Plazomicin sulfateProduct ingredient for Plazomicin
- Name
- Plazomicin sulfate
- Drug Entry
- Plazomicin
Developed by Achaogen biopharmaceuticals, plazomicin is a next-generation aminoglycoside synthetically derived from Sisomicin. The structure of plazomicin was established via appending hydroxylaminobutyric acid to Sisomicin at position 1 and 2-hydroxyethyl group at position 6' 1. It was designed to evade all clinically relevant aminoglycoside-modifying enzymes, which contribute to the main resistance mechanism for aminoglycoside therapy 1. However, acquired resistance of aminoglycosides may arise through over expression of efflux pumps and ribosomal modification by bacteria, which results from amino acid or rRNA sequence mutations 1. Like other aminoglycosides, plazomicin is ineffective against bacterial isolates that produce 16S rRNA methyltransferases Label. Plazomicin mediates the antibacterial activity against pathogens including carbapenem-resistant (CRE) and extended-spectrum beta-lactamase (ESBL) producing Enterobacteriaceae. It mediates the antibacterial activity by binding to bacterial 30S ribosomal subunit and inhibiting protein synthesis Label. On June 28th, 2018, plazomicin sulfate was approved by the FDA for use in adult patients for the treatment of complicated urinary tract infections (cUTI) including Pyelonephritis. It is marketed as Zemdri and is administered via once-daily intravenous infusion.
- Accession Number
- DBSALT002742
- Structure
- Synonyms
- Plazomicin sulphate
- UNII
- A78L6MT746
- CAS Number
- 1380078-95-4
- Weight
- Average: 690.76
Monoisotopic: 690.310571488 - Chemical Formula
- C25H50N6O14S
- InChI Key
- SFTBRKHJMASSAP-BGJNVEJLSA-N
- InChI
- InChI=1S/C25H48N6O10.H2O4S/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;1-5(2,3)4/h3,13-21,23-24,29-30,32-35,37H,4-11,26-28H2,1-2H3,(H,31,36);(H2,1,2,3,4)/t13-,14+,15-,16+,17+,18-,19-,20+,21-,23-,24-,25+;/m1./s1
- IUPAC Name
- (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-{[(2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)oxan-2-yl]oxy}-3-hydroxycyclohexyl]-2-hydroxybutanamide; sulfuric acid
- SMILES
- OS(O)(=O)=O.[H][C@](O)(CCN)C(=O)N[C@@H]1C[C@H](N)[C@@H](O[C@H]2OC(CNCCO)=CC[C@H]2N)[C@H](O)[C@H]1O[C@H]1OC[C@](C)(O)[C@H](NC)[C@H]1O
- External Links
- ChemSpider
- 28536136
- ChEMBL
- CHEMBL2364623
- Wikipedia
- Plazomicin
- Predicted Properties
Property Value Source Water Solubility 12.3 mg/mL ALOGPS logP -2.2 ALOGPS logP -6.1 Chemaxon logS -1.7 ALOGPS pKa (Strongest Acidic) 12.48 Chemaxon pKa (Strongest Basic) 9.89 Chemaxon Physiological Charge 5 Chemaxon Hydrogen Acceptor Count 15 Chemaxon Hydrogen Donor Count 11 Chemaxon Polar Surface Area 269.29 Å2 Chemaxon Rotatable Bond Count 13 Chemaxon Refractivity 145.09 m3·mol-1 Chemaxon Polarizability 61.95 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon