Enprofylline
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Enprofylline
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CAS No:
41078-02-8
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Formula:
C8H10N4O2
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Chemical Name:
Enprofylline
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Synonyms:
1H-Purine-2,6-dione,3,9-dihydro-3-propyl-;1H-Purine-2,6-dione,3,7-dihydro-3-propyl-;3,9-Dihydro-3-propyl-1H-purine-2,6-dione;Enprofylline;3-Propylxanthine;D 4028;3-Propyl-1H-purine-2,6(3H,9H)-dione;3-Propyl-2,3,6,9-tetrahydro-1H-purine-2,6-dione;3,7-Dihydro-3-propyl-1H-purine-2,6-dione;3-Propyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
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CAS No:
Description
ChEBI: Xanthine bearing a propyl substituent at position 3. A bronchodilator, it is used for the symptomatic treatment of asthma and chronic obstructive pulmonary disease, and in the management of cerebrovascular insufficiency, sickle cell disease, and diabetic n uropathy.
Solid
Enprofylline is xanthine bearing a propyl substituent at position 3. A bronchodilator, it is used for the symptomatic treatment of asthma and chronic obstructive pulmonary disease, and in the management of cerebrovascular insufficiency, sickle cell disease, and diabetic neuropathy. It has a role as a non-steroidal anti-inflammatory drug, a bronchodilator agent, an anti-asthmatic drug and an anti-arrhythmia drug.|Enprofylline is a derivative of theophylline which shares bronchodilator properties. Enprofylline is used in asthma, chronic obstructive pulmonary disease, and in the management of cerebrovascular insufficiency, sickle cell disease, and diabetic neuropathy. Long-term enprofylline administration may be associated with elevation in liver enzyme levels and unpredictable blood levels.
Safety Information
3
20/21/22
36
UO8439700
Xn
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, P501
H302
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Drug Information
Used in the management of symptoms of asthma. Also used in the treatment of peripheral vascular diseases and in the management of cerebrovascular insufficiency, sickle cell disease, and diabetic neuropathy.
Enprofylline is a synthetic dimethylxanthine derivative structurally related to theophylline and caffeine. It antagonizes erythrocyte phosphodiesterase, increasing cAMP activity.
Agents that cause an increase in the expansion of a bronchus or bronchial tubes. (See all compounds classified as Bronchodilator Agents.)|Compounds that selectively bind to and block the activation of ADENOSINE A2 RECEPTORS. (See all compounds classified as Adenosine A2 Receptor Antagonists.)|Drugs that are used to treat asthma. (See all compounds classified as Anti-Asthmatic Agents.)
Rapidly absorbed from the digestive tract
1.9 hours
Enprofylline inhibits erythrocyte phosphodiesterase, resulting in an increase in erythrocyte cAMP activity. Subsequently, the erythrocyte membrane becomes more resistant to deformity. Along with erythrocyte activity, enprofylline also decreases blood viscosity by reducing plasma fibrinogen concentrations and increasing fibrinolytic activity.
3-propylxanthine
Enprofylline Use and Manufacturing
N-propyl urea and cyanoacetic acid are heated in the presence of acetic acid to generate N-propyl-N'-cyanoacetylurea; the cyano group is hydrolyzed and cyclized under the action of sodium hydroxide to generate piperidine derivatives; nitrosation is introduced Nitroso group: Under the catalysis of platinum oxide, in dimethylformamide (DMF) solvent, hydrogen pressure of 0.20MPa hydrogen pressure, hydrogenated nitroso group is amino; formylation and cyclization to obtain enprophylline.
Xanthine derivatives are potent phosphodiesterase inhibitors. The tracheal and bronchial expansion effects are stronger than theophylline, and there is no side effect of theophylline stimulation on the central system. It is clinically applicable to lung diseases such as bronchial asthma and airway obstruction.
Computed Properties
Molecular Weight:194.19
XLogP3:0.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:194.08037557
Monoisotopic Mass:194.08037557
Topological Polar Surface Area:78.1
Heavy Atom Count:14
Complexity:268
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes