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
Thumb
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
PropertyValueSource
Water Solubility11.0 mg/mLALOGPS
logP-0.24ALOGPS
logP-0.55ChemAxon
logS-1.2ALOGPS
pKa (Strongest Basic)-0.92ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area58.44 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity49.83 m3·mol-1ChemAxon
Polarizability18.96 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon