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S7796

Sigma-Aldrich

Sisomicin sulfate salt

≥580 μg/mg (USP)

Synonym(s):

O-3-Deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1->4)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1->6))-2-deoxy-L-streptamine sulfate (2:5) (salt)

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About This Item

Empirical Formula (Hill Notation):
C19H37N5O7 · 2.5H2O4S
CAS Number:
Molecular Weight:
692.72
EC Number:
UNSPSC Code:
51281665
PubChem Substance ID:
NACRES:
NA.85

form

powder

concentration

≥580 μg/mg (USP)

color

white to off-white

antibiotic activity spectrum

Gram-negative bacteria

mode of action

protein synthesis | interferes

storage temp.

−20°C

SMILES string

OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.CN[C@@H]1[C@@H](O)[C@H](OC[C@]1(C)O)O[C@H]2[C@H](N)C[C@H](N)[C@@H](O[C@H]3OC(CN)=CC[C@H]3N)[C@@H]2O.CN[C@@H]4[C@@H](O)[C@H](OC[C@]4(C)O)O[C@H]5[C@H](N)C[C@H](N)[C@@H](O[C@H]6OC(CN)=CC[C@H]6N)[C@@H]5O

InChI

1S/2C19H37N5O7.5H2O4S/c2*1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17;5*1-5(2,3)4/h2*3,9-18,24-27H,4-7,20-23H2,1-2H3;5*(H2,1,2,3,4)/t2*9-,10+,11-,12+,13-,14-,15+,16-,17-,18-,19+;;;;;/m11...../s1

InChI key

CIKNYWFPGZCHDL-ZHFUJENKSA-N

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General description

Chemical structure: aminoglycoside

Application

Sisomicin is an aminoglycoside antibiotic isolated from Micromonopora inyoensis. It is effective against most strains of Klebsiellk spp., Escherichia coli, P. aeruginosa, Enterobacter and Proteus spp.. It is a potential treatment for conjunctiva . It is used in disk and tube dilution sensitivity test.

Biochem/physiol Actions

Sisomicin interferes with protein synthesis at the level of functional ribosome assembly. The mechanism is similar to that of gentamycin. Sisomicin closely resembles gentamicin but is more effective against Pseudomonas aeruginosa and indole-positive Proteus.

Packaging

250MG,1G,5G

Storage and Stability

Keep container tightly closed in a dry and well-ventilated place.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

pictograms

Health hazardExclamation mark

signalword

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Repr. 1B

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges


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Irene Galani et al.
Journal of chemotherapy (Florence, Italy), 24(4), 191-194 (2012-10-09)
The in vitro activity of plazomicin was evaluated against 300 multidrug resistant (MDR) (carbapenemase and/or ESBL-producing) isolates from four hospitals in Athens, an area where carbapenemase-producing organisms are endemic. Most of the isolates were also resistant to the legacy aminoglycosides
Bo Li et al.
Rapid communications in mass spectrometry : RCM, 22(22), 3455-3471 (2008-10-15)
The characterization of unknown impurities present in netilmicin and sisomicin by liquid chromatography (LC) coupled with mass spectrometry (MS) is described. The volatile ion-pairing agent trifluoroacetic acid (TFA) was used for the retention of the main compounds and their impurities
Robert T Cass et al.
Antimicrobial agents and chemotherapy, 55(12), 5874-5880 (2011-09-14)
ACHN-490 is an aminoglycoside with activity against multidrug-resistant pathogens, including those resistant to currently used aminoglycosides. Two randomized, double-blind, placebo-controlled clinical studies investigated the pharmacokinetics (PK), safety, and tolerability of ACHN-490 injection in healthy subjects. Study 1 used a parallel-group
David Landman et al.
The Journal of antimicrobial chemotherapy, 66(2), 332-334 (2010-12-07)
Multidrug-resistant Acinetobacter baumannii and Pseudomonas aeruginosa have become a global problem, often leaving the polymyxins as therapeutic agents of last resort. ACHN-490, a next-generation aminoglycoside with activity against a broad range of Gram-positive and Gram-negative pathogens, was examined against clinical
D M Livermore et al.
The Journal of antimicrobial chemotherapy, 66(1), 48-53 (2010-11-17)
the emergence of carbapenemases in Enterobacteriaceae is driving a search for therapeutic alternatives. We tested ACHN-490, a sisomicin derivative that evades all plasmid-mediated aminoglycoside-modifying enzymes, against 82 carbapenem-resistant Enterobacteriaceae isolates. Comparators included internationally and locally available aminoglycosides. Methods The isolates

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