A colorless crystalline alkaloid, C7H8N4O2, derived from tea leaves or made synthetically, used in medicine especially as a bronchial dilator.
[THEO(BROMINE) + PHYLL(O)- + -INE2.]
theophylline
Dictionary:
the·oph·yl·line (thē-ŏf'ə-lĭn)  |
n.
A colorless crystalline alkaloid, C7H8N4O2, derived from tea leaves or made synthetically, used in medicine especially as a bronchial dilator.
A colorless crystalline alkaloid, C7H8N4O2, derived from tea leaves or made synthetically, used in medicine especially as a bronchial dilator.
| 5min Related Video: theophylline |
| Chemistry Dictionary: theophylline |
Variant: 1,3-dimethylxanthine
An alkaloid, C7 H8 N4 O2, structurally related to caffein. It is found in small quantities in tea and is used medicinally for certain respiratory conditions. See also methylxanthines.
| Food and Nutrition: theophylline |
| Drug Info: Theophylline, Aminophylline |
Brand names: Elixophyllin®Quibron® TQuibron® T/SRRespbid®Slo Bid®Slo-Phyllin®T-Phyl®Theo-24®Theo-Bid® DuracapTheo-Dur®Theo-Dur® SprinkleTheo-X®TheoCap™Theochron®Theolair®Theolair® SRTheovent® LAUni-Dur®Uniphyl®
Chemical formula:
- Drug Forms:
- Theophylline, Anhydrous Oral tablet, extended-release (below)
- Theophylline, Anhydrous Oral capsule, extended-release
- Theophylline Oral tablet, extended-release
- Theophylline Oral capsule, extended-release
- Theophylline, Anhydrous Oral tablet, extended release 24 hour
- Theophylline, Aminophylline tablets or capsules
- Theophylline, Aminophylline extended-release tablets or capsules
- Theophylline Oral solution
- Aminophylline Oral tablet
- Theophylline Elixir
- Theophylline, Anhydrous Oral syrup
- Español:
- Teofilina; Anhidra, Tableta oral de liberación prolongada
- Teofilina Anhidra, Cápsula oral de liberación prolongada
- Teofilina, Tableta oral de liberación prolongada
- Teofilina, Cápsula oral de liberación prolongada
- Teofilina; Anhidra, Tableta oral de liberación prolongada-24 horas
- Tabletas o cápsulas de teofilina, aminofilina
- Cápsulas o tabletas de liberación prolongada de teofilina, aminofilina
- Teofilina, Solución oral
- Aminofilina, Tableta oral
- Teofilina, Elixir
- Teofilina ; Anhidra, Jarabe oral
Theophylline, Anhydrous Oral tablet, extended-release
What is this medicine?
THEOPHYLLINE is a bronchodilator. It helps open up the airways in your lungs to make it easier to breathe. This medicine is used to treat the symptoms of asthma, bronchitis, and emphysema.
This medicine may be used for other purposes; ask your health care provider or pharmacist if you have questions.
What should I tell my health care provider before I take this medicine?
They need to know if you have any of these conditions:
•heart disease
•if you smoke
•irregular heartbeat
•liver disease
•seizures
•stomach problems like ulcers
•thyroid disease
•an unusual or allergic reaction to theophylline, aminophylline, caffeine, theobromine, other medicines, foods, dyes, or preservatives
•pregnant or trying to get pregnant
•breast-feeding
How should I use this medicine?
Take this medicine by mouth with a glass of water. Follow the directions on the prescription label. Take this medicine on an empty stomach, at least 1 hour before eating. Do not crush or chew. Take your doses at the same time each day. Do not take your medicine more often than directed. Do not stop taking except on your doctor's advice.
Talk to your pediatrician regarding the use of this medicine in children. While this drug may be prescribed for selected conditions, precautions do apply.
Overdosage: If you think you have taken too much of this medicine contact a poison control center or emergency room at once.
NOTE: This medicine is only for you. Do not share this medicine with others.
What if I miss a dose?
If you miss a dose, take it as soon as you can. If it is almost time for your next dose, take only that dose. Do not take double or extra doses.What may interact with this medicine?
•adenosine
•allopurinol
•aminoglutethimide
•caffeine
•cimetidine
•disulfiram
•ephedrine
•fluvoxamine
•interferon
•isoproterenol
•lithium
•medicines for anxiety or sleep
•medicines for colds and breathing difficulties
•methotrexate
•pentoxifylline
•some antibiotics or anti infectives
•some medicines for irregular heart rhythms
•some medicines for treating seizures
•some medicines used during surgery
•sulfinpyrazone
•tacrine
This list may not describe all possible interactions. Give your health care provider a list of all the medicines, herbs, non-prescription drugs, or dietary supplements you use. Also tell them if you smoke, drink alcohol, or use illegal drugs. Some items may interact with your medicine.
What should I watch for while using this medicine?
Visit your doctor or health care professional for regular checks on your progress. Your doctor or health care professional may schedule regular blood tests, especially at first. Tell your doctor if your symptoms do not improve or if they get worse.
There are many different brands of this medicine. Do not change your brand without checking with your health care professional. Different brands of this medicine may act differently in your body.
Tell all of your doctors that you are taking this medicine. Talk to your doctor before you start or stop ANY over-the-counter or prescription medicines. Also talk to your health care professional about foods that affect this medicine, like chocolate, coffee, teas and charcoal-broiled foods. If you smoke tobacco or marijuana you may affect the level of this medicine in your body. Alcohol may interfere with the effect of this medicine. Avoid alcoholic drinks.
What side effects may I notice from receiving this medicine?
Side effects that you should report to your doctor or health care professional as soon as possible:
•allergic reactions like skin rash, itching or hives, swelling of the face, lips, or tongue
•fast or irregular breathing or heartbeat
•feeling faint or lightheaded, falls
•fever, infection
•nausea, vomiting
•seizures
Side effects that usually do not require medical attention (report to your doctor or health care professional if they continue or are bothersome):
•anxiety, irritable, restless
•diarrhea
•headache
•increased need to pass urine
•tremors
•trouble sleeping
This list may not describe all possible side effects. Call your doctor for medical advice about side effects. You may report side effects to FDA at 1-800-FDA-1088.
Where should I keep my medicine?
Keep out of the reach of children.
Store at room temperature below 25 degrees C (77 degrees F). Keep container tightly closed. Protect from light and moisture. Throw away any unused medicine after the expiration date.
Last updated: 7/1/2002
Important Disclaimer: The drug information provided here is for educational purposes only. It is intended to supplement, not substitute for, the diagnosis, treatment and advice of a medical professional. This drug information does not cover all possible uses, precautions, side effects and interactions. It should not be construed to indicate that this or any drug is safe for you. Consult your medical professional for guidance before using any prescription or over the counter drugs.
| Veterinary Dictionary: theophylline |
An alkaloid derived from tea or produced synthetically; it is a smooth muscle relaxant used chiefly for its bronchodilator effect in the treatment of chronic obstructive pulmonary emphysema, bronchial asthma, chronic bronchitis and bronchospastic distress. It also has myocardial stimulant, coronary vasodilator, diuretic and respiratory center stimulant effects.
- t. cholinate — oxtriphylline, a smooth muscle relaxant, myocardial stimulant and diuretic.
- t. ethylenediamine — a smooth muscle relaxant, myocardial stimulant and diuretic. Called also aminophylline.
| Wikipedia: Theophylline |
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This article needs additional citations for verification. Please help improve this article by adding reliable references. Unsourced material may be challenged and removed. (October 2009) |
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| Systematic (IUPAC) name | |
|---|---|
| 1,3-dimethyl-7H-purine-2,6-dione | |
| Identifiers | |
| CAS number | 58-55-9 |
| ATC code | R03DA04 |
| PubChem | 2153 |
| DrugBank | APRD00082 |
| ChemSpider | 2068 |
| Chemical data | |
| Formula | C7H8N4O2 |
| Mol. mass | 180.164 g/mol |
| SMILES | eMolecules & PubChem |
| Pharmacokinetic data | |
| Bioavailability | 100% |
| Protein binding | 40%, primarily to albumin |
| Metabolism | hepatic to 1-methyluric acid |
| Half life | 5-8 hours |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. | |
| Legal status | |
| Routes | oral, IV |
 (what is this?) (verify) |
|
Theophylline, also known as dimethylxanthine, is a methylxanthine drug used in therapy for respiratory diseases such as COPD or asthma under a variety of brand names. Due to its numerous side-effects, these drugs are now rarely administered for clinical use. As a member of the xanthine family, it bears structural and pharmacological similarity to caffeine. It is naturally found in tea, although in trace quantities (~1 mg/L),[1] significantly less than therapeutic doses.[2]
The main actions of theophylline involve:
- relaxing bronchial smooth muscle
- increasing heart muscle contractility and efficiency: positive inotropic
- increasing heart rate: positive chronotropic
- increasing blood pressure
- increasing renal blood flow
- some anti-inflammatory effects
- central nervous system stimulatory effect mainly on the medullary respiratory center.
Contents |
History
Theophylline was first extracted from tea leaves and chemically identified around 1888 by the German biologist Albrecht Kossel.[3][4] Just seven years after its discovery, a chemical synthesis starting with 1,3-dimethyluric acid was described by Emil Fischer and Lorenz Ach.[5] The Traube synthesis, an alternative method to synthesize Theophylline has been introduced in 1900 by another German scientist, Wilhelm Traube.[6] Theophylline's first clinical use came in 1902 as diuretic.[7] It took additional 20 years until its first description in asthma treatment.[8]
Pharmacokinetics
Absorption
Bioavailability is 100%. However, taking the drug late in the evening may slow the absorption process, without affecting the bioavailability. Taking the drug after a meal high in fat content will also slow down the absorption process, without affecting the bioavailability.[citation needed]
Distribution
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 suffering from obesity.
Metabolism
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 in caffeine is also important in the infant population. Smokers and people with hepatic (liver) impairment metabolize it differently.
Elimination
Theophylline is excreted unchanged in the urine (up to 10%). Clearance of the drug is increased in these conditions: children 1 to 12, teenagers 12 to 16, adult smokers, elderly smokers, cystic fibrosis, 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.
Indications
The main therapeutic uses of theophylline are aimed at:
- chronic obstructive pulmonary disease (COPD)
- asthma
- infant apnea
Uses Under Investigation
A clinical study reported in 2008 that theophylline was helpful in improving the sense of smell in study subjects with anosmia.[9]
Mechanisms of action
The main mechanism of action of theophylline is that of adenosine receptor antagonism.[citation needed] Theophylline is a non-specific adenosine antagonist, antagonizing A1, A2, and A3 receptors almost equally, which explains many of its cardiac effects and some of its anti-asthmatic effects.[citation needed]
Another proposed mechanism of action includes a non-specific inhibition of phosphodiesterase enzymes, producing an increase in intracellular cyclic AMP; however, this is not known with certainty.[10][11][12]
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.[13]
It has been shown that theophylline may reverse the clinical observations of steroid insensitivity in patients with COPD and asthmatics that 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.[14] Furthermore, theophylline has been shown to directly activate HDAC2.[15] (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-KB 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.) Thus theophylline could prove to be a novel form of adjunct therapy in improving the clinical response to steroids in smoking asthmatics.[citation needed]
Side-effects
The use of theophylline is complicated by the fact that it interacts with various drugs, chiefly cimetidine and phenytoin, and that it has a narrow therapeutic index, so its use must be monitored to avoid toxicity. It can also cause nausea, diarrhea, increase in heart rate, arrhythmias, and CNS excitation (headaches, insomnia, irritability, dizziness and lightheadedness) [16][17]. Its toxicity is increased by erythromycin, cimetidine, and fluoroquinolones, such as "cipro" (ciprofloxacin). It can reach toxic levels when taken with fatty meals, an effect called dose dumping.[18]
Synthesis
Theophylline can be prepared synthetically starting from dimethylurea and ethyl 2-cyanoacetate.
References
- ^ MAFF Food Surveillance Information Sheet
- ^ RXlist dosage and administration information for theophylline
- ^ Kossel A. (1888). "Über eine neue Base aus dem Pflanzenreich.". Ber. Dtsch. Chem. Ges. 21: 2164–2167..
- ^ Kossel A. (1889). "Über das Theophyllin, einen neuen Bestandtheil des Thees.". Hoppe Seylers Z. Physiol. Chem. 13: 298–308..
- ^ Fischer E., Ach L. (1895). "Synthese des Caffeins.". Ber. Dtsch. Chem. Ges. 28: 3139..
- ^ Traube W (1900). "Der synthetische Aufbau der Harnsäure, des Xanthins, Theobromins, Theophyllins und Caffeïns aus der Cyanessigsäure]". Chem. Ber. 33: 3035–3056. doi:.
- ^ Minkowski O. (1902). "Über Theocin (Theophyllin) als Diureticum.". Ther. Gegenwart 43: 490–493..
- ^ Schultze-Werninghaus G., Meier-Sydow J. (1982). "The clinical and pharmacological history of theophylline: first report on the bronchospasmolytic action in man by S. R. Hirsch in Frankfurt (Main) 1922.". Clin. Allergy 12: 211–215. PMID 7042115..
- ^ For Some Who Have Lost Their Sense Of Smell, A Once Popular Asthma Drug Could Help. Science Daily, American Physiological Society
- ^ Theophylline at Priory.com
- ^ Ito K, Lim S, Caramori G, et al. (2002). "A molecular mechanism of action of theophylline: Induction of histone deacetylase activity to decrease inflammatory gene expression". Proc. Natl. Acad. Sci. U.S.A. 99 (13): 8921–6. doi:. PMID 12070353.
- ^ RxList.com
- ^ Yano, Biochem and Biophys Res Comm V341-3, 2006
- ^ Ito et al., 2002a
- ^ Ito et al., 2002b
- ^ MedlinePlus Drug Information: Theophylline
- ^ THEOPHYLLINE - ORAL 24 HOUR TABLET (Uni-Dur) side effects, medical uses, and drug interactions
- ^ Food-induced "dose-dumping" from a once-a-day theophylline product as a cause of theophylline toxicity.
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 | diprophylline |
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| Chemistry Dictionary. A Dictionary of Chemistry. Sixth Edition. Copyright © Market House Books Ltd, 2008. All rights reserved. Read more |
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