TERBUTALINE

First approved in 1974

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 Search

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
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
beta(2)-adrenoceptor agonist suppresses renal tumour necrosis factor and enhances interleukin-6 gene expression induced by endotoxin.	2000 Dec	11096136
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
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
The bronchodilator test with increasing doses of terbutaline in chronic obstructive pulmonary disease patients.	2001	11162421
Profile of ligand binding to the porcine beta2-adrenergic receptor.	2001 Apr	11325192
beta2-Adrenoceptor desensitization in human alveolar macrophages induced by inhaled terbutaline in vivo is not counteracted by budesonide.	2001 Apr	11256987
Contribution of amiloride-insensitive pathways to alveolar fluid clearance in adult rats.	2001 Apr	11247951
Interaction between beta-adrenergic signaling and protein kinase C increases cytoplasmic Ca2+ in alveolar type II cells.	2001 Apr 13	11350007
Glucocorticoid enhances the response of type II cells from newborn rats to surfactant secretagogues.	2001 Apr 30	11325615
Pharmacological similarities and differences between beta2-agonists.	2001 Aug	11534896
Antibacterial activity of apical surface fluid from the human airway cell line Calu-3: pharmacologic alteration by corticosteroids and beta(2)-agonists.	2001 Aug	11509329
Beta-adrenoceptor-mediated cell signaling in the neonatal heart and liver: responses to terbutaline.	2001 Dec	11705775
Regulation of SP-B and SP-C secretion in rat type II cells in primary culture.	2001 Dec	11704537
Efficacy and safety of Ascoril in the management of cough--National Study Group report.	2001 Feb	11482804
Intraocular pressure-lowering activity and in vivo disposition of dipivalyl terbutalone in rabbits.	2001 Feb	11266225
Use of vancomycin silica stationary phase in packed capillary electrochromatography I. Enantiomer separation of basic compounds.	2001 Feb	11258766
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
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	11219455
BAPS prize-1999: Lung growth induced by prenatal tracheal occlusion and its modifying factors: a study in the rat model of congenital diaphragmatic hernia.	2001 Feb	11172410
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
Clinical characteristics of asthmatic patients prescribed various beta-agonist metered-dose inhalers at Yamagata University Hospital.	2001 Jan	11201164
Nebulization of a suspension of budesonide and a solution of terbutaline into a neonatal ventilator circuit.	2001 Jan	11175237
Involvement of beta1- and beta2- but not beta3-adrenoceptor activation in adrenergic PYY secretion from the isolated colon.	2001 Jan	11139781
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
Brittle asthma: a separate clinical phenotype of asthma?	2001 Jan-Mar	11370504
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
The effect of the beta(2) adrenoceptor gene Thr164Ile polymorphism on human adipose tissue lipolytic function.	2001 Jul	11429395
Determination of the optical purity of (R)-terbutaline by 1H-NMR and RP-LC using chiral derivatizing agent, (S)-(-)-alpha-methylbenzyl isocyanate.	2001 Jul	11377078
Beta1-adrenoceptor stimulation by high-dose terbutaline downregulates terbutaline-stimulated alveolar fluid clearance in ex vivo rat lung.	2001 Jul-Aug	11480585
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
Attenuation of insulin resistance by chronic beta2-adrenergic agonist treatment possible muscle specific contributions.	2001 Jun 22	11510954
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
Comparison of the acute effects of salbutamol and terbutaline on heart rate variability in adult asthmatic patients.	2001 May	11488317
[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
Efficacy of 'functional relaxation' in comparison to terbutaline and a 'placebo relaxation' method in patients with acute asthma. A randomized, prospective, placebo-controlled, crossover experimental investigation.	2001 May-Jun	11340417
Hypoxia reduces alveolar epithelial sodium and fluid transport in rats: reversal by beta-adrenergic agonist treatment.	2001 Nov	11713096
[Long-acting beta 2-stimulants].	2001 Oct	11676141
[Japanese guideline for the diagnosis and management of bronchial asthma (1998)--its results and reversion].	2001 Oct	11676124
Perinatal factors associated with severe intracranial hemorrhage.	2001 Oct	11641666
Fatal adverse drug events: the paradox of drug treatment.	2001 Oct	11576320
Uterine contractility: vaginal administration of the beta-adrenergic agonist, terbutaline. Evidence of direct vagina-to-uterus transport.	2001 Sep	11594537
Fast enantiomeric separation of basis drugs by electrokinetic chromatography. Application to the quantitation of terbutaline in a pharmaceutical preparation.	2001 Sep	11589279
Pulmonary clearance rate of two chemically different forms of inhaled pertechnetate.	2001 Summer	11681652

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 Jul 05 23:59:35 UTC 2023` Edited by `admin` on `Wed Jul 05 23:59:35 UTC 2023`
Record UNII	N8ONU3L3PG
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TERBUTALINE

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

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