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Research Article

Clarithromycin laurate salt: physicochemical properties and pharmacokinetics after oral administration in humans

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Pages 607-615 | Received 16 Dec 2017, Accepted 25 Oct 2018, Published online: 07 Dec 2018

References

  • Alkhalidi BA, Al-Ghazawi M, AlKhatib HS, Sallam A. 2010. Development of a predictive in vitro dissolution for clarithromycin granular suspension based on in vitro-in vivo correlations. Pharm Dev Technol. 15:286–295.
  • Amsden GW. 1996. Erythromycin, clarithromycin, and azithromycin: are the differences real? Clin Ther. 18: 56–72.
  • Aungst BJ, Hussain MA. 1992. Sustained propranolol delivery and increased oral bioavailability in dogs given a propranolol laurate salt. Pharm Res. 9:1507–1509.
  • Cannon JB, Adeyinka WN, Papp KJ. 1995. Reduction of pain on intravenous infusion with bile salt formulations for a macrolide antibiotic. Int J Pharm. 114:65–74.
  • Dawber JG, Shaw JMA. 1989. A nuclear magnetic resonance and molecular-modelling study of cyclohexylamine and several N-substituted derivatives and their hydrochloride salts. J Chem Soc, Perkin Trans 2. 9:1249–1254.
  • Forner K, Holm R, Morakul B, Junyaprasert VB, Ackermann M, Mazur J, Langguth P. 2017. Dissolution and dissolution/permeation experiments for predicting systemic exposure following oral administration of the BCS class II drug clarithromycin. Eur J Pharm Sci. 101:211–219.
  • Fujiki S, Iwao Y, Kobayashi M, Miyagishima A, Itai S. 2011. Stabilization mechanism of clarithromycin tablets under gastric pH conditions. Chem Pharm Bull. 59:553–558.
  • Green PG, Hadgraft J. 1987. Facilitated transfer of cationic drugs across a lipoidal membrane by oleic acid and lauric acid. Int J Pharm. 37:251–255.
  • [ICH] The International Council for Harmonization of Technical Requirements for Registration of Pharmaceuticals for Human U. 2016. E6 (R2) Integrated addendum to ICH E6 (R1): guideline for good clinical practice. [Accessed 2018 July 12] http://www.ich.org/fileadmin/Public_Web_Site/ICH_Products/Guidelines/Efficacy/E6/E6_R1_Guideline.pdf.
  • Ishii K, Saito Y, Itai S, Nemoto M, Takayama K, Nagai T. 1998. Comparative study of pharmacokinetic parameters between clarithromycin and erythromycin stearate in relation to their physicochemical properties. Drug Dev Ind Pharm. 24:129–137.
  • Labes D, Schuetz H, Lang B. 2017. R package Power TOST: Power and sample size based on two one-sided t-tests (TOST) for (bio) equivalence studies. Retrieved from: http://www.r-project.org
  • Lee Y-C, Dalton C, Regler B, Harris D. 2018. Drug solubility in fatty acids as a formulation design approach for lipid-based formulations: a technical note. Drug Dev Ind Pharm. 44:1551–1556.
  • Li S, He H, Parthiban LJ, Yin H, Serajuddin AT. 2005. IV-IVC considerations in the development of immediate-release oral dosage form. J Pharm Sci. 94:1396–1417.
  • Maggio B, Lucy JA. 1975. Studies on mixed monolayers of phospholipids and fusogenic lipids. Biochem J. 149:597–608.
  • McFarland JW, Berger CM, Froshauer SA, Hayashi SF, Hecker SJ, Jaynes BH, Jefson MR, Kamicker BJ, Lipinski CA, Lundy KM, et al. 1997. Quantitative structure-activity relationships among macrolide antibacterial agents: in vitro and in vivo potency against Pasteurella multocida. J Med Chem. 40:1340.
  • Morakul B, Suksiriworapong J, Chomnawang MT, Langguth P, Junyaprasert VB. 2014. Dissolution enhancement and in vitro performance of clarithromycin nanocrystals produced by precipitation-lyophilization-homogenization method. Eur J Pharm Biopharm. 88:886–896.
  • Mordi MN, Pelta MD, Boote V, Morris GA, Barber J. 2000. Acid-catalyzed degradation of clarithromycin and erythromycin B: a comparative study using NMR spectroscopy. J Med Chem. 43:467–474.
  • Morimoto S, Misawa Y, Asaka T, Kondoh H, Watanabe Y. 1990. Chemical modification of erythromycins. VI. Structure and antibacterial activity of acid degradation products of 6-O-methylerythromycins A. J Antibiot. 43:570–573.
  • Morimoto S, Takahashi Y, Watanabe Y, Omura S. 1984. Chemical modification of erythromycins. I. Synthesis and antibacterial activity of 6-O-methylerythromycins A. J Antibiot. 37:187–189.
  • Muranishi S. 1985. Modification of intestinal absorption of drugs by lipoidal adjuvants. Pharm Res. 2:108–118.
  • Nakagawa Y, Itai S, Yoshida T, Nagai T. 1992. Physicochemical properties and stability in the acidic solution of a new macrolide antibiotic, clarithromycin, in comparison with erythromycin. Chem Pharm Bull. 40:725–728.
  • Noguchi S, Takiyama K, Fujiki S, Iwao Y, Miura K, Itai S. 2014. Polymorphic transformation of antibiotic clarithromycin under acidic condition. J Pharm Sci. 103:580–586.
  • [OECD] The Organisation for Economic Co-operation and Development series on principles of good laboratory practice and compliance monitoring. 1997. Number 1 – OECD principles on good laboratory practice.[accessed 2018 July 12] http://www.oecd.org/officialdocuments/publicdisplaydocumentpdf/?cote=env/mc/chem%2898%2917&doclanguage=en.
  • Peterson WL, Graham DY, Marshall B, Blaser MJ, Genta RM, Klein PD, Stratton CW, Drnec J, Prokocimer P, Siepman N. 1993. Clarithromycin as monotherapy for eradication of Helicobacter pylori: a randomized, double-blind trial. Am J Gastroenterol. 88:1860–1864.
  • R Core Team. 2017. R: A language and environment for statistical computing. Vienna, Austria: R Foundation for Statistical Computing. https://www.R-project.org/ Accessed July 12th, 2018.
  • Rezhdo O, Speciner L, Carrier R. 2016. Lipid associated oral delivery: mechanism and analysis of oral absorption enhancement. J Control Release. 240:544–560.
  • Salem II. 1996. Analytical profiles of drug substances and excipients. Clarithromycin. San Diego: Academic Press. 24: 45–50
  • Suwa T, Yoshida H, Fukushima K, Nagate T. 1988. Metabolic fate of TE-031 (A-56268) III. Absorption, distribution and excretion of 14C-TE -0341 in rats, mice and dogs. Chemotherapy. 36:213–226.
  • Wadhwa H. 2003. Controlled release macrolide pharmaceutical formulations, U.S. patent 20030077325 A1.
  • [WMA] World Medical Association Declaration of Helsinki. Ethical principles for medical research involving human subjects; 2013. [accessed 2018 July 12] https://www.wma.net/wp-content/uploads/2016/11/DoH-Oct2013-JAMA.pdf.
  • Zhang XR, Zhang YF, Wang J, Zhou HB, Li SM, Zhong DF. 2008. Pharmacokinetics of clarithromycin citrate salt after oral administration to beagle dogs and food effects on its absorption. PDA J Pharm Sci Technol. 62:445–453.

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