CFF

CAFFEINE

Created: 2000-05-16
Last modified:  2020-06-05

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Chemical Details

Formal Charge0
Atom Count24
Chiral Atom Count0
Bond Count25
Aromatic Bond Count10
2D diagram of CFF
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Chemical Component Summary

NameCAFFEINE
Synonyms3,7-DIHYDRO-1,3,7-TRIMETHYL-1H-PURINE-2,6-DIONE
Systematic Name (OpenEye OEToolkits)1,3,7-trimethylpurine-2,6-dione
FormulaC8 H10 N4 O2
Molecular Weight194.191
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C2N(c1ncn(c1C(=O)N2C)C)C
SMILESCACTVS3.341Cn1cnc2N(C)C(=O)N(C)C(=O)c12
SMILESOpenEye OEToolkits1.5.0Cn1cnc2c1C(=O)N(C(=O)N2C)C
Canonical SMILESCACTVS3.341 Cn1cnc2N(C)C(=O)N(C)C(=O)c12
Canonical SMILESOpenEye OEToolkits1.5.0 Cn1cnc2c1C(=O)N(C(=O)N2C)C
InChIInChI1.03 InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3
InChIKeyInChI1.03 RYYVLZVUVIJVGH-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank IDDB00201 
NameCaffeine
Groups approved
DescriptionCaffeine is a drug of the methylxanthine class used for a variety of purposes, including certain respiratory conditions of the premature newborn, pain relief, and to combat drowsiness. Caffeine is similar in chemical structure to [Theophylline] and [Theobromine].[A187691,L9851] It can be sourced from coffee beans, but also occurs naturally in various teas and cacao beans, which are different than coffee beans.[T716] Caffeine is also used in a variety of cosmetic products and can be administered topically, orally, by inhalation, or by injection.[T716] The caffeine citrate injection, used for apnea of the premature newborn, was initially approved by the FDA in 1999.[L9863] According to an article from 2017, more than 15 million babies are born prematurely worldwide. This correlates to about 1 in 10 births. Premature birth can lead to apnea and bronchopulmonary dysplasia, a condition that interferes with lung development and may eventually cause asthma or early onset emphysema in those born prematurely.[A187694] Caffeine is beneficial in preventing and treating apnea and bronchopulmonary dysplasia in newborns, improving the quality of life of premature infants.[T716]
Synonyms
  • Guaranine
  • 1,3,7-trimethyl-2,6-dioxopurine
  • 1,3,7-trimethylpurine-2,6-dione
  • Methyltheobromine
  • Caféine
Brand Names
  • Extraprin
  • Texaclear Pain Reliever
  • First Aid Shot Therapy Pain Relief
  • Ru-21 Hangover Relief
  • Basic Care Headache Relief
IndicationCaffeine is indicated for the short term treatment of apnea of prematurity in infants and off label for the prevention and treatment of bronchopulmonary dysplasia caused by premature birth.[T716,L9851] In addition, it is indicated in combination with sodium benzoate to treat respiratory depression resulting from an overdose with CNS depressant drugs.[L9899] Caffeine has a broad range of over the counter uses, and is found in energy supplements, athletic enhancement products, pain relief products, as well as cosmetic products.[T716,L9854,L9872]
Categories
  • Alkaloids
  • Anorexigenic Agents & Respiratory and CNS Stimulants
  • BCRP/ABCG2 Inhibitors
  • Caffeine and Caffeine Containing Products
  • Central Nervous System Agents
ATC-Code
  • D11AX26
  • R03DA20
  • V04CG30
  • N06BC01
CAS number58-08-2

Drug Targets

NameTarget SequencePharmacological ActionActions
Adenosine receptor A1MPPSISAFQAAYIGIEVLIALVSVPGNVLVIWAVKVNQALRDATFCFIVS...unknownantagonist
Adenosine receptor A2aMPIMGSSVYITVELAIAVLAILGNVLVCWAVWLNSNLQNVTNYFVVSLAA...unknownantagonist
Adenosine receptor A2bMLLETQDALYVALELVIAALSVAGNVLVCAAVGTANTLQTPTNYFLVSLA...unknownantagonist
Adenosine receptor A3MPNNSTALSLANVTYITMEIFIGLCAIVGNVLVICVVKLNPSLQTTTFYF...unknownantagonist
Phosphodiesterase enzymesMELSPRSPPEMLEESDCPSPLELKSAPSKKMWIKLRSLLRYMVKQLENGE...unknowninhibitor
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL113
PubChem 2519
ChEMBL CHEMBL113
ChEBI CHEBI:27732
CCDC/CSD AFEREK, AFEMIJ, AFERAG, AFEQEJ, AFEQIN, AFEQUZ, BEBFUM, AFEQOT, BOXVOC, CIHDUV, ARIFUE, CUYLAM, CESKAN01, CESKAN, AYOROW, BIKPUG, GANXUP, DIPHUH, AGIKUY, ABUWIE, FAKKUA, DASZIH, CAFBAR20, DOZGUX, DIJVOH, DIJWAU, DIPHUH01, EXUQUJ, EXUQUJ05, AGIGEE, CAFINE01, DIJVUN, EXUQUJ01, BOLBAH, EXUQUJ07, EXUQUJ08, EKOQAZ
COD 4510852, 1514629, 1514630, 1514631, 1514632, 1514633, 1514634, 1514635, 4500222, 4500223, 7201982, 2231464, 7108131, 4502539, 2242434, 7205199, 4504936, 4504937, 4504939, 4504938, 4504940, 2105780, 2105781, 2105782, 2105783, 2105785, 2105786, 2105787, 2105788, 4505575, 4505576, 7217869, 7217871, 7217870, 7102559, 7102560, 7207660, 7207661, 7207663, 7207662, 7207664, 7207665, 7207667, 7207674, 7218771, 4507751, 5000108, 7229895, 7229904, 4509292, 4509293, 4509294, 4509296, 1505183, 4509298, 1505182, 4509297, 1505184, 4509299, 1505186