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Details

Stereochemistry RACEMIC
Molecular Formula C12H19NO3
Molecular Weight 225.2846
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TERBUTALINE

SMILES

CC(C)(C)NCC(c1cc(cc(c1)O)O)O

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

HIDE SMILES / InChI

Molecular Formula C12H19NO3
Molecular Weight 225.2846
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
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

Curator's Comment:: may cause some cardiostimulatory effects and CNS stimulation.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.16 µM [EC50]
2.3 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Terbutaline SULFATE

Approved Use

indicated 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 Date

1.41851519E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
24 nM
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

AUC

ValueDoseCo-administeredAnalytePopulation
148.6 nM × h
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

T1/2

ValueDoseCo-administeredAnalytePopulation
13.7 h
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

Doses

DosePopulationAdverse events​
2 mg single, transdermal
Overdose
Dose: 2 mg
Route: transdermal
Route: single
Dose: 2 mg
Sources:
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)
Systolic murmur (1 patient)
Tremor (1 patient)
Sources:
50 mg single, oral
Overdose
Dose: 50 mg
Route: oral
Route: single
Dose: 50 mg
Sources:
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)
Jitteriness (1 patient)
Palpitations (1 patient)
Sources:
500 mg single, oral
Overdose
Dose: 500 mg
Route: oral
Route: single
Dose: 500 mg
Sources:
unhealthy, 22 years
Health Status: unhealthy
Age Group: 22 years
Sex: F
Sources:
Other AEs: Nausea, Tachycardia...
Other AEs:
Nausea (1 patient)
Tachycardia (1 patient)
Tremor (1 patient)
Hyperglycemia (1 patient)
Hypokalemia (1 patient)
Sources:
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...
Other AEs:
Tachycardia (1 patient)
Sources:
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...
Other AEs:
Tremor
Palpitation
Sources:
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...
Other AEs:
Cardiotoxicity (3 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Systolic murmur 1 patient
2 mg single, transdermal
Overdose
Dose: 2 mg
Route: transdermal
Route: single
Dose: 2 mg
Sources:
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
Dose: 2 mg
Route: transdermal
Route: single
Dose: 2 mg
Sources:
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
Dose: 2 mg
Route: transdermal
Route: single
Dose: 2 mg
Sources:
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
Dose: 50 mg
Route: oral
Route: single
Dose: 50 mg
Sources:
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
Dose: 50 mg
Route: oral
Route: single
Dose: 50 mg
Sources:
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
Dose: 50 mg
Route: oral
Route: single
Dose: 50 mg
Sources:
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
Dose: 500 mg
Route: oral
Route: single
Dose: 500 mg
Sources:
unhealthy, 22 years
Health Status: unhealthy
Age Group: 22 years
Sex: F
Sources:
Hypokalemia 1 patient
500 mg single, oral
Overdose
Dose: 500 mg
Route: oral
Route: single
Dose: 500 mg
Sources:
unhealthy, 22 years
Health Status: unhealthy
Age Group: 22 years
Sex: F
Sources:
Nausea 1 patient
500 mg single, oral
Overdose
Dose: 500 mg
Route: oral
Route: single
Dose: 500 mg
Sources:
unhealthy, 22 years
Health Status: unhealthy
Age Group: 22 years
Sex: F
Sources:
Tachycardia 1 patient
500 mg single, oral
Overdose
Dose: 500 mg
Route: oral
Route: single
Dose: 500 mg
Sources:
unhealthy, 22 years
Health Status: unhealthy
Age Group: 22 years
Sex: F
Sources:
Tremor 1 patient
500 mg single, oral
Overdose
Dose: 500 mg
Route: oral
Route: single
Dose: 500 mg
Sources:
unhealthy, 22 years
Health Status: unhealthy
Age Group: 22 years
Sex: F
Sources:
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:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Tox targets
PubMed

PubMed

TitleDatePubMed
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
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
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
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
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
[Long-acting beta 2-stimulants].
2001 Oct
[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
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
Lung deposition and protective effect of terbutaline delivered from pressurized metered-dose inhalers and the Turbuhaler in asthmatic individuals.
2001 Oct 15
Uterine contractility: vaginal administration of the beta-adrenergic agonist, terbutaline. Evidence of direct vagina-to-uterus transport.
2001 Sep
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
Patents

Sample Use Guides

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
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 Fri Jun 25 23:50:29 UTC 2021
Edited
by admin
on Fri Jun 25 23:50:29 UTC 2021
Record UNII
N8ONU3L3PG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TERBUTALINE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
TERBUTALIN
Common Name English
(RS)-5-(2-(TERT-BUTYLAMINO)-1-HYDROXYETHYL)BENZENE-1,3-DIOL
Systematic Name English
ASTHMASIAN
Brand Name English
TERBUTALINE [MI]
Common Name English
TERBUTALINE [WHO-DD]
Common Name English
TERBUTALINE [VANDF]
Common Name English
TERBUTALINE [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C48149
Created by admin on Fri Jun 25 23:50:29 UTC 2021 , Edited by admin on Fri Jun 25 23:50:29 UTC 2021
WHO-ATC R03CC53
Created by admin on Fri Jun 25 23:50:29 UTC 2021 , Edited by admin on Fri Jun 25 23:50:29 UTC 2021
WHO-ATC R03CC03
Created by admin on Fri Jun 25 23:50:29 UTC 2021 , Edited by admin on Fri Jun 25 23:50:29 UTC 2021
WHO-ATC R03AC03
Created by admin on Fri Jun 25 23:50:29 UTC 2021 , Edited by admin on Fri Jun 25 23:50:29 UTC 2021
WHO-VATC QR03CC03
Created by admin on Fri Jun 25 23:50:29 UTC 2021 , Edited by admin on Fri Jun 25 23:50:29 UTC 2021
LIVERTOX 938
Created by admin on Fri Jun 25 23:50:29 UTC 2021 , Edited by admin on Fri Jun 25 23:50:29 UTC 2021
WHO-VATC QR03CC53
Created by admin on Fri Jun 25 23:50:29 UTC 2021 , Edited by admin on Fri Jun 25 23:50:29 UTC 2021
WHO-VATC QR03AC03
Created by admin on Fri Jun 25 23:50:29 UTC 2021 , Edited by admin on Fri Jun 25 23:50:29 UTC 2021
NCI_THESAURUS C319
Created by admin on Fri Jun 25 23:50:29 UTC 2021 , Edited by admin on Fri Jun 25 23:50:29 UTC 2021
Code System Code Type Description
CAS
23031-25-6
Created by admin on Fri Jun 25 23:50:29 UTC 2021 , Edited by admin on Fri Jun 25 23:50:29 UTC 2021
PRIMARY
NCI_THESAURUS
C61965
Created by admin on Fri Jun 25 23:50:29 UTC 2021 , Edited by admin on Fri Jun 25 23:50:29 UTC 2021
PRIMARY
IUPHAR
560
Created by admin on Fri Jun 25 23:50:29 UTC 2021 , Edited by admin on Fri Jun 25 23:50:29 UTC 2021
PRIMARY
DRUG CENTRAL
2598
Created by admin on Fri Jun 25 23:50:29 UTC 2021 , Edited by admin on Fri Jun 25 23:50:29 UTC 2021
PRIMARY
EVMPD
SUB10915MIG
Created by admin on Fri Jun 25 23:50:29 UTC 2021 , Edited by admin on Fri Jun 25 23:50:29 UTC 2021
PRIMARY
ECHA (EC/EINECS)
245-385-8
Created by admin on Fri Jun 25 23:50:29 UTC 2021 , Edited by admin on Fri Jun 25 23:50:29 UTC 2021
PRIMARY
INN
2616
Created by admin on Fri Jun 25 23:50:29 UTC 2021 , Edited by admin on Fri Jun 25 23:50:29 UTC 2021
PRIMARY
LACTMED
Terbutaline
Created by admin on Fri Jun 25 23:50:29 UTC 2021 , Edited by admin on Fri Jun 25 23:50:29 UTC 2021
PRIMARY
RXCUI
10368
Created by admin on Fri Jun 25 23:50:29 UTC 2021 , Edited by admin on Fri Jun 25 23:50:29 UTC 2021
PRIMARY RxNorm
WIKIPEDIA
TERBUTALINE
Created by admin on Fri Jun 25 23:50:29 UTC 2021 , Edited by admin on Fri Jun 25 23:50:29 UTC 2021
PRIMARY
DRUG BANK
DB00871
Created by admin on Fri Jun 25 23:50:29 UTC 2021 , Edited by admin on Fri Jun 25 23:50:29 UTC 2021
PRIMARY
ChEMBL
CHEMBL1760
Created by admin on Fri Jun 25 23:50:29 UTC 2021 , Edited by admin on Fri Jun 25 23:50:29 UTC 2021
PRIMARY
PUBCHEM
5403
Created by admin on Fri Jun 25 23:50:29 UTC 2021 , Edited by admin on Fri Jun 25 23:50:29 UTC 2021
PRIMARY
EPA CompTox
23031-25-6
Created by admin on Fri Jun 25 23:50:29 UTC 2021 , Edited by admin on Fri Jun 25 23:50:29 UTC 2021
PRIMARY
FDA UNII
N8ONU3L3PG
Created by admin on Fri Jun 25 23:50:29 UTC 2021 , Edited by admin on Fri Jun 25 23:50:29 UTC 2021
PRIMARY
MESH
D013726
Created by admin on Fri Jun 25 23:50:29 UTC 2021 , Edited by admin on Fri Jun 25 23:50:29 UTC 2021
PRIMARY
MERCK INDEX
M10572
Created by admin on Fri Jun 25 23:50:29 UTC 2021 , Edited by admin on Fri Jun 25 23:50:29 UTC 2021
PRIMARY Merck Index
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