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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H48N6O10
Molecular Weight 592.6828
Optical Activity UNSPECIFIED
Defined Stereocenters 12 / 12
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PLAZOMICIN

SMILES

CN[C@@H]1[C@@H](O)[C@@H](O[C@H]2[C@@H](C[C@H](N)[C@@H](O[C@H]3OC(CNCCO)=CC[C@H]3N)[C@@H]2O)NC(=O)[C@@H](O)CCN)OC[C@]1(C)O

InChI

InChIKey=IYDYFVUFSPQPPV-PEXOCOHZSA-N
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

HIDE SMILES / InChI

Molecular Formula C25H48N6O10
Molecular Weight 592.6828
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 12 / 12
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Plazomicin is a novel aminoglycoside antibiotic that binds to the bacterial 30S ribosomal subunit, thus inhibiting protein synthesis in a concentration-dependent manner. Plazomicin displays a broad spectrum of activity against aerobic gram-negative bacteria including extended-spectrum β-lactamase-producing Enterobacteriaceae, carbapenem-resistant Enterobacteriaceae, and organisms with aminoglycoside-modifying enzymes. Plazomicin resistance in Enterobacteriaceae is via modification of the ribosomal binding site due to expression of 16S rRNA methyltransferases. ZEMDRI (plazomicin) injection for intravenous use is indicated for the treatment of patients 18 years of age or older with Complicated Urinary Tract Infections (cUTI) including Pyelonephritis.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ZEMDRI
PubMed

PubMed

TitleDatePubMed
Synthesis and spectrum of the neoglycoside ACHN-490.
2010 Nov
Activity of a novel aminoglycoside, ACHN-490, against clinical isolates of Escherichia coli and Klebsiella pneumoniae from New York City.
2010 Oct
Plazomicin: A Novel Aminoglycoside for the Treatment of Resistant Gram-Negative Bacterial Infections.
2019 Feb
Plazomicin: A Next-Generation Aminoglycoside.
2019 Jan
Patents

Sample Use Guides

In Vivo Use Guide
Administer ZEMDRI 15 mg/kg every 24 hours by intravenous (IV) infusion over 30 minutes to patients 18 years of age or older with creatinine clearance greater than or equal to 90 mL/min.
Route of Administration: Intravenous
In Vitro Use Guide
MIC50/MIC90 values for plazomicin were the lowest of all the drugs tested: 0.5/0.5 mg/L for 96 KPC-producing Klebsiella pneumoniae isolates and 0.5/1 mg/L for all 110 carbapenemase-producing isolates. Plazomicin (ACHN-490) inhibited the growth of AG-resistant Enterobacteriaceae (MIC(90), ≤4 μg/ml), with the exception of Proteus mirabilis and indole-positive Proteae (MIC(90), 8 μg/ml and 16 μg/ml, respectively). ACHN-490 was more active alone in vitro against Pseudomonas aeruginosa and Acinetobacter baumannii isolates with AG-modifying enzymes than against those with altered permeability/efflux. The MIC(90) of ACHN-490 against AG-resistant staphylococci was 2 μg/ml.
Substance Class Chemical
Created
by admin
on Tue Mar 06 13:21:18 UTC 2018
Edited
by admin
on Tue Mar 06 13:21:18 UTC 2018
Record UNII
LYO9XZ250J
Record Status Validated (UNII)
Record Version
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Name Type Language
PLAZOMICIN
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
(2S)-4-AMINO-N-((1R,2S,3S,4R,5S)-5-AMINO-4-(((2S,3R)-3-AMINO-6-(((2-HYDROXYETHYL)AMINO)METHYL)-3,4-DIHYDRO-2H-PYRAN-2-YL)OXY)-2-((3-DEOXY-4-C-METHYL-3-(METHYLAMINO)-.BETA.-L-ARABINOPYRANOSYL)OXY)-3-HYDROXYCYCLOHEXYL)-2-HYDROXYBUTANAMIDE
Common Name English
PLAZOMICIN [WHO-DD]
Common Name English
PLAZOMICIN [INN]
Common Name English
ACHN-490
Code English
PLAZOMICIN [USAN]
Common Name English
Code System Code Type Description
INN
9522
Created by admin on Tue Mar 06 13:21:18 UTC 2018 , Edited by admin on Tue Mar 06 13:21:18 UTC 2018
PRIMARY
WIKIPEDIA
Plazomicin
Created by admin on Tue Mar 06 13:21:18 UTC 2018 , Edited by admin on Tue Mar 06 13:21:18 UTC 2018
PRIMARY
CAS
1154757-24-0
Created by admin on Tue Mar 06 13:21:18 UTC 2018 , Edited by admin on Tue Mar 06 13:21:18 UTC 2018
PRIMARY
ChEMBL
CHEMBL1650559
Created by admin on Tue Mar 06 13:21:18 UTC 2018 , Edited by admin on Tue Mar 06 13:21:18 UTC 2018
PRIMARY
PUBCHEM
42613186
Created by admin on Tue Mar 06 13:21:18 UTC 2018 , Edited by admin on Tue Mar 06 13:21:18 UTC 2018
PRIMARY SWITZERF
Related Record Type Details
ACTIVE MOIETY