Caffeine citrate

Caffeine citrate
Clinical data
Trade namesCafcit, Gencebok, Cafnea, others
AHFS/Drugs.comMonograph
License data
Routes of
administration		By mouth, intravenous (IV)
ATC code
Legal status
Legal status
Identifiers
IUPAC name
  • 1,3,7-trimethylpurine-2,6-dione; 2-hydroxypropane-1,2,3-tricarboxylic acid
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.125.472
Chemical and physical data
FormulaC14H18N4O9
Molar mass386.317 g·mol−1
3D model (JSmol)
SMILES
  • CN1C=NC2=C1C(=O)N(C(=O)N2C)C.C(C(=O)O)C(CC(=O)O)(C(=O)O)O
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) Y
  • Key:RCQXSQPPHJPGOF-UHFFFAOYSA-N Y
  (verify)

Caffeine citrate, sold under the brand name Cafcit among others, is a medication used to treat a lack of breathing in premature babies.[5] Specifically it is given to babies who are born at less than 35 weeks or weigh less than 2 kilograms (4.4 lb) once other causes are ruled out.[6] It is given by mouth or slow injection into a vein.[5]

Side effects can include problems feeding, increased heart rate, low blood sugar, necrotizing enterocolitis, and kidney problems.[5][6] Testing blood caffeine levels is occasionally recommended.[5] Although it is often referred to as a citric acid salt of caffeine,[7] as implied by its name, caffeine citrate in fact consists of cocrystals of the two components.[8] Caffeine citrate is in the xanthine family of medication.[6] It works by stimulating the respiratory centers in the brain.[5]

Although caffeine was isolated in 1819,[9] it was not until 1977 that caffeine citrate was first used for treating apnea of prematurity.[10][11] It is on the World Health Organization's List of Essential Medicines.[12] The intravenous form may also be taken by mouth.[13]

In June 2020, the Committee for Medicinal Products for Human Use (CHMP) of the European Medicines Agency (EMA) recommended the approval of Gencebok.[14] It was approved for use in the European Union in August 2020.[3]

  1. ^ "Regulatory Decision Summary - Peyona". Health Canada. 23 October 2014. Retrieved 5 June 2022.
  2. ^ "Cafcit- caffeine citrate injection". DailyMed. 3 January 2020. Retrieved 27 August 2020.
  3. ^ a b "Gencebok EPAR". European Medicines Agency (EMA). 19 June 2020. Retrieved 27 August 2020.
  4. ^ "Gencebok Product information". Union Register of medicinal products. Retrieved 3 March 2023.
  5. ^ a b c d e "Caffeine; Caffeine and Sodium Benzoate Injection; Caffeine Citrate". The American Society of Health-System Pharmacists. Archived from the original on 16 July 2017. Retrieved 8 December 2016.
  6. ^ a b c World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 485. hdl:10665/44053. ISBN 9789241547659.
  7. ^ Donn SM, Sinha SK (2012). Manual of Neonatal Respiratory Care. Springer Science & Business Media. p. 457. ISBN 9781461421559. Archived from the original on 30 December 2016.
  8. ^ Cite error: The named reference Smit_2015 was invoked but never defined (see the help page).
  9. ^ Brown N (2015). In Silico Medicinal Chemistry: Computational Methods to Support Drug Design. Royal Society of Chemistry. p. 20. ISBN 9781782621638. Archived from the original on 29 December 2016.
  10. ^ Shrestha B, Jawa G (October 2017). "Caffeine citrate - Is it a silver bullet in neonatology?". Pediatrics and Neonatology. 58 (5): 391–397. doi:10.1016/j.pedneo.2016.10.003. PMID 28446386.
  11. ^ Aranda JV, Gorman W, Bergsteinsson H, Gunn T (March 1977). "Efficacy of caffeine in treatment of apnea in the low-birth-weight infant". The Journal of Pediatrics. 90 (3): 467–472. doi:10.1016/S0022-3476(77)80718-X. PMID 14241.
  12. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  13. ^ Ainsworth SB (2014). Neonatal Formulary: Drug Use in Pregnancy and the First Year of Life (7 ed.). John Wiley & Sons. p. 120. ISBN 9781118819517. Archived from the original on 30 December 2016.
  14. ^ "Gencebok: Pending EC decision". European Medicines Agency (EMA). 25 June 2020. Archived from the original on 27 June 2020. Retrieved 26 June 2020.
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