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.

See full entry for Plazomicin

Accession Number

DBSALT002742

Structure

Similar Structures

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

Plazomicin sulfateProduct ingredient for Plazomicin

Structure for Plazomicin sulfate (DBSALT002742)