| Identification | More | [Name]
Aminophylline | [CAS]
317-34-0 | [Synonyms]
AMINOPHYLLINE
THEOPHYLLINE COMPOUND WITH ETHYLENEDIAMINE
THEOPHYLLINE ETHYLENEDIAMINE
1h-purine-2,6-dione,3,7-dihydro-1,3-dimethyl-,compd.with1,2-ethanediamine
1h-purine-2,6-dione,3,7-dihydro-1,3-dimethyl-,compd.with1,2-ethanediamine(
1h-purine-2,6-dione,3,7-dihydro-1,3-dimethyl-,compdwith1,2-ethanediamine(2
3,7-dihydro-1,3-dimethyl-1h-purine-2,6-dionecompd.with1,2-ethanediamine(2
aminocadol
aminocardol
aminodur
aminofilina
aminophyllin
Amminofillina
ammophyllin
cardiofilina
cardiomin
cardophylin
cardophyllin
carena
cariomin | [EINECS(EC#)]
206-264-5 | [Molecular Formula]
C7H8N4O2 | [MDL Number]
MFCD00013221 | [Molecular Weight]
180.16 | [MOL File]
317-34-0.mol |
| Chemical Properties | Back Directory | [Appearance]
white to slightly yellowish powder | [Melting point ]
269-270 °C
| [storage temp. ]
−20°C
| [solubility ]
H2O: 3.7 mg/mL solutions should be freshly prepared.
| [form ]
powder
| [pka]
pKa 5.0 (Uncertain) | [color ]
white to off-white
| [Water Solubility ]
soluble | [Merck ]
13,464 | [InChI]
InChI=1S/C7H8N4O2.C2H8N2/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13;3-1-2-4/h3H,1-2H3,(H,8,9);1-4H2 | [Contact allergens]
This drug is a 2:1 mixture of the alkaloid theophylline
and ethylenediamine (see below). It caused contact
dermatitis in industrial plants, pharmacists, and nurses.
Ethylenediamine is the sensitizer and patch testing is
generally positive to both ethylenediamine and aminophylline
and negative to theophylline. | [InChIKey]
LHRHXWBJUQKYEL-UHFFFAOYSA-N | [SMILES]
O=C1N(C(=O)N(C)C2NC=NC1=2)C.C(N)CN | [LogP]
-0.175 (est) | [CAS DataBase Reference]
317-34-0(CAS DataBase Reference) | [EPA Substance Registry System]
317-34-0(EPA Substance) |
| Hazard Information | Back Directory | [Chemical Properties]
white to slightly yellowish powder | [Uses]
Aminophylline is a bronchodilator and a non-selective phosphodiesterase (PDE) inhibitor. | [Uses]
Bronchodilatator;Mastocytes degranulation inhibitor | [Originator]
Memcophylline,Memphis Co. | [Definition]
ChEBI: Aminophylline is a mixture comprising of theophylline and ethylenediamine in a 2:1 ratio. It has a role as a bronchodilator agent and a cardiotonic drug. It contains a theophylline and an ethylenediamine. | [Manufacturing Process]
A mixture of 198 g (1 mol) theophylline and 60-78 g (0.75-1 mol)
ethylenediamine hydrate in 300 g of water was stirred at 50°C and then the
mixture was concentrated in vacuo. The product (aminophylline) was
separeted by suction filtration. Aminophylline was used as an aqueous
solution. | [Brand name]
Phyllocontin
(Purdue Frederick); Somophyllin (Fisons); Truphylline (G
& W);Afonilum;Aminomal;Aminophylline injection;Aminophylline mudrane;Aminophylline oral;Amino-slow;Amnivent;Asmafilin;Cardophylline;Carine;Colonofilin;Corfilamine;Corophylline;Corphyllamin;Duraphyllin;Escophylline;Eudiamine;Euphyllin 0.48;Euphyllin retard;Euphylllin cr;Euphylllina;Fadfilina;Godafilin;Jaa aminophylline;Mini-lix;Mudrane gg;Mundiphyllin;Palaran;Palaron;Pecram;Pecran;Peterphylin;Phyllotemp;Planphylline;Somophyllin-12;Syntophyllin;Teophyllamin;Thodrox;Variaphylline. | [Therapeutic Function]
Diuretic, Cardiac stimulant, Smooth muscle relaxant,
Vasodilator | [World Health Organization (WHO)]
Aminophylline, the ethylenediamine salt of theophylline, was
introduced many years ago as a treatment for asthma and is listed in the 8th WHO
Model List of Essential Drugs. It has been recognized for some 10 years that
aminophylline preparations are not interchangeable because bioavailability can
vary considerably. The resulting variability in drug absorption can lead to adverse
effects including irritation of the mucosa. Allergic reation can also be an adverse
effect of aminophylline. Theophylline functions similarly but is considered less of
an irritant. | [Hazard]
Cardiovascular and respiratory collapse. | [Clinical Use]
Reversible airways obstruction
Acute severe asthma | [Veterinary Drugs and Treatments]
The theophyllines are used primarily for their bronchodilatory effects,
often in patients with myocardial failure and/or pulmonary
edema. While they are still routinely used, the methylxanthines
must be used cautiously due to their adverse effects and toxicity. | [Drug interactions]
Potentially hazardous interactions with other drugs
Antibacterials: increased concentration with
azithromycin, clarithromycin, erythromycin,
ciprofloxacin, norfloxacin and isoniazid; decreased
erythromycin levels if erythromycin is given
orally; increased risk of convulsions if given with
quinolones; rifampicin accelerates metabolism of
aminophylline.
Antidepressants: concentration increased by
fluvoxamine - avoid or halve theophylline dose and
monitor levels; concentration reduced by St John’s
wort - avoid.
Antiepileptics: metabolism increased by
carbamazepine, phenobarbital and primidone;
concentration of both drugs increased with
fosphenytoin and phenytoin.
Antifungals: concentration increased by fluconazole
and ketoconazole.
Antivirals: metabolism of aminophylline increased
by ritonavir; concentration possibly increased by
aciclovir.
Calcium-channel blockers: concentration increased
by diltiazem and verapamil and possibly other
calcium-channel blockers.
Deferasirox: concentration of aminophylline
increased.
Feboxostat: use with caution.
Interferons: reduced metabolism of aminophylline.
Tacrolimus: may increase tacrolimus levels.
Ulcer-healing drugs: metabolism inhibited by
cimetidine; absorption possibly reduced by sucralfate. | [Metabolism]
Aminophylline is metabolised to theophylline in vivo.
Theophylline is excreted in the urine as metabolites,
mainly 1,3-dimethyluric acid and 3-methylxanthine, and
about 10% is excreted unchanged. |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,C | [Risk Statements ]
R22:Harmful if swallowed.
R42/43:May cause sensitization by inhalation and skin contact .
R34:Causes burns.
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S36:Wear suitable protective clothing . | [RIDADR ]
UN 2811 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
XH5600000
| [F ]
10-23 | [TSCA ]
Yes | [HazardClass ]
6.1(b) | [PackingGroup ]
III | [HS Code ]
29339900 | [Hazardous Substances Data]
317-34-0(Hazardous Substances Data) | [Toxicity]
LD50 orally in mice: 540 mg/kg (Thompson, Warren) |
| Questions And Answer | Back Directory | [Description]
Aminophylline is a drug combination consisting of bronchodilator theophylline and ethylenediamine in 2: 1 ratio. It is a kind of non-selective adenosine receptor blocker, histone deacetylase activator and phosphodiesterase inhibition. It is mainly indicated for the treatment of various kinds of lung diseases including asthma, COPD, chronic bronchitis and emphysema. Aminophylline exerts its effect through the component of theophylline in vivo. Theophylline can relax the smooth muscle of the bronchial airways and pulmonary blood vessels. It can competitively inhibits type III and type IV phosphodiesterase (PDE), which breaks down cyclic AMP in smooth muscle cells, possibly leading to bronchodilation. Theophylline also binds to the adenosine A2B receptor to block the adenosine mediated bronchoconstriction. Furthermore, during the inflammatory states, theophylline can activate the histone deacetylase to prevent transcription of inflammatory genes that require the acetylation of histones to initiate the transcription.
| [References]
https://www.drugbank.ca/drugs/DB01223
https://en.wikipedia.org/wiki/Aminophylline
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