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Details

Stereochemistry ACHIRAL
Molecular Formula C7H8N4O2.C4H11NO2
Molecular Weight 285.2997
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of THEOPHYLLINE DIETHANOLAMINE

SMILES

OCCNCCO.CN1C2=C(NC=N2)C(=O)N(C)C1=O

InChI

InChIKey=XYBFIZMXHHNHKG-UHFFFAOYSA-N
InChI=1S/C7H8N4O2.C4H11NO2/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13;6-3-1-5-2-4-7/h3H,1-2H3,(H,8,9);5-7H,1-4H2

HIDE SMILES / InChI

Molecular Formula C4H11NO2
Molecular Weight 105.1356
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

Molecular Formula C7H8N4O2
Molecular Weight 180.164
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

Since its discovery as component of the tea leaf by Albert Kossel in 1888, the history of theophylline (CAS 58-55-9) has been a long and successful one. At the turn of the century, theophylline became less expensive due to chemical synthesis and was primarily used as diuretic in subsequent years. It was Samuel Hirsch who discovered the bronchospasmolytic effect of theophylline in 1992, however, despite this pioneering discovery theophylline continued to be used primarily as diuretic and cardiac remedy. The molecular mechanism of bronchodilatation is inhibition of phosphodiesterase(PDE)3 and PDE4, but the anti-inflammatory effect may be due to histone deacetylase (HDAC) activation, resulting in switching off of activated inflammatory genes. Theophylline is indicated for the treatment of acute exacerbations of the symptoms and reversible airflow obstruction associated with asthma and other chronic lung diseases, e.g., emphysema and chronic bronchitis.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
THEOPHYLLINE AND DEXTROSE 5% IN PLASTIC CONTAINER

Cmax

ValueDoseCo-administeredAnalytePopulation
7.3 μg/mL
200 mg single, oral
THEOPHYLLINE serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
95.5 μg × h/mL
200 mg single, oral
THEOPHYLLINE serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
8.51 h
200 mg single, oral
THEOPHYLLINE serum
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
41%
200 mg single, oral
THEOPHYLLINE serum
Homo sapiens

Doses

AEs

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
For a given population there is no single theophylline dose that will provide both safe and effective serum concentrations for all patients. The dose of theophylline must be individualized on the basis of serum theophylline concentration measurements in order to achieve a dose that will provide maximum potential benefit with minimal risk of adverse effects.
Route of Administration: Other
In Vitro Use Guide
1 mM theophylline inhibited histamine release from human skin mast cells
Substance Class Chemical
Record UNII
X3D62BXX1R
Record Status Validated (UNII)
Record Version