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Caffeine citrate

April 14, 2024

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]

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
  • 1,3,7-trimethylpurine-2,6-dione; 2-hydroxypropane-1,2,3-tricarboxylic acid
CAS Number
  • 69-22-7 Y
PubChem CID
  • 6241
ChemSpider
  • 6005 Y
UNII
  • U26EO4675Q
KEGG
  • D07603
ChEMBL
  • ChEMBL1200569
CompTox Dashboard (EPA)
  • DTXSID5046938
ECHA InfoCard100.125.472
Chemical and physical data
FormulaC14H18N4O9
Molar mass386.317 g·mol−1
3D model (JSmol)
  • Interactive image
  • CN1C=NC2=C1C(=O)N(C(=O)N2C)C.C(C(=O)O)C(CC(=O)O)(C(=O)O)O
  • 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)

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]

Medical uses edit

Caffeine citrate is generally the preferred treatment for apnea of prematurity for infants born 28 to 32 weeks or earlier than 28 weeks.[6][13] It has fewer side effects as compared to theophylline.[6]

Caffeine improves airway function in asthma, increasing forced expiratory volume (FEV1) by 5% to 18%, with this effect lasting for up to four hours.[14]

Mechanism edit

In method of action, the preparation is identical to that of caffeine base as the citrate counter ion dissociates in water. Doses of caffeine citrate, due to the added weight of the citrate moiety, are understandably higher than with caffeine base, i.e., it takes a larger dose to get the same amount of caffeine.[11] The ratio of therapeutic doses of caffeine base to its citrate salt is typically 1:2.[11] Dosing should therefore be clearly distinguished.[11]

Manufacture edit

The drug is prepared by combining anhydrous caffeine with citric acid monohydrate and sodium citrate dihydrate. Caffeine citrate cocrystals can take on at least two anhydrous polymorphs.[8]

References edit

  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. from the original on 16 July 2017. Retrieved 8 December 2016.
  6. ^ a b c d e 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. from the original on 30 December 2016.
  8. ^ a b Smit JP, Hagen EJ (1 March 2015). "Polymorphism in Caffeine Citric Acid Cocrystals". Journal of Chemical Crystallography. 45 (3): 128–133. doi:10.1007/s10870-015-0573-3. ISSN 1572-8854. S2CID 96712417.
  9. ^ Brown N (2015). In Silico Medicinal Chemistry: Computational Methods to Support Drug Design. Royal Society of Chemistry. p. 20. ISBN 9781782621638. 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. ^ a b c d Ainsworth SB (2014). Neonatal Formulary: Drug Use in Pregnancy and the First Year of Life (7 ed.). John Wiley & Sons. p. 120. ISBN 9781118819517. from the original on 30 December 2016.
  12. ^ . European Medicines Agency (EMA). 25 June 2020. Archived from the original on 27 June 2020. Retrieved 26 June 2020.
  13. ^ "NIH-funded research leads to pediatric labeling updates for doxycycline, clindamycin and caffeine citrate". National Institutes of Health (NIH). 2 April 2020. Retrieved 27 July 2022.
  14. ^ Welsh EJ, Bara A, Barley E, Cates CJ (January 2010). "Caffeine for asthma". The Cochrane Database of Systematic Reviews. 2010 (1): CD001112. doi:10.1002/14651858.CD001112.pub2. PMC 7053252. PMID 20091514.

External links edit

  • "Caffeine Citrate (CUI C0054436)". NCI Metathesaurus.

April 14, 2024
caffeine, citrate, sold, under, brand, name, cafcit, among, others, medication, used, treat, lack, breathing, premature, babies, specifically, given, babies, born, less, than, weeks, weigh, less, than, kilograms, once, other, causes, ruled, given, mouth, slow,. 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 Caffeine citrateClinical dataTrade namesCafcit Gencebok Cafnea othersAHFS Drugs comMonographLicense dataUS DailyMed Caffeine citrateRoutes ofadministrationBy mouth intravenous IV ATC codeN06BC01 WHO Legal statusLegal statusAU Unscheduled CA only 1 US only 2 EU Rx only 3 4 IdentifiersIUPAC name 1 3 7 trimethylpurine 2 6 dione 2 hydroxypropane 1 2 3 tricarboxylic acidCAS Number69 22 7 YPubChem CID6241ChemSpider6005 YUNIIU26EO4675QKEGGD07603ChEMBLChEMBL1200569CompTox Dashboard EPA DTXSID5046938ECHA InfoCard100 125 472Chemical and physical dataFormulaC 14H 18N 4O 9Molar mass386 317 g mol 13D model JSmol Interactive imageSMILES CN1C NC2 C1C O N C O N2C C C C O O C CC O O C O O OInChI 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 YKey RCQXSQPPHJPGOF UHFFFAOYSA N Y verify 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 Contents 1 Medical uses 2 Mechanism 3 Manufacture 4 References 5 External linksMedical uses editCaffeine citrate is generally the preferred treatment for apnea of prematurity for infants born 28 to 32 weeks or earlier than 28 weeks 6 13 It has fewer side effects as compared to theophylline 6 Caffeine improves airway function in asthma increasing forced expiratory volume FEV1 by 5 to 18 with this effect lasting for up to four hours 14 Mechanism editIn method of action the preparation is identical to that of caffeine base as the citrate counter ion dissociates in water Doses of caffeine citrate due to the added weight of the citrate moiety are understandably higher than with caffeine base i e it takes a larger dose to get the same amount of caffeine 11 The ratio of therapeutic doses of caffeine base to its citrate salt is typically 1 2 11 Dosing should therefore be clearly distinguished 11 Manufacture editThe drug is prepared by combining anhydrous caffeine with citric acid monohydrate and sodium citrate dihydrate Caffeine citrate cocrystals can take on at least two anhydrous polymorphs 8 References edit 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 d e 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 amp Business Media p 457 ISBN 9781461421559 Archived from the original on 30 December 2016 a b Smit JP Hagen EJ 1 March 2015 Polymorphism in Caffeine Citric Acid Cocrystals Journal of Chemical Crystallography 45 3 128 133 doi 10 1007 s10870 015 0573 3 ISSN 1572 8854 S2CID 96712417 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 a b c d Ainsworth SB 2014 Neonatal Formulary Drug Use in Pregnancy and the First Year of Life 7 ed John Wiley amp 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 NIH funded research leads to pediatric labeling updates for doxycycline clindamycin and caffeine citrate National Institutes of Health NIH 2 April 2020 Retrieved 27 July 2022 Welsh EJ Bara A Barley E Cates CJ January 2010 Caffeine for asthma The Cochrane Database of Systematic Reviews 2010 1 CD001112 doi 10 1002 14651858 CD001112 pub2 PMC 7053252 PMID 20091514 External links edit Caffeine Citrate CUI C0054436 NCI Metathesaurus Portal nbsp Medicine Retrieved from https en wikipedia org w index php title Caffeine citrate amp oldid 1214317060, wikipedia, wiki, book, books, library,

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