Aminophylline


Aminophylline
Aminophylline
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 cat.  ?
Legal status P (UK)
Routes oral, i.v.
Pharmacokinetic data
Protein binding 60%
Half-life 7-9 hours
Identifiers
CAS number 317-34-0 YesY
ATC code R03DA05
PubChem CID 9433
DrugBank APRD00329
ChemSpider 9062 YesY
UNII 27Y3KJK423 YesY
KEGG D00227 YesY
ChEMBL CHEMBL1210 N
Chemical data
Formula C16H24N10O4 
Mol. mass 420.427 g/mol
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

Aminophylline is a bronchodilator. It 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]

Contents

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. One 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 [2] which raises intracellular cAMP, activates PKA, inhibits TNF-alpha [3][4] and leukotriene [5] synthesis, and reduces inflammation and innate immunity [5] and
  2. nonselective adenosine receptor antagonist.[6]

Aminophylline is less potent and shorter-acting than theophylline. Its most common use is in the treatment of bronchial asthma.

Causes bronchodilatation, diuresis, CNS and cardiac stimulation, and gastric acid secretion by blocking phosphodiesterase which increases tissue concentrations of cyclic adenine monophosphate (cAMP) which in turn promotes catecholamine stimulation of lipolysis, glycogenolysis, and gluconeogenesis and induces release of epinephrine from adrenal medulla cells

Other uses

Aminophylline is used to reverse dypridamole or adenosine based infusions during nuclear cardiology stress testing.

Aminophylline has shown some promise as a bodyfat reducer when used as a topical cream (sometimes referred to as "cutting gel").[7] Aminophylline is also a treatment option for anaphylactic shock.[8]

Brand names

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

References

  1. ^ "Aminophylline Professional Monograph". http://www.drugs.com/pro/aminophylline-injection.html. 
  2. ^ Essayan DM. (2001). "Cyclic nucleotide phosphodiesterases.". J Allergy Clin Immunol. 108 (5): 671–80. doi:10.1067/mai.2001.119555. PMID 11692087. 
  3. ^ Deree J, Martins JO, Melbostad H, Loomis WH, Coimbra R. (2008). "Insights into the regulation of TNF-alpha production in human mononuclear cells: the effects of non-specific phosphodiesterase inhibition.". Clinics (Sao Paulo). 63 (3): 321–8. doi:10.1590/S1807-59322008000300006. PMC 2664230. PMID 18568240. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2664230. 
  4. ^ Marques LJ, Zheng L, Poulakis N, Guzman J, Costabel U (February 1999). "Pentoxifylline inhibits TNF-alpha production from human alveolar macrophages". Am. J. Respir. Crit. Care Med. 159 (2): 508–11. PMID 9927365. http://ajrccm.atsjournals.org/cgi/pmidlookup?view=long&pmid=9927365. 
  5. ^ a b Peters-Golden M, Canetti C, Mancuso P, Coffey MJ. (2005). "Leukotrienes: underappreciated mediators of innate immune responses.". J Immunol. 174 (2): 589–94. PMID 15634873. http://www.jimmunol.org/cgi/content/full/174/2/589. 
  6. ^ Daly JW, Jacobson KA, Ukena D. (1987). "Adenosine receptors: development of selective agonists and antagonists.". Prog Clin Biol Res. 230 (1): 41–632. PMID 3588607. 
  7. ^ Caruso MK, Pekarovic S, Raum WJ, Greenway F (May 2007). "Topical fat reduction from the waist". Diabetes, obesity & metabolism 9 (3): 300–3. doi:10.1111/j.1463-1326.2006.00600.x. PMID 17391155. http://www.blackwell-synergy.com/openurl?genre=article&sid=nlm:pubmed&issn=1462-8902&date=2007&volume=9&issue=3&spage=300. 
  8. ^ Blackbourne LH. Surgical Recall. Lippincott Williams and Wilkins, 2009. pp169

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Look at other dictionaries:

  • aminophylline — ● aminophylline nom féminin Dérivé de la théophylline utilisé essentiellement en thérapeutique comme bronchodilatateur. aminophylline [aminofilin] n. f. ÉTYM. XXe; de amino , et (théo)phylline. ❖ ♦ Pharmacol. Médicament dérivé de la théophylline …   Encyclopédie Universelle

  • aminophylline — noun Etymology: amino + theophylline Date: 1934 a theophylline derivative C16H24N10O4 used especially to stimulate the heart in congestive heart failure and to dilate the air passages in respiratory disorders (as asthma) …   New Collegiate Dictionary

  • aminophylline — An inhibitor of cAMP phosphodiesterase …   Dictionary of molecular biology

  • aminophylline — /euh mee noh fil uyn, een, am euh noh /, n. Pharm. a theophylline derivative, C16H24N10O4, used chiefly to relieve bronchial spasm in asthma, in the treatment of certain heart conditions, and as a diuretic. [1955 60; AMINO + (THEO)PHYLLINE] * * * …   Universalium

  • aminophylline — noun A bronchodilator comprising theophylline and ethylenediamine in a 2:1 ratio …   Wiktionary

  • aminophylline — A solubilized form of theophylline; a diuretic, vasodilator, and cardiac stimulant; also used as a bronchodilator in asthma and in veterinary medicine. SYN: theophylline ethylenediamine …   Medical dictionary

  • aminophylline — n. medication for asthma and heart problems …   English contemporary dictionary

  • aminophylline — ami·no·phyl·line …   English syllables

  • aminophylline — n. a drug that relaxes smooth muscle and stimulates respiration. It is widely used to dilate the air passages in the treatment of severe asthma and some cases of chronic obstructive pulmonary disease. Administered by mouth or injection, it may… …   The new mediacal dictionary

  • aminophylline — a•mi•no•phyl•line [[t]əˌmi noʊˈfɪl aɪn, in, ˌæm ə noʊ [/t]] n. pha a theophylline derivative, C16H24N10O4, used chiefly to relieve bronchial spasm in asthma, in the treatment of certain heart conditions, and as a diuretic • Etymology: 1955–60;… …   From formal English to slang


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