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Aminophylline

Description References

Aminophylline

CAS No.317-34-0
Chemical Name:Aminophylline
CBNumber:CB8145350
Molecular Formula:C9H16N6O2
Formula Weight:240.27
MOL File:317-34-0.mol

Aminophylline Property

Melting point 269-270 °C
storage temp. Inert atmosphere,Store in freezer, under -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 14,465
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
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)
FDA 21 CFR 310.545
EWG's Food Scores 1-3
FDA UNII 27Y3KJK423
NCI Drug Dictionary aminophylline
ATC code R03DA05,R03DA55
EPA Substance Registry System 1H-Purine-2,6-dione, 3,7-dihydro-1,3-dimethyl-, compd. with 1,2-ethanediamine (2:1) (317-34-0)

Safety

Hazard Codes :Xn,C
Risk Statements :22-42/43-34-36/37/38-20/21/22
Safety Statements :45-36/37/39-26-23-36
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)

NFPA 704:

	0
2		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordDanger
Hazard statements H301
Precautionary statements P301+P310

Aminophylline Chemical Properties,Usage,Production

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
Description Aminophylline is a 2/1 mixture of theophylline and ethylenediamine. It caused contact dermatitis in industrial plants, in pharmacists, and in nurses. Ethylenediamine is the sensitizer, and patch testing is generally positive to both ethylenediamine and aminophylline, but negative to theophylline.
Chemical Properties white to slightly yellowish powder
Originator Memcophylline,Memphis Co.
Uses Bronchodilatator;Mastocytes degranulation inhibitor
Uses Aminophylline exhibits vasodilatory and anti-inflammatory activity and is occasionally clinically used to treat chronic obstructive pulmonary disorder (COPD). In animal models of allergen-induced lung inflammation, aminophylline decreases levels of IL-5, IL-8, and eosinophils. It is mostly used to prepare solutions for intravenous injections.
Uses Aminophylline is a bronchodilator and a non-selective phosphodiesterase (PDE) inhibitor.
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.
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.
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.