Daptomycin: Physicochemical, analytical, and pharmacological properties

Therapeutic Drug Monitoring

Volumn 37, Issue 6, 2015, Pages 699-710

  Tótoli, Eliane Gandolpho ^a   Garg, Sanjay ^b   Nunes Salgado, Hérida Regina ^a  

^a SÃO PAULO STATE UNIVERSITY UNESP   (Brazil)

^b UNIVERSITY OF SOUTH AUSTRALIA   (Australia)

Author keywords

Analytical methods; Antimicrobial; Cyclic lipopeptides; Daptomycin; Resistant strains

Indexed keywords

AMINO ACID; CALCIUM ION; CARBOXYLIC ACID; CREATINE KINASE; CYTOCHROME P450; DAPTOMYCIN; WATER; ANTIINFECTIVE AGENT;

ANALYTIC METHOD; ANTIBACTERIAL ACTIVITY; ANTIBIOTIC THERAPY; AREA UNDER THE CURVE; BACTERIAL INFECTION; BACTERIAL MEMBRANE; BACTERICIDAL ACTIVITY; CREATINE KINASE BLOOD LEVEL; DRUG ABSORPTION; DRUG CLEARANCE; DRUG CONFORMATION; DRUG DISTRIBUTION; DRUG ELIMINATION; DRUG HALF LIFE; DRUG MARKETING; DRUG MECHANISM; DRUG METABOLISM; DRUG MONITORING; DRUG QUALITY; DRUG SOLUBILITY; DRUG STABILITY; DRUG STRUCTURE; DRUG TOLERABILITY; DRUG URINE LEVEL; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HYDROPHOBICITY; KIDNEY DYSFUNCTION; LIPOPHILICITY; MAXIMUM PLASMA CONCENTRATION; MUSCULOSKELETAL INJURY; NONHUMAN; PH; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; QUALITY CONTROL; RENAL CLEARANCE; REVIEW; SIDE EFFECT; TOXIC HEPATITIS; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY; VOLUME OF DISTRIBUTION; ANTIBIOTIC RESISTANCE; DRUG EFFECTS; GRAM POSITIVE BACTERIUM; GRAM-POSITIVE BACTERIAL INFECTIONS; MICROBIOLOGY; PROCEDURES;

ANTI-BACTERIAL AGENTS; DAPTOMYCIN; DRUG MONITORING; DRUG RESISTANCE, BACTERIAL; GRAM-POSITIVE BACTERIA; GRAM-POSITIVE BACTERIAL INFECTIONS; HUMANS;

EID: 84947911000     PISSN: 01634356     EISSN: 15363694     Source Type: Journal    
DOI: 10.1097/FTD.0000000000000222     Document Type: Review

References (92)

1. Silveira GP, Nome F, Gesser JC, et al. Estratégias utilizadas no combate à resistência bacteriana [in Portuguese]. Quim Nova. 2006;29:844-855.
2. Wright GD. Molecular mechanisms of antibiotic resistance. Chem Com-mun (Camb). 2011;47:4055-4061.
3. Guimarães DO, Momesso LS, Pupo MT. Antibióticos: importância ter-apêutica e perspectivas para a descoberta e desenvolvimento de novos agents [in Portuguese]. Quim Nova. 2010;33:667-679.
4. Brunton LL, Chabner BA, Knollman BB. As Bases Farmacológicas da Terapêutica de Goodman & Gilman. 12th ed. São Paulo: AMGH; 2012.
5. Silverman JA, Perlmutter NG, Shapiro HM. Correlation of daptomycin bactericidal activity and membrane depolarization in Staphylococcus aureus. Antimicrob Agents Chemother. 2003;47:2538-2544.
6. Bubalo JS, Munar MY, Cherala G, et al. Daptomycin pharmacokinetics in adult oncology patients with neutropenic fever. Antimicrob Agents Chemother. 2009;53:428-434.
7. Cubist Pharmaceuticals. Cubicin. Available at: http://www.cubicin.com. Accessed December 8, 2014.
8. Picazo JJ, Betriu C, Culebras E, et al. Staphylococcus aureus resistente a meticilina: sensibilidad a la daptomicina a lo largo de un periodo de 10 años (2001-2010) [in Spanish]. Rev Esp Quimioter. 2011;24:107-111.
9. Chitnis S, Katara G, Hemvani N, et al. In vitro activity of daptomycin & linezolid against methicillin resistant Staphylococcus aureus & vancomycin resistant enterococci isolated from hospitalized cases in Central India. Indian J Med Res. 2013;137:191-196.
10. Sader HS, Farrell DJ, Flamm RK, et al. Daptomycin activity tested against 164.457 bacterial isolates from hospitalised patients: summary of 8 years of a worldwide surveillance programme (2005-2012). Int J Antimicrob Agents. 2014;43:465-469.
11. Sweetman SC, ed. Martindale: The Complete Drug Reference. 37th ed. London: RPS Publishing; 2011.
12. Cubicin. Worldwide commercialization of daptomycin. Available at: http://www.drugs.com/international/daptomycin.html. Accessed December 2, 2014.
13. Pea F, Cojutti P, Sbrojavacca R, et al. TDM-guided therapy with daptomycin and meropenem in a morbidly obese, critically ill patient. Ann Pharmacother. 2011;45:e37.
14. Di Paolo A, Tascini C, Polillo M, et al. Population pharmacokinetics of daptomycin in patients affected by severe Gram-positive infections. Int J Antimicrob Agents. 2013;42:250-255.
15. Falcone M, Russo A, Cassetta MI, et al. Variability of pharmacokinetic parameters in patients receiving different dosages of daptomycin: is therapeutic drug monitoring necessary? J Infect Chemother. 2013;19:732-739.
16. Baietto L, D'Avolio A, Pace S, et al. Development and validation of an UPLC-PDA method to quantify daptomycin in human plasma and in dried plasma spots. JPharm Biomed Anal. 2014;88:66-70.
17. Jung D, Rozek A, Okon M, et al. Structural transitions as determinants of the action of the calcium-dependent antibiotic daptomycin. Chem Biol. 2004;11:949-957.
18. Eliopoulos GM, Willey S, Reiszner E, et al. In vitro and in vivo activity of LY 146032, a new cyclic lipopeptide antibiotic. Antimicrob Agents Chemother. 1986;30:532-535.
19. Schneider T, Müller A, Miess H, et al. Cyclic lipopeptides as antibacterial agents-potent antibiotic activity mediated by intriguing mode of actions. Int J Med Microbiol. 2014;304:37-43.
20. Muangsiri W, Kearney WR, Teesch LM, et al. Studies on the reactions between daptomycin and glyceraldehyde. Int J Pharm. 2005;289:33-150.
21. Hancock REW. Mechanisms of action of newer antibiotics for Gram-positive pathogens. Lancet Infect Dis. 2005;5:209-218.
22. Bambeke FV, Mingeot-Leclercq MP, Struelens MJ, et al. The bacterial envelope as a target for novel anti-MRSA antibiotics. Trends Pharmacol Sci. 2008;29:124-134.
23. Munoz-Price LS, Lolans K, Quinn JP. Emergence of resistance to dap-tomycin during treatment of vancomycin-resistant Enterococcus faecalis infection. Clin Infect Dis. 2005;41:565-566.
24. Sabol K, Patterson JE, Lewis JS II, et al. Emergence of daptomycin resistance in Enterococcus faecium during daptomycin therapy. Antimi-crob Agents Chemother. 2005;49:1664-1665.
25. Green MR, Anasetti C, Sandin R, et al. Development of daptomycin resistance in a bone marrow transplant patient with vancomycin-resistant Enterococcus durans. J Oncol Pharm Pract. 2006;12:179-181.
26. Skiest DJ. Treatment failure resulting from resistance of Staphylococcus aureus to daptomycin. J Clin Microbiol. 2006;44:655-656.
27. Hidron AI, Schuetz AN, Nolte FS, et al. Daptomycin resistance in Enterococcus faecalis prosthetic valve endocarditis. J Antimicrob Che-mother. 2008;61:1394-1396.
28. Gasch O, Camoez M, Domínguez MA, et al. Emergence of resistance to daptomycin in a cohort of patients with methicillin-resistant Staphylo-coccus aureus persistent bacteraemia treated with daptomycin. J Antimi-crob Chemother. 2014;69:568-571.
29. Traczewski MM, Katz BD, Steenbergen JN, et al. Inhibitory and bactericidal activities of daptomycin, vancomycin, and teicoplanin against methicillin-resistant Staphylococcus aureus isolates collected from 1985 to 2007. Antimicrob Agents Chemother. 2009;53:1735-1738.
30. Bell JM, Turnidge JD, Sader HS, et al. Antimicrobial activity and spectrum of daptomycin: results from the surveillance program in Australia and New Zealand (2008). Pathology. 2010;42:470-473.
31. Hayden MK, Rezai K, Hayes RA, et al. Development of daptomycin resistance in vivo in methicillin-resistant Staphylococcus aureus. J Clin Microbiol. 2005;43:5285-5287.
32. Cafiso V, Bertuccio T, Purrello S, et al. dltA overexpression: a strain-independent keystone of daptomycin resistance in methicillin-resistant Staphylococcus aureus. Int J Antimicrob Agents. 2014;43:26-31.
33. Sakoulas G, Alder J, Thauvin-Eliopoulos C, et al. Induction of daptomycin heterogeneous susceptibility in Staphylococcus aureus by exposure to van-comycin. Antimicrob Agents Chemother. 2006;50:1581-1585.
34. Lopes HV. Daptomicina: finalmente disponível para a América do Sul [in Portuguese]. Rev Panam Infectol. 2008;10:70-71.
35. Kullar R, Chin JN, Edwards DJ, et al. Pharmacokinetics of single-dose daptomycin in patients with suspected or confirmed neurological infections. Antimicrob Agents Chemother. 2011;55:3505-3509.
36. Estes KS, Derendorf H. Comparison of the pharmacokinetic properties of vancomycin, linezolid, tigecyclin, and daptomycin. Eur J Med Res. 2010; 15:533-543.
37. Oleson FB, Berman CL, Li AP. An evaluation of the P450 inhibition and induction potential of daptomycin in primary human hepatocytes. Chem Biol Interact. 2004;150:137-147.
38. Woodworth JR, Nyhart EH Jr, Brier GL, et al. Single-dose pharmaco-kinetics and antibacterial activity of daptomycin, a new lipopeptide antibiotic, in healthy volunteers. Antimicrob Agents Chemother. 1992;36:318-325.
39. Dvorchik BH, Brazier D, DeBruin MF, et al. Daptomycin pharmacoki-netics and safety following administration of escalating doses once daily to healthy subjects. Antimicrob Agents Chemother. 2003;47:1318-1323.
40. Abdel-Rahman SM, Benziger DP, Jacobs RF, et al. Single-dose pharma-cokinetics of daptomycin in children with suspected or proved gram-positive infections. Pediatr Infect Dis J. 2008;27:330-334.
41. Dvorchik B, Damphousse D. Single-dose pharmacokinetics of daptomycin in young and geriatric volunteers. J Clin Pharmacol. 2004;44:612-620.
42. Silverman JA, Mortin LI, VanPraagh ADG, et al. Inhibition of daptomy-cin by pulmonary surfactant: in vitro modelling and clinical impact. J Infect Dis. 2005;191:2149-2152.
43. Wenisch JM, Meyer B, Fuhrmann V, et al. Multiple-dose pharmacoki-netics of daptomycin during continuous venovenous haemodiafiltration. J Antimicrob Chemother. 2012;67:977-983.
44. Falcone M, Russo A, Cassetta MI, et al. Daptomycin serum levels in critical patients undergoing continuous renal replacement. J Antimicrob Chemother. 2012;24:253-256.
45. Ravina K, Ian M, Matthew G, et al. Efficacy and safety of daptomycin in patients with renal impairment: a multicenter retrospective analysis. Pharmacotherapy. 2014;34:582-589.
46. Pea F, Crapis M, Cojutti P, et al. Daptomycin underexposure in a young intravenous drug user who was affected by life-threatening Staphylococcus aureus-complicated skin and soft tissue infection associated with bacteraemia. Infection. 2014;42:207-210.
47. EUCAST-European Committee on Antimicrobial Susceptibility Testing. Breakpoint Tables for Interpretation ofMICs and Zone Diameters. Version 4.0. 2014. Sweden: European Society of Clinical Microbiology and Infectious Diseases.
48. CLSI-Clinical and Laboratory Standards Institute. Performance Standards for Antimicrobial Susceptibility Testing; Twenty-second Informational Supplement. Wayne: CLSI; 2011.
49. Gould IM, Miró JM, Rybak MJ. Daptomycin: the role of high-dose and combination therapy for Gram-positive infections. Int J Antimicrob Agents. 2013;42:202-210.
50. Shea K, Hilburger E, Baroco A, et al. Successful treatment of vancomycin-resistant Enterococcus faecium pyelonephritis with daptomycin during pregnancy. Ann Pharmacother. 2008;42:722-725.
51. Jeffrey S, James W, Terry B. Use of daptomycin in a pregnant patient with Staphylococcus aureus endocarditis. Ann Pharmacother. 2010;44:746-749.
52. Klibanov OM, Vickery S, Nortey C. Successful treatment of infective panniculitis with daptomycin in a pregnant, morbidly obese patient. Ann Pharmacother. 2014;5:652-655.
53. Seaton RA, Malizos KN, Viale P, et al. Daptomycin use in patients with osteomyelitis: a preliminary report from the EU-CORESM database. J Antimicrob Chemother. 2013;68:1642-1649.
54. Eisenstein BI, Oleson FB Jr, Baltz RH. Daptomycin: from the mountain to the clinic, with essential help from Francis Tally, MD. Clin Infect Dis. 2010;50:S10-S15.
55. Kaya S, Yilmaz G, Kalkan A, et al. Treatment of Gram-positive left-sided infective endocarditis with daptomycin. J Infect Chemother. 2013; 19:698-702.
56. Echevarria K, Datta P, Cadena J, et al. Severe myopathy and possible hepa-totoxicity related to daptomycin. J Antimicrob Chemother. 2005;55:599-600.
57. Bohm N, Makowski C, Machado M, et al. Case report and cohort analysis of drug-induced liver injury associated with daptomycin. Antimicrob Agents Chemother. 2014;58:4902-4903.
58. Travis KS, Walker ED, Cannon CG, et al. Daptomycin-induced rhabdo-myolysis and acute liver injury. Scand J Infect Dis. 2014;46:537-540.
59. Miller BA, Gray A, Leblanc TW, et al. Acute eosinophilic pneumonia secondary to daptomycin: a report of three cases. Clin Infect Dis. 2010; 50:e63-e68.
60. Grégoire C, Brumpt C, Loirat D, et al. A case of daptomycin-induced immune thrombocytopenia Antimicrob Agents Chemother. 2012;56:6430-6431.
61. Christ AP, Machado MS, Rosa P, et al. Development and validation of a stability-indication LC-UV method for determination of daptomycin injectable form and kinetic study in alkaline medium. Anal Methods. 2014;6:1242-1247.
62. Naito T, Yamada T, Yagi T, et al. Simple and validated UHPLC method coupled to UV detection for determination of daptomycin in human plasma and urine. Biomed Chromatogr. 2014;28:317-319.
63. Szultka M, Krzeminski R, Jackowski M, et al. Simultaneous determination of selected chemotherapeutics in human whole blood by molecularly imprinted polymers coated solid phase microextraction fibers and liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2013;940:66-76.
64. Zhou J, Xie Y, Huang J, et al. RRLC determination of daptomycin in fermentation broth. Fujian Fenxi Ceshi. 2012;21:46-49.
65. Bazoti FN, Gikas E, Skoutelis A, et al. Development and validation of an ultra performance liquid chromatography-tandem mass spectrometry method for the quantification of daptomycin in human plasma. J Pharm Biomed Anal. 2011;56:78-85.
66. Verdier MC, Bentué-Ferrer D, Tribut O, et al. Determination of daptomycin in human plasma by liquid chromatography-tandem mass spectrometry. Clin Chem Lab Med. 2011;49:69-75.
67. Baietto L, DAvolio A, Rosa FG, et al. Development and validation of a simultaneous extraction procedure for HPLC-MS quantification of daptomycin, amikacin, gentamicin, and rifampicin in human plasma. Anal Bioanal Chem. 2010;396:791-798.
68. Gika HG, Michopoulos F, Divanis D, et al. Daptomycin determination by liquid chromatography-mass spectrometry in peritoneal fluid, blood plasma, and urine of clinical patients receiving peritoneal dialysis treatment. Anal Bioanal Chem. 2010;397:2191-2197.
69. Gikas E, Bazoti FN, Fanourgiakis P, et al. Development and validation of a UPLC-UV method for the determination of daptomycin in rabbit plasma. Biomed Chromatogr. 2010;24:522-527.
70. Gikas E, Bazoti FN, Fanourgiakis P, et al. Simultaneous quantification of daptomycin and rifampicin in plasma by ultra performance liquid chro-matography: application to a pharmacokinetic study. J Pharm Biomed Anal. 2010;51:901-906.
71. Olszowy P, Szultka M, Fuchs P, et al. New coated SPME fibers for extraction and fast HPLC determination of selected drugs in human blood. J Pharm Biomed Anal. 2010;53:1022-1027.
72. Polillo M, Tascini C, Lastella M, et al. A rapid high-performance liquid chromatography method to measure linezolid and daptomycin concentrations in human plasma. Ther Drug Monit. 2010;32:200-205.
73. Martens-Lobenhoffer J, Kielstein JT, Oye C, et al. Validated high performance liquid chromatography-UV detection method for the determination of daptomycin in human plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2008;875:546-550.
74. Tobin CM, Darville JM, Lovering AM, et al. An HPLC assay for dapto-mycin in serum. J Antimicrob Chemother. 2008;62:1462-1476.
75. WHO-World Health Organization. Quality Assurance of Pharmaceuticals: A Compendium of Guidelines and Related Materials. Good Manufacturing Practices and Inspection. 2nd ed. Geneva, Switzerland: World Health Organization; 2007.
76. ICH-International Conference on Harmonization. Stability Testing of New Drug Substances and Products Q1A (R2). Geneva, Switzerland: International Conference on Harmonization; 2003.
77. Bakshi M, Singh S. Development of validated stability-indicating assay methods. J Pharm Biomed Anal. 2002;28:1011-1040.
78. Kirsch LE, Molloy RM, Debono M, et al. Kinetics of the aspartyl trans-peptidation of daptomycin, a novel lipopeptide antibiotic. Pharm Res. 1989;6:387-393.
79. Sanseverino AM. Síntese orgânica limpa [in Portuguese]. Quim Nova. 2000;23:102-107.
80. Nolasco FR, Tavares GA, Bendassolli JA. Implantação de programas de ger-enciamento de resíduos químicos laboratoriais em universidades: análise crítica e recomendações [in Portuguese]. Eng Sanit Ambient. 2006;11:118-124.
81. Cielecka-Piontek J, Zalewski P, Jelinska A, et al. UHPLC: the greening face of liquid chromatography. Chromatographia. 2013;76:1429-1437.
82. Welch CJ, Wu N, Biba M, et al. Greening analytical chromatography. Trends Anal Chem. 2010;29:667-680.
83. Ribeiro RLV, Bottoli CBG, Collins KE, et al. Reevaluation of ethanol as organic modifier for use in HPLC-RP mobile phases. J Braz Chem Soc. 2004;15:300-306.
84. Shaaban H, Górecki T. Current trends in green liquid chromatography for the analysis of pharmaceutically active compounds in the environmental water compartments. Talanta. 2015;132:739-752.
85. WHO-World Health Organization. International Program On Chemical Safety (IPCS). Environmental Health Criteria 154-Acetonitrile. Geneva, Switzerland: World Health Organization; 1993.
86. Elzanfaly ES, Hegazy MA, Saad SS, et al. Validated green high-performance liquid chromatographic methods for the determination of coformulated pharmaceuticals: a comparison with reported conventional methods. J Sep Sci. 2015;38:757-763.
87. Kogawa AC, Salgado H.R.N. Development and validation of infrared spectroscopy method for the determination of darunavir in tablets. Phys Chem. 2013;33:1-6.
88. Tótoli EG, Salgado H.R.N. Development and validation of the quantitative analysis of ampicillin sodium in powder for injection by Fourier-transform infrared spectroscopy (FT-IR). Phys Chem. 2012;2:103-108.
89. Moreno AH, Salgado H.R.N. Development and validation of the quantitative analysis of ceftazidime in powder for injection by infrared spec-troscopy. Phys Chem. 2012;2:6-11.
90. Vieira DCM, Salgado H.R.N. Development and validation of the quantitative analysis of cefuroxime sodium in powder for injection by infrared spectroscopy. Adv Anal Chem. 2012;2:80-87.
91. Kogawa AC, Salgado H.R.N. Validation of a stability indicating capillary elec-trophoresis method for the determination of darunavir in tablets and comparison with the of infrared absorption spectroscopic method. WJPPS. 2014;3:283-297.
92. Tótoli EG, Salgado H.R.N. Development and validation of an economic, environmental friendly and stability-indicating analytical method for determination of ampicillin sodium for injection by RP-HPLC. WJPPS. 2014;3:1928-1943.