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	ClH
Molecular Weight	36.461
Charge	0
Count

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

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 2678		3.16 µM [EC50]
cAMP biosynthetic process 6 Target ID: GO:0006171 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10516654	Partial Agonist 290		2.3 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Asthma 241 Sources: https://www.drugs.com/pro/terbutaline.html	Preventing		Approved 8429	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 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 1612

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 1647	inhibitor 1626 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
Disodium cromoglycate does not prevent terbutaline-induced desensitization of beta 2-adrenoceptor-mediated cardiovascular in vivo functions in human volunteers.	1999 May	10226872
Effect of beta(2)-adrenoceptor activation and angiotensin II on tumour necrosis factor and interleukin 6 gene transcription in the rat renal resident macrophage cells.	1999 Oct	10525314
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
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
Nocturnal asthma uncontrolled by inhaled corticosteroids: theophylline or long-acting beta2 agonists?	2001	11293649
Profile of ligand binding to the porcine beta2-adrenergic receptor.	2001 Apr	11325192
Contribution of amiloride-insensitive pathways to alveolar fluid clearance in adult rats.	2001 Apr	11247951
Antenatal terbutaline administration decreases the lung hyaluronan concentration in preterm rabbit pups.	2001 Aug	11509820
Beta-adrenoceptor-mediated cell signaling in the neonatal heart and liver: responses to terbutaline.	2001 Dec	11705775
Quantitative determination of clenbuterol, salbutamol and tulobuterol enantiomers by capillary electrophoresis.	2001 Feb	11293696
Beta1-adrenergic agonist is a potent stimulator of alveolar fluid clearance in hyperoxic rat lungs.	2001 Feb	11286398
Denopamine, a beta(1)-adrenergic agonist, increases alveolar fluid clearance in ex vivo rat and guinea pig lungs.	2001 Jan	11133887
A single bout of exercise induces beta-adrenergic desensitization in human adipose tissue.	2001 Jan	11124148
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
Beta1-adrenoceptor stimulation by high-dose terbutaline downregulates terbutaline-stimulated alveolar fluid clearance in ex vivo rat lung.	2001 Jul-Aug	11480585
Pharmacological characterization of KUR-1246, a selective uterine relaxant.	2001 May	11303056
Hypoxia reduces alveolar epithelial sodium and fluid transport in rats: reversal by beta-adrenergic agonist treatment.	2001 Nov	11713096
Sulindac to prevent recurrent preterm labor: a randomized controlled trial.	2001 Oct	11576567
Fatal adverse drug events: the paradox of drug treatment.	2001 Oct	11576320
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 `Sat Dec 16 19:01:07 GMT 2023` Edited by `admin` on `Sat Dec 16 19:01:07 GMT 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