inc.
- Physicians Total Care Inc.
- Rebel Distributors Corp.
- Redpharm Drug
- Remedy Repack
- Resource Optimization and Innovation LLC
- Rite Aid Corp.
- Teva Pharmaceutical Industries Ltd.
- Tya Pharmaceuticals
- West-Ward Pharmaceuticals
- Dosage forms
Form Route Strength Tablet Oral 2.5 mg Tablet Oral 5 mg Powder, metered Respiratory (inhalation) 0.5 mg Injection Subcutaneous 1 mg/1mL Injection, solution Subcutaneous 1 mg/1mL Tablet Oral 2.5 mg/1 Tablet Oral 5 mg/1 - Prices
Unit description Cost Unit Terbutaline sulfate powder 38.4USD g Terbutaline Sulfate 1 mg/ml vial 12.99USD vial Terbutaline sulf 1 mg/ml vial 4.8USD ml Brethine 5 mg tablet 0.83USD tablet Terbutaline sulfate 5 mg tablet 0.63USD tablet Brethine 2.5 mg tablet 0.57USD tablet Terbutaline sulfate 2.5 mg tablet 0.47USD tablet Bricanyl Turbuhaler 0.5 mg/dose Metered Inhalation Powder 0.08USD dose DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 119-122 °C Not Available water solubility 213 mg/mL Not Available logP 0.90 TACAKS-NOVAK,K ET AL. (1995) Caco2 permeability -6.38 ADME Research, USCD - Predicted Properties
Property Value Source Water Solubility 5.84 mg/mL ALOGPS logP 0.55 ALOGPS logP 0.44 ChemAxon logS -1.6 ALOGPS pKa (Strongest Acidic) 8.86 ChemAxon pKa (Strongest Basic) 9.76 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 72.72 Å2 ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 63.04 m3·mol-1 ChemAxon Polarizability 24.78 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption + 0.987 Blood Brain Barrier - 0.9355 Caco-2 permeable - 0.8404 P-glycoprotein substrate Substrate 0.6335 P-glycoprotein inhibitor I Non-inhibitor 0.8954 P-glycoprotein inhibitor II Non-inhibitor 0.9672 Renal organic cation transporter Non-inhibitor 0.9067 CYP450 2C9 substrate Non-substrate 0.7678 CYP450 2D6 substrate Non-substrate 0.7922 CYP450 3A4 substrate Non-substrate 0.6291 CYP450 1A2 substrate Non-inhibitor 0.9516 CYP450 2C9 inhibitor Non-inhibitor 0.9303 CYP450 2D6 inhibitor Non-inhibitor 0.923 CYP450 2C19 inhibitor Non-inhibitor 0.9115 CYP450 3A4 inhibitor Non-inhibitor 0.8766 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9117 Ames test Non AMES toxic 0.9119 Carcinogenicity Non-carcinogens 0.8484 Biodegradation Not ready biodegradable 0.9808 Rat acute toxicity 2.1080 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9548 hERG inhibition (predictor II) Non-inhibitor 0.9467
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Taxonomy
- Description
- This compound belongs to the class of organic compounds known as resorcinols. These are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Phenols
- Sub Class
- Benzenediols
- Direct Parent
- Resorcinols
- Alternative Parents
- Aralkylamines / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Secondary alcohols / 1,2-aminoalcohols / Dialkylamines / Organopnictogen compounds / Hydrocarbon derivatives / Aromatic alcohols
- Substituents
- Resorcinol / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Aralkylamine / Monocyclic benzene moiety / 1,2-aminoalcohol / Secondary alcohol / Secondary amine / Secondary aliphatic amine / Aromatic alcohol
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- phenylethanolamines, resorcinols (CHEBI:9449)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Protein homodimerization activity
- Specific Function
- 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 ...
- Gene Name
- ADRB2
- Uniprot ID
- P07550
- Uniprot Name
- Beta-2 adrenergic receptor
- Molecular Weight
- 46458.32 Da
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. [PubMed:10226872]
- 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:11120594]
- 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:11256987]
- 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:11675405]
- 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:12569076]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- 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. 2011 Jan;25(1):59-66. doi: 10.1016/j.bbi.2010.07.248. Epub 2010 Jul 30. [PubMed:20674738]
- 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. doi: 10.2337/dc08-0520. Epub 2008 Sep 9. [PubMed:18782903]
- 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:1358833]
- 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:2062329]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Protein homodimerization activity
- Specific Function
- Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. Beta-3 is involved in the regulation of lipolysis and thermogenesis.
- Gene Name
- ADRB3
- Uniprot ID
- P13945
- Uniprot Name
- Beta-3 adrenergic receptor
- Molecular Weight
- 43518.615 Da
References
- Hoffmann C, Leitz MR, Oberdorf-Maass S, Lohse MJ, Klotz KN: Comparative pharmacology of human beta-adrenergic receptor subtypes--characterization of stably transfected receptors in CHO cells. Naunyn Schmiedebergs Arch Pharmacol. 2004 Feb;369(2):151-9. Epub 2004 Jan 17. [PubMed:14730417]
- Behr B, Hoffmann C, Ottolina G, Klotz KN: Novel mutants of the human beta1-adrenergic receptor reveal amino acids relevant for receptor activation. J Biol Chem. 2006 Jun 30;281(26):18120-5. Epub 2006 Apr 28. [PubMed:16648137]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Receptor signaling protein activity
- Specific Function
- Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...
- Gene Name
- ADRB1
- Uniprot ID
- P08588
- Uniprot Name
- Beta-1 adrenergic receptor
- Molecular Weight
- 51322.1 Da
References
- Hoffmann C, Leitz MR, Oberdorf-Maass S, Lohse MJ, Klotz KN: Comparative pharmacology of human beta-adrenergic receptor subtypes--characterization of stably transfected receptors in CHO cells. Naunyn Schmiedebergs Arch Pharmacol. 2004 Feb;369(2):151-9. Epub 2004 Jan 17. [PubMed:14730417]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Identical protein binding
- Specific Function
- Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
- Gene Name
- BCHE
- Uniprot ID
- P06276
- Uniprot Name
- Cholinesterase
- Molecular Weight
- 68417.575 Da
References
- 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:15449725]
Drug created on June 13, 2005 07:24 / Updated on February 22, 2019 22:55