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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:
53179-09-2
Molecular Weight:
692.72
EC Number:
258-414-4
UNSPSC Code:
51281665
PubChem Substance ID:
329824589
NACRES:
NA.85

Key Documents

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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

Preparation Note

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
GHS08,GHS07

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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Certificates of Analysis (COA)

Lot/Batch Number
039M4893V
SLCC4231
SLBW7171
SLBV1849
SLBP1781V

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Gengrong Lin et al.
Antimicrobial agents and chemotherapy, 54(5), 2258-2261 (2010-02-11)
Synergy time-kill studies of 47 methicillin-resistant Staphylococcus aureus strains with differing resistance phenotypes showed that combinations of subinhibitory concentrations of ACHN-490 and daptomycin yielded synergy against 43/47 strains at 24 h, while the combination was indifferent against the remaining 4
Stephen Hanessian et al.
Chemical communications (Cambridge, England), 46(12), 2013-2015 (2010-03-12)
Aminoglycoside 66-40C, an unprecedented 16-membered bis-azadiene macrocyclic natural product isolated from the Micromonospora producer of the antibiotic sisomicin, was synthesized following a biomimetic strategy which definitively established its origin as arising from a remarkably selective non-enzymatic macro-dimerization.
Comparison of Preoperative 3-day Topical Levofloxacin versus 1-day Topical Sisomicin Sulfate in the Reduction of Bacterial Flora on Conjunctiva at the End of Cataract Surgery
Y. Kusano, T. Yamaguchi, et al.
Investigative Ophthalmology & Visual Science, 46, 4894-4894 (2005)
Clinical Pharmacology of Sisomicin
Victorio Rodriguez, Gerald P. Bodey, et al.
Antimicrobial Agents and Chemotherapy, 7, 182-195 (1975)
David Landman et al.
The Journal of antimicrobial chemotherapy, 65(10), 2123-2127 (2010-07-30)
Reports of Enterobacteriaceae resistant to all commonly used antimicrobial agents, including β-lactams, fluoroquinolones and aminoglycosides, are increasing in hospitals worldwide. The activity of ACHN-490, a next-generation aminoglycoside, was examined against clinical isolates of Escherichia coli and Klebsiella pneumoniae from hospitals
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