Details
Stereochemistry | RACEMIC |
Molecular Formula | 2C12H19NO3.H2O4S |
Molecular Weight | 548.647 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OS(O)(=O)=O.CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1.CC(C)(C)NCC(O)C2=CC(O)=CC(O)=C2
InChI
InChIKey=KFVSLSTULZVNPG-UHFFFAOYSA-N
InChI=1S/2C12H19NO3.H2O4S/c2*1-12(2,3)13-7-11(16)8-4-9(14)6-10(15)5-8;1-5(2,3)4/h2*4-6,11,13-16H,7H2,1-3H3;(H2,1,2,3,4)
Molecular Formula | H2O4S |
Molecular Weight | 98.078 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C12H19NO3 |
Molecular Weight | 225.2842 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
DescriptionSources: http://www.drugbank.ca/drugs/DB00871Curator's Comment: Description was created based on several sources, including
Sources: http://www.drugbank.ca/drugs/DB00871
Curator's Comment: Description was created based on several sources, including
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. 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. Terbutaline is used 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.
CNS Activity
Sources: http://www.drugbank.ca/drugs/DB00871
Curator's Comment: may cause some cardiostimulatory effects and CNS stimulation.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL210 Sources: http://www.drugbank.ca/drugs/DB00871 |
3.16 µM [EC50] | ||
Target ID: GO:0006171 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10516654 |
2.3 µM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Sources: https://www.drugs.com/pro/terbutaline.html |
Preventing | Terbutaline SULFATE Approved Useindicated for the prevention and reversal of bronchospasm in patients 12 years of age and older with asthma and reversible bronchospasm associated with bronchitis and emphysema. Launch Date2014 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
24 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2706188/ |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
TERBUTALINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
148.6 nM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2706188/ |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
TERBUTALINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
13.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2706188/ |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
TERBUTALINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
2 mg single, transdermal Overdose |
unhealthy, 15 years n = 1 Health Status: unhealthy Age Group: 15 years Sex: M Population Size: 1 Sources: |
Other AEs: Tachycardia, Systolic murmur... Other AEs: Tachycardia (1 patient) Sources: Systolic murmur (1 patient) Tremor (1 patient) |
50 mg single, oral Overdose |
pregnant, 21 years n = 1 Health Status: pregnant Age Group: 21 years Sex: F Population Size: 1 Sources: |
Other AEs: Abdominal pain, Jitteriness... Other AEs: Abdominal pain (1 patient) Sources: Jitteriness (1 patient) Palpitations (1 patient) |
500 mg single, oral Overdose |
unhealthy, 22 years |
Other AEs: Nausea, Tachycardia... Other AEs: Nausea (1 patient) Sources: Tachycardia (1 patient) Tremor (1 patient) Hyperglycemia (1 patient) Hypokalemia (1 patient) |
2.5 mg single, subcutaneous Overdose Dose: 2.5 mg Route: subcutaneous Route: single Dose: 2.5 mg Sources: |
pregnant, 35 years n = 1 Health Status: pregnant Age Group: 35 years Sex: F Population Size: 1 Sources: |
Other AEs: Tachycardia... |
10 mg 3 times / day multiple, oral Highest studied dose Dose: 10 mg, 3 times / day Route: oral Route: multiple Dose: 10 mg, 3 times / day Sources: |
unhealthy, 56 years (range: 44-68 years) n = 12 Health Status: unhealthy Condition: bronchial asthma Age Group: 56 years (range: 44-68 years) Sex: M+F Population Size: 12 Sources: |
Other AEs: Tremor, Palpitation... |
10 ug/kg single, intravenous (starting) Dose: 10 ug/kg Route: intravenous Route: single Dose: 10 ug/kg Sources: |
unhealthy, 9.1 years n = 29 Health Status: unhealthy Condition: severe asthma Age Group: 9.1 years Sex: M+F Population Size: 29 Sources: |
Other AEs: Cardiotoxicity... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Systolic murmur | 1 patient | 2 mg single, transdermal Overdose |
unhealthy, 15 years n = 1 Health Status: unhealthy Age Group: 15 years Sex: M Population Size: 1 Sources: |
Tachycardia | 1 patient | 2 mg single, transdermal Overdose |
unhealthy, 15 years n = 1 Health Status: unhealthy Age Group: 15 years Sex: M Population Size: 1 Sources: |
Tremor | 1 patient | 2 mg single, transdermal Overdose |
unhealthy, 15 years n = 1 Health Status: unhealthy Age Group: 15 years Sex: M Population Size: 1 Sources: |
Abdominal pain | 1 patient | 50 mg single, oral Overdose |
pregnant, 21 years n = 1 Health Status: pregnant Age Group: 21 years Sex: F Population Size: 1 Sources: |
Jitteriness | 1 patient | 50 mg single, oral Overdose |
pregnant, 21 years n = 1 Health Status: pregnant Age Group: 21 years Sex: F Population Size: 1 Sources: |
Palpitations | 1 patient | 50 mg single, oral Overdose |
pregnant, 21 years n = 1 Health Status: pregnant Age Group: 21 years Sex: F Population Size: 1 Sources: |
Hyperglycemia | 1 patient | 500 mg single, oral Overdose |
unhealthy, 22 years |
Hypokalemia | 1 patient | 500 mg single, oral Overdose |
unhealthy, 22 years |
Nausea | 1 patient | 500 mg single, oral Overdose |
unhealthy, 22 years |
Tachycardia | 1 patient | 500 mg single, oral Overdose |
unhealthy, 22 years |
Tremor | 1 patient | 500 mg single, oral Overdose |
unhealthy, 22 years |
Tachycardia | 1 patient | 2.5 mg single, subcutaneous Overdose Dose: 2.5 mg Route: subcutaneous Route: single Dose: 2.5 mg Sources: |
pregnant, 35 years n = 1 Health Status: pregnant Age Group: 35 years Sex: F Population Size: 1 Sources: |
Palpitation | 10 mg 3 times / day multiple, oral Highest studied dose Dose: 10 mg, 3 times / day Route: oral Route: multiple Dose: 10 mg, 3 times / day Sources: |
unhealthy, 56 years (range: 44-68 years) n = 12 Health Status: unhealthy Condition: bronchial asthma Age Group: 56 years (range: 44-68 years) Sex: M+F Population Size: 12 Sources: |
|
Tremor | 10 mg 3 times / day multiple, oral Highest studied dose Dose: 10 mg, 3 times / day Route: oral Route: multiple Dose: 10 mg, 3 times / day Sources: |
unhealthy, 56 years (range: 44-68 years) n = 12 Health Status: unhealthy Condition: bronchial asthma Age Group: 56 years (range: 44-68 years) Sex: M+F Population Size: 12 Sources: |
|
Cardiotoxicity | 3 patients | 10 ug/kg single, intravenous (starting) Dose: 10 ug/kg Route: intravenous Route: single Dose: 10 ug/kg Sources: |
unhealthy, 9.1 years n = 29 Health Status: unhealthy Condition: severe asthma Age Group: 9.1 years Sex: M+F Population Size: 29 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Enhanced responsiveness of the myocardial beta-adrenoceptor-adenylate cyclase system in the perfused rat heart (I). | 1998 Oct |
|
Functional, biochemical and molecular biological evidence for a possible beta(3)-adrenoceptor in human near-term myometrium. | 2000 Aug |
|
beta(2)-adrenoceptor agonist suppresses renal tumour necrosis factor and enhances interleukin-6 gene expression induced by endotoxin. | 2000 Dec |
|
L-Dopa uptake and dopamine production in proximal tubular cells are regulated by beta(2)-adrenergic receptors. | 2000 Jul |
|
Systemic capillary leak syndrome preceding plasma cell leukaemia. | 2001 |
|
Bronchodilators for the prevention and treatment of chronic lung disease in preterm infants. | 2001 |
|
Alveolar epithelial type II cell: defender of the alveolus revisited. | 2001 |
|
Treatment of fetal congenital complete heart block with maternal administration of beta-sympathomimetics (terbutaline): a case report. | 2001 |
|
Long-acting beta-agonist treatment in patients with persistent asthma already receiving inhaled corticosteroids. | 2001 |
|
Choices of therapy for exercise-induced asthma in children. | 2001 |
|
Inhaled short-acting beta2-agonists versus ipratropium for acute exacerbations of chronic obstructive pulmonary disease. | 2001 |
|
Nocturnal asthma uncontrolled by inhaled corticosteroids: theophylline or long-acting beta2 agonists? | 2001 |
|
Profile of ligand binding to the porcine beta2-adrenergic receptor. | 2001 Apr |
|
Glucocorticoid enhances the response of type II cells from newborn rats to surfactant secretagogues. | 2001 Apr 30 |
|
Improved preparative-scale. continuous, free-flow electrophoretic separation of the enantiomers of terbutaline utilizing equal-but-opposite enantiomer mobilities. | 2001 Aug |
|
Pharmacological similarities and differences between beta2-agonists. | 2001 Aug |
|
Off-label prescribing and the standard of care. | 2001 Aug 20 |
|
Regulation of SP-B and SP-C secretion in rat type II cells in primary culture. | 2001 Dec |
|
Quantitative determination of clenbuterol, salbutamol and tulobuterol enantiomers by capillary electrophoresis. | 2001 Feb |
|
Beta1-adrenergic agonist is a potent stimulator of alveolar fluid clearance in hyperoxic rat lungs. | 2001 Feb |
|
Intraocular pressure-lowering activity and in vivo disposition of dipivalyl terbutalone in rabbits. | 2001 Feb |
|
Blunted cardiac responses to receptor activation in subjects with Thr164Ile beta(2)-adrenoceptors. | 2001 Feb 27 |
|
A single bout of exercise induces beta-adrenergic desensitization in human adipose tissue. | 2001 Jan |
|
Brittle asthma: a separate clinical phenotype of asthma? | 2001 Jan-Mar |
|
The effect of the beta(2) adrenoceptor gene Thr164Ile polymorphism on human adipose tissue lipolytic function. | 2001 Jul |
|
Attenuation of insulin resistance by chronic beta2-adrenergic agonist treatment possible muscle specific contributions. | 2001 Jun 22 |
|
On-demand relief treatment for asthma. | 2001 Jun 9 |
|
The effectiveness of high-dose inhaled budesonide therapy in the treatment of acute asthma exacerbations in children. | 2001 Mar |
|
The essential role of cytosolic Cl- in Ca2+ regulation of an amiloride-sensitive channel in fetal rat pneumocyte. | 2001 Mar 1 |
|
Tocolysis with nifedipine or beta-adrenergic agonists: a meta-analysis. | 2001 May |
|
The oxytocin antagonist atosiban versus the beta-agonist terbutaline in the treatment of preterm labor. A randomized, double-blind, controlled study. | 2001 May |
|
Effects of terbutaline on NGF formation in allergic inflammation of the rat. | 2001 May |
|
Pharmacological characterization of KUR-1246, a selective uterine relaxant. | 2001 May |
|
Alveolar epithelial barrier functions in ventilated perfused rabbit lungs. | 2001 May |
|
Efficacy of 'functional relaxation' in comparison to terbutaline and a 'placebo relaxation' method in patients with acute asthma. A randomized, prospective, placebo-controlled, crossover experimental investigation. | 2001 May-Jun |
|
Hypoxia reduces alveolar epithelial sodium and fluid transport in rats: reversal by beta-adrenergic agonist treatment. | 2001 Nov |
|
Beta-adrenoceptor signaling in the developing brain: sensitization or desensitization in response to terbutaline. | 2001 Nov 26 |
|
Sulindac to prevent recurrent preterm labor: a randomized controlled trial. | 2001 Oct |
|
Fatal adverse drug events: the paradox of drug treatment. | 2001 Oct |
|
Regulation of fetal cardiac and hepatic beta-adrenoceptors and adenylyl cyclase signaling: terbutaline effects. | 2001 Oct |
|
Fast enantiomeric separation of basis drugs by electrokinetic chromatography. Application to the quantitation of terbutaline in a pharmaceutical preparation. | 2001 Sep |
|
A cost-effectiveness study comparing the as-needed use of formoterol (Oxis) and terbutaline (Bricanyl) in patients with moderate to severe asthma. | 2001 Sep |
|
A single dose of nebulized budesonide decreases exhaled nitric oxide in children with acute asthma. | 2001 Sep |
|
An advanced and detailed in vitro validation procedure for the radiolabeling of carrier-free terbutaline sulphate dry powder. | 2001 Summer |
|
Pulmonary clearance rate of two chemically different forms of inhaled pertechnetate. | 2001 Summer |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/terbutaline.html
Usual Adult Dose for Asthma - Maintenance
Tablets: 5 mg orally 3 times a day at 6 hour intervals during waking hours. May decrease to 2.5 mg/dose if side effects are pronounced. Do not exceed 15 mg in 24 hours.
Inhalation aerosol: 2 inhalations separated by 60 seconds every 4 to 6 hours. Do not repeat more often than every 4 to 6 hours.
Usual Adult Dose for Asthma - Acute
Inhalation aerosol: 2 inhalations separated by 60 seconds every 4 to 6 hours. Do not repeat more often than every 4 to 6 hours.
Subcutaneous Injection: 0.25 mg into the lateral deltoid area. A second 0.25 mg dose can be administered in 15 to 30 minutes if needed. Do not exceed 0.5 mg in 4 hours.
Continuous intravenous infusion: 0.08 to 6 mcg/kg/min.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20012638
Terbutaline elicited a relaxation response in isolated rat's tracheal smooth muscle at a dose of 10(-6) M or more
Substance Class |
Chemical
Created
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Edited
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Record UNII |
576PU70Y8E
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Record Status |
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NCI_THESAURUS |
C48149
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NCI_THESAURUS |
C319
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100000084794
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m10572
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757336
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C47748
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23031-32-5
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DBSALT000297
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245-386-3
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CHEMBL1760
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576PU70Y8E
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1643500
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |
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IMPURITY -> PARENT |
sum of impurities other than C: not more than twice the area of the principal peak in the chromatogram obtained with reference solution (b) (0.4 per cent)
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
sum of impurities other than C: not more than twice the area of the principal peak in the chromatogram obtained with reference solution (b) (0.4 per cent)
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY |