Basic information
- CAS
23031-25-6- Standard SMILES
CC(C)(C)NCC(O)c1cc(O)cc(O)c1- InChIKey
XWTYSIMOBUGWOL-UHFFFAOYSA-N- Molecular formula
- C12H19NO3
- Average molar mass
- 225.28 g/mol
- Monoisotopic mass
- 225.13649347
Overview
Terbutaline is a member of the class of phenylethanolamines that is catechol substituted at position 5 by a 2-(tert-butylamino)-1-hydroxyethyl group. It has a role as a beta-adrenergic agonist, a bronchodilator agent, a sympathomimetic agent, a hypoglycemic agent, an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an anti-asthmatic drug and a tocolytic agent. It is a member of phenylethanolamines and a member of resorcinols.
Names & identifiers
- Preferred name
- Terbutaline
- IUPAC
- 5-[2-(tert-butylamino)-1-hydroxyethyl]benzene-1,3-diol
- English name
- 5-(1-Hydroxy-2-tert-butylamino-ethyl)benzene-1,3-diol
- Molecular formula
- C12H19NO3
- Molecular weight
- 225.28
Names & synonyms
terbutaline23031-25-6TerbutalinTerbutalinumTerbutalina5-[2-(tert-butylamino)-1-hydroxyethyl]benzene-1,3-diolAsthmasian5-(2-(tert-Butylamino)-1-hydroxyethyl)benzene-1,3-diol1,3-Benzenediol, 5-[2-[(1,1-dimethylethyl)amino]-1-hydroxyethyl]-ButalitabN8ONU3L3PGTerbutalin ratiopharm
Show more names
Bambuterol EP Impurity AC07129Terbutaline-d3D3-(±)-TerbutalineTibolone Impurity 19CarButerol impurity ABambuterol impurity 1Carbuterol Impurity 1Terbutaline Impurity 29
5-(2-((1,1-DIMETHYLETHYL)AMINO)-1-HYDROXYETHYL)-1,3-BENZENEDIOL5-[2-[(1,1-dimethylethyl)amino]-1-hydroxyethyl]-1,3-benzenediolCHEBI:9449DTXSID70213101,3-Benzenediol, 5-(2-((1,1-dimethylethyl)amino)-1-hydroxyethyl)-RefChem:56527DTXCID001310R03AC03
Database identifiers
- CAS
23031-25-6
Properties
Computed structural properties
- XLogP
- 0.9
- Topological polar surface area
- 72.7 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 205
Experimental & physicochemical properties
DrugsPharmaceuticals
LogP
1.4
0.08
Solubility5.84e+00 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Bronchodilator Agents; Beta Adrenergic Agonists
Pharmaceuticals
Antiasthmatic and medicines for chronic obstructive pulmonary disease
Melting Point119 - 122 °C
Physical DescriptionSolid
Dissociation Constants
8.65
8.7
Collision Cross Section
155.28 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
154.9 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
155.27 Ų [M+H]+
Physicochemical properties
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H361 (100%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
P203, P260, P280, P318, P319, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Other Safety InformationIMAP assessments - 1,3-Benzenediol, 5-[2-[(1,1-dimethylethyl)amino]-1-hydroxyethyl]-: Environment tier I assessment
Hazard Classes and CategoriesRepr. 2 (100%)
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
terbutaline
DILI Positive
Oral
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
EPA Human Health Benchmarks for Pharmaceuticals
Terbutaline
0.2
0.7
The usual oral dose of terbutaline sulfate for adults is 5 mg administered at approximately six-hour intervals, three times daily, during the hours the patient is usually awake. If side effects are particularly disturbing, the dose may be reduced to 2.5 mg three times daily, and still provide a clinically significant improvement.
Data used to generate the benchmarks include the following: Lowest Daily Dose (LDD): 7.5 mg/day, Lowest Therapeutic Dose (LTD): 0.1 mg/kg-day, and Screening Dose: 0.00003 mg/kg-day.
Chemistry & industry
Pharmacology
ATC Code
R - Respiratory system
R - Respiratory system
QR - Respiratory system
QR - Respiratory system
Protein BindingTerbutaline is not highly bound to protein in plasma.
Pharmacodynamics
Terbutaline is a beta-2 adrenergic receptor agonist indicated to treat reversibly bronchospasm in asthmatic patients with bronchitis and emphysema. It has a short duration as the inhaled form is taken up to three times daily, and the therapeutic window is wide.
Mechanism of Action
Terbutaline is a selective beta-2 adrenergic receptor agonist. Agonism of these receptors in bronchioles activates adenylyl cyclase, increasing intracellular cyclic adenosine monophosphate (cAMP). Increased cAMP decreases intracellular calcium, activating protein kinase A, inactivating myosin light-chain kinase, activating myosin light-chain phosphatase, and finally relaxing smooth muscle in the bronchiole.
Biological Half-LifeAn oral dose of terbutaline has an elimination half life of 3.4 hours, while a subcutaneous dose has an elimination half life of 2.9 hours.
Metabolism/MetabolitesTerbutaline is sulphated or glucuronidated prior to elimination.
MeSH Pharmacological Classification
Agents that cause an increase in the expansion of a bronchus or bronchial tubes.
Drugs that mimic the effects of stimulating postganglionic adrenergic sympathetic nerves. Included here are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters.
Drugs that prevent preterm labor and immature birth by suppressing uterine contractions (TOCOLYSIS). Agents used to delay premature uterine activity include magnesium sulfate, beta-mimetics, oxytocin antagonists, calcium channel inhibitors, and adrenergic beta-receptor agonists. The use of intravenous alcohol as a tocolytic is now obsolete.
Related reactions
1 records
Compound notes
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