Terbutaline

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
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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatAsthmaCombination Product in combination with: Guaifenesin (DB00874)••••••••••••••••••••••
Treatment ofBronchospasm•••••••••••••••••••••• ••••••
Prevention ofBronchospasm•••••••••••••••••••••• ••••••
Used in combination for symptomatic treatment ofBronchospasmCombination Product in combination with: Guaifenesin (DB00874)•••••••••••••••••
Used in combination to treatBronchospasmCombination Product in combination with: Guaifenesin (DB00874)••••••••••••••••••• ••••••
Associated Therapies
Contraindications & Blackbox Warnings
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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

TargetActionsOrganism
ABeta-2 adrenergic receptor
agonist
Humans
UBeta-3 adrenergic receptor
agonist
Humans
UBeta-1 adrenergic receptor
antagonist
Humans
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
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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.
DrugInteraction
AbacavirTerbutaline may decrease the excretion rate of Abacavir which could result in a higher serum level.
AcebutololThe therapeutic efficacy of Terbutaline can be decreased when used in combination with Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Terbutaline is combined with Aceclofenac.
AcemetacinThe risk or severity of hypertension can be increased when Terbutaline is combined with Acemetacin.
AcetaminophenAcetaminophen may decrease the excretion rate of Terbutaline which could result in a higher serum level.
Food Interactions
No interactions found.

Products

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dosage, form, labeller, route of administration, and marketing period.
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Product Ingredients
IngredientUNIICASInChI Key
Terbutaline sulfate576PU70Y8E23031-32-5KFVSLSTULZVNPG-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
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Bricanyl Tab 2.5 mgTablet2.5 mgOralAstra Zeneca1978-12-312000-07-20Canada flag
Bricanyl Tab 5 mgTablet5 mgOralAstra Zeneca1975-12-312001-07-23Canada flag
Bricanyl TurbuhalerPowder, metered0.5 mg / actRespiratory (inhalation)Astra Zeneca1990-12-31Not applicableCanada flag
Truemed Group LLCTablet5 mg/5mgOralTruemed Group LLC2022-09-17Not applicableUS flag
Truemed Group LLCInjection, powder, for solution1 mg/1mgIntramuscularTruemed Group LLC2022-09-17Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Terbutaline SulfateTablet2.5 mg/1OralAv Kare, Inc.2001-06-262015-12-09US flag
Terbutaline SulfateTablet5 mg/1OralChartwell Rx, Llc.2005-03-25Not applicableUS flag
Terbutaline SulfateTablet5 mg/1OralAmneal Pharmaceuticals of New York Llc2001-06-26Not applicableUS flag
Terbutaline SulfateInjection1 mg/1mLSubcutaneousUnited Biomedical Inc., Asia2014-12-15Not applicableUS flag
Terbutaline SulfateInjection, solution1 mg/1mLSubcutaneousGeneral Injectables & Vaccines, Inc2011-11-162024-03-31US flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ASMALIN SYRUP 1.5 mg/5 mlSyrup1.5 mg/5mlOralSUNWARD PHARMACEUTICAL PRIVATE LIMITED1992-12-06Not applicableSingapore flag
ASMALIN TABLET 2.5 mgTablet2.5 mgOralSUNWARD PHARMACEUTICAL PRIVATE LIMITED1991-08-07Not applicableSingapore flag
BUTYLIN SYRUP 1.5 mg/5 mlSyrup1.5 mg/5mlOralGOLDPLUS UNIVERSAL PTE LTD1995-03-18Not applicableSingapore flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
BECONYL 1,5 MG + 66,5 MG / 5 ML ŞURUP, 100 MLTerbutaline sulfate (1.5 mg/5mL) + Guaifenesin (66.5 mg/5mL)SyrupOralABAY PHARMA SAĞLIK ÜRÜNLERİ SAN. VE TİC. A.Ş.2019-02-04Not applicableTurkey flag
BİCANA 1.5 MG/5 ML+66.5 MG/5 ML ŞURUP, 100 MLTerbutaline sulfate (1.5 mg/5ml) + Guaifenesin (66.5 mg/5ml)SyrupOralDROGSAN İLAÇLARI SAN. VE TİC. A.Ş.2019-11-05Not applicableTurkey flag
BRELAX 1,5 MG+66,5 MG/5 ML ŞURUP, 100 MLTerbutaline sulfate (1.5 mg/mL) + Guaifenesin (66.5 mg/mL)SyrupOralBİLİM İLAÇ SAN. VE TİC. A.Ş.2019-03-06Not applicableTurkey flag
BRICANYL EKSPEKTORAN SURUP, 100 MLTerbutaline sulfate (1.5 mg/5ml) + Guaifenesin (66.5 mg/5ml)SyrupOralASTRAZENECA İLAÇ SAN. VE TİC. LTD. ŞTİ.2000-01-21Not applicableTurkey flag
NASMINE N.F. JARABETerbutaline sulfate (30 mg) + Loratadine (100 mg) + Noscapine hydrochloride (50 mg)SyrupOralARBOFARMA S.A.S.2009-10-062021-10-01Colombia flag

Categories

ATC Codes
R03CC53 — Terbutaline, combinationsR03CC03 — TerbutalineR03AC03 — Terbutaline
Drug Categories
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
  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. [Article]
  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. [Article]
  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. [Article]
  4. 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]
  5. Nilsson HT, Persson K, Tegner K: The Metabolism of Terbutaline in Man Xenobiotica. 1972 Mar 16;2(4):363-373. [Article]
  6. Ripe E, Hornblad Y, Tegner K: Oral administration of terbutaline in asthmatic patients. Eur J Respir Dis Suppl. 1984;134:171-9. [Article]
  7. Tegner K, Nilsson HT, Persson CG, Persson K, Ryrfeldt A: Elimination pathways of terbutaline. Eur J Respir Dis Suppl. 1984;134:93-100. [Article]
  8. Nyberg L: Pharmacokinetic parameters of terbutaline in healthy man. An overview. Eur J Respir Dis Suppl. 1984;134:149-60. [Article]
  9. 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]
  10. Lee DC: Terbutaline sulfate overdose. Ann Emerg Med. 1995 Jul;26(1):107-8. doi: 10.1016/s0196-0644(95)70249-0. [Article]
  11. 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]
  12. 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]
  13. Sharma S, Hashmi MF, Chakraborty RK: Asthma Medications . [Article]
  14. Spiller H (2014). Terbutaline. In Encyclopedia of Toxicology (Third Edition) (3rd ed., pp. 484-485). Elsevier. [ISBN:978-0-12-386455-0]
  15. FDA Approved Drug Products: Bricanyl (Terbutaline Sulfate) Injection [Link]
  16. Dailymed: Terbutaline Sulfate Subcutaneous Injection [Link]
  17. Dailymed: Terbutaline Sulfate Oral Tablet [Link]
Human Metabolome Database
HMDB0015009
KEGG Compound
C07129
PubChem Compound
5403
PubChem Substance
46506887
ChemSpider
5210
BindingDB
25770
RxNav
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
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableSevere Chronic Obstructive Pulmonary Disease1
4CompletedTreatmentAsthma1
4CompletedTreatmentHeart Failure1
4CompletedTreatmentStatus Asthmaticus1
4TerminatedTreatmentExternal Cephalic Version1

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
FormRouteStrength
Aerosol, powderRespiratory (inhalation)0.5 mg/mg
Powder, meteredRespiratory (inhalation)
Injection, solutionParenteral0.5 mg/ml
SolutionRespiratory (inhalation)2.5 mg
AerosolRespiratory (inhalation)10 mg
Aerosol, powderRespiratory (inhalation)0.41 mg/0.5mg
PowderRespiratory (inhalation)
Powder, meteredRespiratory (inhalation)0.5 mg / act
PowderRespiratory (inhalation)100 mg
Aerosol; solutionRespiratory (inhalation)2.5 mg/ml
SyrupOral
SyrupOral
SolutionRespiratory (inhalation)
InjectionSubcutaneous
SolutionOral30 mg
SolutionIntravenous; Subcutaneous0.5 mg
SyrupOral30 mg
Capsule, extended releaseOral7.5 mg
SolutionRespiratory (inhalation)10 mg
SolutionParenteral0.5 mg
InjectionSubcutaneous1 mg/1mL
Injection, solutionSubcutaneous1 mg/1mL
TabletOral2.5 mg/1
TabletOral5 mg/1
TabletOral
Injection, powder, for solutionIntramuscular1 mg/1mg
TabletOral5 mg/5mg
Injection, solution0.5 mg/1ml
Solution0.5 mg/1ml
Tablet
TabletOral2.5 mg
Elixir
TabletOral5 mg
Solution
Tablet, film coated2.5 mg
Tablet, coatedOral
Suspension
SyrupOral1.5 mg/5ml
Prices
Unit descriptionCostUnit
Terbutaline sulfate powder38.4USD g
Terbutaline Sulfate 1 mg/ml vial12.99USD vial
Terbutaline sulf 1 mg/ml vial4.8USD ml
Brethine 5 mg tablet0.83USD tablet
Terbutaline sulfate 5 mg tablet0.63USD tablet
Brethine 2.5 mg tablet0.57USD tablet
Terbutaline sulfate 2.5 mg tablet0.47USD tablet
Bricanyl Turbuhaler 0.5 mg/dose Metered Inhalation Powder0.08USD dose
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)247Encyclopedia of Toxicology (Third Edition)
water solubility1 g/1.5 mLEncyclopedia of Toxicology (Third Edition)
logP0.90TACAKS-NOVAK,K ET AL. (1995)
Caco2 permeability-6.38ADME Research, USCD
Predicted Properties
PropertyValueSource
logP0.44Chemaxon
pKa (Strongest Acidic)8.86Chemaxon
pKa (Strongest Basic)9.76Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area72.72 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity63.04 m3·mol-1Chemaxon
Polarizability24.78 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.987
Blood Brain Barrier-0.9355
Caco-2 permeable-0.8404
P-glycoprotein substrateSubstrate0.6335
P-glycoprotein inhibitor INon-inhibitor0.8954
P-glycoprotein inhibitor IINon-inhibitor0.9672
Renal organic cation transporterNon-inhibitor0.9067
CYP450 2C9 substrateNon-substrate0.7678
CYP450 2D6 substrateNon-substrate0.7922
CYP450 3A4 substrateNon-substrate0.6291
CYP450 1A2 substrateNon-inhibitor0.9516
CYP450 2C9 inhibitorNon-inhibitor0.9303
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.9115
CYP450 3A4 inhibitorNon-inhibitor0.8766
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9117
Ames testNon AMES toxic0.9119
CarcinogenicityNon-carcinogens0.8484
BiodegradationNot ready biodegradable0.9808
Rat acute toxicity2.1080 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9548
hERG inhibition (predictor II)Non-inhibitor0.9467
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-000i-9600000000-883d61ad257dffc64a5d
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0290000000-8c26dbc913131cf49bc4
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0900000000-3148282c5452a80b16c3
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0900000000-9122151a6e70e6f2b536
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-004i-0090000000-aab7f309385309d8884b
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-0920000000-1e85cd2bf4a0358c22d7
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-0900000000-82b70479a4e38921e06b
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-2900000000-aff994ffd107ef3b6e71
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a6r-7900000000-cfe77aa0133facea1c75
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-0udi-0900000000-1a0ccd393797b19105a0
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0190000000-f9271bb736a512dbdbab
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0900000000-a70c8697ca7633839444
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a6r-1900000000-4a9c0ddb9af4ce93b4ae
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a6r-6900000000-0cc68c4a50196d6ffab6
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-9400000000-e1cec349ffb2fcd3ebe2
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-acec7d209f90cccc572b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0090000000-66224d689d8eaa3dc0d3
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-3900000000-07ac2fe38be94e1555c8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00dr-1940000000-15e56999a3e89ad96ee3
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9200000000-ac1be744c4ca43379d48
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-052b-9700000000-13230bd34ff7617c2a47
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-acec7d209f90cccc572b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0090000000-66224d689d8eaa3dc0d3
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-3900000000-07ac2fe38be94e1555c8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00dr-1940000000-15e56999a3e89ad96ee3
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9200000000-ac1be744c4ca43379d48
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-052b-9700000000-13230bd34ff7617c2a47
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-163.9607946
predicted
DarkChem Lite v0.1.0
[M-H]-151.51012
predicted
DeepCCS 1.0 (2019)
[M-H]-163.9607946
predicted
DarkChem Lite v0.1.0
[M-H]-163.9607946
predicted
DarkChem Lite v0.1.0
[M-H]-151.51012
predicted
DeepCCS 1.0 (2019)
[M-H]-151.51012
predicted
DeepCCS 1.0 (2019)
[M+H]+164.4871946
predicted
DarkChem Lite v0.1.0
[M+H]+153.86813
predicted
DeepCCS 1.0 (2019)
[M+H]+164.4871946
predicted
DarkChem Lite v0.1.0
[M+H]+164.4871946
predicted
DarkChem Lite v0.1.0
[M+H]+153.86813
predicted
DeepCCS 1.0 (2019)
[M+H]+153.86813
predicted
DeepCCS 1.0 (2019)
[M+Na]+164.2764946
predicted
DarkChem Lite v0.1.0
[M+Na]+159.96138
predicted
DeepCCS 1.0 (2019)
[M+Na]+164.2764946
predicted
DarkChem Lite v0.1.0
[M+Na]+164.2764946
predicted
DarkChem Lite v0.1.0
[M+Na]+159.96138
predicted
DeepCCS 1.0 (2019)
[M+Na]+159.96138
predicted
DeepCCS 1.0 (2019)

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
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  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. 2011 Jan;25(1):59-66. doi: 10.1016/j.bbi.2010.07.248. Epub 2010 Jul 30. [Article]
  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. doi: 10.2337/dc08-0520. Epub 2008 Sep 9. [Article]
  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. [Article]
  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. [Article]
  11. 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]
  12. 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]
  13. 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]
  14. 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]
  15. 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]
  16. 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
  1. 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]
  2. 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
  1. 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
  1. 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
  1. 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
  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. [Article]
  2. 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
  1. 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
  1. 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 March 28, 2024 03:23