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Theophylline, also known as 1,3-dimethylxanthine, 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 in the liver.
1 Medical uses
1.1 Uses under investigation
2 Adverse effects
3.1 Proton Nuclear Magnetic Resonance Spectroscopy
3.2 Carbon Nuclear Magnetic Resonance Spectroscopy
4 Mechanisms of action
5 Natural occurrences
8 Future Studies
10 External links
The main actions of theophylline involve:
relaxing bronchial smooth muscle
increasing heart muscle contractility and efficiency; as a positive inotrope
increasing heart rate: (positive chronotropic )
increasing blood pressure
increasing renal blood flow
central nervous system stimulatory effect mainly on the medullary respiratory center.
The main therapeutic uses of theophylline are aimed at:
chronic obstructive pulmonary disease ( COPD )
Blocks the action of adenosine ; an inhibitory neurotransmitter that induces sleep, contracts the smooth muscles and relaxes the cardiac muscle.
Uses under investigation
A clinical study reported in 2008 that theophylline was helpful in improving the sense of smell in study subjects with anosmia.
The use of theophylline is complicated by its interaction with various drugs and by the fact that it has a narrow therapeutic window.
Proton Nuclear Magnetic Resonance Spectroscopy
The characteristic signals, distinguishing theophylline from related methylxanthines, are approximately 3.23δ and 3.41δ, corresponding to the unique methylation possessed by theophylline. The remaining proton signal, at 8.01δ, corresponds to the proton on the imidazole ring, not transferred between the nitrogen. The transferred proton between the nitrogen is a variable proton and only exhibits a signal under certain conditions.
Carbon Nuclear Magnetic Resonance Spectroscopy
The unique methylation of theophylline corresponds to the following signals: 27.7δ and 29.9δ. The remaining signals correspond to carbons characteristic of the xanthine backbone.
Mechanisms of action
Like other methylated xanthine derivatives, theophylline is both a
competitive nonselective phosphodiesterase inhibitor,
nonselective adenosine receptor antagonist, antagonizing A1, A2, and A3 receptors almost equally, which explains many of its cardiac effects
Theophylline has been shown to inhibit TGF-beta -mediated conversion of pulmonary fibroblasts into myofibroblasts in COPD and asthma via cAMP-PKA pathway and suppresses COL1 mRNA, which codes for the protein collagen.
It has been shown that theophylline may reverse the clinical observations of steroid insensitivity in patients with COPD and asthmatics who are active smokers (a condition resulting in oxidative stress ) via a distinctly separate mechanism. Theophylline in vitro can restore the reduced HDAC (histone deacetylase) activity that is induced by oxidative stress (i.e., in smokers), returning steroid responsiveness toward normal. ( Corticosteroids switch off the inflammatory response by blocking the expression of inflammatory mediators through deacetylation of histones, an effect mediated via histone deacetylase-2 (HDAC2). Once deacetylated, DNA is repackaged so that the promoter regions of inflammatory genes are unavailable for binding of transcription factors such as NF-κB that act to turn on inflammatory activity. It has recently been shown that the oxidative stress associated with cigarette smoke can inhibit the activity of HDAC2, thereby blocking the anti-inflammatory effects of corticosteroids.)
Theophylline is naturally found in cocoa beans. Amounts as high as 3.7 mg/g have been reported in Criollo cocoa beans.
Trace amounts of theophylline are also found in brewed tea, although brewed tea provides only about 1 mg/L, which is significantly less than a therapeutic dose.
Trace amounts of theophylline are also found in guarana ( Paullinia cupana ) and in kola nuts cola (plant)
When theophylline is administered intravenously, bioavailability is 100%
Theophylline is distributed in the extracellular fluid, in the placenta, in the mother’s milk and in the central nervous system. The volume of distribution is 0.5 L/kg. The protein binding is 40%. The volume of distribution may increase in neonates and those suffering from cirrhosis or malnutrition, whereas the volume of distribution may decrease in those who are obese.
Theophylline is metabolized extensively in the liver (up to 70%). It undergoes N -demethylation via cytochrome P450 1A2. It is metabolized by parallel first order and Michaelis-Menten pathways. Metabolism may become saturated (non-linear), even within the therapeutic range. Small dose increases may result in disproportionately large increases in serum concentration. Methylation to caffeine is also important in the infant population. Smokers and people with hepatic (liver) impairment metabolize it differently. Both THC and nicotine have been shown to increase the rate of theophylline metabolism.
Theophylline is excreted unchanged in the urine (up to 10%). Clearance of the drug is increased in children (age 1 to 12), teenagers (12 to 16), adult smokers, elderly smokers, as well as in cystic fibrosis, and hyperthyroidism. Clearance of the drug is decreased in these conditions: elderly, acute congestive heart failure, cirrhosis, hypothyroidism and febrile viral illness.
The elimination half-life varies: 30 hours for premature neonates, 24 hours for neonates, 3.5 hours for children ages 1 to 9, 8 hours for adult non-smokers, 5 hours for adult smokers, 24 hours for those with hepatic impairment, 12 hours for those with congestive heart failure NYHA class I-II, 24 hours for those with congestive heart failure NYHA class III-IV, 12 hours for the elderly.
Theophylline was first extracted from tea leaves and chemically identified around 1888 by the German biologist Albrecht Kossel. 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.
Theophylline, despite its adverse effects and narrow therapeutic range, as discussed above, is still a potent bronchodilator. Current research regarding theophylline-based therapies are oriented towards employing theophylline, as well as other methylxanthines as natural scaffolding for new bronchodilatory pharmaceuticals. In 2017, Mohammed, et al
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