CHEBI:28177 - theophylline

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ChEBI Name theophylline
ChEBI ID CHEBI:28177
Definition A dimethylxanthine having the two methyl groups located at positions 1 and 3. It is structurally similar to caffeine and is found in green and black tea.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:45950, CHEBI:9523, CHEBI:26940
Supplier Information eMolecules:27517656, eMolecules:493944, ZINC000000001084
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Caffeine is a central nervous system (CNS) stimulant of the methylxanthine class and is the most commonly consumed psychoactive substance globally. It is mainly used for its eugeroic (wakefulness promoting), ergogenic (physical performance-enhancing), or nootropic (cognitive-enhancing) properties. Caffeine acts by blocking binding of adenosine at a number of adenosine receptor types, inhibiting the centrally depressant effects of adenosine and enhancing the release of acetylcholine. Caffeine has a three-dimensional structure similar to that of adenosine, which allows it to bind and block its receptors. Caffeine also increases cyclic AMP levels through nonselective inhibition of phosphodiesterase, increases calcium release from intracellular stores, and antagonizes GABA receptors, although these mechanisms typically occur at concentrations beyond usual human consumption. Caffeine is a bitter, white crystalline purine, a methylxanthine alkaloid, and is chemically related to the adenine and guanine bases of deoxyribonucleic acid (DNA) and ribonucleic acid (RNA). It is found in the seeds, fruits, nuts, or leaves of a number of plants native to Africa, East Asia and South America and helps to protect them against herbivores and from competition by preventing the germination of nearby seeds, as well as encouraging consumption by select animals such as honey bees. The best-known source of caffeine is the coffee bean, the seed of the Coffea plant. People may drink beverages containing caffeine to relieve or prevent drowsiness and to improve cognitive performance. To make these drinks, caffeine is extracted by steeping the plant product in water, a process called infusion. Caffeine-containing drinks, such as coffee, tea, and cola, are consumed globally in high volumes. In 2020, almost 10 million tonnes of coffee beans were consumed globally. Caffeine is the world's most widely consumed psychoactive drug. Unlike most other psychoactive substances, caffeine remains largely unregulated and legal in nearly all parts of the world. Caffeine is also an outlier as its use is seen as socially acceptable in most cultures with it even being encouraged. Caffeine has both positive and negative health effects. It can treat and prevent the premature infant breathing disorders bronchopulmonary dysplasia of prematurity and apnea of prematurity. Caffeine citrate is on the WHO Model List of Essential Medicines. It may confer a modest protective effect against some diseases, including Parkinson's disease. Some people experience sleep disruption or anxiety if they consume caffeine, but others show little disturbance. Evidence of a risk during pregnancy is equivocal; some authorities recommend that pregnant women limit caffeine to the equivalent of two cups of coffee per day or less. Caffeine can produce a mild form of drug dependence – associated with withdrawal symptoms such as sleepiness, headache, and irritability – when an individual stops using caffeine after repeated daily intake. Tolerance to the autonomic effects of increased blood pressure and heart rate, and increased urine output, develops with chronic use (i.e., these symptoms become less pronounced or do not occur following consistent use). Caffeine is classified by the U.S. Food and Drug Administration (FDA) as generally recognized as safe. Toxic doses, over 10 grams per day for an adult, are much higher than the typical dose of under 500 milligrams per day. The European Food Safety Authority reported that up to 400 mg of caffeine per day (around 5.7 mg/kg of body mass per day) does not raise safety concerns for non-pregnant adults, while intakes up to 200 mg per day for pregnant and lactating women do not raise safety concerns for the fetus or the breast-fed infants. A cup of coffee contains 80–175 mg of caffeine, depending on what "bean" (seed) is used, how it is roasted, and how it is prepared (e.g., drip, percolation, or espresso). Thus it requires roughly 50–100 ordinary cups of coffee to reach the toxic dose. However, pure powdered caffeine, which is available as a dietary supplement, can be lethal in tablespoon-sized amounts.
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Formula C7H8N4O2
Net Charge 0
Average Mass 180.16418
Monoisotopic Mass 180.06473
InChI InChI=1S/C7H8N4O2/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13/h3H,1-2H3,(H,8,9)
InChIKey ZFXYFBGIUFBOJW-UHFFFAOYSA-N
SMILES Cn1c2nc[nH]c2c(=O)n(C)c1=O
Metabolite of Species Details
Citrus limon (NCBI:txid2708) See: DOI
Citrus maxima (NCBI:txid37334) See: DOI
Citrus x paradisi (NCBI:txid37656) See: DOI
Homo sapiens (NCBI:txid9606) Found in blood serum (BTO:0000133). See: MetaboLights Study
Roles Classification
Biological Role(s): EC 3.1.4.* (phosphoric diester hydrolase) inhibitor
An EC 3.1.* (ester hydrolase) inhibitor that interferes with the action of a phosphoric diester hydrolase (EC 3.1.4.*).
immunomodulator
Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
adenosine receptor antagonist
An antagonist at any adenosine receptor.
drug metabolite

fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
human blood serum metabolite
Any metabolite (endogenous or exogenous) found in human blood serum samples.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): muscle relaxant
A drug used to produce muscle relaxation (excepting neuromuscular blocking agents). Its primary clinical and therapeutic use is the treatment of muscle spasm and immobility associated with strains, sprains, and injuries of the back and, to a lesser degree, injuries to the neck. Also used for the treatment of a variety of clinical conditions that have in common only the presence of skeletal muscle hyperactivity, for example, the muscle spasms that can occur in multiple sclerosis.
bronchodilator agent
An agent that causes an increase in the expansion of a bronchus or bronchial tubes.
vasodilator agent
A drug used to cause dilation of the blood vessels.
immunomodulator
Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
anti-inflammatory agent
Any compound that has anti-inflammatory effects.
anti-asthmatic drug
A drug used to treat asthma.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing theophylline (CHEBI:28177) has role adenosine receptor antagonist (CHEBI:71232)
theophylline (CHEBI:28177) has role anti-asthmatic drug (CHEBI:49167)
theophylline (CHEBI:28177) has role anti-inflammatory agent (CHEBI:67079)
theophylline (CHEBI:28177) has role bronchodilator agent (CHEBI:35523)
theophylline (CHEBI:28177) has role drug metabolite (CHEBI:49103)
theophylline (CHEBI:28177) has role EC 3.1.4.* (phosphoric diester hydrolase) inhibitor (CHEBI:50218)
theophylline (CHEBI:28177) has role fungal metabolite (CHEBI:76946)
theophylline (CHEBI:28177) has role human blood serum metabolite (CHEBI:85234)
theophylline (CHEBI:28177) has role immunomodulator (CHEBI:50846)
theophylline (CHEBI:28177) has role muscle relaxant (CHEBI:51371)
theophylline (CHEBI:28177) has role vasodilator agent (CHEBI:35620)
theophylline (CHEBI:28177) is a dimethylxanthine (CHEBI:23818)
Incoming aminophylline (CHEBI:2659) has part theophylline (CHEBI:28177)
IUPAC Name
1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione
Synonyms Sources
1,3-dimethyl-7H-purine-2,6-dione IUPHAR
1,3-Dimethylxanthine KEGG COMPOUND
Theophyllin ChemIDplus
Theophylline KEGG COMPOUND
THEOPHYLLINE PDBeChem
theophylline UniProt
théophylline ChEBI
theophylline anhydrous ChemIDplus
Brand Names Sources
Elixophyllin KEGG DRUG
Respbid ChemIDplus
Theo-Dur ChemIDplus
Theolair KEGG DRUG
Uniphyl KEGG DRUG
Manual Xrefs Databases
1801 VSDB
2620 DrugCentral
C00001510 KNApSAcK
C07130 KEGG COMPOUND
CPD-12479 MetaCyc
D00371 KEGG DRUG
DB00277 DrugBank
HMDB0001889 HMDB
TEP PDBeChem
Theophylline Wikipedia
View more database links
Registry Numbers Types Sources
13463 Reaxys Registry Number Reaxys
51226 Gmelin Registry Number Gmelin
58-55-9 CAS Registry Number KEGG COMPOUND
58-55-9 CAS Registry Number NIST Chemistry WebBook
58-55-9 CAS Registry Number ChemIDplus
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Last Modified
22 February 2017