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Plazomicin

Synonym(s): ACHN-490  |  Zemdri  |  plazomicina  |  plazomicine

Class: Aminoglycoside

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Protein synthesis inhibitor. Binds to the bacterial 30S ribosomal subunit to disrupt protein synthesis.
Target Pathogen: Multidrug-resistant Enterobacterales (including Escherichia coli, Klebsiella pneumoniae, Enterobacter spp.); Pseudomonas aeruginosa and other Gram-negative pathogens; limited activity against Staphylococcus aureus including MRSA.
Propensity to select resistant mutants: Moderate. Low frequency of resistance compared with older aminoglycosides due to engineered AME stability.
Description: Semisynthetic derivative of sisomicin designed to overcome common aminoglycoside resistance mechanisms. FDA approved on 26 June 2018 for complicated urinary tract infections, including acute pyelonephritis, caused by susceptible Gram-negative bacteria.
Institute where first reported: Achaogen Inc
Year first mentioned: 2007
Highest development stage: Approved by FDA in 2018
Development status: Approved
Chemical structure(s):
Click here for structure editor
Molecular weight: 592.68
Iso. SMILES: C[C@@]1(CO[C@@H]([C@@H]([C@H]1NC)O)O[C@H]2[C@@H](C[C@@H]([C@H]([C@@H]2O)O[C@@H]3[C@@H](CC=C(O3)CNCCO)N)N)NC(=O)[C@H](CCN)O)O
InChI Key: IYDYFVUFSPQPPV-PEXOCOHZSA-N
Can. SMILES: C[C@@]1(CO[C@@H]([C@@H]([C@H]1NC)O)O[C@H]2[C@@H](C[C@@H]([C@H]([C@@H]2O)O[C@@H]3[C@@H](CC=C(CNCCO)O3)N)N)NC(=O)[C@H](CCN)O)O
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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/42613186
Guide to Pharmacology: plazomicin
Citations:
  • http://aac.asm.org/content/58/5/2554.full
  • https://aac.asm.org/content/63/4/e02329-18
  • https://accpjournals.onlinelibrary.wiley.com/doi/full/10.1002/phar.2203
  • https://www.nature.com/articles/s42003-021-02261-4
    • Patent: WO2009067692A1

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