Plazomicin

Plazomicin
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
CAS Number	1154757-24-0;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1650559;
KEGG	D10151;
PubChem CID	42613186;
UNII	LYO9XZ250J;
CompTox Dashboard (EPA)	DTXSID001031303 ;
	InChI InChI=1S/C25H48N6O10/c1-25(37)11-38-24(18(35)21(25)29-2)41-20-15(31-22(36)16(33)5-6-26)9-14(28)19(17(20)34)40-23-13(27)4-3-12(39-23)10-30-7-8-32/h3,13-21,23-24,29-30,32-35,37H,4-11,26-28H2,1-2H3,(H,31,36)/t13-,14+,15-,16+,17+,18-,19-,20+,21-,23-,24-,25+/m1/s1 Key: IYDYFVUFSPQPPV-PEXOCOHZSA-N;
	SMILES CN[C@@H]1[C@@H](O)[C@@H](O[C@@H]2[C@@H](O)[C@H](O[C@H]3OC(=CC[C@H]3N)CNCCO)[C@@H](N)C[C@H]2NC(=O)[C@@H](O)CCN)OC[C@]1(C)O;
Properties
Chemical formula	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]

References

^ "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.
^ 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.
^ ^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.
^ 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.
^ "Achaogen Announces Plazomicin Granted QIDP Designation by FDA". GlobeNewswire, Inc. Retrieved 27 April 2016.
^ "Achaogen — Plazomicin". Achaogen, Inc. Retrieved 27 April 2016.
^ "Plazomicin — AdisInsight". Springer International Publishing AG. Retrieved 27 April 2016.

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[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.

[Zhanel-3] 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.

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See also

References