Aminophylline

Title: Aminophylline
CAS Registry Number: 317-34-0
CAS Name: 3,7-Dihydro-1,3-dimethyl-1H-purine-2,6-dione compd with 1,2-ethanediamine (2:1)
Additional Names: theophylline compd with ethylenediamine; theophylline ethylenediamine; theophyllamine
Trademarks: Afonilum (Knoll); Aminodur (Berlex); Cardophylin (Rh>e-Poulenc); Euphyllina (Byk Gulden); Pecram (Novartis); Phyllocontin (Purdue Frederick); Phyllotemp (Mundipharma); Planphylline (Viatris); Pulmovet (Solvay); Tefamin (Recordati)
Molecular Formula: C16H24N10O4
Molecular Weight: 420.43
Percent Composition: C 45.71%, H 5.75%, N 33.32%, O 15.22%
Literature References: Prepn: Grüter, US 919161 (1909 to Byk). Toxicity data: C. R. Thompson, M. R. Warren, J. Lab. Clin. Med. 31, 1337 (1946). Comprehensive description: K. D. Thakker, L. T. Grady, Anal. Profiles Drug Subs. 11, 1-44 (1982). Reviews of clinical experience: J. A. Stirt, S. F. Sullivan, Anesth. Analg. 60, 587-602 (1981); A. G. Perry, AACN Clin. Issues 6, 297-306 (1995).
Properties: Occurs as the dihydrate. White or slightly yellowish granules or powder. Slight ammoniacal odor. Bitter taste. Gradually absorbs carbon dioxide from the air and becomes incompletely sol due to liberation of theophylline. One gram dissolves in about 5 ml water, but the soln may become turbid on standing. Insol in alcohol, ether. Keep tightly closed. LD50 orally in mice: 540 mg/kg (Thompson, Warren).
Toxicity data: LD50 orally in mice: 540 mg/kg (Thompson, Warren)
CAUTION: Potential symptoms of overexposure include acute restlessness, anorexia, nausea, fever, vomiting, dehydration; followed by tremors, delirium, convulsions and coma; may result in cardiovascular and respiratory collapse, shock, cyanosis and death. See Clinical Toxicology of Commercial Products, R. E. Gosselin et al., Eds. (Williams & Wilkins, Baltimore, 5th ed., 1984) Section III, pp 17-21.
Therap-Cat: Bronchodilator.
Therap-Cat-Vet: Bronchodilator.
Keywords: Bronchodilator; Xanthine Derivatives.
Aminopromazine Aminopropylon Aminopterin Aminopyrine Aminoquinuride

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
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 DB01223
ChemSpider 9062 YesY
UNII 27Y3KJK423 YesY
KEGG D00227 YesY
ChEMBL CHEMBL1210 N
Chemical data
Formula C16H24N10O4 
Mol. mass 420.427 g/mol
 N (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]