Compound: Plazomicin
SMILES: O=C(N[C@H]1[C@H](O[C@H]2OC[C@@](O)(C)[C@@H]([C@H]2O)NC)[C@@H](O)[C@H](O[C@H]3OC(=CC[C@H]3N)CNCCO)[C@H](C1)N)[C@@H](O)CCN
InChIKey: IYDYFVUFSPQPPV-PEXOCOHZSA-N
Synonyms: Plazomicin, 1154757-24-0, ACHN-490, plazomicina, plazomicine, LYO9XZ250J, ACHN490, (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, DTXSID001031303, plazomicinum, (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, Zemdri (plazomicin), RefChem:57056, J01GB14, DTXCID901516308, Plazomicin [USAN], ACHN 490, Plazomicin (USAN), (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, Plazomicin [USAN:INN], UNII-LYO9XZ250J, 6'-(Hydroxylethyl)-1-(haba)-sisomicin, Sisomicin Impurity 10, PLAZOMICIN [MI], PLAZOMICIN [INN], PLAZOMICIN [WHO-DD], orb1702932, CHEMBL1650559, SCHEMBL11928040, GTPL10847, GLXC-21869, D-Streptamine, O-2-amino-2,3,4,6-tetradeoxy-6-[(2-hydroxyethyl)amino]-a-D-glycero-hex-4-enopyranosyl-(1?4)-O-[3-deoxy-4-C-methyl-3-(methylamino)-b-L-arabinopyranosyl-(1?6)]-N1-[(2S)-4-amino-2-hydroxy-1-oxobutyl]-2-deoxy-, EBC-27364, AKOS040746239, DB12615, NS00072892, D10151, EN300-20605720, Q15426988, (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, (2S)-4-Amino-N-((1R,2S,3S,4R,5S)-5-amino-4-((2-amino-2,3,4,6-tetradeoxy-6-((2- hydroxyethyl)amino)-alpha-D-glycero-hex-4-enopyranosyl)oxy)-2-((3-deoxy-4-C-methyl-3- (methylamino)-beta-L-arabinopyranosyl)oxy)-3-hydroxycyclohexyl)-2-hydroxybutanamide, (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-y, (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, (S)-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)tetrahydro-2H-pyran-2-yl)oxy)-3-hydroxycyclohexyl)-2-hydroxybutanamide, D-Streptamine, O-2-amino-2,3,4,6-tetradeoxy-6-((2-hydroxyethyl)amino)-alpha-D-glycero- hex-4-enopyranosyl-(1->4)-O-(3-deoxy-4-C-methyl-3-(methylamino)-beta-L- arabinopyranosyl-(1->6))-N(sup 1)-((2S)-4-amino-2-hydroxy-1-oxobutyl)-2-deoxy-, l]oxy}-2-{[3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl]oxy}-3-hydroxycyclohexyl]-2-hydroxybutanamide
Theoretical properties:
molecular_formula: C25H48N6O10
molecular_weight: 592.7 g/mol
exact_mass: 592.34319175 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 11
hydrogen_bond_acceptor_count: 15
rotatable_bond_count: 13
heavy_atom_count: 41
topological_polar_surface_area: 269 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
chembl: PLAZOMICIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Plazomicin, sold under the brand name Zemdri, is an aminoglycoside antibiotic used to treat complicated urinary tract infections. As of 2019 it is recommended only for those in whom alternatives are not an option. It is given by injection into a vein.
Common side effects include kidney problems, diarrhea, nausea, and blood pressure changes. Other severe side effects include hearing loss, Clostridioides difficile-associated diarrhea, anaphylaxis, and muscle weakness. Use during pregnancy may harm the baby. Plazomicin works by decreasing the ability of bacteria to make protein.
Plazomicin was approved for medical use in the United States in 2018. It is on the World Health Organization's List of Essential Medicines.