Aminophylline
Aminophylline Basic information
- Product Name:
- Aminophylline
- Synonyms:
-
- AMinophylline(Phyllocontin, Truphylline)
- Theophylline-ethylenediaMine anhydrous COS
- (Theophylline)2 Ethylenediamine, Theophylline hemiethylenediamine complex, 3,7-Dihydro-1,3-dimethyl-1H-purine-2,6-dione, cmpd. with 1,2-ethanediamine (2:1)
- Aminophylline,99%
- Theophylline-e
- Aminophylline hydrat
- AMINOPHYLLINE
- THEOPHYLLINE COMPOUND WITH ETHYLENEDIAMINE
- CAS:
- 317-34-0
- MF:
- C9H16N6O2
- MW:
- 240.27
- EINECS:
- 206-264-5
- Product Categories:
-
- Somopphyllin, Aminocadol, Phyllocontin
- Miscellaneous Biochemicals
- API's
- 317-34-0
- Mol File:
- 317-34-0.mol
Aminophylline Chemical Properties
- 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)
- 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 Information
- 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)
MSDS
- Language:English Provider:Theophylline-ethylenediamine-addition compound (2:1)
- Language:English Provider:ACROS
Aminophylline Usage And Synthesis
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 is a bronchodilator and a non-selective phosphodiesterase (PDE) 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.
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.
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Aminophylline(317-34-0)Related Product Information
- Purine
- Dimethyl fumarate
- Dimethyl sulfoxide
- Dihydromyrcenol
- Theophylline
- N,N,N',N'-Tetramethylethylenediamine
- Ethylenediamine dihydrochloride
- Dimethyl phthalate
- 2-(2-Aminoethylamino)ethanol
- Dimethyl ether
- N-(1-Naphthyl)ethylenediamine dihydrochloride
- ETHANE
- Lysergic acid diethylamide
- Ethylenediamine
- Acefylline Piperazine
- 2-[(4-AMINO-PHENYL)-ETHYL-AMINO]-ETHANOL
- promethazine teoclate
- 8-[2-(4-benzhydrylpiperazin-1-yl)ethyl]-1-methyl-3-(2-methylpropyl)-7H-purine-2,6-dione