TERBUTALINE HYDROCHLORIDE

First approved in 1974

Details

Stereochemistry	RACEMIC
Molecular Formula	C12H19NO3.ClH
Molecular Weight	261.745
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1

InChI

InChIKey=YEEMIJDLFDKGBE-UHFFFAOYSA-N

InChI=1S/C12H19NO3.ClH/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;1H

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	( + / - )

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Beta-2 adrenergic receptor 209 Target ID: CHEMBL210 Sources: http://www.drugbank.ca/drugs/DB00871	Agonist 2752		3.16 µM [EC50]
cAMP biosynthetic process 6 Target ID: GO:0006171 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10516654	Partial Agonist 297		2.3 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Asthma 244 Sources: https://www.drugs.com/pro/terbutaline.html	Preventing		Approved 8583	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

C_max

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

T_1/2

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 Dose: 2 mg Route: transdermal Route: single Dose: 2 mg Sources: https://pubmed.ncbi.nlm.nih.gov/8400938	unhealthy, 15 years Health Status: unhealthy Age Group: 15 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/8400938	Other AEs: Tachycardia, Systolic murmur... Other AEs: Tachycardia (1 patient) Systolic murmur (1 patient) Tremor (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/8400938
50 mg single, oral Overdose Dose: 50 mg Route: oral Route: single Dose: 50 mg Sources: https://pubmed.ncbi.nlm.nih.gov/7793711	pregnant, 21 years Health Status: pregnant Age Group: 21 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/7793711	Other AEs: Abdominal pain, Jitteriness... Other AEs: Abdominal pain (1 patient) Jitteriness (1 patient) Palpitations (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/7793711
500 mg single, oral Overdose Dose: 500 mg Route: oral Route: single Dose: 500 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3692499	unhealthy, 22 years Health Status: unhealthy Age Group: 22 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/3692499	Other AEs: Nausea, Tachycardia... Other AEs: Nausea (1 patient) Tachycardia (1 patient) Tremor (1 patient) Hyperglycemia (1 patient) Hypokalemia (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/3692499
2.5 mg single, subcutaneous Overdose Dose: 2.5 mg Route: subcutaneous Route: single Dose: 2.5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/6102210	pregnant, 35 years Health Status: pregnant Age Group: 35 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/6102210	Other AEs: Tachycardia... Other AEs: Tachycardia (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/6102210
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: https://pubmed.ncbi.nlm.nih.gov/2806513	unhealthy, 56 years (range: 44-68 years) Health Status: unhealthy Age Group: 56 years (range: 44-68 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/2806513	Other AEs: Tremor, Palpitation... Other AEs: Tremor Palpitation Sources: https://pubmed.ncbi.nlm.nih.gov/2806513
10 ug/kg single, intravenous Dose: 10 ug/kg Route: intravenous Route: single Dose: 10 ug/kg Sources: https://pubmed.ncbi.nlm.nih.gov/10891825	unhealthy, 9.1 years Health Status: unhealthy Age Group: 9.1 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10891825	Other AEs: Cardiotoxicity... Other AEs: Cardiotoxicity (3 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/10891825

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
		Cav1.2 4

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
Cav1.2 63	inducer 28 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0024320509003361 Page: 570.0
hERG 2263	inhibitor 2237 Sources: https://link.springer.com/article/10.1007/s10928-018-9583-z Page: 6.0

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:9449	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9449
ChemicalBook	CB02131227	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB02131227
eMolecules	27524076	https://www.emolecules.com/cgi-bin/more?vid=27524076
eMolecules	31228026	https://www.emolecules.com/cgi-bin/more?vid=31228026
MolPort	MolPort-003-850-418	https://www.molport.com/shop/molecule-link/MolPort-003-850-418

PubMed

Title	Date	PubMed
Beta-adrenoceptor-mediated cell signaling in the neonatal heart and liver: responses to terbutaline.	2001-12	11705775
Regulation of SP-B and SP-C secretion in rat type II cells in primary culture.	2001-12	11704537
Beta-adrenoceptor signaling in the developing brain: sensitization or desensitization in response to terbutaline.	2001-11-26	11718842
Hypoxia reduces alveolar epithelial sodium and fluid transport in rats: reversal by beta-adrenergic agonist treatment.	2001-11	11713096
Activation of beta(2)-adrenoceptor prevents shiga toxin 2-induced TNF-alpha gene transcription.	2001-11	11675405
Lung deposition and protective effect of terbutaline delivered from pressurized metered-dose inhalers and the Turbuhaler in asthmatic individuals.	2001-10-15	11704585
[Long-acting beta 2-stimulants].	2001-10	11676141
[Japanese guideline for the diagnosis and management of bronchial asthma (1998)--its results and reversion].	2001-10	11676124
Perinatal factors associated with severe intracranial hemorrhage.	2001-10	11641666
Sulindac to prevent recurrent preterm labor: a randomized controlled trial.	2001-10	11576567
Fatal adverse drug events: the paradox of drug treatment.	2001-10	11576320
Regulation of fetal cardiac and hepatic beta-adrenoceptors and adenylyl cyclase signaling: terbutaline effects.	2001-10	11557613
Uterine contractility: vaginal administration of the beta-adrenergic agonist, terbutaline. Evidence of direct vagina-to-uterus transport.	2001-09	11594537
Fast enantiomeric separation of basis drugs by electrokinetic chromatography. Application to the quantitation of terbutaline in a pharmaceutical preparation.	2001-09	11589279
A cost-effectiveness study comparing the as-needed use of formoterol (Oxis) and terbutaline (Bricanyl) in patients with moderate to severe asthma.	2001-09	11575897
A single dose of nebulized budesonide decreases exhaled nitric oxide in children with acute asthma.	2001-09	11562625
Off-label prescribing and the standard of care.	2001-08-20	11550443
Discriminative capacity of bronchodilator response measured with three different lung function techniques in asthmatic and healthy children aged 2 to 5 years.	2001-08-15	11520714
Beta1-adrenoceptor stimulation by high-dose terbutaline downregulates terbutaline-stimulated alveolar fluid clearance in ex vivo rat lung.	2001-08-02	11480585
Improved preparative-scale. continuous, free-flow electrophoretic separation of the enantiomers of terbutaline utilizing equal-but-opposite enantiomer mobilities.	2001-08	11545386
Pharmacological similarities and differences between beta2-agonists.	2001-08	11534896
Formoterol in clinical practice--safety issues.	2001-08	11534893
Formoterol used as needed--clinical effectiveness.	2001-08	11534891
Chiral separation of beta2-agonists by capillary electrophoresis using hydroxypropyl-alpha-cyclodextrin as a chiral selector.	2001-08	11534757
Antenatal terbutaline administration decreases the lung hyaluronan concentration in preterm rabbit pups.	2001-08	11509820
Antibacterial activity of apical surface fluid from the human airway cell line Calu-3: pharmacologic alteration by corticosteroids and beta(2)-agonists.	2001-08	11509329
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.	2001-07	11453313
The effect of the beta(2) adrenoceptor gene Thr164Ile polymorphism on human adipose tissue lipolytic function.	2001-07	11429395
Determination of the optical purity of (R)-terbutaline by 1H-NMR and RP-LC using chiral derivatizing agent, (S)-(-)-alpha-methylbenzyl isocyanate.	2001-07	11377078
Attenuation of insulin resistance by chronic beta2-adrenergic agonist treatment possible muscle specific contributions.	2001-06-22	11510954
The Ile164 beta(2)-adrenoceptor polymorphism alters salmeterol exosite binding and conventional agonist coupling to G(s).	2001-06-15	11516429
On-demand relief treatment for asthma.	2001-06-09	11417576
On-demand relief treatment for asthma.	2001-06-09	11417575
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.	2001-06-01	11420606
Protection against cold air and exercise-induced bronchoconstriction while on regular treatment with Oxis.	2001-06	11421506
Does the mode of inhalation affect the bronchodilator response in patients with severe COPD?	2001-06	11421505
Brittle asthma: a separate clinical phenotype of asthma?	2001-05-24	11370504
Comparison of the acute effects of salbutamol and terbutaline on heart rate variability in adult asthmatic patients.	2001-05	11488317
[Local necrosis of finger following stab with needle used to pump terbutaline sulfate (Bricalin)].	2001-05	11419060
Efficacy and safety of Ascoril in the management of cough--National Study Group report.	2001-02	11482804
Systemic capillary leak syndrome preceding plasma cell leukaemia.	2001	11713377
Bronchodilators for the prevention and treatment of chronic lung disease in preterm infants.	2001	11687053
Alveolar epithelial type II cell: defender of the alveolus revisited.	2001	11686863
An advanced and detailed in vitro validation procedure for the radiolabeling of carrier-free terbutaline sulphate dry powder.	2001	11681654
Pulmonary clearance rate of two chemically different forms of inhaled pertechnetate.	2001	11681652
Treatment of fetal congenital complete heart block with maternal administration of beta-sympathomimetics (terbutaline): a case report.	2001	11586045
Long-acting beta-agonist treatment in patients with persistent asthma already receiving inhaled corticosteroids.	2001	11437672
Choices of therapy for exercise-induced asthma in children.	2001	11421936
Inhaled short-acting beta2-agonists versus ipratropium for acute exacerbations of chronic obstructive pulmonary disease.	2001	11406052
Age- and gender-specific asthma death rates in patients taking long-acting beta2-agonists: prescription event monitoring pharmacosurveillance studies.	2001	11368253

Patents

Sample Use Guides

In Vivo Use Guide

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

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 `Wed Apr 02 13:17:08 GMT 2025` Edited by `admin` on `Wed Apr 02 13:17:08 GMT 2025`
Record UNII	K44B97GY85
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

(±)-TERBUTALINE HYDROCHLORIDE

Preferred Name

English

TERBUTALINE HYDROCHLORIDE

Common Name

English

1,3-BENZENEDIOL, 5-(2-((1,1-DIMETHYLETHYL)AMINO)-1-HYDROXYETHYL)-, HYDROCHLORIDE (1:1)

Systematic Name

English

1,3-BENZENEDIOL, 5-(2-((1,1-DIMETHYLETHYL)AMINO)-1-HYDROXYETHYL)-, HYDROCHLORIDE

Systematic Name

English

Code System Code Type Description

FDA UNII

K44B97GY85