Plazomicin

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Plazomicin
Plazomicin structure.svg
Names
IUPAC name
(2S)-4-Amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[[(2S,3R)-3-amino-6-[(2-hydroxyethylamino)methyl]-3,4-dihydro-2H-pyran-2-yl]oxy]-2-[(2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)oxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxybutanamide
Other names
6'-(hydroxylethyl)-1-(HABA)-sisomicin
Identifiers
1154757-24-0
ChEMBL ChEMBL1650559
Jmol 3D model Interactive image
KEGG D10151
PubChem 42613186
UNII LYO9XZ250J
Properties
C25H48N6O
Molar mass 592.683 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Plazomicin (INN,[1] codenamed ACHN-490) is a next-generation aminoglycoside ("neoglycoside") antibacterial derived from sisomicin by appending a hydroxy-aminobutyric acid (HABA) substituent at position 1 and a hydroxyethyl substituent at position 6'.[2][3]

Plazomicin has been reported to demonstrate in vitro synergistic activity when combined with daptomycin or ceftobiprole versus methicillin-resistant Staphylococcus aureus (MRSA), vancomycin-resistant S. aureus (VRSA) and against Pseudomonas aeruginosa when combined with cefepime, doripenem, imipenem or piperacillin/tazobactam.[3] It also demonstrates potent in vitro activity versus carbapenem-resistant Acinetobacter baumannii.[4]

In 2012, U.S. Food and Drug Administration granted fast track designation for the development and regulatory review of plazomicin.[5]

It is being developed by Achaogen, Inc. to treat serious bacterial infections due to multidrug-resistant Enterobacteriaceae, including carbapenem-resistant Enterobacteriaceae (CRE)[6] and is in Phase III clinical trials as of April 7, 2016.[7]

See also[edit]

References[edit]

  1. ^ "WHO Drug Information, Vol. 26, No. 3, 2012. International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names: List 68" (PDF). World Health Organization. p. 314. Retrieved 27 April 2016. 
  2. ^ Aggen, JB; Armstrong, ES; Goldblum, AA; Dozzo, P; Linsell, MS; Gliedt, MJ; Hildebrandt, DJ; Feeney, LA; Kubo, A; Matias, RD; Lopez, S; Gomez, M; Wlasichuk, KB; Diokno, R; Miller, GH; Moser, HE (30 August 2010). "Synthesis and Spectrum of the Neoglycoside ACHN-490" (PDF). Antimicrobial Agents and Chemotherapy 54 (11): 4636–4642. doi:10.1128/AAC.00572-10. Retrieved 27 April 2016. 
  3. ^ a b Zhanel, GG; Lawson, CD; Zelenitsky, S; Findlay, B; Schweizer, F; Adam, H; Walkty, A; Rubinstein, E; Gin, AS; Hoban, DJ; Lynch, JP; Karlowsky, JA (10 January 2014). "Comparison of the Next-Generation Aminoglycoside Plazomicin to Gentamicin, Tobramycin and Amikacin". Expert Review of Anti-infective Therapy 10 (4): 459–73. doi:10.1586/eri.12.25. PMID 22512755. 
  4. ^ García-Salguero, C; Rodríguez-Avial, I; Picazo, JJ; Culebras, E (October 2015). "Can Plazomicin Alone or in Combination Be a Therapeutic Option against Carbapenem-Resistant Acinetobacter baumannii?" (PDF). Antimicrobial Agents and Chemotherapy 59 (10): 5959–66. doi:10.1128/AAC.00873-15. Retrieved 27 April 2016. 
  5. ^ "Achaogen Announces Plazomicin Granted QIDP Designation by FDA". GlobeNewswire, Inc. Retrieved 27 April 2016. 
  6. ^ "Achaogen — Plazomicin". Achaogen, Inc. Retrieved 27 April 2016. 
  7. ^ "Plazomicin — AdisInsight". Springer International Publishing AG. Retrieved 27 April 2016.