Details
Stereochemistry | RACEMIC |
Molecular Formula | C12H19NO3 |
Molecular Weight | 225.2842 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1
InChI
InChIKey=XWTYSIMOBUGWOL-UHFFFAOYSA-N
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
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 |
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 |
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 |
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) Health Status: unhealthy Age Group: 56 years (range: 44-68 years) Sex: M+F Sources: |
Other AEs: Tremor, Palpitation... |
10 ug/kg single, intravenous Dose: 10 ug/kg Route: intravenous Route: single Dose: 10 ug/kg Sources: |
unhealthy, 9.1 years Health Status: unhealthy Age Group: 9.1 years Sex: M+F Sources: |
Other AEs: Cardiotoxicity... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Systolic murmur | 1 patient | 2 mg single, transdermal Overdose |
unhealthy, 15 years |
Tachycardia | 1 patient | 2 mg single, transdermal Overdose |
unhealthy, 15 years |
Tremor | 1 patient | 2 mg single, transdermal Overdose |
unhealthy, 15 years |
Abdominal pain | 1 patient | 50 mg single, oral Overdose |
pregnant, 21 years |
Jitteriness | 1 patient | 50 mg single, oral Overdose |
pregnant, 21 years |
Palpitations | 1 patient | 50 mg single, oral Overdose |
pregnant, 21 years |
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 |
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) Health Status: unhealthy Age Group: 56 years (range: 44-68 years) Sex: M+F 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) Health Status: unhealthy Age Group: 56 years (range: 44-68 years) Sex: M+F Sources: |
|
Cardiotoxicity | 3 patients | 10 ug/kg single, intravenous Dose: 10 ug/kg Route: intravenous Route: single Dose: 10 ug/kg Sources: |
unhealthy, 9.1 years Health Status: unhealthy Age Group: 9.1 years Sex: M+F Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Functional, biochemical and molecular biological evidence for a possible beta(3)-adrenoceptor in human near-term myometrium. | 2000 Aug |
|
Choices of therapy for exercise-induced asthma in children. | 2001 |
|
Nocturnal asthma uncontrolled by inhaled corticosteroids: theophylline or long-acting beta2 agonists? | 2001 |
|
beta2-Adrenoceptor desensitization in human alveolar macrophages induced by inhaled terbutaline in vivo is not counteracted by budesonide. | 2001 Apr |
|
Interaction between beta-adrenergic signaling and protein kinase C increases cytoplasmic Ca2+ in alveolar type II cells. | 2001 Apr 13 |
|
Formoterol in clinical practice--safety issues. | 2001 Aug |
|
Formoterol used as needed--clinical effectiveness. | 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 |
|
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 |
|
Effects of the perfusion of beta-, beta2-, or beta3-adrenergic agonists or epinephrine on in situ adipose tissue lipolysis measured by microdialysis in underfed ewes. | 2001 Feb |
|
Involvement of beta1- and beta2- but not beta3-adrenoceptor activation in adrenergic PYY secretion from the isolated colon. | 2001 Jan |
|
Denopamine, a beta(1)-adrenergic agonist, increases alveolar fluid clearance in ex vivo rat and guinea pig lungs. | 2001 Jan |
|
Beta1-adrenoceptor stimulation by high-dose terbutaline downregulates terbutaline-stimulated alveolar fluid clearance in ex vivo rat lung. | 2001 Jul-Aug |
|
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 |
|
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 |
|
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 |
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
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N8ONU3L3PG
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NCI_THESAURUS |
C48149
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R03CC53
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R03AC03
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QR03CC03
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938
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QR03CC53
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QR03AC03
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NCI_THESAURUS |
C319
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Terbutaline
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TERBUTALINE
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DB00871
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9449
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D013726
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m10572
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PRIMARY | Merck Index |
Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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TARGET -> AGONIST | |||
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SALT/SOLVATE -> PARENT |
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PRODRUG -> METABOLITE ACTIVE |
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METABOLITE -> PARENT |
MAJOR
URINE
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METABOLITE -> PARENT |
MAJOR
URINE
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METABOLITE -> PARENT |
MAJOR
URINE
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METABOLITE -> PARENT |
MAJOR
URINE
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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