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 203 Target ID: CHEMBL210 Sources: http://www.drugbank.ca/drugs/DB00871	Agonist 2662		3.16 µM [EC50]
cAMP biosynthetic process 6 Target ID: GO:0006171 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10516654	Partial Agonist 288		2.3 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Asthma 237 Sources: https://www.drugs.com/pro/terbutaline.html	Preventing		Approved 8360	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

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 n = 1 Health Status: unhealthy Age Group: 15 years Sex: M Population Size: 1 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 n = 1 Health Status: pregnant Age Group: 21 years Sex: F Population Size: 1 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 n = 1 Health Status: pregnant Age Group: 35 years Sex: F Population Size: 1 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) n = 12 Health Status: unhealthy Condition: bronchial asthma Age Group: 56 years (range: 44-68 years) Sex: M+F Population Size: 12 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 (starting) Dose: 10 ug/kg Route: intravenous Route: single Dose: 10 ug/kg Sources: https://pubmed.ncbi.nlm.nih.gov/10891825	unhealthy, 9.1 years n = 29 Health Status: unhealthy Condition: severe asthma Age Group: 9.1 years Sex: M+F Population Size: 29 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 1599

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
		Cav1.2 4

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
Cav1.2 49	inducer 27 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0024320509003361 Page: 570.0
hERG 1632	inhibitor 1613 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
MolPort	MolPort-003-850-418	https://www.molport.com/shop/molecule-link/MolPort-003-850-418
eMolecules	27524076	https://www.emolecules.com/cgi-bin/more?vid=27524076
eMolecules	31228026	https://www.emolecules.com/cgi-bin/more?vid=31228026

PubMed

Title	Date	PubMed
Enhanced responsiveness of the myocardial beta-adrenoceptor-adenylate cyclase system in the perfused rat heart (I).	1998 Oct	10192281
Decreased expression and activity of G-protein-coupled receptor kinases in peripheral blood mononuclear cells of patients with rheumatoid arthritis.	1999 Apr	10094932
Diesel exhaust particulate induces airway hyperresponsiveness in a murine model: essential role of GM-CSF.	1999 Nov	10550748
Effects of a range of beta2 adrenoceptor agonists on changes in intracellular cyclic AMP and on cyclic AMP driven gene expression in cultured human airway smooth muscle cells.	1999 Oct	10516654
Functional, biochemical and molecular biological evidence for a possible beta(3)-adrenoceptor in human near-term myometrium.	2000 Aug	10952688
Disturbed neuroendocrine-immune interactions in chronic fatigue syndrome.	2000 Feb	10690878
beta-adrenergic stimulation restores rat lung ability to clear edema in ventilator-associated lung injury.	2000 Jul	10903255
L-Dopa uptake and dopamine production in proximal tubular cells are regulated by beta(2)-adrenergic receptors.	2000 Jul	10894789
Beta2-adrenoceptor agonist suppresses tumour necrosis factor production in rat mesangial cells.	2000 May	10857765
Alveolar epithelial type II cell: defender of the alveolus revisited.	2001	11686863
Treatment of fetal congenital complete heart block with maternal administration of beta-sympathomimetics (terbutaline): a case report.	2001	11586045
Choices of therapy for exercise-induced asthma in children.	2001	11421936
Age- and gender-specific asthma death rates in patients taking long-acting beta2-agonists: prescription event monitoring pharmacosurveillance studies.	2001	11368253
The bronchodilator test with increasing doses of terbutaline in chronic obstructive pulmonary disease patients.	2001	11162421
Contribution of amiloride-insensitive pathways to alveolar fluid clearance in adult rats.	2001 Apr	11247951
Glucocorticoid enhances the response of type II cells from newborn rats to surfactant secretagogues.	2001 Apr 30	11325615
Chiral separation of beta2-agonists by capillary electrophoresis using hydroxypropyl-alpha-cyclodextrin as a chiral selector.	2001 Aug	11534757
Efficacy and safety of Ascoril in the management of cough--National Study Group report.	2001 Feb	11482804
Effectiveness and safety of the oxytocin antagonist atosiban versus beta-adrenergic agonists in the treatment of preterm labour. The Worldwide Atosiban versus Beta-agonists Study Group.	2001 Feb	11236112
Determination of terbutaline enantiomers in human urine by coupled achiral-chiral high-performance liquid chromatography with fluorescence detection.	2001 Feb 10	11232857
Blunted cardiac responses to receptor activation in subjects with Thr164Ile beta(2)-adrenoceptors.	2001 Feb 27	11222464
The efficacy of terbutaline and magnesium sulfate in the management of preterm labor.	2001 Jan	11281506
Nebulization of a suspension of budesonide and a solution of terbutaline into a neonatal ventilator circuit.	2001 Jan	11175237
A single bout of exercise induces beta-adrenergic desensitization in human adipose tissue.	2001 Jan	11124148
Comparison of formoterol and terbutaline for as-needed treatment of asthma: a randomised trial.	2001 Jan 27	11214127
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	11453313
Protection against cold air and exercise-induced bronchoconstriction while on regular treatment with Oxis.	2001 Jun	11421506
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	11420606
The Ile164 beta(2)-adrenoceptor polymorphism alters salmeterol exosite binding and conventional agonist coupling to G(s).	2001 Jun 15	11516429
The effectiveness of high-dose inhaled budesonide therapy in the treatment of acute asthma exacerbations in children.	2001 Mar	11289332
FeNO measured at fixed exhalation flow rate during controlled tidal breathing in children from the age of 2 yr.	2001 Mar	11254527
Neurohormonal regulation of secretion from isolated rat stomach ECL cells: a critical reappraisal.	2001 Mar 2	11164953
[Local necrosis of finger following stab with needle used to pump terbutaline sulfate (Bricalin)].	2001 May	11419060
Tocolysis with nifedipine or beta-adrenergic agonists: a meta-analysis.	2001 May	11336775
The oxytocin antagonist atosiban versus the beta-agonist terbutaline in the treatment of preterm labor. A randomized, double-blind, controlled study.	2001 May	11328217
Effects of terbutaline on NGF formation in allergic inflammation of the rat.	2001 May	11325809
Alveolar epithelial barrier functions in ventilated perfused rabbit lungs.	2001 May	11290513
Regulation of fetal cardiac and hepatic beta-adrenoceptors and adenylyl cyclase signaling: terbutaline effects.	2001 Oct	11557613
A cost-effectiveness study comparing the as-needed use of formoterol (Oxis) and terbutaline (Bricanyl) in patients with moderate to severe asthma.	2001 Sep	11575897
A single dose of nebulized budesonide decreases exhaled nitric oxide in children with acute asthma.	2001 Sep	11562625

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 `Fri Jul 07 00:15:40 UTC 2023` Edited by `admin` on `Fri Jul 07 00:15:40 UTC 2023`
Record UNII	K44B97GY85
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

TERBUTALINE HYDROCHLORIDE

Common Name

English

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

Systematic Name

English

(±)-TERBUTALINE HYDROCHLORIDE

Common 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