Aminophylline

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Cat Number

API0232261

CAS Number

317-34-0

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CAS Number

317-34-0

EINECS

206-264-5

Storage

Store at room temperature

Synonyms

Aminophyllin; Cardophyllin; Linampheta; Phyllocontin; Syntophyllin; Truphylline

Molecular Formula

C16H24N10O4

Molecular Weight

420.43

Smiles

CN1C2=C(C(=O)N(C1=O)C)NC=N2.CN1C2=C(C(=O)N(C1=O)C)NC=N2.C(CN)N

Appearance

White to slightly yellowish powder

Melting Point

269-270°C

Boiling Point

454.1°C at 760 mmHg

General Description

Aminophylline is a salt of theophylline and ethylenediamine, with a molecular weight of 420.4 Da. Its chemical structure is C₁₃H₂₄N₁₀O₄ (theophylline ethylenediamine complex). Aminophylline is a white to off-white powder, soluble in water. It is a bronchodilator and a respiratory stimulant, belonging to the class of xanthine derivatives.

Mechanism of Action

Aminophylline dissociates to theophylline, which acts as a non-selective phosphodiesterase inhibitor, increasing the concentration of cAMP in bronchial smooth muscle. This leads to bronchodilation, relaxation of the airways, and inhibition of mast cell mediator release. The drug also has positive inotropic and chronotropic effects on the heart and acts as a central nervous system stimulant.

Application

Aminophylline is indicated for the treatment of asthma, chronic obstructive pulmonary disease (COPD), and for the management of bronchospasm. It is also used for the treatment of apnea of prematurity and for the management of bradycardia in neonates. The drug is effective in improving respiratory function and reducing the frequency of asthma exacerbations.

Aminophylline, a bronchodilator, inhibited stress‑induced defecation in rats via A₂B adenosine receptors and phosphodiesterase 4, and reduced visceral hypersensitivity via A₂A and A₂B receptors. It effectively prevented both stress‑induced defecation and visceral pain, two key features of irritable bowel syndrome with diarrhea. Given its clinical safety, aminophylline is proposed as a candidate drug for IBS‑D.

Fig. 1 The relationship between the inhibitory effect of aminophylline on defecation and the bronchodilatory effect of aminophylline in mice. (Asano T, et al., 2017)

References

Asano T, et al. Aminophylline suppresses stress-induced visceral hypersensitivity and defecation in irritable bowel syndrome. Sci Rep. 2017;7:40214.

In Xenopus oocytes expressing EAAT3, aminophylline and ephedrine significantly decreased EAAT3 activity by reducing Vmax (not Km), via PKC and PI3K pathways. Both drugs abolished the propofol-induced enhancement of EAAT3 activity. This reveals a novel site of action for aminophylline and ephedrine and a potential interaction with propofol at the EAAT3 level.

Fig. 2 Reversible effects of aminophylline or ephedrine on enhanced activity of excitatory amino acid transporter type 3 (EAAT3) by propofol (30 and 100 μM). (Moon S, Baik HJ. 2018)

References

Moon S, Baik HJ. Aminophylline and Ephedrine, but Not Flumazenil, Inhibit the Activity of the Excitatory Amino Acid Transporter 3 Expressed in Xenopus Oocytes and Reverse the Increased Activity by Propofol. Biomed Res Int. 2018;2018:6817932.

Does Aminophylline require protection from carbon dioxide during storage?

Yes, it can absorb atmospheric CO₂, leading to the precipitation of theophylline. Store in tightly sealed containers, preferably with a desiccant and minimal headspace.

What is the recommended storage temperature for Aminophylline?

Store at controlled room temperature (15-25°C). Avoid excessive heat above 30°C, which accelerates degradation and discoloration.

Is Aminophylline stable in solution for intravenous use?

Aqueous solutions are stable when protected from light and stored at room temperature. However, they should not be refrigerated, as theophylline may crystallize.

How is the impurity theophylline (free base) monitored during stability?

This dissociation product is specifically quantified using a stability-indicating HPLC method, ensuring it remains within pharmacopoeial limits.