519-37-9

Hazards Identification

Pictogram(s):

Signal:

Warning

GHS Hazard Statements:

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

Precautionary Statement Codes:

P264, P270, P301+P317, P330, and P501

Hazard Classes and Categories:

Acute Tox. 4 (100%)

Usage

Uses

Used in Pharmaceutical Industry:
7-(2-HYDROXYETHYL)THEOPHYLLINE is used as a therapeutic agent for its diuretic, muscle relaxant, bronchial dilation, and CNS stimulant activities. It is particularly effective in treating conditions that require these specific properties.
Used in Chemical Synthesis:
7-(2-HYDROXYETHYL)THEOPHYLLINE is used as a synthetic intermediate for the preparation of 7-substituted xanthines, which are important compounds in the development of various pharmaceuticals.
Used in Cardiac Treatment:
7-(2-HYDROXYETHYL)THEOPHYLLINE is used as a cardiac analeptic, which means it helps to stimulate the heart and improve its function.
Used in Enzyme Inhibition:
7-(2-HYDROXYETHYL)THEOPHYLLINE is used as a Phosphodiesterase inhibitor, which can have various therapeutic applications, such as treating certain respiratory conditions and enhancing the effects of certain medications.

Therapeutic Function

Antihyperlipidemic

Biochem/physiol Actions

Pharmacological profile similar to theophylline.

InChI:InChI=1/C9H12N4O3/c1-11-7-6(8(15)12(2)9(11)16)13(3-4-14)5-10-7/h5,14H,3-4H2,1-2H3

Upstream product

• 75-21-8 oxirane 
• 58-55-9 theophylline 
• 107-07-3 2-chloro-ethanol 
• 54504-70-0 Duolip 
• 5614-53-9 1,3-Dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-7-yl-acetaldehyd 
• 479-18-5 diprophylline 

Downstream Products

• 13425-39-3 etofylline nicotinate 
• 69387-85-5 phosphoric acid bis-[2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-yl)-ethyl] ester phenyl ester 
• 100769-71-9 phosphoric acid-[2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-yl)-ethyl ester]-diphenyl ester 
• 5878-61-5 7-(2-chloroethyl)-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione 
• 54504-73-3 1-(Theophyllin-7-yl)-aethyl-2--acetat 
• 54504-79-9 (4-fluoro-phenoxy)-acetic acid 2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-yl)-ethyl ester 
• 54504-70-0 Duolip 
• 54504-74-4 1-(Theophyllin-7-yl)-aethyl-(p-chlorphenoxy)-acetat 
• 54504-77-7 2-(3-trifluoromethyl-phenoxy)-propionic acid 2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-yl)-ethyl ester 
• 54504-80-2 (4-bromo-phenoxy)-acetic acid 2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-yl)-ethyl ester 
• 54504-78-8 (4-iodo-phenoxy)-acetic acid 2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-yl)-ethyl ester 
• 54504-76-6 2-(2-chloro-phenoxy)-2-methyl-propionic acid 2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-yl)-ethyl ester 
• 54504-75-5 2-(4-chloro-phenoxy)-propionic acid 2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-yl)-ethyl ester 
• 169563-63-7 1,2,3,6-Tetrahydro-1,3-dimethyl-2,6-dioxo-7H-purine-7-acetic acid 2-(1,2,3,6-tetrahydro-1,3-dimethyl-2,6-dioxo-7H-purin-7-yl)ethyl ester 

Relevant academic research and scientific papers

Method for treating benign prostate hyperplasia

A method of treating and/or preventing renal dysfunction in a patient, such as renal colic or contrast nephropathy by administering to a patient, a compound of the formula: is described herein. Administration of dyphylline in a sustained release oral dosage form is preferred.

Synthesis of new 7-alkylated theophyllines by chemical modification of dyphylline

Acetylation of 7-(2,3-dihydroxyprop-1-yl)theophylline (1) afforded the di-O-acetyl derivative 2. Reaction of 1 with acetone and benzaldehyde gave the 1,3-dioxolane derivatives 4 and 5, respectively. Periodate oxidation of 1 gave theophylline-7-acetaldehyde (6). Treatment of 6 with hydroxylamine hydrochloride, thiosemicarbazide and benzoylhydrazine afforded the corresponding oxime 9, thiosemicarbazone 10 and benzoylhydrazone 11. Treatment of 10 and 11 with boiling acetic anhydride afforded the respective 1,3,4-thiadiazoline 12 and oxadiazoline 13. Condensation of 6 with dimedone followed by boiling with dilute hydrochloric acid afforded the xanthene derivative 15.

Method of kidney treatment

A method of treating and/or preventing renal dysfunction in a patient, such as renal colic or contrast nephropathy by administering to a patient, a compound of the formula: is described herein. Administration of dyphylline in a sustained release oral dosage form is preferred.

Potentiation of cADPR-induced Ca2+-release by methylxanthine analogues

Caffeine and other methylxanthines are known to induce Ca2+-release from intracellular stores via the ryanodine receptor. In the present work, a range of caffeine analogues, in which methyl groups at the 1 and 7 positions were replaced with alkyl chains containing different functional groups (oxo, hydroxyl, propargyl, ester, and acids), were synthesized. These compounds were then screened for their ability to potentiate Ca2+-release induced by cADPR (an endogenous modulator of ryanodine receptors) in sea urchin egg homogenates. Two of the synthesized methylxanthines, 1,3-dimethyl-7-(7- hydroxyoctyl)xanthine (37) and 3-methyl-7-(7-oxooctyl)-1-propargylxanthine (66), were shown to be more potent than caffeine in potentiating cADPR- induced Ca2+-release, while 1,3-dimethyl-7-(5-ethylcarboxypentyl)xanthine (14) was shown to be more efficacious. The development of new methylxanthine analogues may lead to a better understanding of ryanodine receptor function and could possibly provide novel therapeutic agents.

Metabolism and pharmacokinetics of etofylline clofibrate, a new hypolipidaemic agent

Upon investigations on metabolism and pharmacokinetics of 1-(theophyllin-7-yl)-ethyl-2-[2-(p-chlorophenoxy)-2-methyl-propionate] (etofylline clofibrate, ML 1024, Duolip) is reported. As can be seen from in vivo tests in rats and dogs ML 1024 is cleaved to the metabolites clofibric acid and etofylline. This could be further demonstrated in vitro by incubation with lipases and human serum. The phrmacokinetic parameters of the metabolites after oral application of 2 capsules Duolip, corresponding to 500 mg etofylline clofibrate, were evaluated in 7 healthy volunteers. The serum fluctuations of the main metabolites could be adapted to an open two-compartment model (clofibric acid) and to a one-compartment model (etofylline). The following mean values were found: the invasion half-life is 1 h 4 min for clofibric acid and 1 h 52 min for etofylline. The maximum concentration after approximately 4 h is 22.75 μg/ml for clofibric acid and 6.57 μg/ml for etofylline. The elimination half-life is 12.12 h for clofibric and 4.33 h for etofylline. Via urine 20 mg clofibric acid and 15.7 mg etofylline were excreted within 8 hr. The elimination process after 8 h is not yet terminated.