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Theophylline (Molecule of the Month for October 2018)

Theolair, Slo-Bid, 1,3-dimethylxanthine



Theophylline is a methylxanthine drug used in therapy for respiratory diseases such as chronic obstructive pulmonary disease (COPD) and asthma under a variety of brand names. As a member of the xanthine family, it bears structural and pharmacological similarity to theobromine and caffeine, and is readily found in nature, and is present in tea (Camellia sinensis) and cocoa (Theobroma cacao). A small amount of theophylline is one of the products of caffeine metabolic processing.

Theophylline was first extracted from tea leaves and chemically identified around 1888 by the German biologist Albrecht Kossel. Seven years later, a chemical synthesis starting with 1,3-dimethyluric acid was described by Emil Fischer and Lorenz Ach. Theophylline's first clinical use came in 1902 as a diuretic. It took an additional 20 years until it was first reported as an asthma treatment. The drug was prescribed in a syrup up to the 1970s as Theostat 20 and Theostat 80, and by the early 1980s in a tablet form called Quibron.

The use of theophylline is complicated by its interaction with various drugs and by the fact that it has a narrow therapeutic window.[quantify] Its use must be monitored by direct measurement of serum theophylline levels to avoid toxicity. It can also cause nausea, diarrhea, increase in heart rate, abnormal heart rhythms, and CNS excitation (headaches, insomnia, irritability, dizziness and lightheadedness). Seizures can also occur in severe cases of toxicity, and are considered to be a neurological emergency. Its toxicity is increased by erythromycin, cimetidine, and fluoroquinolones, such as ciprofloxacin.

Formal Chemical Name (IUPAC)
1,3-Dimethyl-3,7-dihydro-1H-purine-2,6-dione

References

https://en.wikipedia.org/wiki/Theophylline

Picture of Theophylline 3D model

click on the picture of  Theophylline above to interact
with the 3D model of the
Theophylline structure
(this will open a new browser window)

Picture of Theophylline

C7 H8 N4 O2



Update by Karl Harrison
(Molecule of the Month for October 2018 )

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