Caffeine citrateProduct ingredient for Caffeine
- Name
- Caffeine citrate
- Drug Entry
- Caffeine
Caffeine 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.4,16 It can be sourced from coffee beans, but also occurs naturally in various teas and cacao beans, which are different than coffee beans.12 Caffeine is also used in a variety of cosmetic products and can be administered topically, orally, by inhalation, or by injection.12
The caffeine citrate injection, used for apnea of the premature newborn, was initially approved by the FDA in 1999.19 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.5 Caffeine is beneficial in preventing and treating apnea and bronchopulmonary dysplasia in newborns, improving the quality of life of premature infants.12
- Accession Number
- DBSALT000866
- Structure
Structure for Caffeine citrate (DBSALT000866)
- Synonyms
- 3,7-dihydro-1,3,7-trimethyl-1h-purine-2,6-dione citrate / Caffeine, citrated / Citrated caffeine
- UNII
- U26EO4675Q
- CAS Number
- 69-22-7
- Weight
- Average: 386.317
Monoisotopic: 386.107378176 - Chemical Formula
- C14H18N4O9
- InChI Key
- RCQXSQPPHJPGOF-UHFFFAOYSA-N
- InChI
- InChI=1S/C8H10N4O2.C6H8O7/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2;7-3(8)1-6(13,5(11)12)2-4(9)10/h4H,1-3H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
- IUPAC Name
- 1,3,7-trimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione; 2-hydroxypropane-1,2,3-tricarboxylic acid
- SMILES
- OC(=O)CC(O)(CC(O)=O)C(O)=O.CN1C=NC2=C1C(=O)N(C)C(=O)N2C
- External Links
- PubChem Compound
- 6241
- ChemSpider
- 6005
- ChEMBL
- CHEMBL1200569
- Wikipedia
- Caffeine_citrate
- Predicted Properties
Property Value Source Water Solubility 11.0 mg/mL ALOGPS logP -0.24 ALOGPS logP -0.55 Chemaxon logS -1.2 ALOGPS pKa (Strongest Basic) -0.92 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 58.44 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 49.83 m3·mol-1 Chemaxon Polarizability 18.96 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon