Details
Stereochemistry | ACHIRAL |
Molecular Formula | C8H10N4O2 |
Molecular Weight | 194.1906 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCN1C2=C(N=CN2)C(=O)NC1=O
InChI
InChIKey=SIQPXVQCUCHWDI-UHFFFAOYSA-N
InChI=1S/C8H10N4O2/c1-2-3-12-6-5(9-4-10-6)7(13)11-8(12)14/h4H,2-3H2,1H3,(H,9,10)(H,11,13,14)
Molecular Formula | C8H10N4O2 |
Molecular Weight | 194.1906 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Enprofylline is a xanthine derivative that shares theophylline's bronchodilator properties. It can be considered a relatively selective, though not potent adenosine A2B receptors antagonist. 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 the elevation in liver enzyme levels and unpredictable blood levels.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9443164 |
156.0 µM [Ki] | ||
Target ID: CHEMBL251 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9443164 |
32.0 µM [Ki] | ||
Target ID: CHEMBL255 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9443164 |
7.0 µM [Ki] | ||
Target ID: CHEMBL256 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9443164 |
65.0 µM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Sources: http://pharmacycode.com/Enprofylline.html |
Palliative | Unknown Approved UseUnknown |
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Palliative | Unknown Approved UseUnknown |
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Palliative | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Effects of enprofylline, a xanthine lacking adenosine receptor antagonism, in patients with chronic obstructive lung disease. | 1982 |
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Continuous treatment of asthmatic patients with enprofylline and theophylline. | 1984 Oct |
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Additive bronchodilator effects of terbutaline and enprofylline in asthma. | 1987 |
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Proliferation, migration, and ERK activation in human retinal endothelial cells through A(2B) adenosine receptor stimulation. | 2001 Aug |
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Adenosine receptor antagonists and retinal neovascularization in vivo. | 2001 Dec |
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Alkylxanthine-induced recovery of respiratory function following cervical spinal cord injury in adult rats. | 2001 Mar |
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Adenosine A(2A) and A(2B) receptor activation of erythropoietin production. | 2001 Nov |
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Structure-activity relationships at human and rat A2B adenosine receptors of xanthine derivatives substituted at the 1-, 3-, 7-, and 8-positions. | 2002 May 23 |
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Direct effects of caffeine and theophylline on p110 delta and other phosphoinositide 3-kinases. Differential effects on lipid kinase and protein kinase activities. | 2002 Oct 4 |
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Regional differences in the adenosine A(2) receptor-mediated modulation of contractions in rat vas deferens. | 2003 Jan 24 |
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Characterization of adenosine receptor(s) involved in adenosine-induced bronchoconstriction in an allergic mouse model. | 2003 Jun |
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The Quintiles Prize Lecture 2004. The identification of the adenosine A2B receptor as a novel therapeutic target in asthma. | 2005 Aug |
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Adenosine A2A receptor stimulation increases angiogenesis by down-regulating production of the antiangiogenic matrix protein thrombospondin 1. | 2005 May |
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Possible involvement of organic anion and cation transporters in renal excretion of xanthine derivatives, 3-methylxanthine and enprofylline. | 2007 Sep 22 |
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Comparative diffusion of drugs through bronchial tissue. | 2008 Jun 5 |
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Theophylline inhibits the differentiation of human monocyte into dendritic cell potentially via adenosine receptor antagonism. | 2009 Dec |
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Progress in the discovery of selective, high affinity A(2B) adenosine receptor antagonists as clinical candidates. | 2009 Mar |
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Allergen-induced airway inflammation and its therapeutic intervention. | 2009 Oct |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7956392
The dosage of enprofylline was incremented from 150 mg twice daily at initiation to 300 and later 450 mg twice daily depending on the patient's tolerance.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3002801
Enprofylline antagonized the 5'-N-ethylcarboxamidoadenosine (NECA)-induced stimulation of platelet adenylate cyclase activity with a Kb of 130 microM. In human platelets, enprofylline did not antagonize but potentiated the NECA-induced inhibition of aggregation. This potentiation was abolished in the presence of the phosphodiesterase inhibitor papaverine. An adenosine antagonistic effect of enprofylline could not be evaluated on A2 receptors of the guinea-pig lung because the xanthine enhanced basal and NECA-stimulated cyclic AMP accumulation. Enprofylline antagonized the N6-R-(-)-phenylisopropyladenosine (R-PIA)-induced inhibition of rat fat cell adenylate cyclase with a Kb of 32 microM. The Ki value for inhibition of [3H]PIA binding to rat fat cell membranes was 45 microM. Enprofylline inhibited cyclic AMP phosphodiesterase activity of human platelets, guinea-pig lung and rat fat cells with Ki values of 15, 130 and 110 microM, respectively.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:11:25 UTC 2023
by
admin
on
Fri Dec 15 16:11:25 UTC 2023
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Record UNII |
DT7DT5E518
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Record Status |
Validated (UNII)
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Record Version |
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C257
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255-201-8
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SUB06547MIG
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100000080238
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126237
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C034347
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ENPROFYLLINE
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1015
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4878
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C74327
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DB00824
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CHEMBL279898
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41078-02-8
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