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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
Structure of TERBUTALINE

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

HIDE SMILES / InChI

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 ( + / - )

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

2014
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
Health Status: unhealthy
Age Group: 15 years
Sex: M
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
Health Status: pregnant
Age Group: 21 years
Sex: F
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
Health Status: pregnant
Age Group: 35 years
Sex: F
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)
Health Status: unhealthy
Age Group: 56 years (range: 44-68 years)
Sex: M+F
Sources:
Other AEs: Tremor, Palpitation...
Other AEs:
Tremor
Palpitation
Sources:
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...
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
Health Status: unhealthy
Age Group: 15 years
Sex: M
Sources:
Tachycardia 1 patient
2 mg single, transdermal
Overdose
Dose: 2 mg
Route: transdermal
Route: single
Dose: 2 mg
Sources:
unhealthy, 15 years
Health Status: unhealthy
Age Group: 15 years
Sex: M
Sources:
Tremor 1 patient
2 mg single, transdermal
Overdose
Dose: 2 mg
Route: transdermal
Route: single
Dose: 2 mg
Sources:
unhealthy, 15 years
Health Status: unhealthy
Age Group: 15 years
Sex: M
Sources:
Abdominal pain 1 patient
50 mg single, oral
Overdose
Dose: 50 mg
Route: oral
Route: single
Dose: 50 mg
Sources:
pregnant, 21 years
Health Status: pregnant
Age Group: 21 years
Sex: F
Sources:
Jitteriness 1 patient
50 mg single, oral
Overdose
Dose: 50 mg
Route: oral
Route: single
Dose: 50 mg
Sources:
pregnant, 21 years
Health Status: pregnant
Age Group: 21 years
Sex: F
Sources:
Palpitations 1 patient
50 mg single, oral
Overdose
Dose: 50 mg
Route: oral
Route: single
Dose: 50 mg
Sources:
pregnant, 21 years
Health Status: pregnant
Age Group: 21 years
Sex: F
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
Health Status: pregnant
Age Group: 35 years
Sex: F
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)
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:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Tox targets
PubMed

PubMed

TitleDatePubMed
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
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 Mon Mar 31 18:31:35 GMT 2025
Edited
by admin
on Mon Mar 31 18:31:35 GMT 2025
Record UNII
N8ONU3L3PG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ASTHMASIAN
Preferred Name English
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
TERBUTALINE [MI]
Common Name English
5-[2-[(1,1-Dimethylethyl)amino]-1-hydroxyethyl]-1,3-benzenediol
Systematic Name English
5-[(1RS)-2-(tert-butylamino)-1-hydroxyethyl]benzene-1,3-diol
Systematic Name English
BAMBUTEROL HYDROCHLORIDE IMPURITY A [EPIMPURITY]
Common Name English
1,3-Benzenediol, 5-[2-[(1,1-dimethylethyl)amino]-1-hydroxyethyl]-
Systematic Name English
TERBUTALINE [VANDF]
Common Name English
terbutaline [INN]
Common Name English
Terbutaline [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C48149
Created by admin on Mon Mar 31 18:31:35 GMT 2025 , Edited by admin on Mon Mar 31 18:31:35 GMT 2025
WHO-ATC R03CC53
Created by admin on Mon Mar 31 18:31:35 GMT 2025 , Edited by admin on Mon Mar 31 18:31:35 GMT 2025
WHO-ATC R03CC03
Created by admin on Mon Mar 31 18:31:35 GMT 2025 , Edited by admin on Mon Mar 31 18:31:35 GMT 2025
WHO-ATC R03AC03
Created by admin on Mon Mar 31 18:31:35 GMT 2025 , Edited by admin on Mon Mar 31 18:31:35 GMT 2025
WHO-VATC QR03CC03
Created by admin on Mon Mar 31 18:31:35 GMT 2025 , Edited by admin on Mon Mar 31 18:31:35 GMT 2025
LIVERTOX 938
Created by admin on Mon Mar 31 18:31:35 GMT 2025 , Edited by admin on Mon Mar 31 18:31:35 GMT 2025
WHO-VATC QR03CC53
Created by admin on Mon Mar 31 18:31:35 GMT 2025 , Edited by admin on Mon Mar 31 18:31:35 GMT 2025
WHO-VATC QR03AC03
Created by admin on Mon Mar 31 18:31:35 GMT 2025 , Edited by admin on Mon Mar 31 18:31:35 GMT 2025
NCI_THESAURUS C319
Created by admin on Mon Mar 31 18:31:35 GMT 2025 , Edited by admin on Mon Mar 31 18:31:35 GMT 2025
Code System Code Type Description
CAS
23031-25-6
Created by admin on Mon Mar 31 18:31:35 GMT 2025 , Edited by admin on Mon Mar 31 18:31:35 GMT 2025
PRIMARY
NCI_THESAURUS
C61965
Created by admin on Mon Mar 31 18:31:35 GMT 2025 , Edited by admin on Mon Mar 31 18:31:35 GMT 2025
PRIMARY
IUPHAR
560
Created by admin on Mon Mar 31 18:31:35 GMT 2025 , Edited by admin on Mon Mar 31 18:31:35 GMT 2025
PRIMARY
DRUG CENTRAL
2598
Created by admin on Mon Mar 31 18:31:35 GMT 2025 , Edited by admin on Mon Mar 31 18:31:35 GMT 2025
PRIMARY
EVMPD
SUB10915MIG
Created by admin on Mon Mar 31 18:31:35 GMT 2025 , Edited by admin on Mon Mar 31 18:31:35 GMT 2025
PRIMARY
ECHA (EC/EINECS)
245-385-8
Created by admin on Mon Mar 31 18:31:35 GMT 2025 , Edited by admin on Mon Mar 31 18:31:35 GMT 2025
PRIMARY
INN
2616
Created by admin on Mon Mar 31 18:31:35 GMT 2025 , Edited by admin on Mon Mar 31 18:31:35 GMT 2025
PRIMARY
SMS_ID
100000082686
Created by admin on Mon Mar 31 18:31:35 GMT 2025 , Edited by admin on Mon Mar 31 18:31:35 GMT 2025
PRIMARY
LACTMED
Terbutaline
Created by admin on Mon Mar 31 18:31:35 GMT 2025 , Edited by admin on Mon Mar 31 18:31:35 GMT 2025
PRIMARY
DAILYMED
N8ONU3L3PG
Created by admin on Mon Mar 31 18:31:35 GMT 2025 , Edited by admin on Mon Mar 31 18:31:35 GMT 2025
PRIMARY
RXCUI
10368
Created by admin on Mon Mar 31 18:31:35 GMT 2025 , Edited by admin on Mon Mar 31 18:31:35 GMT 2025
PRIMARY RxNorm
WIKIPEDIA
TERBUTALINE
Created by admin on Mon Mar 31 18:31:35 GMT 2025 , Edited by admin on Mon Mar 31 18:31:35 GMT 2025
PRIMARY
DRUG BANK
DB00871
Created by admin on Mon Mar 31 18:31:35 GMT 2025 , Edited by admin on Mon Mar 31 18:31:35 GMT 2025
PRIMARY
CHEBI
9449
Created by admin on Mon Mar 31 18:31:35 GMT 2025 , Edited by admin on Mon Mar 31 18:31:35 GMT 2025
PRIMARY
ChEMBL
CHEMBL1760
Created by admin on Mon Mar 31 18:31:35 GMT 2025 , Edited by admin on Mon Mar 31 18:31:35 GMT 2025
PRIMARY
PUBCHEM
5403
Created by admin on Mon Mar 31 18:31:35 GMT 2025 , Edited by admin on Mon Mar 31 18:31:35 GMT 2025
PRIMARY
EPA CompTox
DTXSID7021310
Created by admin on Mon Mar 31 18:31:35 GMT 2025 , Edited by admin on Mon Mar 31 18:31:35 GMT 2025
PRIMARY
FDA UNII
N8ONU3L3PG
Created by admin on Mon Mar 31 18:31:35 GMT 2025 , Edited by admin on Mon Mar 31 18:31:35 GMT 2025
PRIMARY
MESH
D013726
Created by admin on Mon Mar 31 18:31:35 GMT 2025 , Edited by admin on Mon Mar 31 18:31:35 GMT 2025
PRIMARY
MERCK INDEX
m10572
Created by admin on Mon Mar 31 18:31:35 GMT 2025 , Edited by admin on Mon Mar 31 18:31:35 GMT 2025
PRIMARY Merck Index
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