Record Information
Version1.0
Creation date2010-04-08 22:04:34 UTC
Update date2018-05-29 00:29:07 UTC
Primary IDFDB000453
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameTheophylline
DescriptionConstituent of tea leaves (Camellia thea) and maté (Ilex paraguariensis) Theophylline, also known as dimethylxanthine, is a methylxanthine drug used in therapy for respiratory diseases such as COPD and asthma under a variety of brand names. As a member of the xanthine family, it bears structural and pharmacological similarity to caffeine. It is naturally found in tea and in cocoa beans.
CAS Number58-55-9
Structure
Thumb
Synonyms
SynonymSource
1,3-Dimethyl-7H-purine-2,6-dioneChEBI
1,3-DimethylxanthineChEBI
ElixophyllinChEBI
RespbidChEBI
Theo-durChEBI
TheolairChEBI
TheophyllinChEBI
Theophylline anhydrousChEBI
UniphylChEBI
Quibron-tKegg
Theo-24Kegg
Theodur gKegg
AccurbronHMDB
Acet-theocinHMDB
AerolateHMDB
Aerolate IIIHMDB
Aerolate SRHMDB
AminophyllineHMDB
AquaphyllinHMDB
ArmophyllineHMDB
AsbronHMDB
AsmaxHMDB
AustynHMDB
BronkodylHMDB
Bronkodyl SRHMDB
Choledyl saHMDB
Constant-THMDB
DiphyllinHMDB
DoraphyllinHMDB
DuraphylHMDB
Dyspne-inhalHMDB
ElixexHMDB
ElixiconHMDB
ElixominHMDB
Elixophyllin SRHMDB
ElixophyllineHMDB
EuphyllineHMDB
EuphylongHMDB
LabidHMDB
LanophyllinHMDB
LiquophyllineHMDB
LiquoriceHMDB
MaphyllineHMDB
MedaphyllinHMDB
NuelinHMDB
OptiphyllinHMDB
ParkophyllinHMDB
PseudotheophyllineHMDB
Quibron t/srHMDB
Quibron-t/srHMDB
Slo-bidHMDB
Slo-phyllinHMDB
SolosinHMDB
Somophyllin-CRTHMDB
Somophyllin-DFHMDB
Somophyllin-THMDB
Spophyllin retardHMDB
SustaireHMDB
SynophylateHMDB
Synophylate-l.a. cenulesHMDB
T-PhylHMDB
TefaminHMDB
TeofilinaHMDB
TeofyllaminHMDB
TeolairHMDB
TheacitinHMDB
Theal tabl.HMDB
Theal tabletsHMDB
Theo-dur-sprinkleHMDB
TheobidHMDB
Theobid jr.HMDB
TheochronHMDB
TheocinHMDB
Theoclair-SRHMDB
Theoclear 80HMDB
Theoclear l.a.-130HMDB
Theoclear laHMDB
Theoclear-200HMDB
Theoclear-80HMDB
TheocontinHMDB
TheodelHMDB
TheofolHMDB
TheogradHMDB
Theolair-SRHMDB
TheolixHMDB
TheolixirHMDB
Theona pHMDB
TheophylHMDB
Theophyl-225HMDB
Theophyl-SRHMDB
TheophylineHMDB
Theophylline-SRHMDB
Theostat 80HMDB
TheoventHMDB
Uni-durHMDB
UnifylHMDB
UniphyllinHMDB
XanthiumHMDB
XantiventHMDB
AerobinHMDB
BronchoparatHMDB
Glycine theophyllinateHMDB
Nuelin s.a.HMDB
Slo phyllinHMDB
SloPhyllinHMDB
Somophyllin THMDB
Theo24HMDB
Theoconfin continuousHMDB
TheoniteHMDB
CT Arzneimittel brand OF theophylline sodium glycinateHMDB
Von CT, theoHMDB
Mundipharma brand OF theophylline sodium glycinateHMDB
Quibron T SRHMDB
Quibron T-SRHMDB
Sodium glycinate, theophyllineHMDB
Theo 24HMDB
Theophyllinate, glycineHMDB
Theophylline sodium glycinateHMDB
TheospanHMDB
UniphyllineHMDB
CT-Arzneimittel brand OF theophylline sodium glycinateHMDB
ConstantTHMDB
Fameasan brand OF theophylline sodium glycinateHMDB
LodraneHMDB
MonospanHMDB
Quibron TSRHMDB
TheodurHMDB
TheonHMDB
TheopekHMDB
TheostatHMDB
CT, Theo vonHMDB
Theo von CTHMDB
1,3 DimethylxanthineHMDB
3,7-Dihydro-1,3-dimethyl-1H-purine-2,6-dioneHMDB
Afonilum retardHMDB
Anhydrous, theophyllineHMDB
Constant THMDB
Fujisawa brand OF theophylline sodium glycinateHMDB
Glycinate, theophylline sodiumHMDB
SomophyllinTHMDB
Theo durHMDB
1,3-Dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurinebiospider
1,3-Dimethyl-3,7-dihydro-1H-purine-2,6-dionebiospider
1,3-Dimethyl-3,9-dihydro-1H-purine-2,6-dionebiospider
1H-Purine-2,6-dione, 3,7-dihydro-1,3-dimethyl-biospider
1H-Purine-2,6-dione, 3,9-dihydro-1,3-dimethyl-biospider
2,6-Dihydroxy-1,3-dimethylpurinebiospider
3,7-Dihydro-1,3-dimethyl-1H-purine-2,6-dione, 9CIdb_source
Aerolate srHMDB
Bronkodyl srHMDB
Constant-tHMDB
Elixophyllin srHMDB
Labophyllinebiospider
Mudranebiospider
Purine-2,6(1H,3H)-dione, 1,3-dimethyl-biospider
Slophyllinbiospider
Somophyllin-crtHMDB
Somophyllin-dfHMDB
Somophyllin-tHMDB
T-phylHMDB
Teonovadb_source
Theoclair-srHMDB
Theokinbiospider
Theolair-srHMDB
Theona PHMDB
Theophyl-srHMDB
Theophylline-srHMDB
Xanthine, 1,3-dimethyl-biospider
Predicted Properties
PropertyValueSource
Water Solubility22.9 g/LALOGPS
logP-0.26ALOGPS
logP-0.77ChemAxon
logS-0.9ALOGPS
pKa (Strongest Acidic)7.82ChemAxon
pKa (Strongest Basic)-0.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area69.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity44.93 m³·mol⁻¹ChemAxon
Polarizability16.86 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC7H8N4O2
IUPAC name1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
InChI IdentifierInChI=1S/C7H8N4O2/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13/h3H,1-2H3,(H,8,9)
InChI KeyZFXYFBGIUFBOJW-UHFFFAOYSA-N
Isomeric SMILESCN1C2=C(NC=N2)C(=O)N(C)C1=O
Average Molecular Weight180.164
Monoisotopic Molecular Weight180.06472552
Classification
Description belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentXanthines
Alternative Parents
Substituents
  • Xanthine
  • 6-oxopurine
  • Purinone
  • Alkaloid or derivatives
  • Pyrimidone
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Urea
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 46.67%; H 4.48%; N 31.10%; O 17.76%DFC
Melting PointMp 264°DFC
Boiling PointNot Available
Experimental Water Solubility7.36 mg/mL at 25 oCYALKOWSKY,SH & HE,Y (2003)
Experimental logP-0.02HANSCH,C ET AL. (1995)
Experimental pKapKa2 8.6 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
ChemSpider ID2068
ChEMBL IDCHEMBL190
KEGG Compound IDC07130
Pubchem Compound ID2153
Pubchem Substance IDNot Available
ChEBI ID28177
Phenol-Explorer IDNot Available
DrugBank IDDB00277
HMDB IDHMDB01889
CRC / DFC (Dictionary of Food Compounds) IDBCK73-S:BCK73-S
EAFUS IDNot Available
Dr. Duke IDTHEOPHYLLINE| DIMETHYLXANTHINE
BIGG IDNot Available
KNApSAcK IDC00001510
HET IDTEP
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDTheophylline
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
(+)-inotropicDUKE
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
anti apneic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti asthmatic49167 A drug used to treat asthma.DUKE
anti bradyarrhythmic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
anti bronchitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti cellulitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antidote50247 Any protective agent counteracting or neutralizing the action of poisons.DUKE
anti emphysemic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti neuralgic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti rhinitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
arteriodilatorDUKE
bronchodilator35523 An agent that causes an increase in the expansion of a bronchus or bronchial tubes.DUKE
cAMP inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
cAMP-phosphodiesterase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
cardiovascular38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
cGMP inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
cGMP-phosphodiesterase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
cholereticDUKE
central nervous system stimulant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
fetotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
herbicide24527 A substance used to destroy plant pests.DUKE
hypertensiveDUKE
hyperuricemicDUKE
hypoglycemic35526 A drug which lowers the blood glucose level.DUKE
myocardiotonic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
myorelaxantDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
prostaglandin secretorDUKE
stimulantDUKE
tachycardic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
teratogenic50905 A role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect.DUKE
vasodilator35620 A drug used to cause dilation of the blood vessels.DUKE
Enzymes
NameGene NameUniProt ID
Adenosine deaminaseADAP00813
Adenosine receptor A1ADORA1P30542
Adenosine receptor A2aADORA2AP29274
Adenosine receptor A2bADORA2BP29275
Pathways
NameSMPDB LinkKEGG Link
Caffeine MetabolismSMP00028 map00232
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.