It07:Terbutaline Sulphate

Terbutaline Sulphate
IUPAC Systematic name
tert-butyl-[2-(3,5-dihydroxyphenyl)-2-hydroxyethyl]azanium sulfate
Other name
Bricanyl
Indentifiers
ATC Code	R03AC03R03CC03
CAS number	{{{CASNo}}}
PubChem (CID)	36120
SMILES	[NH2+CC(C1=CC(=CC(=C1)O)O)O.CC(C)(C) [NH2+]CC(C1=CC(=CC(=C1)O)O)O.[O-]S(=O)(=O)[O- CC(C)(C)[NH2+]CC(C1=CC(=CC(=C1)O)O)O.CC(C)(C) [NH2+]CC(C1=CC(=CC(=C1)O)O)O.[O-]S(=O)(=O)[O-]
Chemical Data
Molecular formula	(C12H20NO3)2 SO4
Molar mass	548.6468 g/mol
Pharmacokinetic Data
Bioavailability	{{{Bioavailability}}}
Protein Binding	{{{Protein_binding}}}
Metabolism	GI tract (oral), liver; CYP450: unknown
Half life	urine 90% (60% unchanged), bile/faeces; Half-life: 3-4h
Excretion	{{{Excretion}}}
Therapeutic considerations
Pregnancy cat.	B
Legal status	POM
Routes	SQ, Oral, Inhaled

Structure

mo_terbutaline_sulphate.pdb

Crystal Structure

TESU.cif

Terbutaline sulphate belongs to a class of drugs known as short acting beta 2 agonistslike salbutamol. It is a bronchodilator These drugs work by acting on the lungs' beta 2 receptors. Stimulation of these recpetors cause the relaxation of muscles in the airway, thus allowing the opening of the airway. Terbutaline sulphate is used in the treatment of conditions that cause the narrowing of airways such as asthma, bronchitis and emphysema. Terbutaline sulphate is mainly administered as an inhaler, where the drug can directly get to the lungs. It can also be taken in tablet form if the inhaler is being used frequently to ease shortness of breath. The tablets can be taken regularly to help keep the airways constantly open and reduce inhaler usage. However the inhaler has the advantage of reducing the chance of side effects occuring in other body parts, as the quantity of the drug absorbed by the blood via inhalation is smaller than the quantity taken orally.

Conditions where the drug is used

Chronic obstructive pulmonary disease (COPD)

Bronchospasm (narrowing of the airways) in other lung conditions (e.g. bronchitis and emphysema)

Asthma

Side Effects

Chest discomfort

Breathing difficulty

Dizziness

Drowsiness

Fast, irregular heartbeat

Headache

Increased heart rate

Nausea

Sweating

Tremors

Weakness

Synthesis

To synthesise terbutaline sulphate, first terbutaline needs to be formed from the parent cyanohydrin. This done via a Ritter reaction to convert the nitrile group into an N-alkyl amide.

When the N-alkyl amide has been made; treat with sulphuric acid to make terbutaline sulphate.

synthesis of terbutaline sulphate

Image taken from Synthesis of the Adrenergic Bronchodilators (R)-Terbutaline and (R)-Salbutamol from (R)-Cyanohydrins1 Effenberger, F.; Jager, J. J. Org. Chem.; (Article); 1997; 62(12); 3867-3873. DOI: 10.1021/jo970032d

Real Life Product

Below is a Bricanyl inhaler, which contains terbutaline sulphate.

Bricanyl terbutaline sulphate inhaler