Details
Stereochemistry | ACHIRAL |
Molecular Formula | C11H14N4O4 |
Molecular Weight | 266.2533 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1C2=C(N(CC3OCCO3)C=N2)C(=O)N(C)C1=O
InChI
InChIKey=HWXIGFIVGWUZAO-UHFFFAOYSA-N
InChI=1S/C11H14N4O4/c1-13-9-8(10(16)14(2)11(13)17)15(6-12-9)5-7-18-3-4-19-7/h6-7H,3-5H2,1-2H3
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/?term=11268710Curator's Comment: description was created based on several sources, including
http://cathaydrug.ph/product/dilatair/
https://www.ncbi.nlm.nih.gov/pubmed/18376093
Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=11268710
Curator's Comment: description was created based on several sources, including
http://cathaydrug.ph/product/dilatair/
https://www.ncbi.nlm.nih.gov/pubmed/18376093
Doxofylline (7-(1, 3-dioxalan-2-ylmethyl) theophylline) is a novel xanthine bronchodilator which differs from theophylline in that it contains a dioxalane group in position 7. Doxofylline is indicated for the treatment of bronchial asthma, pulmonary disease with spastic bronchial component and Chronic Obstructive Pulmonary Disease (COPD). Doxofylline does not directly inhibit any of the known HDAC enzymes, and did not inhibit any phosphodiesterase (PDE) enzyme sub types or act as an antagonist at any of the known adenosine receptors, except for PDE2A(1), and adenosine A(2A) and only at the highest tested concentration (10(-4) M). Doxofylline has greatly decreased affinity towards adenosine A1 and A2 receptors, which explain its better safety profile. Moreover, it does not interfere with calcium influx into the cells nor antagonize calcium channel blockers. Doxofylline has been shown to be a more potent bronchodilator with fewer side effects than theophylline. This drug should not be administered together with other xanthine derivatives, including beverages and foods containing caffeine.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2652 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22138191 |
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Target ID: CHEMBL251 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22138191 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | Dilatair Approved UseUnknown |
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Palliative | Ddilatair Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Therapeutic potential of adenosine receptor antagonists and agonists. | 2007 Aug |
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Development and validation of a sensitive LC-MS/MS method with electrospray ionization for quantitation of doxofylline in human serum: application to a clinical pharmacokinetic study. | 2008 Jun |
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[Meta-analysis of efficacy and safety of oral theophylline in chronic obstructive pulmonary disease]. | 2010 Mar 2 |
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7-(1,3-Dioxolan-2-ylmethyl)-1,3-di-methyl-2,6-dioxo-2,3,6,7-tetra-hydro-1H-purin-9-ium tetra-chloridoferrate(III). | 2010 Sep 11 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: http://cathaydrug.ph/product/dilatair/
Elderly Patients: 200 mg tablet two or three times daily.
Adults: 400 mg tablet two or three times daily.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2776832
Curator's Comment: Doxofylline inhibited PAF-induced bronchoconstriction in vitro, and the concomitant generation of TXA2-like activity in perfused guinea-pig lungs.
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WHO-VATC |
QR03DA11
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FDA ORPHAN DRUG |
399413
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C744
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R03DA11
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DOXOFYLLINE
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C76317
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CHEMBL1527608
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SUB06390MIG
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ACTIVE MOIETY
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