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Journal of Dietary Supplements Volume 10, 2013 - Issue 3
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Original Articles

pH-Dependent Stability of Creatine Ethyl Ester: Relevance to Oral Absorption

Brandon T. GuffordCollege of Pharmacy University of Nebraska Medical Center, Nebraska Medical Center, Omaha, Nebraska, USA
,
Edward L. EzellEppley Institute for Research in Cancer, University of Nebraska Medical Center, Nebraska Medical Center, Omaha, Nebraska, USA
,
Dennis H. RobinsonCollege of Pharmacy University of Nebraska Medical Center, Nebraska Medical Center, Omaha, Nebraska, USA
,
Donald W. MillerFaculty of Medicine, University of Manitoba, Winnepeg, Manitoba, Canada
,
Nicholas J. MillerFaculty of Medicine, University of Manitoba, Winnepeg, Manitoba, Canada
,
Xiaochen GuFaculty of Pharmacy, University of Manitoba, Winnepeg, Manitoba, Canada
&
Jonathan L. VennerstromCollege of Pharmacy University of Nebraska Medical Center, Nebraska Medical Center, Omaha, Nebraska, USACorrespondence[email protected]
 show all
Pages 241-251 | Received 13 Nov 2012, Accepted 07 May 2013, Published online: 19 Aug 2013

REFERENCES

  • Adriano E, Garbati P, Damonte G, Salis A, Armirotti A, Balestrino M. Searching for a therapy of creatine transporter deficiency: Some effects of creatine ethyl ester in brain slices in vitro. Neuroscience. 2011;199:386–393.
  • Angelis ID, Turco L. Caco-2 cells as a model for intestinal absorption. Curr Protoc Toxicol. 2011;20:1–15.
  • Bird SP. Creatine supplementation and exercise performance: a brief review. J Sports Sci Med. 2003;2:123–132.
  • Buford TW, Krider RB, Stout JR, Greenwood M, Campbell B, Spano M, Ziegenfus T, Lopez H, Landis J, Antonio J. International Society of Sports Nutrition position stand: creatine supplementation and exercise. J Int Soc Sports Nutr. 2007;4:6.
  • Child R, Tallon MJ. Creatine ethyl ester rapidly degrades to creatinine in stomach acid. 4th Annual ISSN Meeting, 2007. International Society of Sports Nutrition (ISSN) 4th Annual Meeting, Las Vegas, NV, USA.
  • Diamond BJ. Temperature and pH dependence of the cyclization of creatine: a study via mass spectrometry. Thesis submitted to The Graduate College of Marshall University 2005. Marshall University, Huntington, WV, USA.
  • Edgar G, Shiver HE. The equilibrium between creatine and creatinine in aqueous solution. The effect of hydrogen ion. J Am Chem Soc. 1925;47:1179–1188.
  • Edgar G, Wakefield RA. The kinetics of the conversion of creatine into creatinine in hydrochloric acid solutions. J Am Chem Soc. 1923;45:2242–2245.
  • Giese MW, Lecher CS. Non-enzymatic cyclization of creatine ethyl ester to creatinine. Biochem Biophys Res Commun. 2009a;388:252–255.
  • Giese MW, Lecher CS. Qualitative in vitro NMR analysis of creatine ethyl ester pronutrient in human plasma. Int J Sports Med. 2009b;30:766–770.
  • Gufford BT, Sriraghavan K, Miller NJ, Miller DW, Gu X, Vennerstrom JL, Robinson DH. Physicochemical characterization of creatine N-methylguanidinium salts. J Diet Supp. 2010;7: 240–252.
  • Johnson CD. Stereoelectronic effects in the formation of 5- and 6-membered rings: the role of Baldwin's rules. Acc Chem Res. 1993;26:476–482.
  • Katseres NS, Reading DW, Shayya L, DiCesare JC, Purser GH. Non-enzymatic hydrolysis of creatine ethyl ester. Biochem Biophys Res Commun. 2009;386:363–367.
  • Kohler F. Buffer solutions. In: K Diem, C Lentner (Eds.), Geigy scientific tables (7th ed., pp. 280–282). Basel: Ciba-Geigy Ltd., 1970.
  • Leland, KM, McDonald TL, Drescher KM. Effect of creatine, creatinine, and creatine ethyl ester on TLR expression in macrophages. Int Immunopharmacol. 2011;11:1341–1347.
  • Miller DW, Hinton M, Chen F. Evaluation of drug efflux transporter liabilities of darifenacin in cell culture models of the blood-brain and blood-ocular barriers. Neurourol Urodyn. 2011;30:1633–1638.
  • Mold JD, Gore RC, Lynch JM, Schantz EJ. Creatine ethyl ester. J Am Chem Soc. 1955; 77:178–180.
  • Persky AM, Brazeau GA, Hochhau. Pharmacokinetics of the dietary supplement creatine. Clin Pharmacokinet. 2003a;42:557–574.
  • Persky AM, Muller M, Derendorf H, Grant M, Brazeau GA, Hochhaus G. Single- and multiple-dose pharmacokinetics of oral creatine. J Clin Pharmacol. 2003b;43:29–37.
  • Portmans JR, Auquier H, Renaut V, Durusel A, Saugy M, Brisson GR. Effect of short-term creatine supplementation on renal responses in men. Eur J Appl Physiol Occup Physiol. 1997;76:566–567.
  • Schedel JM, Tanaka H, Kiyonaga A, Shindo M, Schutz Y. Acute creatine ingestion in human: consequences on serum creatine and creatinine concentrations. Life Sci. 1999;65:2463–2470.
  • Spillane M, Schoch R, Cooke M, Harvey T, Greenwood M, Kreider R. Willoughby DS. The effects of creatine ethyl ester supplementation combined with heavy resistance training on body composition, muscle performance, and serum and muscle creatine levels. J Int Soc Sports Nutr. 2009;6:6.
  • Terjung R, Clarkson P, Eichner R, Greenhaff PL, Hespel PJ, Israel RJ, Kraemer WJ, Meyer RA, Spiet LL, Tarnopolsky MA, Wagenmakers AJM, Williams MH. The physiological and health effects of oral creatine supplementation. Med Sci Sports Exerc. 2000;32:706–717.
  • Velema MS, de Ronde W. Elevated plasma creatinine due to creatine ethyl ester use. Neth J Med. 2011;69:79–81.
  • Vennerstrom JL. Production of creatine esters using in situ acid production. US Patent No. 6,897,334, 2005.
  • Vennerstrom JL, Miller DW. Creatine ester pronutrient compounds and formulations. Eur Patent No. 1 324 760, 2007.

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