Aminophylline

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Aminophylline
Aminophylline Formula V.1.svg
Systematic (IUPAC) name
1,3-dimethyl-7H-purine-2,6-dione; ethane-1,2-diamine
Clinical data
AHFS/Drugs.com Consumer Drug Information
MedlinePlus a601015
Pregnancy
category
  • AU: A
  • US: C (Risk not ruled out)
Legal status
Routes of
administration		 oral, i.v.
Pharmacokinetic data
Protein binding 60%
Biological half-life 7-9 hours
Identifiers
CAS Number 317-34-0 YesY
ATC code R03DA05 (WHO)
PubChem CID: 9433
DrugBank DB01223 YesY
ChemSpider 9062 YesY
UNII 27Y3KJK423 YesY
KEGG D00227 YesY
ChEMBL CHEMBL1210 N
Chemical data
Formula C16H24N10O4
Molecular mass 420.427 g/mol
  • O=C2N(c1ncnc1C(=O)N2C)C.O=C2N(c1ncnc1C(=O)N2C)C.NCCN
  • InChI=1S/2C7H8N4O2.C2H8N2/c2*1-10-5-4(8-3-9-5)6(12)11(2)7(10)13;3-1-2-4/h2*3H,1-2H3,(H,8,9);1-4H2 YesY
  • Key:FQPFAHBPWDRTLU-UHFFFAOYSA-N YesY
 NYesY (what is this?)  (verify)

Aminophylline is a compound of the bronchodilator theophylline with ethylenediamine in 2:1 ratio. The ethylenediamine improves solubility, and the aminophylline is usually found as a dihydrate.[1]

Aminophylline is less potent and shorter-acting than theophylline. Its most common use is in the treatment of airway obstruction from asthma or COPD. It is used off-label as a reversal agent during nuclear stress testing. Aminophylline is a nonselective adenosine receptor antagonist and phosphodiesterase inhibitor.[2]

Medical uses

Aminophylline is used to reverse regadenoson, dipyridamole or adenosine based infusions during nuclear cardiology stress testing.

Aminophylline has shown some promise as a bodyfat reducer when used as a topical cream.[3] Aminophylline is also a treatment option for anaphylactic shock.[4]

While it has been suggested for use in cardiac arrest evidence does not support a benefit.[5][6]

Side effects

Aminophylline can lead to theophylline toxicity. Aminophylline has been found to decrease the sedative effects of propofol[7] and decrease topiramate antiseizure action.[8]

Properties

It is more soluble in water than theophylline. White or slightly yellowish granules or powder, having a slight ammoniacal odor and a bitter taste. Upon exposure to air, it gradually loses ethylenediamine and absorbs carbon dioxide with the liberation of free theophylline. Its solutions are alkaline. 1 g dissolves in 25 mL of water to give a clear solution; 1 g dissolved in 5 mL of water crystallizes upon standing, but redissolves when a small amount of ethylenediamine is added. Insoluble in alcohol and in ether.

Mechanism of action

Like other methylated xanthine derivatives, aminophylline is both a

  1. competitive nonselective phosphodiesterase inhibitor[9] which raises intracellular cAMP, activates PKA, inhibits TNF-alpha[10][11] and leukotriene[12] synthesis, and reduces inflammation and innate immunity[12] and
  2. nonselective adenosine receptor antagonist.[13]

Aminophylline causes bronchodilation, diuresis*, central nervous system and cardiac stimulation, and gastric acid secretion by blocking phosphodiesterase which increases tissue concentrations of cyclic adenosine monophosphate (cAMP) which in turn promotes catecholamine stimulation of lipolysis, glycogenolysis, and gluconeogenesis, and induces release of epinephrine from adrenal medulla cells.

  • Note that diuresis is caused by an increase in cAMP which acts in the CNS to inhibit the release of Anti-diuretic hormone (Arginine-Vasopressin).

Adenosine is an endogenous extracellular messenger that can regulate myocardial oxygen needs.[2][14] It acts through cellular surface receptors which effect intracellular signalling pathways to increase coronary artery blood flow, slow heart rate, block atrioventricular node conduction, suppress cardiac automaticity, and decrease β-adrenergic effects on contractility.[2][14] Adenosine also antagonizes chronotropic and ionotropic effects of circulating catecholamines.[15] Overall, adenosine decreases the heart’s rate and force of contraction, which increases blood supply to the cardiac muscle. Given specific circumstances this mechanism (which is intended to protect the heart) may cause atropine-resistant refractory bradyasystole.[2] Adenosine’s effects are concentration-dependent. Adenosine’s receptors are competitively antagonized by methylxanthines such as aminophylline.[2][14][15] Aminophylline competitively antagonizes the cardiac actions of adenosine at the cell surface receptors.[14] Thus, it increases heart rate and contractility.

Brand names

  • Phyllocontin
  • Truphylline
  • Minomal R 175 mg tab
  • Minomal R 350 mg tab
  • Minomal SR 600 mg tab

References

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  4. ↑ Blackbourne LH. Surgical Recall. Lippincott Williams and Wilkins, 2009. pp169
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  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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  13. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  14. ↑ 14.0 14.1 14.2 14.3 Lua error in package.lua at line 80: module 'strict' not found.
  15. ↑ 15.0 15.1 Lua error in package.lua at line 80: module 'strict' not found.
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