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Caffeine citrate information


Caffeine citrate
Clinical data
Trade namesCafcit, Gencebok, Cafnea, others
AHFS/Drugs.comMonograph
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[1]
  • US: ℞-only[2]
  • EU: Rx-only[3][4]
Identifiers
IUPAC name
  • 1,3,7-trimethylpurine-2,6-dione; 2-hydroxypropane-1,2,3-tricarboxylic acid
CAS Number
  • 69-22-7 checkY
PubChem CID
  • 6241
ChemSpider
  • 6005 checkY
UNII
  • U26EO4675Q
KEGG
  • D07603
ChEMBL
  • ChEMBL1200569
CompTox Dashboard (EPA)
  • DTXSID5046938 Edit this at Wikidata
ECHA InfoCard100.125.472 Edit this at Wikidata
Chemical and physical data
FormulaC14H18N4O9
Molar mass386.317 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) checkY
  • Key:RCQXSQPPHJPGOF-UHFFFAOYSA-N checkY
  (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]

  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. ^ 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.
  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.

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Caffeine citrate

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Caffeine citrate, sold under the brand name Cafcit among others, is a medication used to treat a lack of breathing in premature babies. Specifically it...

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Caffeine

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bronchopulmonary dysplasia of prematurity and apnea of prematurity. Caffeine citrate is on the WHO Model List of Essential Medicines. It may confer a modest...

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Uric acid

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8-Phenyltheophylline Acefylline Aminophylline ATL-444 Bamifylline Cafedrine Caffeine Caffeine citrate Cartazolate CGH-2466 CGS-15943 Choline theophyllinate Ciforadenant...

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Cytosine

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8-Phenyltheophylline Acefylline Aminophylline ATL-444 Bamifylline Cafedrine Caffeine Caffeine citrate Cartazolate CGH-2466 CGS-15943 Choline theophyllinate Ciforadenant...

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Nucleotide

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8-Phenyltheophylline Acefylline Aminophylline ATL-444 Bamifylline Cafedrine Caffeine Caffeine citrate Cartazolate CGH-2466 CGS-15943 Choline theophyllinate Ciforadenant...

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Adenosine

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Caffeine acts by blocking binding of adenosine to the adenosine A1 receptor, which enhances release of the neurotransmitter acetylcholine. Caffeine also...

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Phenolphthalein

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8-Phenyltheophylline Acefylline Aminophylline ATL-444 Bamifylline Cafedrine Caffeine Caffeine citrate Cartazolate CGH-2466 CGS-15943 Choline theophyllinate Ciforadenant...

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Theobromine

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classified as a dimethyl xanthine. Related compounds include theophylline, caffeine, paraxanthine, and 7-methylxanthine, each of which differ in the number...

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Sting Energy

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acid, artificial flavor, maltodextrin, sodium citrate, sodium hexametaphosphate, potassium sorbate, caffeine, sodium benzoate, tartrazine, inositol, calcium...

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Allopurinol

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8-Phenyltheophylline Acefylline Aminophylline ATL-444 Bamifylline Cafedrine Caffeine Caffeine citrate Cartazolate CGH-2466 CGS-15943 Choline theophyllinate Ciforadenant...

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Methotrexate

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8-Phenyltheophylline Acefylline Aminophylline ATL-444 Bamifylline Cafedrine Caffeine Caffeine citrate Cartazolate CGH-2466 CGS-15943 Choline theophyllinate Ciforadenant...

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Uracil

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growth of cancerous cells. Uracil can also be used in the synthesis of caffeine. Uracil has also shown potential as a HIV viral capsid inhibitor. Uracil...

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Inositol

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"Ovulation induction with myo-inositol alone and in combination with clomiphene citrate in polycystic ovarian syndrome patients with insulin resistance". Gynecological...

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Nucleoside

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8-Phenyltheophylline Acefylline Aminophylline ATL-444 Bamifylline Cafedrine Caffeine Caffeine citrate Cartazolate CGH-2466 CGS-15943 Choline theophyllinate Ciforadenant...

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Pyrimidine

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8-Phenyltheophylline Acefylline Aminophylline ATL-444 Bamifylline Cafedrine Caffeine Caffeine citrate Cartazolate CGH-2466 CGS-15943 Choline theophyllinate Ciforadenant...

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Guanine

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8-Phenyltheophylline Acefylline Aminophylline ATL-444 Bamifylline Cafedrine Caffeine Caffeine citrate Cartazolate CGH-2466 CGS-15943 Choline theophyllinate Ciforadenant...

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Quercetin

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vivo study found that quercetin supplementation slows the metabolism of caffeine to a statistically significant extent in a particular genetic subpopulation...

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Theophylline

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S, et al. (19 September 2022). "Comparative efficacy and safety of caffeine citrate and aminophylline in treating apnea of prematurity: A systematic review...

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Xanthine

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other organisms. Several stimulants are derived from xanthine, including caffeine, theophylline, and theobromine. Xanthine is a product on the pathway of...

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Ivermectin

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Fenethylline

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take place. These illicit pills often contain "a mix of amphetamines, caffeine[,] and various fillers", which are sometimes referred to as "captagon"...

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Purine

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notable purines are hypoxanthine, xanthine, theophylline, theobromine, caffeine, uric acid and isoguanine. [contradictory] Aside from the crucial roles...

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Propolis

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8-Phenyltheophylline Acefylline Aminophylline ATL-444 Bamifylline Cafedrine Caffeine Caffeine citrate Cartazolate CGH-2466 CGS-15943 Choline theophyllinate Ciforadenant...

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Dipyridamole

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place. Dipyridamole overdose can be treated with aminophylline: 6  or caffeine which reverses its dilating effect on the blood vessels. Symptomatic treatment...

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Red Bull

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and magnesium carbonate (substituted in some flavours with a trisodium citrate/citric acid buffer, each solution providing electrolytes). To produce Red...

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Uridine

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8-Phenyltheophylline Acefylline Aminophylline ATL-444 Bamifylline Cafedrine Caffeine Caffeine citrate Cartazolate CGH-2466 CGS-15943 Choline theophyllinate Ciforadenant...

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Cinnamaldehyde

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Phenol red

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8-Phenyltheophylline Acefylline Aminophylline ATL-444 Bamifylline Cafedrine Caffeine Caffeine citrate Cartazolate CGH-2466 CGS-15943 Choline theophyllinate Ciforadenant...

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