Caffeine citrate

Caffeine citrate
Clinical data
Trade names	Cafcit, Gencebok, Cafnea, others
AHFS/Drugs.com	Monograph
License data	US DailyMed: Caffeine_citrate;
Routes of; administration	By mouth, intravenous (IV)
ATC code	N06BC01 (WHO) ;
Legal status
Legal status	AU: Unscheduled; CA: ℞-only; US: ℞-only; EU: Rx-only;
Identifiers
	IUPAC name 1,3,7-trimethylpurine-2,6-dione; 2-hydroxypropane-1,2,3-tricarboxylic acid;
CAS Number	69-22-7 ;
PubChem CID	6241;
ChemSpider	6005 ;
UNII	U26EO4675Q;
KEGG	D07603;
ChEMBL	ChEMBL1200569;
CompTox Dashboard (EPA)	DTXSID5046938 ;
ECHA InfoCard	100.125.472
Chemical and physical data
Formula	C14H18N4O9
Molar mass	386.317 g·mol−1
3D model (JSmol)	Interactive image;
	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) ; Key:RCQXSQPPHJPGOF-UHFFFAOYSA-N ;
	(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]

Caffeine was discovered in 1819.^[9] It is on the World Health Organization's List of Essential Medicines.^[10] The intravenous form may also be taken by mouth.^[11]

In June 2020, the Committee for Medicinal Products for Human Use (CHMP) of the European Medicines Agency (EMA) recommended the approval of Gencebok.^[12] It was approved for use in the European Union in August 2020.^[3]

^ "Regulatory Decision Summary - Peyona". Health Canada. 23 October 2014. Retrieved 5 June 2022.
^ "Cafcit- caffeine citrate injection". DailyMed. 3 January 2020. Retrieved 27 August 2020.
^ ^a ^b "Gencebok EPAR". European Medicines Agency (EMA). 19 June 2020. Retrieved 27 August 2020.
^ "Gencebok Product information". Union Register of medicinal products. Retrieved 3 March 2023.
^ ^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.
^ ^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.
^ 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.
^ Cite error: The named reference Smit_2015 was invoked but never defined (see the help page).
^ 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.
^ 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.
^ 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.
^ "Gencebok: Pending EC decision". European Medicines Agency (EMA). 25 June 2020. Archived from the original on 27 June 2020. Retrieved 26 June 2020.

[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.

[Gencebok_EPAR-3] "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.

[AHFS2016-5] "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.

[WHO2008-6] 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.

[Smit_2015-8] 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.

[WHO21st-10] 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.

[Ai2014-11] 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.

[12] "Gencebok: Pending EC decision". European Medicines Agency (EMA). 25 June 2020. Archived from the original on 27 June 2020. Retrieved 26 June 2020.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

[12]