317-34-0

Basic information

• Product Name: Aminophylline
• Synonyms: AMinophylline(Phyllocontin, Truphylline);Theophylline-ethylenediaMine anhydrous COS;1,3-diMethyl-1H-purine-2,6(3H,7H)-dione coMpound with ethane-1,2-diaMine (1:1);AMinophyllin Anhydrous USP;3,9-dihydro-1,3-dimethyl-1H-purine-2,6-dione;Aminophylline dihydrochloride hyderate;Aminophylline, >=98%;(Theophylline)2 · Ethylenediamine 3,7-Dihydro-1,3-dimethyl-1H-purine-2,6-dione, cmpd. with 1,2-ethanediamine (2:1) Theophylline hemiethylenediamine complex Theophylline, compound with ethylenediamine (2 to 1) dihydrate Theophylli
• CAS NO: 317-34-0
• Molecular Formula: C₂H₈N₂*2C₇H₈N₄O₂
• Molecular Weight: 420.43
• EINECS: 206-264-5
• Product Categories: Somopphyllin, Aminocadol, Phyllocontin;Miscellaneous Biochemicals;API's
• Mol File: 317-34-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 269-270 °C
• Boiling Point: 454.1 °C at 760 mmHg
• Flash Point: 228.4 °C
• Appearance: white to off-white/powder
• Vapor Pressure: 2.62E-32mmHg at 25°C
• Storage Temp.: −20°C
• Solubility: H2O: 3.7 mg/mL solutions should be freshly prepared.
• PKA: pKa 5.0 (Uncertain)
• Water Solubility: soluble
• Merck: 14,465
• CAS DataBase Reference: Aminophylline(CAS DataBase Reference)
• NIST Chemistry Reference: Aminophylline(317-34-0)
• EPA Substance Registry System: Aminophylline(317-34-0)

Safety Data

• Hazard Codes: Xn,C
• 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
• Hazardous Substances Data: 317-34-0(Hazardous Substances Data)

Usage

References

https://www.drugbank.ca/drugs/DB01223 https://en.wikipedia.org/wiki/Aminophylline

Chemical Properties

white to slightly yellowish powder

Originator

Memcophylline,Memphis Co.

Uses

Different sources of media describe the Uses of 317-34-0 differently. You can refer to the following data:
1. 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.
2. Bronchodilatator;Mastocytes degranulation inhibitor
3. Aminophylline is a bronchodilator and a non-selective phosphodiesterase (PDE) inhibitor.

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.

InChI:InChI=1/2C7H8N4O2.C2H8N2.H2O/c2*1-10-5-4(8-3-9-5)6(12)11(2)7(10)13;3-1-2-4;/h2*3H,1-2H3,(H,8,9);1-4H2;1H2

Synthetic route

theophylline (58-55-9) + ethylenediamine (107-15-3) → theophylline ethylenediamine (317-34-0)

Conditions	Yield
In methanol; ethyl acetate at 5 - 80℃; for 2.5h; Temperature;	91.8%

sodium 1,2-naphthoquinone-4-sulfonate (521-24-4) + theophylline ethylenediamine (317-34-0) → 2C7H8N4O2*C22H20N2O4

Conditions	Yield
In sodium hydroxide at 40℃; pH=13.00; Kinetics; Further Variations:; Temperatures;

Upstream product

• 58-55-9 theophylline 
• 107-15-3 ethylenediamine 
• 58-55-9 Theophylline 

Downstream Products

• 107-15-3 ethylenediamine 
• 58-55-9 Theophylline 

Relevant articles and documents

11/2 aminophylline hydrate compound

The invention provides a 11/2 aminophylline hydrate compound and a preparation method thereof, wherein the compound is determined by a powder X-ray diffraction determination method, and characteristicdiffraction peaks are shown at 10.8 degrees, 12.0 degre

LIQUID PHARMACEUTICAL FOR ORAL DELIVERY

A liquid pharmaceutical for oral delivery wherein at the time of use, a solid unit dosage form is added to the liquid wherein the unit dosage form is comprised of a substrate soluble in the liquid and a particulate pharmaceutically active material in a pharmaceutically effective amount. At the time of use, the unit dosage form is added to the liquid, without requiring measurement of the liquid, and the entire liquid is consumed to provide for oral delivery of the pharmaceutically effective amount of material.