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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
Structure of DOXOFYLLINE

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

HIDE SMILES / InChI

Molecular Formula C11H14N4O4
Molecular Weight 266.2533
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Dilatair
Palliative
Ddilatair

Cmax

ValueDoseCo-administeredAnalytePopulation
1.7 μg/mL
100 mg single, intravenous
DOXOFYLLINE plasma
Homo sapiens
1687 ng/mL
400 mg single, oral
DOXOFYLLINE serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1.76 μg × h/mL
100 mg single, intravenous
DOXOFYLLINE plasma
Homo sapiens
4814 ng × h/mL
400 mg single, oral
DOXOFYLLINE serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1 h
100 mg single, intravenous
DOXOFYLLINE plasma
Homo sapiens
3.32 h
400 mg single, oral
DOXOFYLLINE serum
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
7.4%
DOXOFYLLINE plasma
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
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
Unknown
Substance Class Chemical
Record UNII
MPM23GMO7Z
Record Status Validated (UNII)
Record Version