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 |
---|---|---|
Systemic capillary leak syndrome preceding plasma cell leukaemia. | 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 |
|
Age- and gender-specific asthma death rates in patients taking long-acting beta2-agonists: prescription event monitoring pharmacosurveillance studies. | 2001 |
|
Interaction between beta-adrenergic signaling and protein kinase C increases cytoplasmic Ca2+ in alveolar type II cells. | 2001 Apr 13 |
|
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 |
|
Formoterol in clinical practice--safety issues. | 2001 Aug |
|
Formoterol used as needed--clinical effectiveness. | 2001 Aug |
|
Chiral separation of beta2-agonists by capillary electrophoresis using hydroxypropyl-alpha-cyclodextrin as a chiral selector. | 2001 Aug |
|
Antenatal terbutaline administration decreases the lung hyaluronan concentration in preterm rabbit pups. | 2001 Aug |
|
Antibacterial activity of apical surface fluid from the human airway cell line Calu-3: pharmacologic alteration by corticosteroids and beta(2)-agonists. | 2001 Aug |
|
Discriminative capacity of bronchodilator response measured with three different lung function techniques in asthmatic and healthy children aged 2 to 5 years. | 2001 Aug 15 |
|
Off-label prescribing and the standard of care. | 2001 Aug 20 |
|
Beta-adrenoceptor-mediated cell signaling in the neonatal heart and liver: responses to terbutaline. | 2001 Dec |
|
Regulation of SP-B and SP-C secretion in rat type II cells in primary culture. | 2001 Dec |
|
Efficacy and safety of Ascoril in the management of cough--National Study Group report. | 2001 Feb |
|
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 |
|
Use of vancomycin silica stationary phase in packed capillary electrochromatography I. Enantiomer separation of basic compounds. | 2001 Feb |
|
Brittle asthma: a separate clinical phenotype of asthma? | 2001 Jan-Mar |
|
Can asthma treatment in sports be doping? The effect of the rapid onset, long-acting inhaled beta2-agonist formoterol upon endurance performance in healthy well-trained athletes. | 2001 Jul |
|
The effect of the beta(2) adrenoceptor gene Thr164Ile polymorphism on human adipose tissue lipolytic function. | 2001 Jul |
|
Determination of the optical purity of (R)-terbutaline by 1H-NMR and RP-LC using chiral derivatizing agent, (S)-(-)-alpha-methylbenzyl isocyanate. | 2001 Jul |
|
Beta1-adrenoceptor stimulation by high-dose terbutaline downregulates terbutaline-stimulated alveolar fluid clearance in ex vivo rat lung. | 2001 Jul-Aug |
|
Protection against cold air and exercise-induced bronchoconstriction while on regular treatment with Oxis. | 2001 Jun |
|
Does the mode of inhalation affect the bronchodilator response in patients with severe COPD? | 2001 Jun |
|
Adrenergic regulation of ion transport across adult alveolar epithelial cells: effects on Cl- channel activation and transport function in cultures with an apical air interface. | 2001 Jun 1 |
|
The Ile164 beta(2)-adrenoceptor polymorphism alters salmeterol exosite binding and conventional agonist coupling to G(s). | 2001 Jun 15 |
|
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 |
|
On-demand relief treatment for asthma. | 2001 Jun 9 |
|
Comparison of the acute effects of salbutamol and terbutaline on heart rate variability in adult asthmatic patients. | 2001 May |
|
[Local necrosis of finger following stab with needle used to pump terbutaline sulfate (Bricalin)]. | 2001 May |
|
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 |
|
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 |
|
Activation of beta(2)-adrenoceptor prevents shiga toxin 2-induced TNF-alpha gene transcription. | 2001 Nov |
|
Beta-adrenoceptor signaling in the developing brain: sensitization or desensitization in response to terbutaline. | 2001 Nov 26 |
|
[Japanese guideline for the diagnosis and management of bronchial asthma (1998)--its results and reversion]. | 2001 Oct |
|
Perinatal factors associated with severe intracranial hemorrhage. | 2001 Oct |
|
Sulindac to prevent recurrent preterm labor: a randomized controlled trial. | 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 single dose of nebulized budesonide decreases exhaled nitric oxide in children with acute asthma. | 2001 Sep |
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
by
admin
on
Edited
Fri Dec 15 17:58:22 GMT 2023
by
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on
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Record UNII |
576PU70Y8E
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Record Status |
Validated (UNII)
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Record Version |
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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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10369
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DTXSID3045437
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576PU70Y8E
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SUB04724MIG
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576PU70Y8E
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1643500
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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 |