Identification
- Summary
Terbutaline is a beta-2 adrenergic agonist used as a bronchodilator and to prevent premature labor.
- Brand Names
- Bricanyl
- Generic Name
- Terbutaline
- DrugBank Accession Number
- DB00871
- Background
Terbutaline was first synthesized in 196612 and described in the literature in the late 1960s and early 1970s.11 It is a selective beta-2 adrenergic agonist used as a bronchodilator in asthmatic patients.12,16,17
Terbutaline was granted FDA approval on 25 March 1974.15
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Terbutaline (DB00871)
- Weight
- Average: 225.2842
Monoisotopic: 225.136493479 - Chemical Formula
- C12H19NO3
- Synonyms
- Terbutalin
- Terbutalina
- Terbutaline
- Terbutalinum
- External IDs
- KWD 2019
Pharmacology
- Indication
Terbutaline is indicated for prevention and reversal of bronchospasm in patients at least 12 years old, with asthma and reversible bronchospasm associated with bronchitis and emphysema.16,17
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
- Associated Therapies
- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Terbutaline is a beta-2 adrenergic receptor agonist indicated to treat reversibly bronchospasm in asthmatic patients with bronchitis and emphysema.16,17 It has a short duration as the inhaled form is taken up to three times daily, and the therapeutic window is wide.16,17
- Mechanism of action
Terbutaline is a selective beta-2 adrenergic receptor agonist.11 Agonism of these receptors in bronchioles activates adenylyl cyclase, increasing intracellular cyclic adenosine monophosphate (cAMP).13 Increased cAMP decreases intracellular calcium, activating protein kinase A, inactivating myosin light-chain kinase, activating myosin light-chain phosphatase, and finally relaxing smooth muscle in the bronchiole.13
Target Actions Organism ABeta-2 adrenergic receptor agonistHumans UBeta-3 adrenergic receptor agonistHumans UBeta-1 adrenergic receptor antagonistHumans - Absorption
A 0.5 mg subcutaneous dose of terbutaline reaches a mean Cmax of 9.6 ± ng/mL, with a median Tmax of 0.5 hours, and a mean AUC of 29.4 ± 14.2 h*ng/mL.16 A 5 mg oral terbutaline tablet reaches a mean Cmax of 8.3 ± 3.9 ng/mL with a median Tmax of 2 hours, and a mean AUC of 54.6 ± 26.8 h*ng/mL.17 A 5 mg oral terbutaline solution reaches a mean Cmax of 8.6 ± 3.6 ng/mL, with a median Tmax of 1.5 hours, and a mean AUC of 53.1 ± 23.5 h*ng/mL.17
Oral terbutaline has an oral bioavailability of 14-15%.8
- Volume of distribution
Terbutaline has a mean volume of distribution of 1.6 L/kg.8
- Protein binding
Terbutaline is not highly bound to protein in plasma.8
- Metabolism
Terbutaline is sulphated or glucuronidated prior to elimination.4,5,6,9
Hover over products below to view reaction partners
- Route of elimination
An oral dose of terbutaline is 40% eliminated in the urine after 72 hours.6 The major metabolite in the urine was the sulphate conjugated form of terbutaline.6 Parenteral doses of terbutaline are 90% eliminated in the urine, with approximately 2/3 as the unchanged parent drug.7 Less than 1% of a dose of terbutaline is eliminated in the feces.7
- Half-life
An oral dose of terbutaline has an elimination half life of 3.4 hours,17 while a subcutaneous dose has an elimination half life of 2.9 hours.16
- Clearance
The average clearance of terbutaline is 3.0 mL/min/kg.8
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Patients experiencing an overdose may present with abdominal pain, agitation, palpitations, seizures, angina, hypertension, hypotension, tachycardia, arrhythmias, nervousness, headache, tremor, dry mouth, nausea, dizziness, fatigue, malaise, insomnia.10,16,17 Discontinue treatment with terbutaline and initiate symptomatic and supportive therapy.16,17
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Terbutaline may decrease the excretion rate of Abacavir which could result in a higher serum level. Abaloparatide The risk or severity of adverse effects can be increased when Terbutaline is combined with Abaloparatide. Acebutolol The therapeutic efficacy of Terbutaline can be decreased when used in combination with Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when Terbutaline is combined with Aceclofenac. Acemetacin The risk or severity of hypertension can be increased when Terbutaline is combined with Acemetacin. Acetaminophen Acetaminophen may decrease the excretion rate of Terbutaline which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Terbutaline which could result in a lower serum level and potentially a reduction in efficacy. Acetylcholine The risk or severity of adverse effects can be increased when Terbutaline is combined with Acetylcholine. Acetylsalicylic acid The risk or severity of hypertension can be increased when Terbutaline is combined with Acetylsalicylic acid. Aclidinium Terbutaline may increase the neuromuscular blocking activities of Aclidinium. 
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- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Terbutaline sulfate 576PU70Y8E 23031-32-5 KFVSLSTULZVNPG-UHFFFAOYSA-N - Product Images
- International/Other Brands
- Brethaire (Novartis) / Brethine / Bricanyl (AstraZeneca) / Bricardyl (Johnson) / Bricasma (AstraZeneca) / Bricasol (AstraZeneca) / Dracanyl (AstraZeneca) / Terbasmin (AstraZeneca)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image 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 / act Respiratory (inhalation) Astra Zeneca 1990-12-31 Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Terbutaline Sulfate Injection 1 mg/1mL Subcutaneous Bedford Pharmaceuticals 2004-04-28 2011-12-31 US 
Terbutaline Sulfate Injection 1 mg/1mL Subcutaneous Akorn 2010-02-01 Not applicable US Terbutaline Sulfate Tablet 5 mg/1 Oral TWi Pharmaceuticals, Inc. 2020-07-13 Not applicable US Terbutaline Sulfate Injection 1 mg/1mL Subcutaneous Teva Parenteral Medicines, Inc. 2004-07-20 2011-12-31 US Terbutaline Sulfate Tablet 5 mg/1 Oral ANI Pharmaceuticals, Inc. 2018-10-16 Not applicable US Terbutaline Sulfate Injection 1 mg/1mL Subcutaneous Hikma Pharmaceuticals USA Inc. 2009-05-20 Not applicable US Terbutaline Sulfate Injection 1 mg/1mL Subcutaneous Medical Purchasing Solutions. Llc 2009-05-20 Not applicable US Terbutaline Sulfate Tablet 2.5 mg/1 Oral State of Florida DOH Central Pharmacy 2009-07-01 Not applicable US Terbutaline Sulfate Tablet 5 mg/1 Oral Av Kare, Inc. 2001-06-26 2015-12-09 US Terbutaline Sulfate Injection, solution 1 mg/1mL Subcutaneous Medical Purchasing Solutions, Llc 2017-02-22 Not applicable US - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image ASMALIN SYRUP 1.5 mg/5 ml Syrup 1.5 mg/5ml Oral SUNWARD PHARMACEUTICAL PRIVATE LIMITED 1992-06-12 Not applicable Singapore ASMALIN TABLET 2.5 mg Tablet 2.5 mg Oral SUNWARD PHARMACEUTICAL PRIVATE LIMITED 1991-07-08 Not applicable Singapore BUTYLIN SYRUP 1.5 mg/5 ml Syrup 1.5 mg/5ml Oral GOLDPLUS UNIVERSAL PTE LTD 1995-03-18 Not applicable Singapore - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image BECONYL 1,5 MG + 66,5 MG / 5 ML ŞURUP, 100 ML Terbutaline sulfate (1.5 mg/5mL) + Guaifenesin (66.5 mg/5mL) Syrup Oral ABAY PHARMA SAĞLIK ÜRÜNLERİ SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey 
BİCANA 1.5 MG/5 ML+66.5 MG/5 ML ŞURUP, 100 ML Terbutaline sulfate (1.5 mg/5ml) + Guaifenesin (66.5 mg/5ml) Syrup Oral DROGSAN İLAÇLARI SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey BRELAX 1,5 MG+66,5 MG/5 ML ŞURUP (GAYALİN), 100 ML Terbutaline sulfate (1.5 mg/mL) + Guaifenesin (66.5 mg/mL) Syrup Oral BİLİM İLAÇ SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey BRICANYL EKSPEKTORAN SURUP, 100 ML Terbutaline sulfate (1.5 mg/5ml) + Guaifenesin (66.5 mg/5ml) Syrup Oral ASTRAZENECA İLAÇ SAN. VE TİC. LTD. ŞTİ. 2020-08-14 Not applicable Turkey คอฟบรอน Terbutaline sulfate (1.5 mg/5mL) + Guaifenesin (66.5 mg/5mL) Syrup Oral บริษัท แมคโครฟาร์ จำกัด 1993-05-29 2020-09-29 Thailand 
คอฟบรอน-เอ็ม Terbutaline (1.5 MG/5ML) + Guaifenesin (66.5 MG/5ML) Syrup Oral บริษัท แมคโครฟาร์ จำกัด 2012-12-17 Not applicable Thailand นูคอล Terbutaline sulfate (1.5 mg/5mL) + Guaifenesin (66.5 mg/5mL) Syrup Oral บริษัท เอช.เค.ฟาร์มาซูติคอล จำกัด 2015-11-25 Not applicable Thailand บรองเซท เอกซเปคตอแรนท์ Terbutaline sulfate (1.5 mg/5mL) + Guaifenesin (66.5 mg/5mL) Syrup Oral บริษัท ไทยนครพัฒนา จำกัด 2005-07-26 Not applicable Thailand บรองโคลิคซ์ เอ๊กซ์เป็คทอแรนท์ Terbutaline sulfate (1.5 mg/5mL) + Guaifenesin (66.5 mg/5mL) Syrup Oral บริษัท นิวไลฟ์ฟาร์ม่า จำกัด จำกัด 1998-06-15 Not applicable Thailand บรองโคแลค เอ็กซ์เพคทอแรนท์ Terbutaline sulfate (1.5 mg/5mL) + Guaifenesin (66.5 mg/5mL) Syrup Oral บริษัท อินแพคฟาร์มา จำกัด 2002-05-02 2020-09-29 Thailand
Categories
- 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
- Drug 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
- Drugs that are Mainly Renally Excreted
- Ethanolamines
- Neurotransmitter Agents
- OCT2 Substrates
- 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
- Chemical TaxonomyProvided by Classyfire
- 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
- 1,2-aminoalcohol / 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Alcohol / Amine / Aralkylamine / Aromatic alcohol / Aromatic homomonocyclic compound / Hydrocarbon derivative / Monocyclic benzene moiety
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- phenylethanolamines, resorcinols (CHEBI:9449)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- N8ONU3L3PG
- CAS number
- 23031-25-6
- 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
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. [Article]
- 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. [Article]
- 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. [Article]
- Davies DS, George CF, Blackwell E, Conolly ME, Dollery CT: Metabolism of terbutaline in man and dog. Br J Clin Pharmacol. 1974 Apr;1(2):129-36. doi: 10.1111/j.1365-2125.1974.tb00221.x. [Article]
- Nilsson HT, Persson K, Tegner K: The Metabolism of Terbutaline in Man Xenobiotica. 1972 Mar 16;2(4):363-373. [Article]
- Ripe E, Hornblad Y, Tegner K: Oral administration of terbutaline in asthmatic patients. Eur J Respir Dis Suppl. 1984;134:171-9. [Article]
- Tegner K, Nilsson HT, Persson CG, Persson K, Ryrfeldt A: Elimination pathways of terbutaline. Eur J Respir Dis Suppl. 1984;134:93-100. [Article]
- Nyberg L: Pharmacokinetic parameters of terbutaline in healthy man. An overview. Eur J Respir Dis Suppl. 1984;134:149-60. [Article]
- Davies M, Peramuhendige P, King L, Golding M, Kotian A, Penney M, Shah S, Manevski N: Evaluation of In Vitro Models for Assessment of Human Intestinal Metabolism in Drug Discovery. Drug Metab Dispos. 2020 Nov;48(11):1169-1182. doi: 10.1124/dmd.120.000111. Epub 2020 Aug 29. [Article]
- Lee DC: Terbutaline sulfate overdose. Ann Emerg Med. 1995 Jul;26(1):107-8. doi: 10.1016/s0196-0644(95)70249-0. [Article]
- Mattila MJ, Muittari A: Effect of bronchodilator drugs on the peak expiratory flow rate of asthmatic patients: oral orciprenaline and terbutaline (KWD 2019). Ann Med Exp Biol Fenn. 1969;47(4):298-302. [Article]
- Freedman BJ: Trial of new bronchodilator, terbutaline, in asthma. Br Med J. 1971 Mar 20;1(5750):633-6. doi: 10.1136/bmj.1.5750.633. [Article]
- Sharma S, Hashmi MF, Chakraborty RK: Asthma Medications . [Article]
- Spiller H (2014). Terbutaline. In Encyclopedia of Toxicology (Third Edition) (3rd ed., pp. 484-485). Elsevier. [ISBN:978-0-12-386455-0]
- FDA Approved Drug Products: Bricanyl (Terbutaline Sulfate) Injection [Link]
- Dailymed: Terbutaline Sulfate Subcutaneous Injection [Link]
- Dailymed: Terbutaline Sulfate Oral Tablet [Link]
- External Links
- Human Metabolome Database
- HMDB0015009
- KEGG Compound
- C07129
- PubChem Compound
- 5403
- PubChem Substance
- 46506887
- ChemSpider
- 5210
- BindingDB
- 25770
- 10368
- ChEBI
- 9449
- ChEMBL
- CHEMBL1760
- Therapeutic Targets Database
- DAP000246
- PharmGKB
- PA451616
- Guide to Pharmacology
- GtP Drug Page
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Terbutaline
- MSDS
- Download (73.1 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Not Available Severe Chronic Obstructive Pulmonary Disease 1 4 Completed Treatment Asthma 1 4 Completed Treatment Heart Failure 1 4 Completed Treatment Status Asthmaticus 1 4 Terminated Treatment External Cephalic Version 1 4 Unknown Status Not Available Asthma 1 4 Unknown Status Treatment Pain, Labor 1 3 Completed Basic Science Asthma 1 3 Completed Treatment Acute Exacerbation of Chronic Obstructive Airways Disease 1 3 Completed Treatment Asthma 9
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 Aerosol, powder Respiratory (inhalation) 0.5 mg/mg Powder, metered Respiratory (inhalation) Injection, solution Parenteral 0.5 mg/ml Solution Respiratory (inhalation) 2.5 mg Aerosol Respiratory (inhalation) 10 mg Solution Respiratory (inhalation) 10 mg Aerosol, powder Respiratory (inhalation) 0.41 mg/0.5mg Powder Respiratory (inhalation) Powder, metered Respiratory (inhalation) 0.5 mg / act Powder Respiratory (inhalation) 100 mg Aerosol; solution Respiratory (inhalation) 2.5 mg/ml Syrup Oral Syrup Oral 100 mg Syrup Oral Solution Respiratory (inhalation) Injection Subcutaneous Solution Oral 30 mg Solution Intravenous; Subcutaneous 0.5 mg Syrup Oral 30 mg Capsule, extended release Oral 7.5 mg Solution Parenteral 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 Tablet Oral Injection, solution 0.5 mg/1ml Solution 0.5 mg/1ml Tablet Tablet Oral 2.5 mg Elixir Tablet Oral 5 mg Solution Tablet, film coated 2.5 mg Tablet, coated Oral Suspension Syrup Oral 1.5 mg/5ml - 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) 247 Encyclopedia of Toxicology (Third Edition) water solubility 1 g/1.5 mL Encyclopedia of Toxicology (Third Edition) logP 0.90 TACAKS-NOVAK,K ET AL. (1995) Caco2 permeability -6.38 ADME Research, USCD - Predicted Properties
Property Value Source logP 0.44 ChemAxon 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
Targets
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- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Stevenson RS, Thompson GW, Wilkinson M, Murphy DA, Armour JA: Neuronally induced augmentation of cardiac output. Can J Cardiol. 1999 Dec;15(12):1361-6. [Article]
- Nakamura A, Johns EJ, Imaizumi A, Yanagawa Y, Kohsaka T: Modulation of interleukin-6 by beta2-adrenoceptor in endotoxin-stimulated renal macrophage cells. Kidney Int. 1999 Sep;56(3):839-49. doi: 10.1046/j.1523-1755.1999.00630.x. [Article]
- Adding LC, Agvald P, Artlich A, Persson MG, Gustafsson LE: Beta-adrenoceptor agonist stimulation of pulmonary nitric oxide production in the rabbit. Br J Pharmacol. 1999 Feb;126(3):833-9. doi: 10.1038/sj.bjp.0702369. [Article]
- Scott MG, Swan C, Jobson TM, Rees S, Hall IP: Effects of a range of beta2 adrenoceptor agonists on changes in intracellular cyclic AMP and on cyclic AMP driven gene expression in cultured human airway smooth muscle cells. Br J Pharmacol. 1999 Oct;128(3):721-9. doi: 10.1038/sj.bjp.0702829. [Article]
- Lulich KM, Mitchell HW, Sparrow MP: The cat lung strip as an in vitro preparation of peripheral airways: a comparison of beta-adrenoceptor agonists, autacoids and anaphylactic challenge on the lung strip and trachea. Br J Pharmacol. 1976 Sep;58(1):71-9. doi: 10.1111/j.1476-5381.1976.tb07694.x. [Article]
- Ha TN, Posterino GS, Fryer MW: Effects of terbutaline on force and intracellular calcium in slow-twitch skeletal muscle fibres of the rat. Br J Pharmacol. 1999 Apr;126(8):1717-24. doi: 10.1038/sj.bjp.0702482. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
Enzymes
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Sulfotransferase activity
- Specific Function
- Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfonation of steroids and bile acids in the liver and adrenal glands.
Components:
References
- Davies M, Peramuhendige P, King L, Golding M, Kotian A, Penney M, Shah S, Manevski N: Evaluation of In Vitro Models for Assessment of Human Intestinal Metabolism in Drug Discovery. Drug Metab Dispos. 2020 Nov;48(11):1169-1182. doi: 10.1124/dmd.120.000111. Epub 2020 Aug 29. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid binding
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Components:
References
- Davies M, Peramuhendige P, King L, Golding M, Kotian A, Penney M, Shah S, Manevski N: Evaluation of In Vitro Models for Assessment of Human Intestinal Metabolism in Drug Discovery. Drug Metab Dispos. 2020 Nov;48(11):1169-1182. doi: 10.1124/dmd.120.000111. Epub 2020 Aug 29. [Article]
- 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. [Article]
- Kovarik Z, Radic Z, Grgas B, Skrinjaric-Spoljar M, Reiner E, Simeon-Rudolf V: Amino acid residues involved in the interaction of acetylcholinesterase and butyrylcholinesterase with the carbamates Ro 02-0683 and bambuterol, and with terbutaline. Biochim Biophys Acta. 1999 Aug 17;1433(1-2):261-71. doi: 10.1016/s0167-4838(99)00124-7. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Symporter activity
- Specific Function
- Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
- Gene Name
- SLC22A5
- Uniprot ID
- O76082
- Uniprot Name
- Solute carrier family 22 member 5
- Molecular Weight
- 62751.08 Da
References
- Ito N, Ito K, Ikebuchi Y, Kito T, Miyata H, Toyoda Y, Takada T, Hisaka A, Honma M, Oka A, Kusuhara H, Suzuki H: Organic cation transporter/solute carrier family 22a is involved in drug transfer into milk in mice. J Pharm Sci. 2014 Oct;103(10):3342-8. doi: 10.1002/jps.24138. Epub 2014 Aug 29. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Quaternary ammonium group transmembrane transporter activity
- Specific Function
- Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
- Gene Name
- SLC22A2
- Uniprot ID
- O15244
- Uniprot Name
- Solute carrier family 22 member 2
- Molecular Weight
- 62579.99 Da
References
- Ito N, Ito K, Ikebuchi Y, Kito T, Miyata H, Toyoda Y, Takada T, Hisaka A, Honma M, Oka A, Kusuhara H, Suzuki H: Organic cation transporter/solute carrier family 22a is involved in drug transfer into milk in mice. J Pharm Sci. 2014 Oct;103(10):3342-8. doi: 10.1002/jps.24138. Epub 2014 Aug 29. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 28, 2022 22:35